II

Patrick Kennedy wasn’t thinking that far ahead in October 1848 when he made his way on foot—so it is said—from Dunganstown, a town in southwest County Wexford, along the River Barrow, down to New Ross, six miles away, to board a ship to Liverpool and from there, he hoped, to the New World.5 He was just trying to escape an Ireland that was three years into a catastrophic famine.

In 1845, following an unusually wet summer, a mysterious blight caused the potato crop to fail. The disease had crossed the Atlantic on ships bound for European ports and thence reached Ireland, carried across the Irish Sea by rain and wind. Desperate farmers and peasants tried to stop the scourge by cutting off the blackened leaves and stalks, only to find that the tubers had rotted completely. For a time farmers assumed it was a fluke event, a one-off, but early in 1846 the deadly fungus reappeared, and by the end of that summer more than 90 percent of Ireland’s potato crop was gone. By early October, many Irish towns reported having not a single loaf of bread or pound of grain to feed their residents. A harsh winter followed, with cold rains and snow, and in 1847 potato yields were a fraction of what they had been in 1844.6

This might have been less of a problem had not the potato been such a staple of the Irish diet. Introduced to Ireland in the late sixteenth century, it became in time critically important. More than half of the population of eight million relied on it as their main source of nourishment; upwards of a third, including the poorest of the poor, survived on it almost exclusively. The potato was an ideal subsistence food for Irish peasants, since it was highly nutritious (the Irish were among the tallest and most fertile people in Europe, if also perhaps the most impoverished) and since impressive yields could be had on small plots of land and even in poor conditions. Except when the crop failed. As conditions deteriorated, hunger spread, then starvation. Some families took to the road, wandering from village to village, hoping forlornly that someone would take them in. Others waited in their cottages, shared their remaining morsels, and died quietly, one by one. Many who avoided starvation succumbed to typhus, which spread rapidly among the weakened population.

All told, about one million people died between 1846 and 1851 from starvation or disease, a figure amounting to 13 percent of Ireland’s population. The effects were most severe in the west and southwest—in Mayo and Clare and Kerry, people died by the tens of thousands—but Wexford, too, suffered greatly. “Deaths from famine had been numerous…caused by the utter want of food,” reported the Wexford Independent in January 1847, and one shopkeeper wrote that “the young and old are dying as fast as they can bury them, [for] the fever is rageing here at such arate that there are in healthy in the morning knows not but in the Evening may have taken the infection.”7

The worst of the suffering might have been avoided had British authorities been more attentive or compassionate. But Parliament’s response was piecemeal and inadequate, confirming for many Irish what they could expect from their alien oppressors across the Irish Sea. For centuries the English had exploited them, maltreated them; why should it be any different now? Many London observers believed that the famine was God’s work and endorsed the view of Charles Trevelyan, the director of government relief, that Ireland’s “great evil” was not famine but “the selfish, perverse and turbulent character of the people.”8 In the summer of 1847, an officially sanctioned soup kitchen program fed almost three million people, suggesting what kind of relief could be mobilized by the British state, but the program was shut down that fall. Under an Irish Poor Law Extension Act, Parliament shifted the burden of famine relief away from central government to local Irish communities, who would ostensibly raise their own tax funds for poor relief. A clause in the law stipulated that any head of household renting more than a tenth of a hectare of land would be ineligible for public assistance. Some tenants starved to death rather than give up land to their landlord; many others abandoned their farms, accepted relief, and, faced with extreme poverty, chose the route of emigration. All told, two million Irish men and women, the majority of them Catholic and from the south and west of the country, fled for points overseas during the decade following the famine’s outbreak. The vast majority ended up in the United States.9

The less fortunate were the first to leave, but they were not the least fortunate in most cases, because the journey required some savings or other assets that could be converted into cash. In the words of economic historian Cormac Ó Gráda, “In the hierarchy of suffering the poorest of the poor emigrated to the next world; those who emigrated to the New World had the resources to escape.”10

Twenty-six-year-old Patrick Kennedy was among the latter. His exact reasons for leaving remain a mystery, but as the third-born son he knew that even if conditions improved, he would have little chance of inheriting the family farm—or of gaining access to any other parcel of land, for that matter. True, the Kennedys were comparatively well-off in Dunganstown, and had been spared the worst of the famine, but even so, the future for someone in Pat’s position was bleak. So he set his sights on the far side of the Atlantic, on “the States,” that strange and wondrous place so often discussed at family gatherings. America offered hope to people like him, and, what’s more, there were already substantial numbers of Irish in the United States to welcome the newcomers to its shores. Pat surely knew as well that conditions on the ships to New York or Boston or Philadelphia were less brutal than on those bound for Quebec, a destination that, moreover, had the disadvantage of being under British rule. (In 1847, an estimated 30 percent of those bound for British North America perished on board or shortly after their arrival in Quebec.) A ticket to Australia, also under British dominion, was too pricey to consider.11

Still, the voyage to America, typically lasting a month and costing $17 to $20 (the equivalent of $550 to $650 today), including provisions, was arduous enough. Often, the ships were barely seaworthy; always, they were dangerously overcrowded. Only in fair weather were passengers allowed on deck, and often not even then. The steerage below was cramped—a grown man could not stand without stooping—and unsanitary, and in short order the illnesses that the Irish had fled were sweeping through the crammed holds. Typhus was especially pervasive. Water soon turned foul and could be forced down only with the addition of plentiful amounts of vinegar. Food supplies dwindled, and the stench from the privies became overpowering. Day after day the misery raged on, often in rough weather that created its own misery and stress. Mortality rates were high. As nerves frayed and tempers flared, fights broke out, sometimes leaving the combatants a bloodied mess. Single women faced their own agony: the threat of assault by rapacious sailors.12

It took a healthy disposition and a dose of good luck to survive the passage on these “coffin ships” with mind and body intact. Patrick did. Even upon arrival at port in East Boston (or Noddle’s Island, as it was known, which was still accessible from the mainland only by ferry), his challenges were just beginning. Immigrant Boston was a forbidding land. As he emerged from the shadowy steerage, blinking in the daylight, then crossed over the gangplank onto the brimming dock, Pat would have been met by a motley mix of hucksters and con men, eager to take advantage of the disoriented newcomers by promising pleasant lodgings that often turned out to be squalid and windowless, or well-paying jobs that in reality were backbreaking and might pay one dollar for a fourteen-hour workday.

But at least there were jobs to be had, and in Boston no one, not even the most destitute, starved to death. Indeed, East Boston at midcentury was experiencing a boom of sorts, largely because of the shipbuilding that went on there and because it provided transatlantic shipping companies with a deepwater port. One of these companies, the Cunard Line, employed many of the new arrivals as carpenters and dockhands as it built piers and warehouses on the waterfront. Others found work in Donald McKay’s shipyard, maker of the world’s finest clipper ships, beautifully finished and furnished and built for speed. (In 1854, the Flying Cloud, at seventeen hundred tons, made the trip from New York to San Francisco, by way of Cape Horn, in eighty-nine days, eight hours, the fastest on record.^*1) Pat Kennedy, having learned the skills of coopering (barrel and cask making) in Wexford, found work at Daniel Francis’s cooperage and brass foundry on Sumner Street, which made mostly shop castings and whiskey barrels, the latter destined for the taverns that were popping up like mushrooms all over Irish Boston. Soon he was working twelve-hour days, seven days a week. (Like other immigrants, he quickly discovered that in America the workday was longer than anything he had experienced in Ireland.)13

He also found time to marry. Bridget Murphy, another recent arrival from County Wexford, became Pat’s wife in September 1849, in a ceremony at Holy Redeemer Church.14 They bought a modest house on Sumner Street, proof positive that Patrick had established genuine job security and a decent wage. Their first child, Mary, was born in 1851, followed by Joanna in 1852, John in 1854 (who died of cholera before his second birthday), Margaret in 1855, and Patrick Joseph, called “P. J.” so as not to be confused with his father, in early 1858.

All the while, Pat Kennedy maintained his grueling work schedule until, one autumn day, he could do it no more. In November 1858, ten months after the birth of P. J. and nine years after stepping ashore in Boston, Pat died, at age thirty-five, with a wife and four young children, leaving behind no documents or portraits. The immediate cause was either cholera or consumption, but years of punishing work, every day of the week, surely took their toll on his immune system, made him susceptible to infection and then unable to fight it off. The first of this clan of Kennedy men to set foot in America, he was the last to die in anonymity.15

III

It says something about the experience of Irish-born men in Boston at this time that so many of them died young, leaving large numbers of children to be raised by their mothers. According to one estimate, the average Irishman of Patrick’s generation survived only fourteen years in the New World.16 The congested and unsanitary conditions in which many of them lived was a factor—often they made do in cellar apartments in the North End or Fort Hill that offered little light or air and were prone to flooding; it was not unheard of for a hundred people to share one sink and privy—since they made the community a prime target for every scourge and disease. Cholera hit the Irish sections of the city hard in 1849, and there were regular outbreaks of smallpox and tuberculosis. Add to that the extremely long hours in physically taxing jobs in the quarries or on the docks and it becomes easy to see why so many met their end prematurely. Three Irish Americans who in due course would reach the pinnacle of the political scene in Boston—Martin Lomasney, James Michael Curley, and one of John F. Kennedy’s grandfathers, P. J. Kennedy—all lost their fathers in childhood. Kennedy’s other grandfather, John F. Fitzgerald, had barely reached adulthood before his father passed on. (His mother had already died.)17

The constant stream of new arrivals strained Boston’s resources well past the limit. In 1847 the city built two hospitals on Deer Island, in the harbor, to treat “Foreign Diseased Paupers”; both were soon swamped with patients, almost all of them Irish. Acute needs remained. A health inspection committee visiting a teeming Irish area near the harbor in 1849 found horrible conditions (perhaps colored by prejudice on the part of its members):

In Broad Street and all the surrounding neighborhood…the situation of the Irish is particularly wretched….This whole district is a perfect hive of human beings, without comforts and mostly without common necessaries; in many cases, huddled together like brutes, without regard to sex, or age, or sense of decency; grown men and women sleeping together in the same apartment, and sometimes wife and husband, brothers and sisters, in the same bed. Under such circumstances, self-respect, forethought, all high and noble virtues soon die out, and sullen indifference and despair, or disorder, intemperance and utter degradation reign supreme.18

The description speaks to one overriding characteristic of the Boston Irish: their ballooning numbers. In 1800, the city counted little more than a thousand Irish. By 1830 the figure had risen to eight thousand. But in 1847 alone, 37,000 came ashore. (This in a city that, according to an 1845 census, had a total of 114,366 residents.) Many others traveled overland to the city from Canadian ports. On just one spring day that year—April 10—one thousand Irish overwhelmed the port of Boston. By the early 1850s Irish-born Catholics made up a quarter of Boston’s population, and Reverend Theodore Parker remarked that in a single decade Suffolk County had become a “New England County Cork,” and the city of Boston “the Dublin of America.” Catholic churches soon dotted the landscape in Irish Boston, each becoming the unifying center for its neighborhood, around which community life revolved. In 1860, on the eve of the Civil War, the city’s Irish-born population stood at 45,991.19

If there was strength in numbers, young Bridget Kennedy could be forgiven for not seeing it as she contemplated her new life as a single mother. The Boston in which she and her compatriots had arrived was already more than two centuries old, and it possessed a reputation and civic identity that could terrify the newcomer.20 Everywhere she turned, she saw evidence of anti-Irish and anti-Catholic prejudice. Anglo-Saxon Bostonians, steeped in anti-papist rhetoric that coursed deep into their colonial past, saw the immigrants as crude and clannish and uncivilized, prone to crime and public drunkenness. These residents regularly posted “No Irish Wanted” notices when making hires, and excluded even the small band of well-educated, professional Irish Catholics from the city’s rigidly defined and tightly restrictive financial hierarchy. Being Irish and Catholic was an occupational handicap at midcentury that few could overcome.21

Even women who worked as maids, as Bridget Kennedy had done, found themselves under suspicion. “Though Bostonians could not do without the Irish servant girl, distrust of her mounted steadily,” historian Oscar Handlin wrote. “Natives began to regard her as a spy of the Pope who revealed their secrets regularly to priests in confession.” Soon there were newspaper ads like the one for “a good, reliable woman” to care for a two-year-old in Brookline, then a Yankee enclave. The person hired would not have any washing or ironing duty, but the post had one ironclad requirement: “Positively no Irish need apply.”22

Politically, too, the Irish found themselves frozen out. In the early 1850s, the reactionary Know Nothing movement (so named because its adherents would feign ignorance when asked about the organization) swept the immigrant-heavy Eastern Seaboard and became, for a time, an unstoppable force in Massachusetts. With an ideology rooted in anti-Catholicism and opposition to immigrants, the party sought to extend the period for naturalization and the right to vote from the then-current five years to twenty-one years, and ran candidates under the motto “Americans must rule America.” In the state election in 1854, two out of three Massachusetts voters backed Know Nothing candidates, with the result that the party took all but a handful of legislative seats as well as the governor’s office and the Boston mayor’s seat. In short order, the state legislature put forth a program of “Temperance, Liberty, and Protestantism,” which mandated among other things that Protestant hymns and the King James Bible be used in public schools, and which deprived Catholics of the right to hold public office because of their supposed allegiance to Rome.23

The bigotry of the Know Nothings prompted Abraham Lincoln, an up-and-coming Illinois politician, to despair to a friend in 1855, “Our progress in degeneracy appears to me to be pretty rapid. As a nation we began by declaring that ‘all men are created equal.’ We now practically read it ‘all men are created equal, except negroes.’ When the Know-Nothings get control, it will read ‘all men are created equal except negroes, and foreigners, and Catholics.’ ”24

The Know Nothing surge in American politics proved short-lived, thanks to Lincoln’s rapidly growing Republican Party, but Know Nothing sentiments continued to hold sway in Massachusetts state politics for many years to come, and kept the Irish population away from elected office. The nativist press duly chronicled the alleged lawlessness and chronic alcoholism and disease in Boston’s immigrant neighborhoods, and state voters approved laws mandating literacy tests that were designed to keep Irish from the polls. Catholics were discriminated against in hospitals and were prohibited from burying their dead in public cemeteries. Hundreds of impoverished Irish in poorhouses and asylums were deported back to Liverpool on the grounds that they were a drain on the public purse.25

At the same time, the Irish experienced tensions with other immigrant blocs—the Germans, the Scots, the English, the Canadians—who saw their wages diminish on account of the throngs of unskilled newcomers. As John F. Kennedy would later remark about the era of immigration lasting into the early 1900s, “Each wave disliked and distrusted the next. The English said the Irish ‘kept the Sabbath and everything else they could lay their hands on.’ The English and the Irish distrusted the Germans who ‘worked too hard.’ The English and the Irish and the Germans disliked the Italians; and the Italians joined their predecessors in disparaging the Slavs.” From time to time in later years, after the influx of Italian immigrants to Boston in the 1890s, noises were made about the Irish and Italians banding together against the Yankees, but unity proved elusive—the economic and social tensions were simply too deep.26

Under different circumstances, the newcomers might have responded to these restrictions by striking out for greener pastures elsewhere in the United States. But few Irish had the training or the skills to feel confident they could make it out there in the great unknown. Some could not read; others lacked the skills needed to settle on the rural frontier. There was also the simple matter of Boston’s geography, different from that of almost every other major American city in that it was substantially water-locked. To venture out from areas where most immigrants lived required the payment of tolls or fares, which, however modest, were prohibitive for a people struggling to eke out an existence. (As late as 1858, bridges leaving the city charged tolls even for pedestrians.) Most of all, perhaps, this was a place to which they could relate, with an established Irish community—with recognizable faces, a neighborhood parish, an Irish-run saloon.27

Moving was in any event out of the question for a young widow with a brood to raise. So Bridget Kennedy hunkered down and set about doing what needed to be done. In June 1860, a year and a half after Pat’s passing, a Boston census taker reported that she had personal effects worth $75, a respectable sum in the neighborhood at that time. To help make ends meet, she took in boarders occasionally, including Mary Roach, eighteen, who looked after the Kennedy children. Details regarding Bridget’s employment are sketchy, but it seems she worked as a hairdresser and housecleaner before becoming the proprietor of a notions shop near the waterfront in East Boston that in due course started also carrying groceries and baked goods, even some liquor.28

Bridget loved her daughters, but P. J., as the lone son, was the measure of all things. She and the girls coddled him and worked to keep him on the straight and narrow. Determined to give him the opportunity for a better life, Bridget saved every penny she could in order to send him to Sacred Heart, a school run by the Sisters of Notre Dame. Quiet and reserved, with fair skin, blue eyes, and wavy brownish-red hair to go with a sturdy build, the boy was ambitious and blessed with a quick and agile mind, but book learning left him antsy; he lasted in school only until his early or mid teens. He then went to work as a dockhand on East Boston’s busy waterfront, but although he had the strength for physical labor, he lacked the temperament. The hard-drinking, brawling ways of his co-workers left him cold, and, with his mother’s constant encouragement, he aspired to bigger things. Each month he put away part of his earnings and kept on the lookout for an opportunity.

One day it came: a saloon in Haymarket Square was losing money and had been put up for sale. P. J. pounced and acquired it for next to nothing. Before long the enterprising and self-possessed young man, now in his early twenties, turned the tavern into a profitable business, specializing in offerings of lager beer. He carefully plowed the profits back in, becoming part owner of two additional taverns and expanding into whiskey importation and distribution. A teetotaler like his son after him (he did not wish to be associated with the stereotype of the blustering and bellicose Irish drunkard), Kennedy was a popular saloonkeeper, and he looked the part, with his stocky physique and swooping handlebar mustache. His patrons appreciated his friendly and unassuming manner and his willingness to help new arrivals find lodging and work, to straighten out misunderstandings with the police, to find legal assistance and arrange bail. Most of all, he had the great saloonkeeper’s ability to listen, to absorb the constant babbling without complaint, to laugh with the jokesters and commiserate with the down-and-out.29

Owning the taverns also gave Kennedy something else: political influence. As a neighborhood social center, a refuge in the cold and impersonal urban environment, the corner saloon was where the Irishman could stop on his way home from work and rest his tired body, forget his troubles, and tell a tall tale or two while delaying the return to his often dingy tenement apartment, teeming with children and boarders. Invariably, the chatter touched on social issues, and the tavern became a key center of political activity, its owner often a notable figure in the community, second only to the parish priest in power and prestige. Soon Kennedy knew who was running for office, knew the campaign strategies and shenanigans, knew who had dirt on whom. Small wonder, then, that he and many other saloon owners became ward bosses who built their political power through jobs and favors.

With each passing year, the political discussions in the taverns shifted more and more away from the remembered grievances of Ireland and toward local concerns. No longer did England’s serial transgressions against their beloved Emerald Isle generate the most fervor among the men who hunched over the bar; now it mattered more whether fares could be reduced on ferries linking East Boston to the mainland, and whether Boston’s new sewage system would fully encompass Irish neighborhoods. The attachment to Eire and its beauty remained, but America was home now to these men, many of them naturalized citizens who had fought for the Union in the Civil War. They saw meaning in politics and found a home in the Democratic Party, and they flocked to its banner. Kennedy, his influence rising, became a leader of Boston’s Ward Two and, in 1884, at age twenty-six, was appointed precinct officer. Two years later, just shy of his twenty-eighth birthday, he won a seat in the state House of Representatives.30

IV

P. J. Kennedy’s success was one sign among many that the Irish had arrived in Massachusetts politics. The sheer numbers tell the tale, just as farsighted Yankee Protestants had long feared. By the mid-1870s, with the second generation now in adulthood, with the birth rate high and the mortality rate waning, and with more transplants arriving from the motherland by the week (emigration slowed after the end of the famine, but it never disappeared), Irish Americans represented more than a third of Boston’s population of 300,000 and were fast approaching 50 percent.31 The Beacon Hill bluebloods might retain control of the financial and cultural institutions and the social pecking order, but the political contest was a different story. The Boston Irish were electing state legislators and city aldermen, and in 1882 one of their own, Patrick Collins, was elected to the U.S. Congress. Two years after that, Hugh O’Brien became the city’s first Irish and first Catholic mayor. Meanwhile, ward bosses such as Kennedy and the legendary Martin “the Mahatma” Lomasney wielded great power in their areas, as did the cocky John F. Fitzgerald, the rakish ruler of the North End, who in time would become P. J.’s in-law.32

As Kennedy prospered in business and politics, he also found success in his personal life. He began courting Mary Augusta Hickey, a tall, handsome woman with stately grace and formidable intelligence who was two years his senior and hailed from an affluent Irish family in Brockton, then an upscale suburb. Her Irish-born father, James, was a prosperous businessman, and her three brothers had all done well: Charles was the mayor of Brockton, Jim was a police captain, and John, a graduate of Harvard Medical School, was a doctor in nearby Winthrop. If any family can be said to have represented the so-called lace-curtain Irish (solidly middle class, and to be distinguished from the down-at-the-heels “shanty” Irish), it was the Hickeys. On Thanksgiving eve 1887, P. J. and Mary Augusta (“Mame,” he called her) were married at Sacred Heart Church. A little over nine months later, on September 6, 1888, they had their first child, Joseph Patrick Kennedy. In 1891 followed Francis Benedict, who died of diphtheria about a year later, then Mary Loretta, in 1892, and Margaret Louise, in 1898.

Bridget Kennedy, for her part, lived long enough to see her son find success in the world in which she had struggled to survive, and to see his first son born into it. She died in her home in December 1888, at age sixty-seven.33

Her daughter-in-law, it turned out, was much like her in one respect: she was intensely ambitious for her son. Just as P. J. had been the star in his family firmament, so Joseph would be in his, the child on whom Mary Augusta lavished her primary attention. “My Joe,” she called him as she immersed herself in his daily life, doting on him, engaging him on his school activities, and reminding him that his uncle John had gone to Harvard. Joe felt the bond, rushing home from the local parish school every day to have lunch with her. “He missed me,” Mary Augusta remembered delightedly years later, after he had begun to make his mark on Boston society. “He missed me and wanted to hurry home and see me again.”34

Initially, the family resided at 151 Meridian Street, in the business district of East Boston, a three-story dark-red brick house, which we would today call a townhouse and which was near one of P. J.’s taverns. But before long they moved up—in both senses of the word—to a large house at 165 Webster Street, an elegant, tree-lined avenue on Jeffries Point, overlooking the harbor, with a backyard that sloped down to the water. Young Joe had the run of the place, the Irish servant girls treating him like a young prince and his sisters constantly deferring to him. “I thought he was a god,” Margaret said of her brother many years afterwards. “I’d be thrilled even if he asked me to put something away for him—anything, just as long as he noticed me.” Loretta, meanwhile, remarked on the authority Joe seemed to possess within the family, even at a young age. In this largely female world, he was the pivot around which all things circled, an arrangement he took to be the normal order of things.35

The details of Joe Kennedy’s boyhood are largely lost to us, in part because in later years he showed little interest in talking about it. He offered few clues as to the nature of life within the household, or about his relationships with his sisters, though in adulthood he corresponded with them via letters and phone calls and backed them financially.36 Never one to look back, Joe was also keen to hide the fact that he had grown up in a life of privilege, wanting for nothing and with advantages others did not have. (“Joe did not come in on a raft,” his niece Mary Lou McCarthy would subsequently remark. “His life was very comfortable.”37) To admit such a thing would be to admit that he might not be fully responsible for his own success, and this was something Kennedy was loath to do. A devotee in his boyhood of Horatio Alger Jr. books, he loved their up-from-nothing, against-all-odds theme and came firmly to believe that anyone with God-given talents who worked hard could achieve great things. Kennedy never said or implied he was a child of poverty or that he faced undue hardships growing up, but he did push the narrative that his success was entirely his own.38

Young Joe looked up to his father, and recalled with satisfaction being allowed to tag along with him to campaign rallies and torchlight parades. He took pride in being the son of one of East Boston’s most prominent figures, someone who had achieved rare distinction in business and politics. He admired his father’s shrewdness and talent for organization, could see the respect he carried in the community. Yet there was also a sense, no doubt encouraged by his strong-willed mother, Mary Augusta, that he should set his own sights higher, that his father’s success, however great, was too bounded, too local. And indeed, P. J. Kennedy, for all his determination to make good, did not have a driving ambition to extend his influence beyond his corner of the city. A mediocre public speaker with scant interest in chatting up voters on street corners, Kennedy preferred to wield his political power from behind the scenes. His tenure in the state house was undistinguished, and he achieved little after being elected to the state senate in 1892. After two one-year terms in the upper chamber, he stepped aside. East Boston was the heart of his political world; being ward boss was his calling.39

Mary Augusta felt differently. Although she was proud of her husband’s accomplishments and of her Irish roots, she also chafed at them, aware that among the “proper” Bostonians against whom she measured herself and her family—the Yankee Protestants of Beacon Hill and the Back Bay—parochial politics of the type her husband practiced was not altogether honorable. And she was less willing than P. J. to accept the unwritten regulations of the social game: equal but separate. She wanted something more for her Joe, wanted him to be on equal footing with the Brahmins who ruled Boston society, wanted him to go to Harvard, not the Jesuit-run Boston College or Holy Cross, where the lace-curtain Irish typically sent their sons. She urged him to introduce himself as “Joe” rather than “Joe Kennedy,” the better to hide his Irish heritage.40 One detects her strong influence behind the couple’s decision to send the boy, upon his completion of the seventh grade in parochial school in 1901, to Boston Latin, the oldest and most distinguished public school in the country, whose alumni included five signers of the Declaration of Independence (Franklin, Hancock, Hooper, Paine, and Samuel Adams) as well as Cotton Mather, Ralph Waldo Emerson, and Henry Ward Beecher. By the start of the twentieth century, most upper-class Protestants no longer sent their sons to Boston Latin—they preferred the even more exclusive Northeast prep schools now dotting the landscape—but it was still a forbidding Yankee institution, and even the preternaturally confident Joe must have felt some butterflies on his first day, September 12, as he boarded the ferry that would carry him across the canal and into an environment wholly new to him.41

The curriculum was classical and rigorous, focused on preparing students for the Harvard entrance examinations. Six years of Latin were compulsory, as were six years of science, math, and English, five years of history, and four years of French. In this hothouse atmosphere, Joe struggled. Though he did not lack for brains—he possessed a fine analytical intelligence and a superior memory—his transcript shows a string of C’s and D’s and failing grades in elementary French, elementary physics, and advanced Latin. So poorly did he perform in the classroom that he had to repeat his senior year. Curiously, these dismal results did not seem to dampen the boy’s ego, at least in any lasting way. He looked with scorn on the bookish and humorless types who grubbed for grades and focused his energies instead on the social realm and on athletic pursuits.42

Tall, trim, and physically graceful, Joe excelled on the sports field. He captained the tennis team, played basketball, and became proficient as well at military drill, a high-status activity at the school. When, as a colonel, he led the Boston Latin team to victory in a citywide drill competition, he became a heroic figure on campus. But it was on the baseball diamond that Joe really dazzled. A superb line-drive hitter, he maintained an astonishing .667 batting average as a senior, a feat that earned him the Mayor’s Cup for batting in the city high school league, and gave him a trophy in a ceremony presided over by his future father-in-law, Mayor John F. Fitzgerald. In subsequent years, Joe would recall individual games in perfect detail, and offer highlights to any listener who made the mistake of showing even a modicum of interest.43

Then as now in American high schools, athletes were accorded more than their share of respect. Add to this Joe’s self-assurance, indefatigable energy, and good looks—he had strikingly blue eyes, gleaming white teeth, and brownish-red hair to go with an athletic build—and it’s no surprise that he was popular with the faculty and with fellow students. In the span of a few glorious weeks in the fall of 1907, he was reelected manager of the football team (The Boston Globe had the story, along with a large photo), elected senior class president, and named captain of the baseball team. Many years later, he called Boston Latin “a shrine that somehow seemed to make us all feel that if we could stick it out we were made of just a little bit better stuff than the fellows our age who were attending what we always thought were easier schools.”44

Perhaps so, but to our modern sensibility, it still surprises that the boy with the awful grades, who had to repeat a year and who was Irish Catholic to boot, would be admitted into the Harvard College class of 1912. But so he was. Joe’s rousing success in extracurricular endeavors no doubt helped, as did the fact that Boston Latin was a feeder school, sending more students to Harvard—twenty-five, half of the graduating class—than did any other high school in the country, public or private. That Harvard took more public school graduates and more Catholics (and Jews) than did Yale or Princeton may have mattered as well.45 And the admissions office was surely aware that the boy with the spotty record happened to be the son of one of Boston’s leading political figures.

V

And so, on the first day of October 1908, Joseph Patrick Kennedy headed across the Charles River and onto the grounds of the most prestigious university in the country. Though physically outside the city, in neighboring Cambridge, Harvard at the start of the century was at the epicenter of “proper Boston”; as a calling card to the city’s privileged elite, the university was more important than either occupation or address. The nineteenth-century Yankee and alumnus Edmund Quincy, whose father had been president of the college, expressed the prevailing sentiment: “If a man’s in there,” he remarked, tapping his Harvard Triennial Catalogue, with its full list of graduates, “that’s who he is. If he’s not, who is he?”46

Joe understood the point, as did his mother, who had dreamed of this moment since the day he was born. He knew, she knew, her husband knew, that Joe’s grandmother had been a servant, her first name so common and obviously Irish that the patrician women called their female servants “our Bridgets.” Yet now here he was, however improbably, a Harvard man. If Joe felt nervous about what lay ahead, he didn’t show it. Academically, he saw no reason to worry, given that Boston Latin was widely known to be more demanding than anything Harvard could throw at him. The rigid curriculum of the former gave way now to an elective system in which there were no core requirements and no need even to select a major. With the barest of effort, one could avoid difficult subjects and choose a path of least resistance. Kennedy did. Though he had a good head for numbers, he took no math or science but instead concentrated in government and economics, with a smattering of humanities courses thrown in.

As at Boston Latin, academics at Harvard mattered less to Joe than did the goings-on outside the classroom. He rarely opened a book unless it was required for class. But this time he would have a much harder time scaling the social and sporting peaks of the school. Like the journalist Walter Lippmann, who was two years ahead of him in the class of 1910, he did not fully realize how many Harvards there were, and how little they overlapped.47 There was the Harvard of the privileged young men from proper families such as the Cabots, Bancrofts, Winthrops, Welds, Lodges, and Saltonstalls, with their “final clubs” such as the Porcellian, the A.D., and the Fly, who might or might not go to class and aimed only for a “gentleman’s C” average. There was the Harvard of athletes; the Harvard of intellectuals intent on an academic career; the Harvard of socialites focused mostly on having a good time and securing a gig on Wall Street; the Harvard of iconoclastic outsiders looking to find their way; and the Harvard of public school graduates, many of whom commuted from home every morning and returned home every night.48

Joe Kennedy was firmly in the last group, even though he lived in residence in Harvard Yard. It didn’t take him long to realize that, despite the fact that freshmen were thrown together in the dormitories and dining halls in the Yard, sharp class distinctions defined the social environment. Being accepted into the right organization was the coin of the realm for many students, and the Catholic Joe, like the Jewish Lippmann, would never be tapped for membership at the elite ones—or even come close.

It was not for lack of trying. Where another student with his profile might have avoided the pursuit for fear of being rejected, or simply seen it as a lost cause, Joe charged ahead. When one door closed in his face, he knocked on the next. It was his nature to be irrepressible, not to mention ultracompetitive; both attributes would serve him well in his business activities in the years ahead, but at Harvard they did not get him through the narrow gate to a top final club. He had the wrong surname, the wrong family background, the wrong religious denomination. Perhaps, too, the very aggressiveness of his pursuit hurt his cause; he simply tried too hard, and lacked the finesse to hide it. Joe did gain membership to other university groups, including the Hasty Pudding Club and, in his senior year, Delta Upsilon, a lesser club where even Jews and scholarship boys were welcome, but for the rest of his life it stung him that no emissaries from the “Porc” or the Fly ever showed up at his door, depriving him of the recognition he most craved. (Franklin Delano Roosevelt, class of 1904, likewise never forgot being passed over by the Porcellian.) In the ultimate determination of in or out at Harvard, Joe Kennedy was out.49

On the athletic field, too, Kennedy experienced disappointment. Like many who had starred in high school, he had the sudden, unnerving realization in college that he was merely ordinary. Superior talents were all around him. Though he suited up for baseball his first three years, and remained a potent hitter, his fielding and baserunning were liabilities, and he never made the varsity squad until late in his junior year; although he earned a coveted letter, he played in only four games and had seven at-bats.50 He did not try out for the team as a senior.

All in all, then, Joe Kennedy’s Harvard experience was a mixed one. Continuing his lax approach to his studies, he did just well enough to squeak by, earning mostly C’s and not a single A.51 Sporting success eluded him. And despite all-consuming effort, he failed to grab hold of the college’s most desired status symbol, membership in a top final club, which left him envious and scornful. On the flip side, he had his degree and would always be a Harvard man. Gregarious and bright, he proved quite popular among those classmates who didn’t mind his social climbing. And he made some connections with elite Bostonians that would prove useful going forward.

Most notable of all, it was during his Harvard years that Joe positioned himself as the leading suitor of Rose Fitzgerald, the mayor’s daughter.

VI

They had first met many years before, as children, when the Kennedys and the Fitzgeralds vacationed at Old Orchard Beach, Maine. A newspaper photo from that year shows Joe, age seven, and Rose, age five, standing a few feet apart, but in later years neither could recall this initial encounter. And there might have been other fleeting meetings, since, after all, their fathers were prominent political figures who occasionally brought their firstborn to campaign events.

Then again, P. J. Kennedy and John F. Fitzgerald (“Fitzie” to many, or “Johnny Fitz,” or, somewhat later, “Honey Fitz”) were also rivals of sorts, so perhaps the opportunities for chance encounters were fewer than one might imagine. Like the Kennedys, the Fitzgeralds were now second-generation Irish Americans. But where P. J. was restrained and unflashy, even a little severe, Fitzgerald was merry and pugnacious and dashing, a dynamo who could pontificate on any subject at machine-gun speed, the words gushing forth at a rate that astonished first-time listeners.

In other ways too, the two men were polar opposites. Kennedy was systematic in his climb to power, pragmatic and calculating, working patiently behind the scenes and considering his every move carefully. Fitzgerald, on the other hand, was the prototypical gate-crasher, glad-handing and histrionic and bombastic, inclined to shoot first and ask questions later. Short of stature at five feet, five inches, with a large, round face, blue eyes, and sandy hair parted down the middle, he was a natty dresser who reveled in his Irishness and refused to follow the guidelines of any party strategy. A buffoon to some, he had street smarts in spades, and a keen political antenna, and he vowed always to “work harder than anyone else.” And so he did. Ever smiling in photographs, he took on a gloomy look when crossed, his brow furrowed, and didn’t mind in the slightest when told it made him look a bit like Napoleon.52

Born in the North End in 1863 to Thomas Fitzgerald, a grocer, and Rosanna Cox Fitzgerald, who hailed from County Wexford and County Cavan, respectively, young John excelled in his studies and attended Boston Latin, one of the first Irishmen (if not the first) to gain admission. Intending to become a doctor, he enrolled at Harvard Medical School but dropped out before the end of his first year when his widowed father died suddenly and he had to support his siblings. Soon Fitzgerald began his ascent up the greasy pole of politics, first as a member of the Boston Common Council, then as a state senator (where he served alongside P. J. Kennedy), then as a U.S. congressman representing the Ninth District for three terms, then, beginning with his election on December 12, 1905, as Boston’s mayor, under the slogan “Bigger, Better, Busier Boston.”53

That he had a gift for politics no one doubted. It was said that Honey Fitz was the first and most expert practitioner of the “Irish switch”—shaking the hand of one person while talking to another and smiling at a third. An oft-told story had it that he could talk with a person for fifteen minutes, at a rate of two hundred words a minute, barely letting the person get a word in, then pat the fellow on the back and say how much he’d loved the conversation. Night after night he was on the go, seemingly indefatigable, often taking in two, even three dinners in a single evening—one account estimated that in just his first two years as mayor Fitzgerald attended twelve hundred dinners, fifteen hundred dances, and two hundred picnics and delivered three thousand speeches.54 This seems implausible, but even if the estimate overshoots by half, one is left with an almost superhuman level of activity. Then again, this is a man who would go to parties with spare collars in his back pocket so that he could dance all night and still appear fresh. On his fiftieth birthday he celebrated by sprinting a hundred yards at 7:00 A.M., running a quarter mile at nine, wrestling at noon, and boxing at one.55

In 1889, Fitzgerald had married his second cousin Mary Josephine (“Josie”) Hannon, of Acton, Massachusetts, whose parents hailed from County Limerick. Slender and petite, with soft brown hair and an erect bearing she would keep into her tenth decade, Josie was bashful and retiring, the antithesis of her husband. A daughter, Rose Elizabeth, arrived in July 1890, and five more children followed. Rose was born in the North End, the center of her father’s political power, in the family’s first home, at 4 Garden Court Street. There followed a stint in a big, rambling house in West Concord, twenty-five miles northwest of Boston, but in 1904 Honey Fitz, wanting to be closer to the action, bought a fifteen-room Italianate home with mansard eaves on Welles Avenue in Dorchester, just south of Boston. Inspired by her father’s lessons and their frequent excursions to see the city’s many landmarks, Rose became deeply interested in history. She was a stellar student, blessed with a sharp intelligence and a prodigious memory. From her mother, meanwhile, she inherited a deep religious faith and a serene disposition.56

From the beginning, “Rosie” was the apple of her father’s eye, and he in turn became the dominant figure in her life, notwithstanding his frequent absences. “Rose was like her father for all the world,” a childhood friend commented years afterwards. “She was always quoting her father—in fact, we used to call her ‘Father Says.’ ”57 From a young age, Rose accompanied Fitzgerald on political trips (in 1897, at age seven, she met President William McKinley in the White House), and she developed a deep and lasting love of politics that neither her mother nor her siblings nor even her future husband—for all his political ambition for himself and his sons—remotely shared. She relished it all, not merely the campaign rallies, with their blaring brass bands and blizzards of confetti, but also the backroom strategizing and the secret maneuvering that made election victories happen and governing take place. “She damn well knows all the nuts and bolts of politics,” her son Jack’s press secretary Pierre Salinger would marvel decades later, after watching her in action in two campaigns. “She knows how to get votes out, how you make the phone calls, raise money, and all that; and as a speaker, she’s an absolute spellbinder.”58

Over time, Rose began taking on some of her mother’s political duties. With her deep shyness, Josie Fitzgerald hated the ceremonial rounds she was expected to make as a political wife; when she relented and took part, her distaste was palpable and she came off as cold and forbidding. Rose, starting in her mid-teens, stepped in, acting as hostess and greeter at myriad Honey Fitz campaign events and joining him at banquets, ship launches, and building dedications. She became, indeed, a kind of substitute wife. She loved every minute, and won accolades from the press for her precocity and striking beauty. There was something regal about her bearing, observers remarked, owing to her perfect posture and the sureness of her movement. Her skill at piano accompaniment came in handy, too, at many of these mayoral events, as her father loved nothing more than to unleash his Irish tenor and belt out “Sweet Adeline” whenever it was requested, and often when it wasn’t.

In June 1906, Rose graduated from Dorchester High. Not yet sixteen, she was the youngest person ever to graduate from the school, and ranked third in a class of 285. Petite and graceful, she had shiny black curly hair and a winning smile, and she radiated poise as she strode across the stage at graduation. On hand to award her the diploma was none other than her father, the mayor, brimming with pride, the moment captured by a photo that ran in The Boston Post the following day. “Most Beautiful Girl Graduate?” blared the headline, no doubt with encouragement from the mayor.59

VII

Rose seemed to have the world in her hand, and she soon had another reason to be thrilled: she found love. That same summer, back at Old Orchard Beach in Maine, she and Joe Kennedy met properly for the first time. Though their encounter was brief, she was smitten by his energy and athletic good looks.60 That fall, he invited her to a dance at Boston Latin. She wanted desperately to say yes but turned down the invitation, because her father “refused to let me go. He disapproved of a girl of sixteen going around to dances in strange places and meeting people who might cause trouble.”61 Undaunted, Rose and Joe carried on a nominally secret relationship that school year while she took college preparatory classes at Dorchester High and attended lectures about European culture and languages at the Lowell Institute, in Boston. He would meet her after lectures and walk her (almost) all the way home, or they would arrange to rendezvous at friends’ parties.

“During that last year at Dorchester High, and the following year,” Rose recalled, “Joe and I managed to see each other rather often. Less often than we would have liked, but more often than my father was aware of.” Joe’s class book in his graduation year at Boston Latin punningly predicted that he would “earn his living in a very round-a-bout way. He will run the flying horses at ‘Severe’ beach [a reference to the carousel at Revere Beach]; on every horse there will be a pretty Rose—that is where the Rose Fitz.”62

Rose’s father had other ideas. Though a union of his daughter with Joe Kennedy would bring together two of the most prominent Irish families in Boston and generate lavish press attention, Fitzgerald frowned on the relationship. Perhaps he felt Joe wasn’t good enough for his daughter, or perhaps he sensed even then that the young man would not be a true and devoted partner. And perhaps, too, Fitzgerald’s own low-wattage rivalry with P. J. Kennedy influenced his thinking, as he seemed much more keen on another Harvard-educated Irish Catholic suitor, Hugh Nawn, the handsome son of a wealthy Dorchester contractor. (Rose liked Hugh well enough but thought he lacked Joe’s charisma.) Whatever the case, when Rose’s ardor for Joe refused to cool, Fitzgerald took a more dramatic step: in 1908 he shipped her and her sister Agnes off to a Sacred Heart convent in the Netherlands.

Her father’s decisions regarding her education frustrated Rose to no end. He had already quashed her desire to attend Wellesley College, to which she had been admitted—too secular, he determined, and besides, at seventeen she was too young to matriculate. Now he was shipping her abroad, and to a convent. Ever the dutiful daughter, however, Rose took the decisions with minimal complaint. Her letters home indicate that she profited in important ways from the experience, not least by cultivating the cosmopolitan interest she had in the world outside the United States. Her proficiency in French improved considerably, and she studied German as well. The convent’s strictly regimented schedule did not keep the two girls from traveling to various parts of the Continent and reporting home rapturously about their experiences. To her surprise, Rose found that she did not mind the devotional emphasis and strict routines of the school.63

She didn’t mention in her letters home that she kept Joe Kennedy’s photo on the table in her room, or that she missed him terribly. The feeling was mutual. For Joe, Mayor Fitzgerald’s opposition to him only sweetened the prize, only made him more determined to have what he considered the prettiest, most famous Catholic girl in the city. Upon Rose’s return to the United States in mid-1909, she and Kennedy picked up right where they had left off, though their meetings were sporadic, as Rose spent the next academic year in New York at the Academy of the Sacred Heart, a girls’ boarding school (which would become Manhattanville College).64 Only in 1910, with her return to Boston, could the romance fully resume, with carefully planned meetings in Harvard Yard, in friends’ homes, and in the Christian Science church, where no one would think to look for them. When, in January 1911, Rose had her coming-out with a splashy debut party at her parents’ home, Joe was present, as were his parents and some four hundred other guests, including every notable Democratic politician in the city. The press was there, too, of course, reporting the following day that the lovely debutante was the belle of Irish Boston, looking sublime in her white chiffon dress.65

Eventually, her father relented in his opposition to Joe Kennedy’s courtship. He could see her determination, and furthermore he had to acknowledge, however grudgingly, that Joe brought a lot of attractive attributes to the table—education, ambition, affability, good looks, and a kind of superhuman stamina that could rival Fitzgerald’s own. In addition, Kennedy was already making impressive moves in his young career. On leaving Harvard, he had set his sights high, aiming to crack Boston’s financial institutions, still tightly controlled by the Yankee Protestants. That is to say, he went into banking. From a young age and right through college, he had shown a talent for profit-making enterprises, and he grasped early on that power came from money.^*2 He had a head for numbers, and had made useful contacts while at Harvard with students whose families controlled the city’s leading banks. Besides, as he later told an interviewer, “Banking could lead a man anywhere, as it played an important part in every business.”66

Upon his graduation, in 1912, Kennedy got himself appointed as a state bank examiner, a position that allowed him to see bank records and books throughout the greater Boston area and to learn how the banks operated and made their money. From there he cleverly maneuvered his way into the presidency of East Boston’s Columbia Trust, a small bank his father had helped found in the mid-1890s. At just twenty-five, he was reportedly the youngest bank president in the state, perhaps in the country. And he was determined to make good. Commuting daily by train from the family home in Winthrop (P. J., after losing a race for street commissioner in 1908, had pulled up stakes and moved the family to a rambling home in this coastal enclave), Joe put in long hours and made use of every possible family connection to breathe new life into a trust company that had been losing assets. Often he skipped lunch or made do with crackers and milk at his desk.

Joe was popular with the immigrants who made up the bulk of the bank’s clientele. Eschewing the stodgy, standoffish reserve of many bankers, he mingled and joked with his clients, many of them poor, and earned their respect with his friendly demeanor and his efforts on their behalf. Strong personal relations with customers were key to business success, Kennedy preached to his staff, and he modeled the message. Stories were legion of his helping clients in desperate economic circumstances who had been turned down by other banks. Less commonly reported was that he always kept an eye on the bottom line—he could be as quick as any banker in calling a loan or foreclosing a mortgage.67

The strenuous efforts paid off: in short order Kennedy, an instinctive businessman for whom dealmaking came easily, boosted deposits and brought in new business for Columbia Trust. Within six months he had increased the bank’s holdings by 27 percent. Even Honey Fitz had to tip his hat.68

For his part, Fitzgerald soon had bigger things to worry about. For years, his mayoralty had been dogged by charges of corruption, with sworn testimony of payoffs and cronyism. Then, in 1913, a fellow Democrat named James Michael Curley announced that he would challenge Fitzgerald’s quest for reelection. An unscrupulous and silver-tongued demagogue, Curley, who at six feet and two hundred pounds dwarfed his opponent, learned that Fitzgerald had been carrying on with a curvaceous blond cigarette girl named Elizabeth “Toodles” Ryan, whom he’d met in a hotel bar. Curley sent a letter to Josie threatening to make the affair public if her husband did not withdraw as a candidate. When Honey Fitz refused to get out of the race, Curley announced publicly that he would give a series of high-profile lectures, including “Great Lovers in History: From Cleopatra to Toodles” and “Libertines: From Henry VIII to the Present Day.” In short order, Fitzgerald’s office announced he would not be running after all. A ditty began making the rounds: “A whiskey glass and Toodles’ ass / made a horse’s ass / out of Honey Fitz.”69

In late December 1913, newspapers began speculating about a possible engagement between Rose Fitzgerald and Joseph Kennedy. The official announcement came on June 20, 1914, after Joe presented Rose with a flawless two-carat diamond he had purchased at discount from a Harvard classmate who had entered his family jewelry business.

One week later, Franz Ferdinand, archduke of Austria-Hungary, was assassinated in Sarajevo, at the hands of a sixteen-year-old Bosnian Serb nationalist. At first, few Americans paid much attention—the crisis seemed no worse than those that had preceded it in the Balkans since 1908 and been resolved peacefully. But this time the Austrians, urged on by their ally Germany, sought to crush the Serbs for good, and the result was a cascade of events that led, in early August, to the start of the First World War. As armies across Europe mobilized, the United States, under President Woodrow Wilson, declared its neutrality, a position the nation would steadfastly maintain for another two and a half years.70

On October 7, 1914, in the midst of a war-induced financial downturn, Rose and Joe were married. Cardinal William O’Connell presided, and Honey Fitz gave the bride away. Acceding to Rose’s wishes, her parents kept the reception small (a prudent move, perhaps, in view of her father’s recent scandal), whereupon bride and groom honeymooned in Philadelphia (where they took in the first two games of the World Series between the Boston Braves and the Philadelphia Athletics) and White Sulphur Springs, West Virginia, where they spent their days riding, golfing, and playing tennis. On Sunday, October 25, they returned to Boston, and that Wednesday, the twenty-eighth, they moved to the sturdy and unassuming house on Beals Street.71

On July 25, 1915, nine months to the day after they returned from the honeymoon, Rose gave birth to the couple’s first child, Joseph Patrick Kennedy Jr. An exuberant Honey Fitz reported of his first grandson that “his mother and father have already decided that he is going to be president of the United States.”72 Twenty-two months after that, on May 29, 1917, on the heels of America’s fateful entry in the war, came child number two. His parents named him John Fitzgerald Kennedy.

II

For the Kennedys, as for many other Americans, the final months of the war had been a blur as they grappled with a more immediate menace: the influenza pandemic that swept the earth in the summer and fall of 1918 and would kill more than twice as many as the Great War itself—somewhere between fifty and a hundred million people. In the United States, nearly 700,000 people died. (Among U.S. soldiers in Europe, the disease claimed more lives—63,000—than did the fighting.) It was an illness like no other. People could be healthy on Monday and dead by Wednesday evening. Some died quickly, experiencing a rapid accumulation of fluid in the lungs that caused them to literally drown. Others lingered before succumbing to secondary bacterial infection. Mortality rates were highest for those in their twenties and thirties.19

The first cases were identified in the American Midwest in the late winter of 1918, and some of the soldiers shipping out to Europe in large numbers unknowingly carried the virus in their lungs. The disease appeared on the Western Front in April, then made its way to Spain, where it killed so many people—some eight million—that it became known as the Spanish flu. There followed a midsummer lull, after which a second, deadlier form of the illness began spreading to various points of the globe, and in September the disease rampaged down the East Coast of the United States, from Boston to New York to Baltimore and beyond. That month, more than twelve thousand Americans perished.

Joe Kennedy was given the task of managing the impact of the crisis at Fore River. With scores of the company’s workers falling ill, he converted shipyard dormitories into infirmaries, hoping to isolate the ailing and prevent further contagion. He stayed put in Quincy for days on end, no doubt partly in order to avoid the risk of contaminating his family. In addition to Rose, Joe Junior, and John, there was now also Rose Marie (later Rosemary, or, to the family, Rosie), born on September 13. “She was,” Rose recalled, “a very pretty baby and she was sweet and peaceable and cried less than the first two had, which at the time I supposed was part of her being a girl.” A clipping in Rose’s scrapbook included the line “A brilliant future is predicted for the baby.”20

In October, the pandemic reached maximum ferocity, hitting almost every corner of the world. In the United States that month, 200,000 perished. Then suddenly, in November, for reasons that remain murky, the crisis eased, and by early 1919 the pandemic was over. With India alone suffering as many as seventeen million deaths, and Samoa losing more than a fifth of its population, it was, in historian Roy Porter’s words, “the greatest single demographic shock mankind has ever experienced.”21 The war was partly responsible for spreading the disease, but so were advances in shipbuilding that for several decades had facilitated global travel and made the world smaller.

The Kennedys survived the epidemic intact, but the long hours and the stress took their toll on Joe, who developed an ulcer and suffered a physical breakdown in late 1918, requiring several weeks of recuperation at a “health farm.” For Rose the absence was not much of a change, for her husband hadn’t been around much during his years at Fore River. Even before that—indeed, from the beginning of their marriage—he had worked brutally long hours at Columbia Trust, including on weekends. Usually he came home at night, but not always. On those occasions, Rose did not question where he had been—or why. “Joe’s time was his own,” she remarked in her memoirs, “as it had been and always would be: School and college had once taken much of it before, and now it was business.”22

Only business? Rose was too discreet to say, but the careful words suggest she had some inkling of what she was getting when she married him, knew there was an area of his life that she would not be a part of, a compartment she could not enter. Of their pre-marriage days, biographer David Nasaw writes, “At Harvard and after graduation, Joe remained faithful to Rose in the way that men of his generation and class remained faithful to their best girls. He did not court any other marriageable women, but neither did he remain chaste until his wedding day.” Afterwards, it seems, the pattern continued. Which is to say, Joe did not give up being a womanizer. He had affairs, lots of them, with secretaries, stenographers, waitresses, actresses, and others.23 How much this surprised his wife—if it did at all—we don’t know. She was well aware that her father had been untrue to her mother, and that many of the other politicians and celebrities she met during her years as Honey Fitz’s hostess and sidekick had likewise cheated on their wives. Even so, and even though she was highly adept at suppressing or ignoring things that made her unhappy (and certainly did not record them for posterity), it can’t have been easy on those occasions when evening came and no husband appeared.

The sheer quietude of those evenings, even when Joe was home, was undoubtedly a shock to Rose’s system. No longer was she the belle of Catholic Boston, written about in the press, attending balls, traveling internationally, meeting famous people, appearing alongside her effervescent father at this or that lavish banquet or campaign rally or ship launching, or in a box on opening night at the theater. She’d loved that life, and even though marriage and domesticity brought their own pleasures, it’s hard to imagine that a wave of nostalgia did not wash over her from time to time. Her new existence gave her scant opportunity to exercise her formidable and capacious intelligence, her passion for politics, and her wide-ranging curiosity about the world.24

All around her she could see the gains that women were experiencing in American society. In August 1920, the Nineteenth Amendment gave women the right to vote, and though they remained excluded from local and national political realms, they found increased opportunities for making their voices heard through a plethora of civic, religious, and voluntary groups and clubs.25 More women were entering the job force as well, albeit in positions men seldom sought—nursing, teaching, and clerical work. Fashions were changing as new fabrics and dyes allowed for more self-expression and less restrictive cuts. Hemlines moved up and necklines crept lower. Corsets went in the trash or in a box in the attic. The boundaries between appropriate and unacceptable behavior for women blurred as drinking, smoking, and frankness about sex became fashionable. Whereas in 1915 most middle- and upper-class young women had to be chaperoned during social engagements, by a decade later they engaged in unsupervised dating, in which a fellow “asked out” a woman and spent money on her. Rose gave little overt indication that she longed for full access to this new world—it conflicted in key respects with the conservative version of Catholic womanhood to which she and her mother adhered—but in a moment of candor she acknowledged that “life was flowing past.”26

Only once that we know of was there a seeming rupture. The details are sketchy, but according to relatives, in early 1920, heavily pregnant with her fourth child—Kathleen would be born on February 20—Rose abruptly moved back to her parents’ home on Welles Avenue in Dorchester. Joe’s constant work and frequent absences were too much, the emotional deprivation too draining. Even when Joe was home, a part of him was not really there, as he refused to talk about work and no longer shared his dreams or plans with her, as he had done during the many years of courtship. She felt isolated, she told her parents, and ached for more. Honey Fitz and Josie had long had their doubts about their son-in-law and his ruthless ambition, but they were not thrilled by the new arrangement. After three weeks, Honey Fitz told his daughter that, in so many words, she had made her bed and must lie in it. The kids needed her, and so did her husband. “You’ve made your commitment, Rosie,” he told her, “and you must honor it now. What is past is past. The old days are gone. [But] you can make things work out. I know you can.”27

Rose complied and, after attending a church retreat, returned to Beals Street, determined to fulfill her duties as wife and mother. If her subsequent unambiguous defense of the marriage in this period—“[You] never heard a cross word, we always understood one another and trusted one another and that was it”—doesn’t exactly have the ring of truth, it’s almost certainly the case that Rose gave little thought to divorce. Her deep Catholic faith proscribed it. Moreover, church teachings provided a measure of comfort, instructing her that all spouses faced pressures, especially in child-rearing, and that there was true nobility in marital sacrifices.28

III

And indeed, there were plenty of good times in these years, too. Often on Saturday evenings, Joe and Rose would attend the symphony in Boston. At Harvard he had developed a deep interest in classical music, and she had studied composition and performance during her school year in Holland. They relished taking in live concerts as well as playing records at home on the family Victrola. At other times Rose would sit down at the piano in the living room and play popular songs, with Joe and the children or family friends joining in with the words. On Sundays they piled the kids into the family Model T and drove the ten miles to Winthrop to visit Joe’s parents. And on weekday mornings, Rose took pleasure in taking the children on excursions in the neighborhood, pulling Rosemary in a kiddie car and holding little Jack (as they called him) by the hand while Joe Junior walked alongside.29 They would stop in a store or two—the five-and-ten in Coolidge Corner was particularly exciting for the boys—and at St. Aidan’s Church, on Freeman Street, to instill in the children the idea, she later said, that “church isn’t just for Sundays and special times on the calendar but should be part of daily life.”30

And so it was. Rose insisted that her children observe the important Catholic rituals, starting with baptism in the days after birth and then, as they grew, First Confession, First Holy Communion, and Confirmation. Before and after meals and before bed, she guided them in prayer. She made sure they never traveled without a rosary in their pocket. Every Sunday, without fail, and on First Fridays, the family attended Mass, and they were in the pews as well on the Holy Days of Obligation—the Epiphany on January 6, the Assumption of the Blessed Virgin Mary on August 15, All Saints’ Day on November 1, and so on. The boys served as altar boys, and the girls wore veils and carried prayer books.31

Joe, meanwhile, could show his tender side, surprising Rose with flowers or a loving note. At the birth of each child, he gave her a thoughtful, often expensive gift. And whenever a child became ill, this workaholic father would become instantly engaged. Jack’s fragile health was a special concern. His birth, in May 1917, had been uncomplicated—Dr. Frederick L. Good, a Boston obstetrician who was summoned along with his nurse to the Kennedy home for the delivery (he would deliver each of the Kennedy children, and a few of the grandchildren after that), pronounced the baby healthy and handsome. But from an early point, little Jack was sickly and frail. Rose tried hard to build up his strength, to no avail. In February 1920, at age two years, nine months, he contracted scarlet fever, mere days after Kathleen’s birth. A leading cause of childhood death in those years, the illness also could have serious aftereffects (kidney disease, rheumatic heart disease, arthritis), and it was highly contagious, a potential disaster in the tight confines of a family home. With the local Brookline hospital refusing to take patients with contagious illnesses, Kennedy enlisted his father’s and his father-in-law’s help to get little Jack admitted to Boston City Hospital, even though he was not a Boston resident.

“By the time he got there,” Rose remembered, “Jack was a very, very sick little boy.” Unable to visit him because she was adhering to the custom of the day to remain in bed for three weeks after childbirth, Rose dispatched Joe, who for two months changed his schedule so he could spend each afternoon and evening at his son’s hospital bedside.32 The situation was acute, and Joe feared the worst. For several agonizing days, Jack hovered between life and death. But eventually he pulled through, aided in no small part by the treatment he received from the attending physician, Dr. Edward Place, widely acknowledged as the nation’s leading authority on measles and scarlet fever. In early July, Joe penned a heartfelt note of thanks to Dr. Place, “for your wonderful work for Jack during his recent illness.” He added that he had “never experienced any serious sickness in my family previous to this case of Jack’s, and I little realized what an effect such a happening could possibly have on me. During the darkest days I felt that nothing else mattered except his recovery.”33

At one point during the harrowing episode, Kennedy pledged—to God, or to himself, or both—that if Jack lived, he would give half of his fortune to the Church. When his son did recover, he wrote a check for $3,740, half of his liquid assets (on paper he was worth infinitely more), to the Guild of Saint Appollonia, which had been formed a decade before to provide free dental care to the city’s Catholic schoolchildren. Jack, for his part, so endeared himself to the nurses with his sweetness and vulnerability that two of them would later pay him a visit at home. “He is such a wonderful boy,” nurse Sara Miller wrote in a letter to Joe. “We all love him very much.” Nurse Anna Pope agreed some weeks later: “Jack is certainly the nicest little boy I have ever seen….I’m afraid I asked for too much when I asked for Jack’s picture but he was so lovable and such an excellent little patient, everyone loved him. I felt very lonesome when I left him.” Upon being discharged, Jack was sent away for several weeks of convalescence at the Mansion House Hotel, in Poland Springs, Maine, as there was worry he might still be contagious. Only in May, three months after falling ill and near his third birthday, did he return home to Brookline. His nurse reported that he had been “an excellent little patient” and that, after meeting his baby sister at last, he appeared “very happy.”34

By this stage the Kennedys were on the move. The previous year, Joe had taken a management position with Hayden, Stone and Company, a leading stockbrokerage firm with offices in Boston and New York. From the start, he thrived, learning market operations and the intricacies of insider trading (not then illegal, but widely considered unethical) from Galen Stone, the portly and mustached co-founder, who became his mentor. With his zest for hard work and his skill at juggling numbers and accounts, Kennedy did well for the company and for himself, investing in stocks on the side and buying and selling real estate, all the while expanding his connections in the financial world. In one case, he learned from Stone that the Pond Creek Coal Company, whose board of directors Stone chaired, was about to be acquired by Henry Ford. Before the plan was made public, Joe bought fifteen thousand shares at $16, mostly with borrowed funds; when news of Ford’s plans broke, Pond Creek skyrocketed, and Kennedy promptly sold, netting more than half a million dollars.35

As socially ambitious as ever, Kennedy dressed for success, ordering tailored suits and custom-made shirts, and he joined first the Woodland Golf Club and then the Middlesex Club, the oldest Republican club in New England (though he kept his Democratic affiliation). And he moved his family to a new Brookline home, at 131 Naples Road.36 The anticipated further expansion of his family made a change of address imperative, but it mattered as well that the new residence was in a fancier neighborhood, with grander houses on bigger plots, more suitable for a man of his station. This home, for which he paid $16,000, sat on an acre, had twelve rooms, high ceilings, a formal entry, curved bay windows, plus an icebox and a washing machine. The Beals Street house they sold to Joe’s loyal assistant and confidant Edward “Eddie” Moore and his wife, Mary, who, with no children of their own, became fixtures at Naples Road, chipping in to help as needed, including as babysitters to the ever-growing brood of Kennedy children.

Rose was delighted with the relocation. She loved the splendor of the new residence, reminiscent as it was of what she had had as a teenager in Dorchester, yet it was close enough to Beals Street that she still knew her way about the neighborhood. Most of all, it had the space her growing family needed. She turned the large wraparound front porch into a playroom, separating the children with folding partitions—“two, three or four of them as the situation at the time indicated. That way they could be with each other and entertain one another for hours at a time with a minimal risk that they would push one another down or stick one another with something sharp or perhaps pile heavy objects inside or on top of the baby carriage.”37 Soon pregnant again, she delivered Eunice in July 1921. Patricia followed in May 1924, and then Robert in November 1925, Jean in February 1928, and finally Edward (named for Eddie Moore) in February 1932.

To manage her ever-expanding family, Rose relied not merely on full-time domestic help but on a detailed cataloging system in which she kept index cards and index tabs listing illnesses, treatments, and measurements for each child. She became an “executive,” as she herself put it, overseeing the kids’ clothes and their daily exercise and managing a complex operation of maids, nurses, and cooks:

I had to be sure there were plenty of good-quality diapers on hand, and that they were changed as needed and properly washed and stored for us….There was also the daily supply of bottles and nipples to be cleaned and sterilized. I didn’t do much of it myself, but I had to make sure it was done properly, and on a schedule that didn’t interfere with another vital schedule. If nursemaids were in the kitchen boiling bottles and nipples and preparing “formulas” and pureeing vegetables (there were no canned baby foods then) when the cook needed the stove and some of the same utensils to prepare supper, there could be a kitchen crisis, sharp words and bruised feelings and, from a management point of view, a precipitous drop in morale and efficiency.38

In later years Rose would be faulted for what some saw as a severe and overly clinical approach to child-rearing, one focused on “efficiency” and order rather than on love and affection. It’s true that she doled out hugs and kisses sparingly, and placed a premium on presentation—proper attire, proper grammar, proper posture. She obsessed about the children’s weight, especially the girls’. It may be, as some have suggested, that she dealt with her husband’s philandering by isolating herself emotionally from her family—and, in part, physically as well, through frequent traveling vacations without her husband and children. Five-year-old Jack’s memorable rebuke, when his mother prepared to depart for a six-week trip to California with her sister Agnes, is telling: “Gee, you’re a great mother to go away and leave your children all alone!”39

Telling behavior—but only to a degree. It bears noting that Rose herself was the source for Jack’s comment, in her diary entry for April 3, 1923, and also that she used it to underscore the young boy’s wit and precociousness. In her memoirs, moreover, she acknowledged that Jack’s comment wounded her, and that she felt miserable the next day as the kids gathered on the porch to see her off. “They looked so forlorn, and when I kissed them good-bye I had tears in my eyes,” she wrote. But then: “After I was down the street a way I suddenly realized there was something I had forgotten and I came back—to find them all laughing and playing on the porch, apparently not missing me much at all. I resumed my journey with an easy conscience.”40

To some extent, at least, an “executive” approach to her task was necessitated by her circumstances. She had five children in six years, from 1915 to 1921, and two more by the end of 1925, with two more still to come after that. Oldest daughter Rosemary, moreover, showed signs of being slow to develop and required extra attention. Rose was effectively a single parent most of the time, as her husband’s work not only kept him in the office until all hours but took him out of town for days, even weeks, on end. The family finances allowed her to have much more domestic help than most mothers of the era—as she herself readily acknowledged—but even so, the logistical demands were extraordinary, especially given her commitment to the then-current ideal of achievement-oriented child-rearing. The right kind of mothering, this Victorian notion held, could set a child on a lifelong path of personal and social significance. From this ideal flowed movements like Republican Motherhood, centered in New England and urging women to be highly engaged with their offspring and to raise patriotic sons who would enter public service.41

Even Rose’s practice of withholding physical affection from her children, so jarring to our modern sensibility and no doubt to many parents at the time, had expert support behind it. With her characteristic hunger for learning, Rose avidly studied the “scientific” child-rearing recommendations of the era and tried to follow them. Eleanor Roosevelt and countless other women did the same. L. Emmett Holt’s bestselling study The Care and Feeding of Children: A Catechism for the Use of Mothers and Children’s Nurses, which made him a kind of Dr. Spock figure of his day, warned mothers against coddling children or playing with them or displaying a lot of affection toward them. Babies, he wrote, should be kissed only on the cheek or forehead, “but the less even of this the better.” Feeding and sleeping schedules should be highly regimented, and children ought to be weighed at standardized intervals. (The data should be collected on, yes, index cards.) They should also get plenty of fresh air and exercise. Rose followed each of these recommendations, and she took to heart as well Holt’s emphasis on dental hygiene. Healthy teeth were imperative to good health and good looks, he declared, and mothers should not fall into the trap of thinking they could delay proper dental care for their offspring. Rose hired an orthodontist to straighten out the children’s teeth, and she insisted on toothbrushings after every meal.42

It wasn’t just Holt. A survey of magazine articles focusing on motherhood between 1910 and 1935 found that the writers considered “too much love” to be the greatest threat to a child’s welfare. And John B. Watson, in his influential book The Psychological Care of Infant and Child (1928), built on Holt’s theories to argue for a stern, controlling, discipline-centered parenting style and to warn against too much maternal affection toward the children. Kissing and hugging, he noted, should be avoided to the greatest extent possible. “If you must, kiss them once on the forehead when they say good night. Shake hands with them in the morning.”43

IV

With a live-in staff that freed her from some of the basic caregiving for the younger children, Rose could focus her attention on the intellectual and social development of the older ones. In addition to outings to points of interest in Brookline, including the public library on Washington Street, she took them on regular visits to see Boston’s historic sites, much as Honey Fitz had done with her when she was little. (Often she would rattle off improvised math challenges en route: “What is two plus two, subtract three, then add two?”) Rose was adamant that “they should know history and especially the history of their own country,” and on their excursions to landmarks she would explain what had happened at the spot and why it mattered, encouraging questions and discussion so the kids would remember. “I was determined about this, and I may have overdone it a little since there can be too much even of a good thing,” she recalled. “In any case they did learn, their interest developed with the years, and I suspect that this may be one reason why as adults they wanted to serve the country in public life.”44

Jack in particular seemed to be fascinated by history, and by the world generally. His curiosity was insatiable. Rose noticed it during these day trips, and also when she read to him in the evenings. He loved adventure stories of all kinds—Sinbad the Sailor, Black Beauty, Peter Pan—and was especially fond of Billy Whiskers, a picture book series by Frances Trego Montgomery featuring a mischievous goat that marries and has two “kids.” Rose found the illustrations crude and harsh, but Jack adored the tales. When he learned in one story that Billy stopped in the Sandwich Islands on his way across the Pacific, Jack asked his mother to get information on this mysterious-sounding place, which she duly did, pulling out the family atlas so Jack could see for himself. Another time, when she read to the older children the Easter story of Christ’s entrance into Jerusalem on a donkey, shortly before the Crucifixion and Resurrection, Jack piped up: “Mother, we know what happened to Jesus Christ, but what happened to the donkey?”45

With his quick wit and irreverent spirit, Jack resembled his maternal grandfather, Honey Fitz, which may explain why the two got on so well. A frequent visitor in these years, “Grandpa Fitz” would take the two older boys for hours at a time, to a sporting event or to the swan boats in the Public Garden, or to the State House where he had formerly been a senator. The boys loved his sense of fun, his infectious love of learning, his sheer delight at being in their presence. (By contrast, their other grandfather, P. J. Kennedy, “wouldn’t let us cut up or even wink in his presence,” Jack remembered.) They never tired of hearing the old man’s well-worn stories, listening with rapt attention and pleading, “Tell that one again, Grandpa!”46

The fifty-nine-year-old Fitzgerald had ample time for his grandsons because his once-storied political career had sputtered. In 1916, two years after the Toodles scandal forced his withdrawal from the mayor’s race, he’d won the Democratic nomination for the U.S. Senate, but he was defeated in the general election by Republican Henry Cabot Lodge. In 1918 he rebounded to claim a seat in Congress, representing the Tenth District, only to be forced out after seven months when a congressional investigation found evidence of voter fraud. Yearning for one more shot at the limelight, Honey Fitz announced in 1922 that he would challenge Lodge a second time for the Senate, then abruptly switched his candidacy to the race for governor. One of Jack Kennedy’s earliest memories was touring the Boston wards with his grandfather, who invariably let loose his patented rendition of “Sweet Adeline” and chatted up anyone and everyone. The crowds loved him, but it was not enough: Honey Fitz lost by a wide margin. His political peak had passed.47

Jack remained frail and prone to sickness, in contrast to his robust and physically imposing older brother. But he did well enough academically at the local Edward Devotion School to enter second grade (under Miss Bicknell) at age six, a year ahead of most kids his age. And he had charm in abundance, not to mention a taste for mischief. Admonished by his mother to get serious in school, he breezily replied, “You know, I’m getting on all right, and if you study too much, you’re liable to go crazy.” That same fall, 1923, Jack and Joe Junior were caught shoplifting false mustaches from a shop, this after they formed a club in which they initiated new members by sticking pins into them. On an eatery sign reading “No dogs allowed in this Restaurant,” they scribbled “Hot” before “dogs.” On another occasion in 1923, soon after a family vacation, Jack confessed to his father, “Well, here I have been home only a few hours and the cops are chasing me already.” He had teased a little girl who had promptly gone to tell a policeman on him, whereupon Jack had raced home and hidden in the cellar until nightfall.48

It was all standard high jinks for two energetic youngsters, but for the family “executive,” Rose Kennedy, it suggested the need for a more structured environment. The point was brought home when Joe Junior cajoled Jack into racing around the block on their bikes in opposite directions and a collision occurred, sending Jack to the hospital for twenty-eight stitches. Another time she caught the two boys in the cellar, surrounded by empty milk bottles they had purloined from the neighborhood in order to resell. She opted to transfer them from Edward Devotion School to the private Noble and Greenough Lower School (soon thereafter renamed Dexter), six blocks from home, which fielded sports teams and where “there would be after-school supervised play” until 4:45 in the afternoon.49

The principal of the school, Miss Myra Fiske, had interviewed the boys in the spring of 1924 and liked what she saw. She noted Jack’s precocious intellect and wrote that she was “very glad that we decided to take this little John Kennedy. He is a fine chap.” That fall the brothers enrolled and instantly entered an elite world, a Brahmin bastion where Catholics were rare and blacks and Jews unknown. “We were probably the first and only ones who were Catholics,” Jack later reflected, which may have been an exaggeration but not by much.50

Inevitably, the taunting and bullying soon followed. “Almost everybody was a Protestant,” schoolmate Augustus Soule recalled. “I think there was a sort of snobbery, which the children adopted. I think that in those days the upper crust Boston families, of which there were a great number sending their children to the school, were very down on the Irish….To be Irish and Catholic was a real, real stigma—and when the other boys got mad at the Kennedys, they would resort to calling them Irish or Catholic.” Sometimes the fists started flying. Joe, older and bigger than his brother, not to mention more pugnacious and combative, seemed to take the encounters in stride, even challenging older boys to fight on occasion. Jack took a different tack, betting on his brother to win the scraps using a popular schoolyard currency. Soule again:

In those days, marbles: that was the big thing. You always carried a little bag of marbles in your pants pocket. And I can remember going back to my father and saying, “I need some more marbles.”

“What happened to the ones you had?” he’d ask.

“Well, I lost them all in a bet.”

“With whom?”

“I bet with Jack Kennedy.”

It’s an indelible memory I have: Joe fighting and getting all bloody, and Jack going around, betting marbles very quietly. To my mind that illustrates how completely different the two brothers were!51

For all the ostracism they suffered, however, both Joe and Jack liked the school. They played sports and eventually earned starting slots on the football team, with Joe as a bruising fullback and Jack as the lithe and scrappy quarterback.52 They had dedicated and able teachers. Miss Fiske, much beloved by the students, would gather them all together for assembly each morning, and they would recite in unison the school motto (“Our best today, better tomorrow”), followed by Lincoln’s Gettysburg Address or his second inaugural address, or a passage from literature or the Bible.53

With his lively wit and natural interest in history, Jack became Miss Fiske’s special pet. One day he asked her to take him to the historic sites of Lexington and Concord, and offered to get his father’s Rolls-Royce for the occasion. “I don’t think Rose came,” Fiske recalled many years later. “All the boys turned out to see the famous Rolls-Royce. And when it came it was a dilapidated old Ford! Jack never got over how the other boys hooted him—something had happened to the Rolls-Royce!”54

V

That Jack could even offer the luxury automobile for an after-school excursion says something about the family’s finances at mid-decade. In actuality, Joseph P. Kennedy owned not one Rolls but two, and his fortune was growing by the day. After leaving Hayden, Stone at the start of 1923 (though highly successful at the firm, he felt certain, no doubt rightly, that as an Irish Catholic he would never make partner), he had struck out on his own, down the hall from his old firm, on Milk Street in Boston’s financial district, behind a door marked “Joseph P. Kennedy, Banker.” At thirty-four, he was in business for himself, with only Eddie Moore, his genial and devoted factotum, and accountant E. B. Derr on his staff. “It’s so easy to make money in this market,” Kennedy told a Harvard friend. “We’d better get it before they pass a law against it.”55

And so he did. His timing was exquisite, as the economy was emerging full-force out of the postwar doldrums. Farmers struggled and would do so through the end of the decade, but the automobile industry zoomed ahead and the manufacturing sector gained enormously from new technologies—electric motors, aluminum, synthetic materials—that allowed for a proliferation of new consumer goods. The expansion of the economy also gave Americans more discretionary income to spend on the new appliances, as well as on restaurant meals, beauty products, and movies. By the late 1920s, the United States produced nearly half of the world’s industrial goods and ranked first among exporters—by 1929, it was responsible for nearly one-sixth of global exports. One in every five Americans now had a car. More and more American companies were looking abroad, with General Electric and Coca-Cola, for example, investing heavily in Germany and with several U.S. firms challenging British companies for control of Middle East petroleum.56

To a degree fully evident only after the fact, the Great War had altered the global power balance as the United States challenged a prostrate and divided Europe for world leadership. During the course of the war, financial predominance had crossed the Atlantic from London to New York as Europe’s international debts skyrocketed and the United States became the world’s largest creditor nation. By the time the shooting stopped, America’s gross domestic product was equal to that of all the European states together. Old World leaders took due notice, and oriented themselves to the prospect of a new American-led global order. In the geopolitical arena, however, Washington punched below its weight, and the postwar peacemaking effort proved difficult—the bitter and protracted battle between Woodrow Wilson and his domestic opponents resulted in the Senate’s rejecting American membership in the newly founded League of Nations. The result preserved the notion (artificial, it would turn out) of a Euro-centered world, and cheered those—like Joseph Kennedy—who wanted the United States to stay out of foreign political entanglements, out of fear that they would encroach on American sovereignty and threaten its way of life. Even many of those who wanted U.S. membership in the League took the defeat in stride, seeing it as a minor bump on the road to growth and prosperity.57

Wall Street reflected the growing popular optimism, though the boom market was still some years off when Joseph Kennedy established his business. Under Galen Stone’s tutelage, he had learned to use inside information to minimize risk and maximize return; with his lack of sentiment and skill with numbers, he became savvy at market schemes that, while then still legal, were considered by many to be disreputable. A favorite tactic was the stock pool, in which a few traders banded together to buy shares of inactive stock and trade them back and forth to create the appearance of a boom and thus draw in less adroit investors. At an agreed-upon top price, the pool would “pull the plug” and leave the duped investors holding the bag as the stock sank back to its real market value. An elaboration of the maneuver added the option of short selling the stock on its way down.58

Decades later, after his sons became prominent political figures, critics would charge that much of Joe Kennedy’s investment capital during the 1920s came from bootlegging operations undertaken with mob figures in what was, after all, an era of Prohibition. (The Eighteenth Amendment, ratified by the states in 1919 and put into effect the following year, prohibited the manufacturing, transportation, and sale of alcohol within the United States.59) No solid evidence ever accompanied these claims, and careful research by Daniel Okrent and David Nasaw has failed to turn up any.^*3 Moreover, as Nasaw notes, the notion of Kennedy as bootlegger runs contrary to what we know about the man. He always moved cautiously in his business affairs, always placed a premium on achieving and maintaining the appearance of respectability. As an Irish Catholic outsider in the WASP financial world, he understood all too well that his opponents were watching him closely, hoping he would trip up; he needed to watch his every step. Though not averse to playing at the margins of legality, or to taking financial risks when the situation warranted, he took care not to cross over into unlawful territory—he had too much to lose.60

By the end of 1925, Joseph P. Kennedy was a millionaire several times over. A vow he had made upon graduating from university—that he would make his first million by thirty-five—had been realized and surpassed.61

Yet he was dissatisfied. Almost on a daily basis, he received reminders that he and his family would never be fully accepted among “proper Bostonians”—even if in material terms he had long since left his patrician Harvard friends in his wake. He saw it in the treatment his boys received at school, in the barriers that would keep his daughters from being invited to the right debutante parties when they came of age, in the glass ceiling he had come up against at Hayden, Stone. When he rented a summerhouse for the family above a rock-studded beach in Cohasset, fifteen miles southeast of Boston, he found pointed evidence of Brahmin prejudice. Many of Boston’s elite families passed the summers there, and made it clear they wanted nothing to do with the Irish American newcomers. The community’s matrons snubbed Rose, and Joe was blackballed when he applied for membership in the Cohasset Country Club.62

A different man would have brushed aside the disappointments, secure in the knowledge that they paled next to his extraordinary financial accomplishments and his large and handsome family. But Joe Kennedy could never rationalize things that way. His pride wouldn’t let him. Beneath his proud and bullish bravado was a deeply insecure man, whose sense of self-worth was so intimately connected to success that even minor defeats or rejections—the social slights at Harvard, the country-club snubs—left deep and lasting wounds. It didn’t matter how many triumphs he achieved along the way. “Goddamn it! I was born here,” he exclaimed in an interview, referring to Boston, his frustration rising with each word. “My children were born here. What the hell do I have to do to be an American?”63

He wanted out: wanted out of Boston’s constrictive social environment, wanted to move the family to a more open and meritocratic place, a place where he was spending more and more of his time anyway—namely, New York City. Boston was “no place to bring up Catholic children,” he later said. Perhaps not, but his very Catholic wife frowned at the idea. Rose Kennedy had moved schools several times as a child herself and had found the experience difficult; she didn’t want the same thing for her kids. And Boston was her town. She cherished its rich history, its status as the cradle of the American Revolution, and she knew her way around its landmarks as few others did. But her husband persisted, and it was her habit to defer to him on matters of consequence. (“The architect of our lives,” she revealingly called him.) She found herself softening. She realized she liked Manhattan on her visits there to see Joe, and enjoyed the Broadway shows they took in. When an outbreak of poliomyelitis—the same disease that crippled Franklin Roosevelt in 1921—broke out in Massachusetts in September 1927, and the Dexter School announced it would not reopen before October, Rose took it as a sign and relented: New York it would be.64

On September 27, 1927, the Kennedy family, numbering nine strong and traveling in a specially hired railway car, made its way south to Riverdale, a leafy part of the Bronx overlooking the Hudson River. There they settled in a rented stucco house at the corner of Independence Avenue and 252nd Street. Not far away stood the Wave Hill estate, once lived in by both Mark Twain and Theodore Roosevelt. Rose had advocated for Riverdale because it resembled Brookline in key respects: a suburb with excellent schools that were within walking distance of home. On September 28, the day after their arrival, the school-age kids enrolled at the private, nonsectarian Riverdale Country School.65

VI

Perhaps Rose Kennedy had one additional motivation in agreeing to the move: she hoped she and the children would see more of Joe, who was increasingly ensconced in the New York financial world. It was not to be. Barely had they settled in when her husband began spending much of his time in Hollywood, to pursue a growing side business in the movies. Years before, while still president of Columbia Trust, Kennedy had remarked to an associate, “We must get into the picture business. This is a new industry and a gold mine.” By early 1920, while at Hayden, Stone, he’d had a hand in a variety of production and distribution efforts, and in short order had gained control of a chain of thirty-one New England theaters. His timing, again, was superb: in total capital investment, the motion picture industry was fast becoming one of the nation’s largest. Some twenty thousand theaters dotted the country, ranging from the modest small-town venue with a hundred seats to the luxurious urban “picture palaces,” with their baroque lobbies and a thousand or more padded seats. In 1922, movies drew some forty million viewers weekly; by 1929 the number approached a hundred million—this at a time when the nation’s population was 122 million and weekly church attendance was sixty million.66

Yet it struck Kennedy that it was a poorly run industry, anarchic and wasteful and lacking a structure, and tailor-made for someone like him, with an eye for numbers and for profits. In 1926 he bought a struggling company called Film Booking Offices and was soon churning out highly profitable Hollywood potboilers at the rate of two or three per month. Artistic distinction mattered not a whit—Kennedy’s sole concern, as producer, was whether the film would make money. Westerns and melodramas predominated, with titles such as The Dude Cowboy and Red Hot Hooves, featuring no-name actors or over-the-hill stars. (He also tried in vain to sign baseball star Babe Ruth.) Budgets seldom exceeded $30,000.67

As he had with the Boston Brahmins, Kennedy expressed private contempt for Hollywood elites while at the same time compulsively seeking their acceptance. In early 1927, he hit upon the idea of bringing the top studio heads to Harvard for a lecture series on the film industry. The dean of the business school signed off, as did President A. Lawrence Lowell, and the invitations went out. Though many of the tycoons were not on speaking terms—a few were even suing each other—the prestige of speaking at the nation’s leading university won them over, just as Kennedy had predicted. One after another they accepted the invitation and soon began descending on the campus, barely able to hide their awed enthusiasm. “I cannot begin to tell you how it impresses me, coming to a great college such as this to deliver a lecture, when I have never even seen the inside of one before,” gushed an emotional Marcus Loew. Other giants, including Alfred Zukor and Harry Warner, spoke in similar terms. For Kennedy the endeavor was a smashing personal success that secured his standing as a leading new fixture on the Hollywood scene.68

Rose was aware, in broad outline, of Joe’s film work (to the delight of the Kennedy children and their stupefied friends, he would screen first-run motion pictures from a projector set up in the family living room), and she assumed he would run his growing empire from New York City. And indeed, Kennedy maintained the main FBO office at 1560 Broadway, off Forty-sixth Street, in Manhattan. But more often than not he was out west, sometimes for weeks at a time. And not just for business. “In those days,” film writer Cy Howard would later observe,

Hollywood was the perfect place for an Eastern banker to have an affair. Separated from the East Coast by three days on a train, there was little worry of the accidental encounter between a wife and a mistress in a restaurant or on a street corner. Beyond that, there was the nature of the film industry, which provided dozens of Hollywood producers just like Joe with the perfect cover for spending their time with any number of beautiful actresses that just happened to work for them. You see, the film industry was actually the cover, allowing men to take their mistresses to dinners or even to parties, providing a form of legalized whoring.69

Kennedy took full advantage, seeing a steady stream of actresses and dancers.

In November 1927, soon after the family’s move to Riverdale, Kennedy met Gloria Swanson, Hollywood’s reigning screen siren and the most powerful woman in the industry. The first actress to turn down a million dollars for a role, she and her films were subjects of feverish discussion in beauty parlors and church picnics across the country. A younger, more sophisticated version of Rose—they had the same dark hair, luminous skin, and petite figures—the twenty-eight-year-old captivated Kennedy with her street smarts and vivacity and her low, sultry voice. “Together we could make millions,” he assured her one night over dinner. Swanson, well aware of Kennedy’s reputation as one of the shrewdest moneymen in Hollywood and taken with his energy and good looks, agreed to let him manage her financial interests, which were a mess after several years of overspending and dubious investing.70

Soon they became lovers. In her memoirs, Swanson recalled the first time they had sex, in a Palm Beach, Florida, hotel in February 1928 (just as Rose Kennedy was preparing to give birth to daughter Jean back in Boston). “Since his kiss on the train, I had known this would happen. And I knew, as I lay there, that it would go on. Why? I thought. We were both happily married with children….All arguments were useless, however. I knew perfectly well that whatever adjustments or deceits must inevitably follow, the strange man beside me, more than my husband, owned me.” There followed many “intimate hours together” at Kennedy’s rented house on Rodeo Drive in Beverly Hills, after which “Joe would have one of his horsemen [often the ubiquitous Eddie Moore] drive me home.”71 Mesmerized with Swanson as with no lover before, Kennedy led a split life, between his wife and family on the one hand, and his Hollywood megastar, the ultimate trophy mistress, on the other. Not completely split, however—Swanson and her husband on one occasion traveled with Rose and Joe in Europe (the two women shopped together at the exclusive Paris couturier Lucien Lelong), and she was a guest of the Kennedy family in their home.72

Swanson tried to resist the European excursion, but it was pointless. “When his mind was made up,” she later wrote, “there was not a big enough lever in the world to move him. I might argue all day, but I knew he would only out-argue me.” So she agreed to “throw a shawl over my scarlet letter and have tea with his wife and my husband and the vicar, doubtless, not to mention the press.”73

Rose Kennedy would always deny that her husband had anything other than a professional relationship with Swanson. According to Eunice Kennedy Shriver, her mother didn’t even hear rumors about the affair until the 1960s, and then waved them off. The claim of ignorance seems hard to believe. More likely, Rose knew about the romance while it was going on but chose to suppress it, to pretend it wasn’t there. “Mrs. Kennedy had this amazing knack for shutting out anything she did not want to know or face or deal with, and conversely of actually believing what she wanted to believe,” an employee in the household recalled. Perhaps some small part of Rose even condoned the relationship, or at least understood it, in view of what appears to have been her highly circumscribed view of what constituted proper sexual behavior for a devout Catholic—in essence, outside of procreation, intercourse should be sharply limited, in both frequency and duration—and her knowledge that it conflicted with her husband’s sex drive.74

For his part, Joe Kennedy knew that his philandering was wrong, that adultery was contrary to God’s word. But he also believed in confession and the forgiveness of sins. So he went on straying from the marriage bed. Obsessively focused on winning, on conquest, he always wanted more, more, more—in all areas of life. A journalist who knew him speculated that for Kennedy, a mistress was “another thing that a rich man had—like caviar. It wasn’t sex, it was part of the image…his idea of manliness.”75

Never, it seems, did Kennedy seriously consider leaving Rose for another woman, not even for Gloria Swanson. The actress hints in her memoirs that he contemplated forsaking Rose for her, but the notion is far-fetched.76 She was a huge catch, one of the most alluring women in the entire world, and dating her gave Kennedy prestige in Hollywood and—even more so—among his astonished Harvard friends. But he spent less time with her than he might have if the affair were as important to him as Swanson wanted it to be. For Kennedy, family was ultimately sacrosanct, even if he often had an odd and callous way of showing it. His preferred arrangement, common enough among men of his station, was having a wife at home and girlfriends away from home. By the fall of 1929 the affair had run its course, and Kennedy was readying to leave Hollywood and the film business behind—$5 million richer, thirty pounds lighter, and fighting an ulcer.77

He needed to rein himself in, he understood, needed to return to the more buttoned-up Northeast, to his wife and kids. Earlier in 1929, P. J. Kennedy had become deathly ill, at age seventy-one. (Mary Augusta had died in 1923.) Joe had spent several days by his father’s bedside in Boston in the final days; when P. J. seemed to rally, the son took it as a sign he could return to California, only for death to come on May 18. Nor did he travel back from Hollywood for the funeral (he sent Rose and Joe Junior in his place), a decision he regretted instantly. Never the introspective sort, Kennedy nonetheless understood that, having turned forty and with his father now gone, he needed to get his priorities in order, lest he lose his family. He had to be home, and home was not the wild west of glitzy young Southern California.78

And besides, even with his gargantuan work ethic, Kennedy found it hard to give sufficient attention from Los Angeles to the chattering stock ticker in New York. Now, as he gradually transitioned back to the East, he could afford to do that. He sensed big things were in the offing on Wall Street and made a major decision, one that went against the crowd and the consensus of expert opinion: he got out. Guy Currier, a well-connected and flamboyant lawyer to whom Kennedy often turned for advice, had warned him that the stock market seemed inflated, edgy, precarious, the danger signs flashing all around. Kennedy, predisposed toward pessimism, agreed, and he systematically went about liquidating much of his vast portfolio, even as the bankers and industrialists and traders around him stayed bullish. When prices began falling in September 1929, he stood at a safe distance. He remained there when the bottom fell out on October 29, Black Tuesday.79

One of Kennedy’s Harvard classmates, historian Frederick Lewis Allen, captured the moment in his classic work Only Yesterday:

The big gong had hardly sounded in the great hall of the Exchange at ten o’clock Tuesday morning before the storm broke out in full force. Huge blocks of stock were thrown upon the market for what they would bring. Five thousand shares, ten thousand shares appeared at a time on the laboring ticker at fearful recessions in price. Not only were innumerable small traders being sold out, but big ones, too, protagonists of the new economic era who a few weeks before had counted themselves millionaires. Again and again the specialist in a stock would find himself surrounded by brokers fighting to sell—and nobody at all even thinking of buying.80

VII

It is tempting to see the Kennedy marriage in this period as little more than an elaborate masquerade, or at best as a sterile collaboration between two people who felt little for each other but were stolidly committed to raising successful children. The temptation should be resisted. If (as some authors assert) the Kennedys’ relationship had become largely sexless by the end of the decade, and if they kept aspects of their emotional lives from each other, it is also true that they maintained a strong bond. The letters between them (especially those from Joe) attest to that fact. There was affection in their long talks about their children, and comfort in their shared history and rituals. Joe was proud of Rose as a dedicated mother and as an intelligent and talented wife, and she admired and treasured his deep commitment to the kids’ welfare and his interest in their many activities and accomplishments.81

Still, the tensions in the marriage in the late 1920s were real enough, visible not only to the household staff but to the older children as well, who knew full well that their father carried on with other women. Joe’s long absences in California (and Palm Beach, where he liked to spend time in winter), combined with Rose’s own weeks-long travels, meant that for significant stretches, the Kennedy children had to make do with surrogate parents, whether in the form of the staff or the ever loyal Eddie and Mary Moore. Did young Jack resent the marital discord in this period, and his mother’s absences? The record is unclear, but surely he did, at least to a degree.82 Any child would. Some later authors would see in Rose’s trips proof of her emotional sterility and lack of maternal love, and of her “managerial” approach to parenting. But though it’s true that she always withheld a part of herself, did not let motherhood consume her, and at times stood slightly apart from the whirlwind of family activity, can one really blame her? She had eight children, with one more to come, and was married to a serial adulterer, one who thought nothing of occasionally bringing a mistress home for dinner. Maintaining a separate identity was for her a form of self-preservation. To numerous contemporary observers, including her son Jack, Rose was the glue that held the family together. As one close friend told a biographer, “Joe provided the fire in the family, but Rose provided the steel, and still does.”83

Decades later, Jack offered a revealing and generous summation of his mother: “She was a little removed and still is, which I think is the only way to survive when you have nine children. I thought she was a very model mother for a big family.”84

Whatever the strains he felt at home after the move to New York, Jack appears to have adjusted reasonably well to the new surroundings, and to Riverdale Country School. His teachers described him as bright, confident, and personable, while friends remembered him as popular, athletic, and girl crazy. In sixth grade, Jack received excellent grades in his history bimonthly reports (with scores consistently in the nineties) and won the school’s commencement prize for best composition. “Far be it from the Kennedys to spoil their children,” Harold Klue, one of his social studies teachers, recalled. “They were taught to do for themselves and think for themselves.”85

Jack, for one, certainly didn’t think he was being spoiled. Although at one time or another all of the Kennedy kids hit their father up for an increased weekly allowance, no effort would be quite as stylish as Jack’s “Plea for a Raise,” issued to “My Mr. J. P. Kennedy” sometime during the first year in New York, and invoking a phrase from I Corinthians 13:

My recent allowance is 40¢. This I used for aeroplanes and other playthings of childhood but now I am a scout and I put away my childish things. Before I would spend 20¢ of my ¢.40 allowance and in five minutes I would have empty pockets and nothing to gain and 20¢ to lose. When I am a scout I have to buy canteens, haversacks, blankets, searchlidgs [sic], ponchos, things that will last for years…and so I put in my plea for a raise of thirty cents for me to buy scout things and pay my own way more around.86

The appeal worked: “Mr. J. P. Kennedy” granted the increase.

In the seventh grade, Jack’s grades slipped into the average range. “Creditable,” his generous headmaster noted of his overall performance, while a classmate recalled that Jack’s main concern that year seemed to be “getting a date for the Saturday afternoon movie.”87 (Like many twelve-year-old boys, he was shy around girls—according to family lore, he could barely bring himself to speak to them when they started calling the house.) Perhaps, too, the disruption caused by another move affected his academic performance: in May 1929 the family moved to a twelve-room colonial on Pondfield Road in Bronxville, a one-square-mile village close to Riverdale. Central Manhattan was fifteen miles to the south. Joe paid $250,000 for the mansion (about $3.7 million today), named Crownlands, which sat on six acres of lush lawns and boasted a grass tennis court, a five-car garage, and gardener’s as well as chauffeur’s cottages. Joe Junior, Jack, and eventually Bobby rode the bus to school in Riverdale, while the girls attended the public Bronxville School.

Crownlands, however, was not Joe’s most important home purchase of the period. After their humiliating snubbing in Cohasset, the family had spent several summers fifty miles to the south, in Hyannis Port, on the Cape Cod peninsula. A small hamlet next to the larger town of Hyannis, Hyannis Port comprised about a hundred well-built, roomy, shingled or clapboard houses, separated from one another by manicured hedges or low stone walls. It was not yet the fashionable place it would become, and was far less of a summer destination for Boston’s elites than Cohasset or Bar Harbor or Newport, but it nevertheless had several things in its favor: good railway access, sandy beaches, a Catholic church, a golf club that was willing to accept Joe Kennedy as a member, and a yacht club where Joe Junior and Jack, and the other children as they grew older, could learn to sail and race. Best of all, Hyannis Port contained no concentration of “proper Bostonians” who would look down their noses at the upstart Irish Catholic Kennedys. And it gave Rose the Massachusetts anchor she desperately missed—and wanted. The family rented Malcolm Cottage, a rambling three-gabled house on Marchant Avenue, with white wooden shingles and black shutters, wide porches, two and a half acres of sloping lawn where the kids could play, a tennis court, and a private beach with a superb view of Nantucket Sound. A breakwater poked out to the left to protect against the battering of the ocean waves.

In 1928, Joe purchased the property in his and Rose’s names and immediately commissioned an addition that more or less doubled the home’s size and gave them fifteen rooms and nine baths, plus an RCA sound theater (unheard of in a private residence at the time) in the basement. It would become, more than any other residence, what the Kennedys meant when they spoke of “home,” the place where Joe, newly returned to the East Coast, would, during days of ceaseless activity, set about molding his children.88

For the two oldest boys in particular, Hyannis Port would take on far more meaning than the Bronxville house ever would. For their days of living at home during the academic year were rapidly coming to a close. Boarding school beckoned.

II

Did Jack resent the favoritism his parents showed toward his brother? One guesses he did, at least somewhat. According to Lem Billings, however, Jack found it fairly easy to forgive the partiality, because he never felt unfairly treated and because he treasured the space and relative anonymity his status as the second son provided. It allowed him to develop his natural inquisitiveness, to lose himself in his reading and thereby escape, if only momentarily, the fever-pitched intensity of life in the Kennedy family. Confident that he matched or outshone his older brother in mental ability, and confined to his bed by frequent maladies, Jack cultivated an intellectual prowess that no one else in the family really had, and this proved irritating to Joe Junior, who expected to be the best in everything.15

Words and their meanings interested Jack. He was the only one in the family, his sister Eunice said, “who looked things up,” the one who “did the best on all the intellectual things and sort of monopolized them.” Rose remembered that “he gobbled books,” and “not necessarily the ones I had so thoughtfully chosen for him from the PTA- and library-approved lists.” More than any of his siblings, he internalized his mother’s mantra that reading constituted “the most important instrument of knowledge.” Biography, history, tales of adventure and chivalry—these were his genres, as he devoured Robert Louis Stevenson and Sir Walter Scott and read and reread Macaulay’s Lays of Ancient Rome. The cadences of historical prose appealed to him, and he had a first-rate memory of what he read, often able to recall scenes and quotations with astonishing accuracy, even decades later. “He had a strong romantic and idealistic streak,” Rose said. “In fact, he was inclined to be somewhat of a dreamer. I often had the feeling his mind was only half occupied with the subject at hand, such as doing his arithmetic homework or picking his clothes up off the floor, and the rest of his thoughts were far away weaving daydreams….I remember him in his boyhood reading and rereading his copy of King Arthur and the Round Table.”16

One also detects from an early point a sense of ironic self-awareness and detachment concerning the Kennedy clan’s peculiarities that his older brother entirely lacked. Jack could be at once of the family and apart from it. In a family that prized punctuality, he was habitually late. Notwithstanding his mother’s obsessive focus on order and decorum, he was sloppy, forgetful, irreverent—and grew more so over time. In the winter of 1932, when two friends picked him up from the Bronxville train station, he remarked sardonically, “I want to stop by the house for a minute, and check the nursery and see if there’s anybody new in the family.” He came out and exclaimed, “By God, there is!” (It was Teddy, born on February 22.)17

As Rose later put it, from boyhood on, Jack “thought his own thoughts, did things his own way, and somehow just didn’t fit any pattern. Now and then, fairly often in fact, that distressed me, since I thought I knew what was best. But at the same time that I was taken aback, I was enchanted and amused. He was a funny little boy, and he said things in such an original, vivid way.” At least compared with his three brothers, a friend noted, Jack was “neither pushy nor calculating.” Another acquaintance expanded on the point, describing Jack as “a loner, a self-contained person. It may be that in the intensely competitive family situation he withdrew somewhat into himself, learned to keep his own counsel, and put a layer of insulation between himself and other people.”18

“Unquestionably,” historian Herbert Parmet would write, “the introspective second son was the one who resembled his father least of all.”19

Yet Jack was also plainly devoted to his family, and fiercely loyal. He cared about what his parents thought, and during his prep school years cherished his vacation visits home. His father was now around much more, having left Hollywood behind, and his parents’ marriage seemed stronger, even with his continued serial womanizing. (Rose Kennedy in her memoirs describes the early 1930s as a golden time, as she and Joe spent long hours with each other, walking hand in hand along the shore at the Cape or through the Bronxville woodlands.) Meanwhile, Jack formed a special bond with Kick, three years younger, who possessed a quick, self-deprecating sense of humor much like his own (Joe Junior’s was more biting and sarcastic) and whose radiant charm and free-spiritedness he found enchanting. He enjoyed spending time with his other younger siblings as well—upon Teddy’s birth he asked his parents if he could be named the godfather, and was granted his wish. (He had less luck with another suggestion: that the boy be named George Washington Kennedy, since he shared a birthday with the first president.) When Teddy got a little older, it was Jack who taught him how to ride a bicycle and sail.20

What’s more, for all the differences with Young Joe and all the intense competition between them, the two brothers shared a common vitality and mutual affection. From an early age they were each other’s number-one playmate, and they had innumerable adventures together—in Brookline, in New York, in Hyannis Port, and later in prep school and college.^*1 From his brother Jack learned how to sail—how to be an effective crewman, how to shift ballast in a jib, how to secure the advantage in tight races. Joe Senior recalled that his two oldest boys “were out in sailboats alone here in Hyannis Port when they were so small you couldn’t see their heads. It looked from shore as if the boats were empty.” The boys christened their first boat the Rose Elizabeth, after their mother, and spent endless hours tinkering with it and learning to sail it with consummate skill and speed. As competitive as they could be with each other, they fought much more fiercely as a team against outsiders, whether on the sporting field or in the schoolyard.21

Years later Jack would write:

I have always felt that Joe achieved his greatest success as the oldest brother. Very early in life he acquired a sense of responsibility towards his brothers and sisters and I do not think that he ever forgot it….He would spend long hours throwing a football with Bobby, swimming with Teddy and teaching the younger girls how to sail….I think that if the Kennedy children amount to anything now or ever amount to anything, it will be due more to Joe’s behavior and his constant example than to any other factor. He made the task of bringing up a large family immeasurably easier for my father and mother for what they taught him, he passed on to us and their teachings were not diluted through him but strengthened.22

Those parental teachings centered on the importance of education, of avoiding idleness, of respecting public service, of loyalty to family. But more than anything, they were about winning. The point, Joe Senior insisted time and again, was not to play well, to compete for the sake of competing, but to defeat all comers, to secure the top prize. Even good sportsmanship paled in comparison. “We want no losers around here, only winners,” he proclaimed. From the time the children were six or seven years old, Joe and Rose entered them in swimming and sailing races, taking care to put them in different categories so they didn’t have to race each other. Always, Joe exhorted them to reach the finish line first. “The thing he always kept telling us was that coming in second was just no good,” remarked Eunice, who became an excellent sailor and all-around athlete. “The important thing was to win—don’t come in second or third, that doesn’t count, but win, win, win.” Small wonder that the Kennedys took on the reputation within the Hyannis community of being graceless competitors, of being willing to do anything to prevail. Though not an accomplished sailor himself, Joe Senior would follow his kids’ boats and make note of deficiencies he saw in performance or effort. Any slacker would be subjected to a stern talking-to at dinner in front of the family and sent in disgrace to eat alone in the kitchen.23

“My husband was quite a strict father,” Rose later acknowledged. “He liked the boys to win at sports and everything they tried. If they didn’t win, he would discuss their failure with them, but he did not have much patience with the loser.”24

One of Jack’s friends, Paul Chase, remembered seeing—and hearing—Mr. Kennedy’s win-at-all-costs approach up close. “Several times, Jack asked me to crew for him when he could not find anyone else. Once we lost badly and caught a half-hour lecture from the old man on our return to shore. He said he had watched the race and that he was disgusted with both of us. There was no sense, he claimed, in going into a race unless you did your damnedest to win, an endeavor at which we had failed miserably. He was really angry with us.”25

Chase’s anecdote hints at the possibility of a more benign assessment of Joe Kennedy’s relentlessness: that it was less about winning than about expending maximum effort in the attempt. The Kennedy kids were expected to always work harder than anyone, Robert Kennedy later wrote, even if others in the competition were more talented. “ ‘After you have done the best you can,’ he used to say, ‘the hell with it.’ ”26

Visitors to the Hyannis Port home marveled at the sheer orchestration of daytime activity. Here the summers were not holidays, filled with lassitude and soaking in the sun. Joe could not abide his offspring lounging around, even briefly, and he insisted on a packed schedule. His wife felt the same. Each evening, she posted a schedule of events for the following day—moving from tennis to golf to swimming to sailing, sometimes with professional instructors alongside. On a bulletin board next to the dining room she pinned articles from magazines and newspapers that she wanted her kids to read, and she scattered special lamps throughout the house to encourage reading.^*2 Friday night was movie night in the basement, with its twenty-seven-seat theater. Saturdays were taken up with more sporting activities, and another movie or a game of charades after dinner. The younger children, supervised by a nurse, were forbidden from riding their bikes off the property; the older ones, watched over by a governess, were expected to be in the house when the lights went on at dusk. All had to be seated at the dining table five minutes before mealtimes, with dinner served promptly at 7:15 each evening. Rose had clocks placed in each room so no one would be late.27

Though the Kennedys were one of the richest families in America, guests encountered few signs of ostentatious wealth or conspicuous consumption. Quite the contrary: “We each had a napkin,” Teddy later related, “and that napkin was expected to last the entire week. If it suffered any stains—which of course is what napkins are designed to do—too bad.” The furniture in the house was comfortable but mostly ordinary; the bicycles and sporting equipment were often weathered and beaten, meant to be used until they fell apart. On birthdays the children could expect to receive no more than one or two gifts, none of them extravagant. Their weekly allowances were kept small.28

In subsequent years the suggestion would be made that the close-knit Kennedys practiced an insular solidarity and didn’t mix much with the other families of Hyannis Port, many of them Protestants from Pittsburgh. Lem Billings, for one, didn’t deny the claim, but he questioned whether anti-Catholic prejudice played much of a role. “The children were invited certainly to every party there was in Hyannis Port and there was no problem about the mixing of the Pittsburgh Protestant children and the Catholic Kennedy children,” Billings said. “I know that when I used to visit the Kennedys I knew a lot of the boys and girls in Hyannis Port better than they did, because I’d been raised with them in Pittsburgh, but this didn’t mean they weren’t invited to whatever went on. I don’t think they probably went as often as they could have, because it was a very self-sufficient family. They had everything they needed at home. They had their own movies; they had all their own athletic facilities.”29

Always, the culture of competition dominated among the children. “Which one of us is the best looking?” visitors would be asked. “Who is the funniest?” “Whose outfit do you prefer?” Seemingly friendly “touch” football games on the family lawn would turn into fierce, bruising affairs, much to the astonishment of unsuspecting guests. The gentle pleasure of skipping stones would become competitive, as would seeing whose seashell floated out the farthest into Nantucket Sound. If the family was waiting for a car and had a few minutes to kill, someone would come up with a game to play. Even board games and charades would be hotly contested. At the ages of twelve and ten, respectively, Joe Junior and Jack started winning local sailing races, and they did not let up. Eunice would soon do the same. Patricia, for her part, became an accomplished golfer. At times, Joe Senior got into the athletic act, taking on his sons in sports in which he knew he would prevail. An excellent low-handicap golfer who regularly shot in the low and mid-eighties, he would challenge Joe and Jack and beat them every time. In tennis, too, he always won comfortably, until one day when Joe Junior, then in his mid-teens, nearly bested him. That was the end of the father-son tennis matches—Kennedy preferred to hang up his racket rather than lose to one of his boys.30

Years later, one weary weekend visitor outlined the “Rules for Visiting the Kennedys”:

Anticipate that each Kennedy will ask what you think of another Kennedy’s (a) dress, (b) hairdo, (c) backhand, (d) latest public achievement. Be sure to answer “terrific.” This should get you through dinner. Now for the football field. It’s “touch,” but it’s murder. If you don’t want to play, don’t come. If you do come, play, or you’ll be fed in the kitchen and no one will speak to you. Don’t let the girls fool you. Even pregnant, they can make you look silly. Above all, don’t suggest any plays, even if you played quarterback at school. The Kennedys have the signal-calling department sewed up, and all of them have A-pluses in leadership….Run madly on every play, and make a lot of noise. Don’t appear to be having too much fun, though. They’ll accuse you of not taking the game seriously enough.31

As a philosophy of life, winning was of course problematic. On some level, Joe and Rose understood as much. Their eldest daughter, Rosemary, pretty and round-faced and sweet-natured, with a lovely smile that dimpled her cheeks, could never compete in the family’s do-or-die ethos. A mere sixteen months younger than Jack, she had been slow to crawl and then to walk. Reading and writing were difficult for her—for a long time, she scrawled her letters from the right side of the page to the left. Like Joe Junior and Jack, she had entered Edward Devotion School, but at the end of kindergarten her teachers determined that she would not be promoted to first grade but would instead repeat the year. This time she passed, with a C, but the struggles went on. She couldn’t balance herself on a bicycle or throw a ball or steer a sled like the others. At the dinner table, she struggled to manage a knife, so her meat was served precut. The intricacies of sailing eluded her; alone among her siblings, she did not have her own boat. Her parents consulted a stream of experts, including the head of the psychology department at Harvard and a specialist in Washington, D.C. “Each of them told me she was retarded,” Rose recalled, “but what to do about her, where to send her, how to help her seemed an unanswered question….I had never heard of a retarded child.”32

For a time the parents opted for what was then an enlightened approach, in the form of what today would be called “mainstreaming.” They determined Rosemary would be sent to regular school, not institutionalized in the draconian way common for the “feebleminded” (as they were then labeled) of the era. When conventional schooling proved unworkable—there were few schools in the United States then for children with special needs—they opted for homeschooling, with hired tutors and with Rose in the supervisory role. Progress was slow and fleeting. Rosemary learned to write but did not progress beyond block letters. Rose avoided using cursive in her letters to her daughter and refrained from sprinkling in French expressions when speaking to the other children, for fear of making Rosemary feel disaffected. At her insistence, Rosemary was included in most social activities, including dances at the Yacht Club, where Joe Junior and Jack, if they saw her sitting by herself, were to make sure she kept dancing, even if it cut into their own fun.33

Years afterwards, Rose would express guilt that her preoccupation with Rosemary may have made her neglectful of Jack, so close to his sister in age. “When his sister was born after him, it was such a shock, and I was frustrated and confused as to what I should do with her or where I could send her or where I could get advice about her, that I did spend a lot of time going to different places or having her tutored or having her physically examined or mentally examined, and I thought he might have felt neglected.” She expressed no similar worry about Kathleen or Eunice, born after Rosemary, who evidently could make do with less mothering than a son could.34

In September 1929, not long before her eleventh birthday, Rosemary was sent away to the Devereux School, in Berwyn, Pennsylvania, which provided specialized instruction for intellectually challenged students. She struggled to adjust to being away from home, and it did not help that the school discouraged parental visits. In mid-November, her father received his first letter and replied right away. “I cannot tell you how excited and pleased I was to get your letter,” he enthused. “You were a darling to write me so soon.” He filled her in on family goings-on and told her that Gloria Swanson would soon send her a letter and a photo, then nudged her to work hard in her studies: “I was very glad to see a lot of improvement in the report card, and I am sure that within the next couple of months it will be even better.” It didn’t happen. Though Rosemary adapted somewhat to the social environment of the school, she plateaued academically—she lacked confidence, her teachers reported, and had difficulty concentrating on any but the simplest tasks. Even elementary concepts eluded her. The parents hoped for improved performance when she returned to Devereux for a second year in 1930, and then for a third in 1931; each time they were disappointed.35

III

As the 1920s ended and Young Joe and Jack entered their teenage years, their father assumed a key role in their educational development, while Rose remained in charge of the girls and Bobby. Rose had wanted her sons to attend Catholic schools, but Joe thought that if they were to compete in the political world, they needed to be with boys from prominent—which meant Protestant—families. “There is nothing wrong with Catholic schools,” he later said. “They’re fine. But I figured the boys could get all the religion they needed in Church, and that it would be broadening for them to attend Protestant schools.” Only such a school, he felt, could make his sons the kind of men he wanted them to be—and, at the same time, pave their path to Harvard.36

But which school should it be? Kennedy consulted widely, including with Russell Ayers, a Harvard classmate who taught history and coached baseball at Choate and who encouraged him to send his boys there. Choate was a highly respected private boarding academy, one that sent many of its graduates to the Ivy League (especially Yale) and had students from forty states and several foreign countries, but it wasn’t the elite of the elite among New England prep schools.37 The scions of New York money went there—Paul Mellon, son of Gilded Age robber baron Andrew W. Mellon, was a graduate—while the true blue-blood families sent their sons to the older and more prestigious St. Mark’s, St. Paul’s, or Groton. Joe Kennedy’s wealth was too new, and his lineage too Irish, to be fully acceptable to these schools.38 At Choate, the Kennedy sons were more likely to be accepted, and it had the further advantage of being closer to Bronxville—sixty-five miles away, in Wallingford, Connecticut—than the other schools.

“My only hesitancy about doing it,” Kennedy wrote C. Wardell St. John, the Choate assistant headmaster (and double cousin of the headmaster), in late April 1929, “is I realize that when the boys go away now to school, they are practically gone forever, because it is three years there and then four years at college, and you realize how little you see of them after that. I may be selfish in wanting to hold on for another year at least….However I am talking the matter over with his mother and will try to come to a decision and make out the applications as you suggest.” A few days later, Kennedy wrote Ayers to say, “I have definitely made up my mind to send them to Choate, provided I can get them in.”39

That September, Joe Junior enrolled at Choate. After a rough start, he adjusted and became a model student, making up with hard work what he lacked in natural aptitude. (“Joe is better at facts than at imagination,” one teacher wrote of him.) Soon he was a standout on the athletic field as well, suiting up for football, wrestling, hockey, and crew. “He has been one of the most livable boys in the whole house,” his housemaster wrote at the conclusion of the spring 1930 term, “and he accepted discipline—not nearly as frequently necessary in the latter portion of the year—with more grace and manliness than any other boy.”40

Initially, Jack was set to follow his brother and enroll in 1931, in the third form (or freshman year); then it was determined he would start a year sooner, in September 1930.41 But then the plan changed again, likely on account of Rose’s advocacy—she suspected Choate of having a Protestant bias. That fall, Jack was dispatched instead to Canterbury, an all-boys Catholic boarding school in New Milford, Connecticut, that aspired to prepare students not just for Catholic colleges but for the Ivy League.42

He showed up, without a uniform, on September 24, 1930, one of thirty-two new students. For the first time in his life he was on his own, in an alien, forbidding place. The campus was bleak, with nondescript buildings scattered about and a stone church at its center. The Housatonic River ran nearby. Just how Jack felt upon being deposited here instead of with his brother down the road in Wallingford is unclear; perhaps a part of him wanted to strike out alone, or imagined so. “It’s a pretty good place but I was pretty homesick the first night,” he acknowledged in a letter to his grandfather Honey Fitz soon after arriving. “The swimming pool is great even though the football team looks pretty bad. You have a whole lot of religion and the studies are pretty hard. The only time you can get out of here is to see the Harvard-Yale and the Army-Yale [games]. This place is freezing at night and pretty cold in the daytime.” To encourage his mother, he noted in another letter, “We have chapel every morning and evening and I will be quite pius [sic] I guess when I get home.”43

Soon he began suffering one malady after another—hives, fevers, lightheadedness, upset stomach, pink eye. The school infirmary became a second home. One wonders if some of these ailments were exacerbated by—if not rooted in—the shock of being away from home, by the pressure to match his brother’s achievements, and by the need to live up to the Kennedy family credo, which decreed that you never gripe too much, never say you miss your parents or siblings. (“My knees are very red with white lumps of skin,” he wrote in a letter home, “but I guess I will pull through.”) Jack’s letters detail his problems with fatigue and with keeping his weight up—he hovered around 117 pounds, not exactly brawny in a thirteen-year-old boy—and the challenges his comparatively small stature presented on the athletic field: “Football practice is pretty hard and I am the lightest fellow about on the squad. My nose my leg and other parts of my anatomy have been pushed around so much that it is beginning to be funny.” Lest his parents think him weaker than his brother, he pointedly reminded them, after describing feeling dizzy and weak to the point of almost blacking out in chapel, that “Joe fainted twice in church so I guess I will live.”44

To his mother, Jack wrote, “I have hives, that is a sickness which everything begins to itch. My face had hands knees and feet. I also have a cold. Outside of that I am O.K. When ever I go out the Doc jumps one on me for not wearing enough all the other boys arent either.” Then again, Jack added, his spelling questionable at best, some classmates had it worse: “One fellow who cracked his head to pieces and broke his collor bone sledding was one of them. They patched up his arm and then let him out two days later. He was a little fellow in the first form two days later he was down with pnemonia. They should not have let him out because he was weak and white. The other boy went to the infirmary with a slight cold and then he got pnemonia.” About his eyesight, Jack added, “It has gotten worse and everything is a blur at over eight feet but if you do want me to wait till Easter I will if you think it best.”45

Rose Kennedy’s index cards from the fall of 1930 indicate that Jack lost weight steadily between October and early December. At her request, Nelson Hume, the headmaster at Canterbury, arranged for the boy to be seen by a local physician named Schloss, who prescribed a special drink for weight gain. “Jack tells me that he has about finished the tonic that Dr. Schloss gave him,” Hume informed Joe Kennedy in January 1931, adding that, as headmaster, he was taking a personal interest in Jack’s health: “I am going to take immediate charge of the question of increasing Jack’s weight myself.” Increased dairy consumption was deemed to be the key, and Hume informed Mr. Kennedy that Jack would be given milk to drink all throughout the day.46

If such protracted ailments would send most parents today racing to the school to provide succor to their child, the Kennedys were not such parents. The record suggests that Rose and Joe paid but one visit to Canterbury during their son’s time there. Few thought this all that unusual at the time (though we can note that the parents of Jack’s fellow student and future brother-in-law Sargent Shriver, who did not suffer similar health problems, came to see their son on numerous weekends in the first year). Joe and Rose did write frequently to Jack, and also communicated via mail with his teachers and with the school administration.47

Little by little, the young teenager acclimated to campus life. Academically, he did better in some subjects than others. In English, where the class read one of his favorite authors, Sir Walter Scott, he earned his best grade, a 95. In math he scored a 93, followed by 80 in history, 78 in science, and 68 in Latin. (Foreign languages would forever be a struggle for him.)48 One senses in his letters a restive momentum, a nascent intellectualism, and an ear for rhetoric. “We are reading Ivanhoe in English,” he wrote his father, “and though I may not be able to remember material things such as tickets, gloves and so on I can remember things like Ivanhoe and the last time we had an exam on it I got a ninety eight.” Then an elegant wrap-up: “There goes the bell and that is not just a form of finish because it really did ring.” He wrote of hearing a visiting speaker give “one of the most interesting talks that I ever heard, about India,” and in another letter he implored his father, one year after the Wall Street crash, to sign him up for a subscription to “Litary Digest because I did not know about the Market Slump until a long time after.” He added, “Please send some golf balls.”49

Latin class presented a special problem: “Today we had a latin test. I handed in my paper the last one and I thought he had it because I gave it to him. He was also handing out some corrected papers so he must have handed out mine because I have not seen it around and I cant convince him that I gave it to him so he gave me a zero which pulls my mark down to about 40 and so I guess my average will be very very low this month. In all my other subject after the first weeks bad start I am doing pretty well but the first week counts ¹/₅ so my average will be around 69 or maybe higher. What a mess!”50

Like other thirteen-year-old boys, Jack puzzled over the alterations to his voice. At choir practice, he thought he sounded like the family dog: “My voice must be changing, because when I go up it sounds as if Buddy is howling. I go up another note and Buddy is choking. Another note and Buddy and me have gasped our last.”51

Then, in April, soon after spring break, came a sudden onset of crippling abdominal pains. Joe Kennedy dispatched a nurse and a surgeon to attend to him, and they soon pinpointed the cause: appendicitis. Jack underwent an appendectomy at nearby Danbury Hospital. Though it was normally a routine procedure, there were unspecified complications, and recovery proved slow. At the beginning of May it was decided that Jack would not return to school but would convalesce at home in Bronxville, with tutors paying periodic visits. He made up the missing work and passed his examinations, but the ordeal marked the end of his lone experience in a Catholic school. For his father had, in the interval, arranged for a fall transfer to Choate.52

IV

How Jack Kennedy felt about the decision, and about the prospect of being reunited with his hard-driving brother, is unknown, but there is no record of an objection. In any case, before he could matriculate at Choate he had to pass the qualifying examinations. He got by in math and English but failed his Latin test by eight points. He was allowed to sit for a makeup, but it meant a summer of preparation and home tutoring in Hyannis Port. The tutor, Bruce Belmore, was impressed by his pupil and wrote to Wardell St. John that Jack was “a fine chap. He will be a credit to Choate.” When September rolled around, however, Jack found he had misplaced the notice telling him when to appear for the Latin exam, prompting Rose to cable the school from Hyannis. On the afternoon of October 2, 1931, Jack signed in at Choate and retook the test. This time he passed, and took his place in the third form.53

One imagines the scene as Jack arrived in the family’s chauffeured Rolls-Royce, laden with luggage that his brother helped him carry up the stairs in Choate House, the rambling brown-shingled, three-story structure where all third-formers lived. He got his first look at the elm-shaded campus, modeled on Eton and situated in the rolling New England countryside, with playing fields, tennis courts, stables, chapel, infirmary, and library. Young Joe, one speculates, showed him around, schooling him about the culture of the place, about the social pecking order among the students, about which teachers to hope to get and which to pray to avoid. They would have eaten together in the dining hall that first evening, whereupon Joe patted his kid brother on the back and headed out in the fall evening air, back to his friends and his dorm, and Jack headed to the headmaster’s home for a welcome party.

Mrs. Kennedy had by then already advised the headmaster, George St. John, that her younger son would need more watching than the older boy. “As a matter of fact,” she said of Jack, “he hates routine work, but loves History and English—subjects which fire his imagination. Again let me thank you for your interest and patience with Jack. He has a very attractive personality—we think—but he is quite different from Joe for whom we feel you have done so much.”54

St. John, an austere, balding pipe smoker who came from a family of teachers and farmers and had worked his way through Harvard, assured Rose early in the term that everything seemed in order. Jack, he told her, “sits at a nearby table in the Dining Hall where I look him in the eye three times a day, and he is fine.” His wife, Clara, sent her own letter to Mrs. Kennedy: “Everyone likes your boy, and he is rapidly making a real place for himself in the life of the school,” joining with the other third-formers in having ice cream and singing around the piano.55

Before long, however, the assessment would change. George St. John, exacting and pedantic, ran the school like a personal fiefdom, with strict regulations not merely for students but for their teachers, who were expected to do double duty as housemasters and live with the boys, and who had to obtain St. John’s permission if they wished to marry. Everyone was under his control. He could be generous in spirit as long as his authority was not questioned, and he cared deeply for his charges. (“If a single boy is lost,” he liked to say, “the school is too large by one.”) A devout Episcopalian Anglophile, St. John would also remark, “We save a boy’s soul at the same time we are saving his algebra,” and he promised parents that the school would provide excellent teaching, rigorous exercise, and “manly discipline.” To go into town required the dean’s permission, and only seniors could go to the movies. The dress code was rigidly enforced—all students wore jackets and ties to class, and suits (with stiff-collared white shirts, in the style of the day) to dinner.56

Into this regimented, bounded environment stepped young Jack Kennedy, absentminded, untidy, casual in manner and appearance. After just a week, his housemaster, Earl “Cap” (or “Cappy”) Leinbach, would write, “Jack has a pleasing personality, and is warmly received by all the boys in the house, but rules bother him a bit.” There were early squabbles with the assigned roommate, Godfrey Kaufmann Jr., whose father owned The Washington Star and who objected to Jack’s penchant for turning their shared closet into a garbage heap and leaving books strewn about the room. Leinbach had to intervene, and things improved, but the two boys continued to spar regularly—at one point they drew a white chalk line down the center of the room that neither was permitted to cross. (Even so, they regularly got in trouble for conversing long past lights-out at night—with the light still on.)

The handsome, blue-eyed Leinbach, who had been a military intelligence officer in World War I and whose beautiful southern wife all the boys fancied, took Jack under his wing and became a kind of mentor. He liked the young man’s wit and vitality, while Jack was impressed by Leinbach’s military courage—during the war he had apparently made a daring escape from his German captors shortly before he was to be taken out and shot. By the end of the first month Leinbach could report a “gradual improvement” in Jack’s attitude, noting that “Jack found it irksome to settle down, is naturally active and impulsive, but he has responded and is now exceedingly cooperative. He is in all respects a fine citizen.”57

Headmaster St. John was less convinced. Not long after Clara St. John reported to Mrs. Kennedy that Joe Junior “is established as one of the ‘big boys’ of the school on whom we are going to depend,” her husband informed Mr. Kennedy that the younger brother’s results “are not yet commensurate with the standard we set for him….His problem is still one of application.” Joe Senior responded in kind, acknowledging that, while Jack had abundant natural talent, he was “careless in applying it.” He urged the headmaster to prod his son, to keep him under strict watch, lest Jack allow this cavalier approach to get the better of him.58

St. John’s solicitous attitude toward the Kennedy parents may have had something to do with a hope that they would respond with a contribution to the school’s coffers. There was irony here, inasmuch as he was wary of Catholic climbers such as Joe Kennedy and didn’t much want their kids at his Episcopal school. But there were bills to pay, and the Kennedys had wealth. When St. John hinted coyly of the need for a sound motion picture projector, Joe Kennedy got the message: he sent the school a high-end model costing $3,500, thus earning the headmaster’s gratitude and cementing his commitment to keeping a watchful eye on the sons. “We’ll try to show our appreciation, our sheer gratitude, in every way we know,” St. John wrote Kennedy. “I’m keeping close to Jack.”59

Still, to the headmaster and his teachers, Jack went on being a square peg who didn’t fit in the round hole they had assigned him. He seems to have determined early on that he would not seek to match, much less exceed, his brother’s exploits, and he viewed with bemused detachment the vaunted Choate values and Choate ways that Joe Junior worked so hard to embody. Jack’s irresponsibility in this sense likely reflected his bid to preserve his individuality, to create a sense of self. Joe worked indefatigably to maintain his grades (which in the end were not that much higher on average than his brother’s); Jack seemed to make a point of hardly studying. Joe was noted for his laser-like focus; Jack, his teachers complained, suffered from an “inability to concentrate effectively.” Joe respected hierarchy and kowtowed to the rule makers and the enforcers; Jack brooked authority and poked fun at the conceit that lay behind it. Joe maintained a neat personal appearance, to the approving eyes of the Choate faculty; Jack was casual, slovenly, raffish—charmingly nonconformist, a different crowd might say.60

Then again, these dichotomies don’t give the full picture. Behind Jack’s insouciance lay the angst of living in the shadow of a brother who was accumulating accolades left and right, and—perhaps—a tacit admission that victory in the sibling rivalry lay beyond reach, at least for now. (You can’t lose if you don’t compete.) And underneath the slacker mien existed a pronounced bookishness and an intense curiosity about the world—as well as knowledge about it. Jack’s friend Ralph “Rip” Horton noticed that whenever a group of boys got together to listen to the popular radio quiz show Information Please, most of them could answer only a few questions, but Jack whizzed through more than half. “How do you know all this stuff?” they’d ask. “I guess I read a lot,” came the reply, neither boastful nor falsely modest.61

“Jack read a great deal but not to the point that he was burdensome about it,” Horton remembered. “I think he could read quite fast, and, yes, he read a great deal but not ostentatiously….He seemed to absorb what he read much better than the rest of us. He also, which I think is rather indicative of his future, always read The New York Times. He read that every single day from cover to cover, and I think that gave him a great insight into the political scene and international activities which he was so interested in.”62

Horton, who hailed from New York City, also saw other sides to his new friend: “He was a boy of many interests. He liked sports, he liked roughhousing, he liked to be sloppy, he liked to play golf, he liked girls. But he would never stick to anything, would never give himself over entirely to anything. He loved to come to New York to see me.”63

In other words: a fairly typical fourteen-year-old. The picture of an unconventional Jack Kennedy, going against the grain at a highly structured, tradition-bound prep school, should not be overdrawn. Careless and inattentive, chafing against rules, he still sought to fit in, to be popular, to win acceptance among his peers, to gain his parents’ approval. Athletics were a means to that end, and Jack’s letters home in the first year reveal his dogged pursuit of sporting success. Results were meager. To his father he expressed confidence that he would make the basketball team and play alongside his brother, but he crashed out in the tryouts. Even more dispiriting, gridiron success eluded him. Football was where a Choate boy could most easily gain campus recognition, but whereas Young Joe did, Jack was simply too light and willowy to withstand the rigors of the game, and had to content himself with playing below the first-team level, on one of the school’s lower teams.64

Only in golf, where Jack could put his excellent hand-eye coordination to good use, did he make the squad, though not the top-six unit. And golf was a minor sport at the school and, as such, small consolation for a boy who had internalized his father’s win-at-all-costs mentality, who understood all too well that his fragile constitution looked pathetic next to the sturdy, irrepressible Joe Junior—not least in his father’s eyes. In a letter in December 1931, Jack made much of playing football in foot-high snow that turned to ice, and then cautioned his father against thinking his brother was all that tough:

The first thing [Joe] did to show me how tough he was was to get sick so that he could not have any thanksgiving dinner. Manly Youth. He was then going to show me how to Indian wrestle. I then through him over on his neck. Did the sixth formers lick him. Oh Man he was all blisters, they almost paddled the life out of him. He was roughhousing in the hall, a sixth former caught him, he led him in and all the sixth formers had a swat or two. What I wouldn’t have given to be a sixth former. They have some pretty strong fellows up there if blisters have anything to do with it.65

The letter was further proof, if such was needed, that the fourteen-year-old, coming to the end of his first term at Choate, was feeling the pressure to perform, to measure up, to meet his father’s approval. Though Jack and Joe led largely separate lives at the school, moving in different circles, living in different dorms, seeing each other only occasionally, the older boy was ever present in his brother’s mental world, as the shining star in the family firmament, the golden child, the one who could do no wrong in the eyes of his parents or Choate’s administration and faculty.

But it was not to be forever. In eighteen months, Jack knew, big brother would graduate from this place and move on to his next success. The burden would be lifted, at least to a degree. Still, as the Choate community prepared to scatter for Christmas break 1931, young Jack Kennedy continued to grapple with his core dilemma: how to be true to his own sensibility and make his own way in the world while remaining a Kennedy, with all that that implied.

II

In one essay that year, Jack pondered how a Christian God could allow evil in the world, and how true justice could be achieved when people were born into such widely varying circumstances. Does God in fact “render to everyone his just due,” Jack asked, given the vast disparities in the human condition?

A boy is born in a rich family, brought up in [a] clean environment with an excellent education and good companions, inherits a fool-proof business from his father, is married and then eventually dies a just and honest man. Take the other extreme. A boy is born in the slums, of a poor family, has evil companions, no education, becomes a loafer, as that is all there is to do, turns into a drunken bum, and dies, worthless. Was it because of the [rich] boys abylity that he landed in the lap of luxery, or was it the poor boys fault that he was born in squalor? The answer will often come back “The poor boy will get his reward in the life hereafter if he is good.” While that is a dubious prospect to many of us, yet [there is] something in it. But how much better chance has [the] boy born with a silver spoon in his mouth of being good than the boy who from birth is surrounded by rottenness and filth. This even to the most religious of us can hardly seem a “square deal.” Thus we see that justice is not always received from “The Most Just” so how can we poor mortals ever hope to attain it.

The young Kennedy, himself a son of privilege, was professing here that he saw little reason why the less fortunate should put much stock in the traditional Christian promise of a heavenly reward for a life well lived. Maybe such a reward would indeed be forthcoming, he allowed, but inequalities of condition and opportunity made the task of living a morally upright life much more daunting for those born into poverty and despair. In sum, injustice in the world remained a problem for which the Bible offered few answers.13

It was a core philosophical position, staked out at sixteen, in the midst of the Great Depression, from which the grown-up Jack Kennedy—congressman, senator, president—would never waver.

Kay Halle, a wealthy socialite friend of Joe Senior’s, got a sense of Jack’s precocity when, accompanied by the father, she visited him in a hospital room where he was laid up with one malady or another. It was her first encounter with him, and it made an impression. “Jack was lying in bed, very pale, which highlighted the freckles across his nose. He was so surrounded by books I could hardly see him. I was very impressed, because at that point this very young child was reading The World Crisis, by Winston Churchill.” Halle did not indicate whether Jack had all six volumes of this epic mega-history of World War I in the hospital room that day, and one wonders, too, what he made of Churchill’s interpretation of the war, so different from his father’s. Whereas the elder Kennedy still clung to his view that the Great War had been a colossal waste, sacrificing millions of young men for no good reason, Churchill, though critical of many aspects of British and Allied strategy, extolled leaders and fighting men who set duty and sacrifice before self-interest, who were driven by something bigger than themselves, and whose cause was entirely just: “Every man a volunteer, inspired not only by love of country but by a widespread conviction that human freedom was challenged by military and Imperial tyranny.”14

Author Barbara Leaming suggests that Jack’s reading of The World Crisis initiated his lifelong fascination with and admiration for Churchill (later in adolescence he read and loved the Englishman’s massive million-word biography of Marlborough, the great military commander, statesman, and Churchill ancestor) and also spurred a deep and lasting interest in the question of how wars begin—and how to prevent them.15 This seems right, and there can be no doubt that, given his growing interest in international affairs, Jack in this period followed current global politics as well—the climb to power in 1933, during his second year at Choate, of Adolf Hitler and his National Socialist Party in depression-ravaged Germany; the deepening crisis of confidence in France and Britain; and the growing tensions in East Asia as a rising Japan flexed its muscles.

With respect to domestic affairs, on the other hand, including the widespread dislocation and deprivation caused by the Great Depression, one doesn’t see the same level of engagement from young Jack—notwithstanding his probing fifth-form paper on injustice. To a considerable extent, the cloistered Choate existence kept the students isolated from the outside world. Then again, from his daily New York Times Jack would have been aware of the devastating effects of the economic downturn on his fellow Americans. Given his superior recall, he might even have known some specifics: that between 1929 and 1933, the gross national product declined by half; that 100,000 businesses in that period shut their doors; that corporate profits fell from $10 billion to $1 billion; that by the time of the presidential election of 1932, a quarter of the nation’s workforce was unemployed, while millions more worked only part-time; and that there was no national safety net: no unemployment compensation, no welfare system, no social security.

On home visits, too, Jack would have observed up close his father’s deepening gloom over the state of the nation. This was something new, for over the previous dozen years Joe Kennedy had shown scant sustained concern about political developments—he’d been too busy making money and producing movies. Even the historic candidacy of fellow Catholic Alfred E. Smith, the Democrats’ choice for president in 1928, had failed to excite him. Although still a Democrat by party affiliation (if more from inheritance than conviction), Kennedy had profited handsomely from the “Coolidge prosperity” of mid-decade, and he had felt strongly that Herbert Hoover stood a better chance than Al Smith of keeping the good times going. (He may also have been embarrassed by the informality of Smith’s campaign style, adhering in core respects to the stereotype of the crude Irish pols of Joe’s Boston youth.)16

The stock market crash and subsequent Depression changed him. Though his vast fortune remained intact and indeed grew, thanks to his expertly timed withdrawal from the stock market prior to the crash and his adept short selling afterwards (in 1935 his wealth would be estimated at $180 million, or $3.6 billion today), he now saw the future in bleak, self-centered terms, fearing a radical upheaval that might bring down the social and economic order and scuttle everything he had built for his family. His political philosophy, such as it was, remained inchoate and cynical—basically, acquiring and maintaining power were all that really mattered—but he intuited that whereas in the twenties business had been supreme, the thirties would be the decade of government, with the reformers running the show, and that he needed to shift his attention accordingly. He saw the limits of his long-held belief that money brought power; real power, he now saw, rested in politics.17

Kennedy hitched his hopes to one man, Franklin Delano Roosevelt, the governor of New York and Democratic candidate for president in 1932. The history between the two men reportedly went back to World War I, when, as manager of the Fore River shipyard, Kennedy negotiated testily with Roosevelt, then assistant secretary of the Navy, over the fate of two Argentine dreadnoughts completed before the war but returned to the Fore River yard for premature repairs. (Kennedy, so the story goes, refused to deliver the vessels until payment was received; Roosevelt objected and, when Kennedy stood firm, dispatched Navy tugs to tow away the ships.)18 Now, a decade and a half later, Kennedy, having seen up close the flaws in the economic system that had made him rich, willed himself to believe that Roosevelt, more than the ineffectual Hoover, represented capitalism’s best hope against revolution from below. And there was cold opportunism, too: Kennedy speculated that FDR would win and that through him he might himself find an entrée into politics. Roosevelt, for his part, saw in Kennedy not only a means of building up his presidential war chest, but a rare and formidable ally in the world of finance.19

“Roosevelt was a man of action,” Kennedy told a journalist later. “He had the capacity to get things done….Long before the campaign, long before his name was even seriously considered, I went out to work for him. I think I was the first man with more than $12 in the bank who openly supported him. I did this because I had seen him in action. I knew what he could do and how he did it, and I felt that after a long period of inactivity we needed a leader who would lead.” To another reporter he said, “I wanted [Roosevelt] in the White House for my own security and for the security of our kids, and I was ready to do anything to elect him.”20

They were a fascinating pair, so similar in some ways, so contrasting in others. Both were intelligent and egotistical men, skilled in the art of concealing their true motives behind guileless masks. Both were impatient with intellectual debate over abstract ideas and theories. (At Harvard, where they were eight years apart, they had been content to scrape by in their classes and to prioritize the social dimensions of collegiate life.) Both were hearty and outgoing, adept at attracting talented and dedicated subordinates, yet were not known for maintaining deep friendships—or being true to their wives. The differences were equally telling. Where Kennedy was fervent and single-minded, Roosevelt was cool and urbane, content to operate on myriad levels at once. Kennedy viewed the human condition in dark, fatalistic terms, whereas Roosevelt usually saw reasons for optimism even in the most difficult circumstances; he had the greater faith in the power of democratic ideals. Kennedy’s intellect, though formidable, had a narrow character, and he was uncomfortable with doubt; Roosevelt, with his more capacious sensibility, liked to entertain differing points of view. Most striking of all, whereas for Kennedy his children were always supreme, Roosevelt seemed at times more responsive to his constituency—his “national family”—than to his own offspring.21

Thus began a marriage of convenience, one that was never free of mutual suspicion but that for a time, in the early and mid-1930s, also featured a degree of affection, or at least commonality based on a shared sense of humor and an appreciation of each other’s talents and achievements. Kennedy poured money and time into Roosevelt’s campaign in 1932, contributing ideas to the candidate’s speeches on the economy and calling wealthy Democrats to urge them to make donations. He also helped persuade newspaper magnate William Randolph Hearst to break the deadlock at the Democratic National Convention that threatened an early FDR win. Kennedy then accompanied the candidate on a whistle-stop train tour to the western states in September, voicing robust support as Roosevelt called for greater government involvement in combating the economic crisis through “a new deal for the American people.” On election night, Kennedy put on a lavish victory party that took up two floors of the Waldorf Astoria, in New York, with Roosevelt’s theme song “Happy Days Are Here Again” blaring through the night. In the weeks thereafter, he laid on the flattery: in one telegram he informed FDR that a nun at his daughter Rosemary’s convent school had declared the new administration to be “like another Resurrection.” (Roosevelt, perhaps recalling what had occurred immediately before the previous Resurrection, replied vaguely with a thank-you for the “awfully nice telegram.”)22

There had been signs during the campaign of what would become two pronounced features of Joe Kennedy’s public persona in the years to come: his cultivation of the press and an obsessive interest in image-building. The right sort of publicity, his Hollywood years had taught him, could endow a person with fame as well as prestige; consequently, he made friends among the reporters who covered Roosevelt and took every chance to chat them up. “He liked being with the press more than he liked being with the politicians,” said Ernest Lindley, a correspondent who two years earlier had penned the first Roosevelt biography. “He liked the repartee.”23

Kennedy hoped to be appointed secretary of the Treasury in the new administration, but, to his intense frustration, there would be no offer of any kind for more than a year after the inauguration, in large part because of opposition at the White House, especially from the gnarled, gnomish, chain-smoking chief secretary, Louis Howe, who loathed the idea of bringing on a man he considered an unscrupulous Wall Street denizen. His pride wounded, Kennedy turned privately critical of Roosevelt—in letters, phone calls, and face-to-face meetings, he unloaded on FDR for his ingratitude and callousness—only to fall under the spell of the president’s mesmerizing charm whenever they met and leave each encounter pledging his undying support. In 1934, after being passed over a second time for the Treasury slot and turning down an offer to become the U.S. representative to Ireland, he agreed to head up the Securities and Exchange Commission, a newly created entity designed to regulate stock exchanges, meaning that the notorious stock speculator would now be the cop on Wall Street’s corner.24 Presidential aides objected to the appointment for that reason, but Roosevelt held firm. Set a thief to catch a thief, he reasoned.25

III

As much as anything, what comes through in the accounts of Jack’s Choate years is his lively wit. It’s a theme in contemporaneous assessments and in subsequent oral histories, and it’s there in his own letters to family and friends. Headmaster St. John, hardly one of the young man’s great champions in this period, acknowledged Jack’s gift for satirizing mundane everyday developments and mining them for laughs.26

The sense of humor and the charm go a long way toward explaining Jack’s most conspicuous talent during his four years in Wallingford: his ability to make friends. Not everyone took to him—a few classmates thought him glib and cavalier. For the most part, however, and even before his brother graduated in 1933 (in a blaze of glory: he won the Harvard Trophy, awarded to the graduating student who best combined sportsmanship and scholarship), Jack was broadly popular, at least among the boys in his year.27 “With Jack,” said Seymour St. John, the headmaster’s son, who would later take over that position himself, “nobody really admired what he did or respected what he did, but they liked his personality. When he flashed his smile, he could charm a bird off a tree.”28 From the start, Jack never lacked for pals, many of whom were drawn in by his irreverence and easy laugh, and by his lack of ostentatiousness despite his family’s wealth. An early companion was Rip Horton, whose family ran a major dairy business in New York City. On occasion the two teens ventured into Manhattan together, with Horton procuring passes that got them into speakeasies and other clubs.

Another acquaintance was Al Lerner, from New York City, who in time would become known as Alan Jay Lerner and who, with Frederick Loewe, would write some of Broadway’s most beloved musicals, among them Brigadoon, My Fair Lady, and Camelot. The last would be a favorite of Jack’s and would become, with its famous “one brief shining moment” line, a sobriquet for his presidency.

But it was Lem Billings who became Jack’s closest friend, a distinction he would keep for the rest of Kennedy’s life. They met toward the end of spring semester in 1933, while working on the school yearbook, The Brief. Handsome and bespectacled, with curly blondish hair and a piercing nasal voice, Billings was tall and strong at six-two and 175 pounds, not all that coordinated but big enough to play first-team football and be a regular on the crew team. With ancestors on his mother’s side who had arrived in America aboard the Mayflower in 1620, Lem was the son of a prominent Pittsburgh doctor who had recently died unexpectedly and left almost nothing behind, having lost his fortune after the Wall Street crash. Like Jack, Lem followed in the footsteps of a more celebrated brother who carried his father’s name: Frederic “Josh” Billings Jr. was president of his Choate class of 1929, chairman of the student council, editor in chief of the yearbook, and captain of the football team; later he was an athletic and academic standout at Princeton and a Rhodes Scholar. The two “second sons” soon bonded. In a postcard to Lem from Hyannis Port that summer, Jack closed with “I’ll see you next fall, which is a damn sight too near for comfort.”29

Their friendship deepened when they returned to school in September. They shared a love of practical jokes and gossiping, as well as an instinct for flouting authority. “Jack had the best sense of humor of anybody I’ve known in my life,” Billings remembered. “And I don’t think I’ve known anybody who was as much fun.”30 Together, they delighted in mocking pomposity and self-importance and blind conformism, all qualities found in abundance on the Choate campus. But they were also powerfully dependent on each other. In Lem, Jack found a loyal, intelligent confidant and caretaker of sorts as he battled through his ailments, while Lem relied on Jack not just for unconditional friendship but for stability following his father’s sudden death. They found they enjoyed each other without rivalry. Over winter break that year, Jack invited Billings to Palm Beach, playground of the wealthy, where Joe Senior had recently paid $115,000 for a six-bedroom, two-story oceanfront vacation home on North Ocean Boulevard, complete with pool and tennis court.31

Lem would become a fixture at the various Kennedy houses in the years to come. He noticed early on that the family seemed to lack a true sense of place, of belonging. “They really didn’t have a real home with their own rooms where they had pictures on the walls or memorabilia on the shelves,” he remarked years afterwards, “but would rather come home for holidays from their boarding schools and find whatever room was available.” Upon arrival Lem would hear Jack say to his mother, “Which room do I have this time?” Yet Billings found himself drawn to the Kennedys just the same—to their intense vitality, their open-mindedness, their frantic activism. “With them, life speeded up.” He loved the informality among the siblings and their penchant for playful teasing, and marveled at their deep loyalty to one another. So frequently did Billings visit that young Teddy for a time thought he was a member of the family. “I was three years old before it dawned on me that Lem wasn’t one more older brother,” Teddy said, adding that Lem kept more clothes in the Hyannis Port home on a continual basis than Jack did.32

Joe Kennedy could sense the bond Billings had not just with Jack but with all the Kennedy kids. A few years later, he sent the young man a letter: “Dear Lem, This is as good a time to tell you that the Kennedy children from young Joe down should be very proud to be your friends, because year in and year out you have given them what few people really enjoy. True Friendship. I’m glad we all know you.—JPK.”33

Jack in many ways dominated the friendship. He enjoyed teasing and needling people, and often his closest friend became the target of his barbs. Soon Lem had a string of nicknames such as “LeMoan,” “Pneumoan,” and “Delemma,” and soon Jack’s letters to him opened with the greeting “Dear Unattractive” or “Dear Crap.” One letter, from April 1934, began, “Received your very uninteresting post card.”34 Most of the time Lem took the taunts in stride, but not always—on occasion he took offense at perceived slights. Jack, for his part, could sometimes get angry, too, especially over suggestions that he treated his friend unfairly. When Lem got upset over a mix-up concerning an invitation to the Palm Beach home, Jack let him have it:

Of all the cheap shit I have ever gotten this is about the cheapest. You were invited down on Thanksgiving when the family was not coming. But then you were too busy and you and Rip [Horton] were going to St. Lawrence. Then you decide to come down as Rip was going to. But by that time, the family had decided to come down. Then you get hot in the arse because there may not be room enough, not forgetting that there was room enough at Thanksgiving but you didn’t want to come until Rip decided he wanted to come….Then I heard from dad saying it was okay. That was the situation: as regards the cheap shit you are pulling, you can do what you want….If you look at this thing you will see you are not so fucking abused.35

Author David Pitts summarizes the dynamic well: “Like many close attachments, their friendship was complicated, and neither boy likely fully understood its nature or limitations at this time in their lives. Lem was clearly the more emotionally involved. He needed Jack and Jack knew it. But it also was apparent that Jack needed Lem, too. In the early years, they tested each other, as boys are prone to do, each seeking dominance.”36

Seymour St. John, who would see the two boys together on his visits home from Yale, where he was an undergraduate, wrote perceptively that “their schoolboy banter was humorously critical, devil-may-care, which gave them a protective veneer and a sense of security.” There was mutual dependence, St. John went on, and Lem “was ready to follow and applaud Jack in every escapade.” The notorious school disciplinarian, J. J. Maher, the housemaster of their West Wing dorm, whom Jack in particular detested, was less forgiving of the boys’ friendship, complaining to the headmaster of their self-centered, “silly, giggling inseparable companionship.” An unyielding disciplinarian, the bachelor Maher was a compact, muscular figure who doubled as the school’s first-team football coach and prided himself on being stronger and faster than any member of his team. He proved an irresistible target for the two boys’ antics, such as the time when, late in the evening, they noisily began carrying Jack’s trunk down the stairs to the basement after a vacation. An incensed Maher came flying out of his room, roaring at them for making a racket and reminding them that such work should be done not at night but in the morning. Jack duly apologized, and they resumed the work the next morning—before sunrise. Maher was furious, much to the boys’ amusement.37

IV

In January 1934, soon after the Christmas break, Rose Kennedy wrote the school to ask if Jack could be permitted to travel to Providence, Rhode Island, to attend a dance with Rosemary. “The reason I am making this seemingly absurd request is because the young lady is his sister and she has an inferiority complex.” George Steele, the dean of students, readily consented. “I appreciate thoroughly how much it would mean to you and Jack’s sister to have him accept….I know Jack will want to do this for Rosemary.”38

Rosemary, age fifteen, was by then in her second year at the Convent of the Sacred Heart School, Elmhurst, in Providence. Her parents, hoping that a new environment would spur her academically, had transferred her from the Devereux School in the fall of 1932. As before, progress was slow and intermittent, her limited attention span thwarting teachers’ efforts to educate her; as before, she craved her family’s approval and attention. “Thank you very much for the lovely letter you sent me,” she wrote her parents in the spring of 1934, perhaps with help from the nuns, her penmanship and grammar similar to those of a ten-year-old. “I got three bottles of perfume, but it is allright. I am satisfied. I like the handkerchief lot….I cannot thank you enough for everything you have done to make Elmhurst so happy. Thanking you again for your kindness.”39

Jack never got the chance to go to Rhode Island, for suddenly he again fell ill—this time ominously so. He had skinned his knee in Palm Beach playing tennis with Billings, and it became infected. Whether for that reason or another, he began feeling terrible. By early February he had been transported to New Haven Hospital. His condition deteriorated further and, according to Billings, he “came very close to dying.” Rumors spread among the students that Jack was at death’s door; heartfelt prayers were issued in the school chapel. Leukemia seemed a possibility, but doctors ruled it out. “It was some very serious blood condition,” Billings recalled, which seems as exact a diagnosis as any. Headmaster St. John got swept up in the emotion of the moment, telling Joe Senior that “Jack is one of the best people that ever lived—one of the most able and interesting. I could go on about Jack!” To Jack himself St. John wrote with warmth and emotional attachment: “I think of you over and over, and wish I had you under my own roof; but I am grateful you are in such good scientific care.”40

As was her pattern, Rose did not visit her son during the weeklong ordeal, choosing to stay put in Palm Beach. (Her husband did come to the hospital, as did Eddie Moore.) Not once during his four years at Choate did she come to Connecticut—even with all his illnesses. She did, however, take numerous solo vacations during those four years, and she also accompanied Joe Senior on trips to Europe. (Between 1929 and 1936 she went abroad seventeen times.) How Jack felt about her absence during his myriad infirmary stays goes unrecorded, but we can guess that it stung. We can imagine that some part of him wished she had come even once to the annual Mother’s Day at the school, held in the spring each year, or had made the two-hour drive from Bronxville on some other occasion. If Rose’s distance had the compensating advantage of making him more self-reliant, more independent, that was small consolation.41

Rose did maintain close written contact with the school and hospital staff during the crisis. “Jack’s sense of humor hasn’t left him for a minute, even when he felt most miserable,” Mrs. St. John reported to her as the situation began to improve. When he had his first meal “after what must have seemed to him a terribly long time…he said to me, ‘It was just as well that they decided to give me breakfast; if they hadn’t, I think the nurse would have come in pretty soon and looked in my bed and not been able to see me at all!’ ”42

As soon as his symptoms abated, Jack was sent down to the family home in Florida for several weeks of rest and recuperation. While there, he kept up with his schoolwork with the help of a tutor, and sent the St. Johns a handwritten letter of thanks for their “numerous kindnesses” while he was in the hospital. He returned to school after Easter break. His weight, which had gone down to 125 pounds, was back up to 140. Exams soon followed, and he acknowledged to his mother that, although “I did not come out with flying colors, still I passed which is in itself a small accomplishment.” To his father he bemoaned the rainy spring weather and the fact that “Mr. Maher came back from his holidays looking blacker than ever.”43 Taskmaster Maher, for his part, conceded in his housemaster’s report that “to say that I understand Jack is more an expression of fond hope than a statement of fact.” His young pupil was “such a complete individualist in theory and practice that the ordinary appeals of group spirit and social consciousness…have no effect.” Jack’s basic approach, Maher continued, was to say, “I’m a lively young fellow with a nimble brain and a bag full of tricks. You’ll spoil my fun if I let you, so here I go; catch me if you can.” The housemaster expressed hope that the “silly game” had lost its zest and that the young man was learning to distinguish between “liberty and license.”44

Then, in June, with the school year just completed, another illness, leading to yet another hospitalization. This time it was determined that Jack should be sent to the famed Mayo Clinic, in Rochester, Minnesota, in the hope of finding out, once and for all, what plagued him. Neither parent accompanied him; instead the honor fell to Eddie Moore. Jack was miserable, not least because he knew that Lem Billings was in Hyannis Port with the rest of the Kennedys enjoying the summer sun. (As it happened, Lem scalded himself in the Kennedys’ shower and was himself laid up in the hospital for three weeks.)45 Humiliating pokes and prods by the Mayo staff came in quick succession, and he wrote a string of letters to Billings describing his ordeal. Many were lewd. “I’m suffering terribly out here and I now have gut ache all the time,” read one missive. “I’m still eating peas and corn for food and I had an enema given by a beautiful blonde. That, my sweet, is the height of cheap thrills.”46

“Here I am in the hottest place, except the Kennedys’ shower, in the country,” he wrote after learning of Lem’s scalding. “A fellow stuck his finger up my rectum today and I, much to my embarrassment, burst out laughing. That rather upset the mgmt. of the whole place. How are you feeling? I hope you are having a pleasant stay….They ask me the most personal questions, and I am blushing terribly especially when they ask me the color of my stool. They also gave my penis a tremendous jerk and I began to giggle coyly.”47

Sex was never far from the seventeen-year-old’s mind. “My virility is being sapped. I’m just a shell of the former man and my penis looks as if it has been through a wringer.” The nurses were “very tantalizing and I’m really the pet of the hospital…and let me tell you, the nurses are almost as dirty as you, you filthy minded shit.” Exhibiting even at this age a chauvinistic view of women, he boasted that one of the nurses “wanted to know if I would give her a workout,” but, to his disappointment, she failed to return to his room.48

The adolescent boasting and obscenity were surely employed to cover what must have been a deeply trying experience. Here he was, half a continent from home, surrounded by strangers and subjected to an endless string of tests, each one seemingly designed to damage his dignity. Yet his letters give little evidence of self-pity or of the other emotion that many teenagers in his condition—or adults, for that matter—would feel, namely, fear. He was sick and hurting but wouldn’t admit it, not even perhaps to himself. Instead he stood detached, a ceaseless observer of his own life, his letters suffused with his characteristic stoicism and a dark and richly inventive sense of humor. “I only had two enemas today and feel kind of full,” he informed Billings on June 30. But finally there was hopeful news: “They have found something wrong with me at last. I don’t know what but it’s probably something revolting like piles or a disease of my vital organ.” No definitive diagnosis was in fact ever made that summer, but the doctors concluded he suffered from allergies as well as from spastic colon (known today as irritable bowel syndrome) or, more seriously, from colitis, which, if true, would explain why it was hard for him to gain weight and could generate worse problems if the colon bled or became ulcerated. Jack returned home with orders to follow a proper diet and also to take steps to relieve emotional stress, at the time thought to be a major contributor to the condition.49

He would have only a few weeks in Hyannis Port that summer, but he was determined to make the most of them. He loved this place more than any other, not least for the opportunity it gave him to be out on the water in Nantucket Sound. He had become, by this point in his young life, a highly skilled racing skipper, with a reputation for boldness and cunning and for catching his opponents by surprise. He and Joe Junior, one observer noted, went for “split-second timing at the start, recklessness at the windward buoy, disregard for the risk of a tiny misjudgment.” They carried full canvas while rival skippers reefed, possessed a deft touch at the tiller, and were adept at picking up the hint of a breeze in light winds. In the early years, the boys used two cleverly named sixteen-footers in the Wianno junior class—Tenovus, followed, after the birth of Teddy, by Onemore—and in 1932 Joe Senior added to the fleet, buying a used twenty-five-foot Wianno senior with a small cuddy for overnight trips. Jack named her Victura (“something to do with winning”), and she became the vehicle for his greatest successes.50

V

In the fall of 1934, Jack returned to Choate for his senior year. He and Lem Billings roomed together. Headmaster St. John had allowed it, over J. J. Maher’s warning—prescient, time would reveal—that mischief would follow. That Jack and Lem would even ask to be roommates is fascinating, in view of what their summer correspondence had revealed: for Lem, this was more than a friendship. At some point over the previous year he had fallen in love with Jack. At first content with the relationship being purely platonic, he found it harder and harder to restrain himself, even though he was pretty sure his feelings were not reciprocated.51

But how should he proceed? Unwilling to risk a termination of the friendship by openly stating his feelings and admitting that his sexual attractions were directed to boys and, in particular, to Jack, he opted to drop a hint. The unspoken tradition at Choate, borrowed from British private schools, was for boys who wanted to have sexual encounters with other boys to exchange notes written on toilet paper (which could be flushed or even swallowed to avoid a paper trail). In early June, Lem had sent such a note to Jack—no doubt after much agonized indecision. The note does not survive, and we don’t know what precisely it said, but we have Jack’s response. “Please don’t write to me on toilet paper anymore,” he wrote from his hospital bed later that month. “I’m not that kind of boy.” As if to assuage any embarrassment on his friend’s part, or cover his own, or both, he devoted the rest of the letter to his medical condition and his sagging manhood.52

Whether Jack had any prior inkling of Lem’s interest in him is unclear. His letters from the period suggest he took Lem to be a ladies’ man like himself. A year before, in June 1933, in his very first letter to Lem, he wrote, “Please give my best to Pussy [Brooks, a girl from Pittsburgh whom Lem knew] and take it easy on the women.” And certainly, a single incident of this nature at an all-boys prep school does not say all that much about a person’s sexual orientation. Yet there were periodic hints that Lem might be cut from a different cloth. Earlier in 1934, the two boys had ventured to Harlem in full evening dress to find a prostitute, in order to lose their virginity in the same evening to the same woman. Jack went into the room with the woman he had selected, while Lem—as he recalled later—waited uncomfortably by the door. When Jack came out, he had to coax his friend into going into the room, where, it seems, Lem did not lose his virginity.53

On another occasion, Jack and Lem and an alumnus of the school, Pete Caesar, left a Choate evening social with two girls, Olive Cawley and Pussy Brooks, and drove to a nearby farm. En route, the quintet noticed they were being followed by one of the school’s cars. On Jack’s suggestion, Pete and Pussy remained in the car while the other three dashed off unseen. When the campus cops arrived, they merely found an alumnus necking with his girl and drove on. Jack and Olive, meanwhile, had found a remote corner of a barn, and Lem planted himself in a haystack in another barn and waited quietly for everyone to finish.54

Having been rebuffed by Jack in no uncertain terms, Lem backed off and, it seems, never made the proposition again. He could only watch as Jack became increasingly infatuated with Cawley, a pretty and vibrant brunette who hailed from New York City and attended the private Kimberley School, in New Jersey.55 But it’s telling that Jack, contrary to what one would expect of a straight man in that era, did not break off the friendship. Even after it became incontrovertibly clear in later years that Lem was gay, the two remained close. “Jack was a hell of a forgiving guy,” their friend Rip Horton said. “He was terribly understanding.” Journalist Charles Bartlett, who befriended Jack and Lem after the Second World War, said much the same thing: “I liked Lem and saw that he was a good friend of Jack’s. Jack was not a judgmental type of guy. He accepted his friends without passing judgment on them.”56

The truth was that Jack enjoyed spending time with Lem, valued his friendship. The perspicacious Seymour St. John, in an interview half a century later, saw Lem as a tragic figure whose identity over time became entirely wrapped up in Jack Kennedy and his family, “who had nothing really to hold onto” until he found Jack. After that, “anything Jack did, he would follow right along with him and be the stooge.” But St. John also perceived the positive side of the friendship, not least for Jack, who could count on his friend to be the jester, to lift his spirits when he might otherwise have sunk into despair, with his chronic ailments and his ongoing rivalry with Joe Junior. “It was Billings’s loyalty that helped [Jack] to emerge from his adolescent trials with his confidence in himself strengthened rather than broken,” St. John said.57

Now, as they entered their final year (Lem could have finished in 1934, but, as if to demonstrate Seymour St. John’s point, he stayed on an extra year in order to be with Jack and their friends), they were determined to have a good time. Maher, sensing trouble, put them in a room right next to his own.58 The trouble came soon enough. Jack had brought with him from Hyannis Port a pristine old Victrola and a bunch of records, and in short order their room became the hangout spot for a dozen friends. Maher informed the headmaster of the noise and messiness, and before long George St. John stood before the student body in the long, formal English dining hall and spoke of a small group of selfish, pleasure-loving troublemakers who seemed intent on destroying the peace of the school. They were “muckers,” the headmaster said, nothing more than muckers, and he would not stand for it.59

Perfect, Jack and his buddies thought as they listened: muckers! The name fit them to a tee. The group promptly went into Wallingford and shelled out $12 each for a small gold charm in the shape of a shovel and engraved with the initials CMC, for Choate Muckers Club. (Another meaning of mucker was someone who, in the days before automobiles, shoveled horse manure off the streets.) Their subsequent antics were misdemeanors at worst—sneaking off school grounds for milkshakes and playing music after hours. Alcohol was never in the equation, and neither was smoking. For Spring Festival they planned to have each member arrive at the dance pulling his date on a shovel, then have photographs taken outside next to a manure pile, shovels in hand.60

St. John was furious when he learned of the scheme. At lunch in the dining hall, he read off the Muckers’ names, accused them of undermining Choate’s morals and integrity, and ordered them into his study. There he expelled them and ordered them to clear out of their rooms and prepare to depart the school. The astonished boys trudged back to their dorms and fretted about how to tell their parents, only to be called back into the headmaster’s study and informed that he had changed his mind: they would not be expelled after all. But there would be no more club, he told them, no more shenanigans, and they would be kept at school over the Easter break.61

At St. John’s request, Joe Kennedy and Lem’s mother, Romaine, traveled to the school to discuss the crisis. Their sons were the ringleaders, he told them, and he wanted them, as parents, to understand the seriousness of the situation. During the Kennedys’ session, father and son nodded politely at the headmaster’s stern words, and Jack expressed contrition. Mr. Kennedy professed to be appalled by the club’s actions, but inside he questioned what all the fuss was about. Himself an outsider in this elite Episcopalian milieu, he wondered if George St. John’s rumored anti-Catholicism played a role in his overheated approach to the affair. (For there was a third meaning of mucker: a lowly Irish Catholic immigrant who worked to clear the swamps of Boston’s Back Bay.) When St. John interrupted their conversation to take a phone call, Joe leaned over and whispered to Jack, “My God, my son, you sure didn’t inherit your father’s directness or his reputation for using bad language. If that crazy Muckers Club had been mine, you can be sure it wouldn’t have started with an M!”62

One detects a sense of entitlement in how both Kennedys—father and son—reacted to the Muckers affair, a sense that the rules didn’t fully apply to Jack, and that St. John couldn’t really touch him. More than that, in Joe Kennedy’s handling of the episode there’s a strong whiff of fatherly pride. Well aware of his reputation for being a domineering, overbearing presence in his children’s lives, he worked to instill in them—and especially the boys—a certain irreverence and independence of mind. When Young Joe graduated from Choate in 1933, his father, upon the recommendation of Harvard Law School professor Felix Frankfurter, dispatched him to the London School of Economics to spend a year studying with Harold Laski, the distinguished socialist theorist and economist, before matriculating at Harvard. Laski’s political and economic philosophies were far from Kennedy’s own, but he reasoned that a sustained period under the Briton’s tutelage would broaden Joe Junior’s intellectual range and hone his ability to defend a more conservative position. Nor was this a newfound philosophy: visitors to the Kennedy home had long noted that during the mealtime seminars, Mr. Kennedy never pushed Joe or Jack or the other children to adopt his positions, but encouraged them to adopt and defend their own points of view.63

But being informed and opinionated was not enough—commitment and responsibility were essential, too. In this regard Jack remained for his father a source of worry, no less at the end of the Choate years than at the beginning. In letter after letter that final year (penned, mind you, while he headed a major new government agency in Washington), he nudged and cajoled his second son, urging him to finish, as he put it, in “a blaze of glory.” A missive from December 1934 gives the flavor:

After long experience in sizing up people, I definitely know you have the goods and you can go a long way. Now aren’t you foolish not to get all there is out of what God has given you and what you can do with it yourself? After all, I would be lacking even as a friend if I did not urge you to take advantage of the qualities you have. It is very difficult to make up fundamentals you have neglected when you were very young, and that is why I am urging you to do the best you can. I am not expecting too much, and I will not be disappointed if you don’t turn out to be a real genius, but I think you can be a really worthwhile citizen with good judgment and understanding.64

In the wake of the near expulsion in the spring, Choate gave three of the troublemakers an opportunity to meet with a Columbia University psychologist, Prescott Lecky. Jack, perhaps at his father’s urging, accepted the offer. Lecky reported that he found the young man to be very able, “but definitely in a trap, psychologically speaking. He has established a reputation in the family for thoughtlessness, sloppiness, and inefficiency, and he feels entirely at home in the role.” When Lecky asked him if he expected to succeed in the world with this attitude, Jack had no answer. “He thinks of himself as a self-reliant, intelligent, and courageous boy,” Lecky continued, “but he has never recognized the difficulty he will have in maintaining those definitions unless he sacrifices the defense devices that he has built up through the years. He does not worry about his sloppiness, he says, and has never been neat in his life; but it is obvious that he must worry sooner or later, or give up the definitions he values most.”

More than anything, Lecky determined, the source of Jack’s troubles could be found in the rivalry with Joe Junior. “My brother is the efficient one in the family,” Jack told him, “and I am the boy who doesn’t get things done. If my brother were not so efficient, it would be easier for me to be efficient. He does it so much better than I do.” Lecky concluded that “Jack is apparently avoiding comparison and withdraws from the race, so to speak, in order to convince himself that he is not trying.”65

It was an astute appraisal of a young man who had yet to find his way. Lecky was surely right that the sibling rivalry and the inferiority complex that resulted from his second-son status helped explain Jack’s anti-establishment flair and slacker ways. Then again, one could go too far with the notion. Perhaps a part of Jack was simply following in the footsteps of his father, a similarly indifferent student during his days at Boston Latin thirty years before.

Whatever the case, as Jack prepared to depart Choate that spring of 1935—aged eighteen, tall and wiry, with an angular, handsome face and a mop of hair that resisted all efforts at control—he could take a certain satisfaction from his four years at the school. His health travails had been at times all-consuming and, partly for that reason, his academic performance seldom went beyond middling. But he experienced a freedom he had never had before, especially after his brother’s departure at the midpoint. He met a lifelong friend in Lem Billings and enjoyed the conviviality of a large circle of other pals. What’s more, he learned during his Choate years how to get along on his own, independently, even in the face of adversity, and saw the degree to which he could use his charm and sense of humor to his advantage. “In any school he would have got away with some things, just on his smile,” George St. John conceded. “He was a very likeable person, very lovable.” One measure of that: despite ranking barely above the median in his class, Jack Kennedy was voted by his classmates “most likely to succeed.” No doubt the result owed a good deal to the Kennedys’ immense wealth, well known on campus, and to the energetic efforts of the ex-Muckers, led by Billings, to round up votes for their leader, but it also resulted from Jack’s popularity among his fellow students.66

The vote was Jack’s final poke in the eye to the Choate establishment, and it must have annoyed the school’s leaders to see their exasperating Mucker recognized in this way. But they could see the promise in the lad, more so than in his accomplished older brother, who lacked his creative intelligence. “Jack has a clever, individualist mind,” George St. John had told Mr. Kennedy some time before. “It is a harder mind to put in harness than Joe’s….When he learns the right place for humor and learns to use his individual way of looking at things as an asset instead of a handicap, his natural gift of an individual outlook and witty expression are going to help him. A more conventional mind and a more plodding and mature point of view would help him a lot more right now; but we have to allow, my dear Mr. Kennedy, with boys like Jack, for a period of adjustment…and growing up; and the final product is often more interesting and more effective than the boy with a more conventional mind who has been to us parents and teachers much less trouble.”67

Assistant headmaster Wardell St. John had a similar inkling. “Jack has it in him to be a great leader of men,” he wrote at the end of spring term, “and somehow I have a feeling that he is going to be just that.”68

It was, time would reveal, a most penetrating pair of assessments.

II

Now here they were, bound for Europe together. It was the first time for both. And what a means of transportation they had! The Normandie was the greatest of all ocean liners (arguably to this day), the largest and fastest passenger ship afloat. Her maiden voyage had taken place just a few months earlier, during which she set a transatlantic speed record, covering Le Havre to New York in just four days, three hours, and fourteen minutes, at an average speed of thirty knots. Her lavish interiors, finished entirely in the Art Deco style, featured spectacular entryways and staircases, as well as a 305-foot-long dining room with silver walls and twenty-four-foot gold ceilings, a room larger than the Hall of Mirrors at Versailles, able to seat seven hundred guests at 157 tables. Other amenities included indoor and outdoor pools, a theater, a chapel, a winter garden, and an open-air tennis court. The Kennedys were enthralled, as Rose made clear in her diary, though Jack’s devouring of the French delicacies caused grumbling from one quarter. “The food here is very pimp-laden,” he wrote Billings, “and my face is causing much comment from the old man, and it is getting damned embarrassing. He really rang the bell when after helping myself to a dessert that was oozing with potential pimps he said my face was getting to look like yours.”13

The Kennedys were to disembark at Plymouth, on England’s south coast, but bad weather compelled the captain to make straight for Le Havre, in Normandy. From nearby Dieppe the family then boarded a small craft for a rough crossing to Newhaven, in East Sussex. “Everyone ill except Joe, Jack, and Kick all of whom stayed on upper deck in rain freezing to death,” Rose wrote in her diary.14

Upon arrival in London they settled in at Claridge’s hotel, in Mayfair, just off Grosvenor Square and the shops of Bond Street. It was an eventful time to be in Europe. A British election was fast approaching, and there were rising tensions on the Continent. Earlier in the year, German leader Adolf Hitler had warned that rival powers should get used to dealing with Germany on an equal footing—in March he announced the existence of a German Luftwaffe (air force) and ordered the conscription of all able-bodied men aged nineteen or over. Both were violations of the Versailles Treaty—the most consequential of a series of treaties imposed by the Allies on the defeated powers at the end of World War I—and caused acute consternation in European chancelleries. The Soviet Union and France responded by signing a treaty of friendship and mutual support. In September, shortly before the Kennedys set sail from New York, Hitler imposed the Nuremberg Laws, in which Jews were denied the rights of German citizenship and marriage, and extramarital relations between Jews and “Aryans” were prohibited. The swastika became the official flag of Germany. On October 2–3, Benito Mussolini’s Italy invaded Abyssinia (Ethiopia), a clear breach of the League of Nations’ sanctions against aggression.15

For informed observers at the time, and for legions of historians later, these were deeply ominous developments, proof positive that the fragile international order was foundering. Coming out of the Great War, the Allied leaders, led by Woodrow Wilson, had championed a new way of conducting world affairs, with the end of secret diplomacy and bilateral deals and the creation of the League of Nations to settle geopolitical crises and head off interstate violence. Disarmament efforts would make the world safer and contribute to the avoidance of another destructive general war. Much to Wilson’s dismay, the U.S. Senate had rejected American membership in the League—the centerpiece of his vision for the postwar world—but under the subsequent Republican administrations, U.S. officials nonetheless participated discreetly in League meetings on a range of issues.16 Hitler’s accession to power in 1933 scuttled the disarmament talks—he walked out of them in short order, rendering further efforts moot, and the World Disarmament Conference adjourned indefinitely. Mussolini’s invasion of Abyssinia, meanwhile, brought sharp verbal condemnation from the world’s powers but little more. Italy swiftly resigned from the League and drew closer to Nazi Germany.17

How much Jack took note of these machinations is unclear. He read the daily newspapers and (following his mother’s example) clipped articles that interested him. But mostly he devoted his early efforts in London to penetrating the city’s social scene. The LSE intrigued him, but he did not take to Harold Laski, finding him humorless and self-important and his socialist ideas impractical and narrow.18 Suddenly the prospect of spending an academic year—or even a term—under this man seemed like a nightmare. Seemingly on cue, another mystery ailment arrived, placing Jack in the hospital and leaving physicians confounded once again. He was jaundiced and had joint pain, and his blood count was off, but he was not fully symptomatic of anything. The doctors settled on hepatitis as the likely diagnosis, but without conviction. “They are doing a number of strange things to me,” he wrote Lem from his bed, “not the least of which is to shove a tremendous needle up my cheeks. Today was most embarrassing as one doctor came in just after I had woken up and was reclining with a semi [erection] on due to the cold weather. His plan was to stick his finger under my pickle and have me cough. His plan quickly changed however when he drew back the covers and there was ‘JJ Maher’ quivering with life.” (Jack had named his penis after his detested Choate housemaster.) The “very sexy” night nurse, meanwhile, “is continually trying to goose me so I always have to be on my guard.”19

In time, much would be made of Jack Kennedy’s exposure to the famous Laski’s teachings. Jack himself talked up the connection, presumably in order to enhance the impression of his academic credentials. References would be made by political operatives to the “term” he spent at the LSE. In fact, he lasted in London all of a month before returning to the United States, his parents feeling his health could be better monitored from there.^*1 Tellingly, he informed Billings in a letter that “Dad says I can go home if I want to.” Not only that, but the elder Kennedy signed off on his son’s request to enroll late at Princeton. (The school granted his appeal.) On October 21, 1935, Billings received the good news via wire: ARRIVING PRINCETON THURSDAY AFTERNOON; HOPE YOU CAN ARRANGE ROOMING.20

Billings was thrilled. He wired back: NOTHING COULD POSSIBLY SOUND BETTER. SO HURRY HOME. And he did have accommodation for his friend, though admittedly it wasn’t much: a dumpy two-bedroom apartment that he shared with Rip Horton on the fourth floor of South Reunion Hall. The main bathroom was in the basement, seventy-two steps away, and the flat had long since seen its best days. It had but a single radiator and a lone cramped closet. But it was cheap, and it offered a splendid view of ivy-covered Nassau Hall, the oldest building on campus, dating to 1756, when the university was known as the College of New Jersey.21

If Jack felt let down by his new digs, he didn’t show it. Never one to live with the ostentation his family wealth afforded him, he entered college with the same casual, even sloppy, manner of dress and lifestyle he had followed at Choate. He happily bunked on a spare cot in Billings’s small bedroom. He was aware, moreover, that the spartan arrangement was made necessary by his friend’s financial constraints. Though he could belittle Lem in letters (in a way Lem never dared do to him), Jack was also deeply loyal. He worried about his friend’s money problems, and pledged to help him out. “Your financial worries have upset me,” he wrote from London, “as Princeton would not be awfully jolly without your sif [syphilis] covered face.” He offered Billings $500 and added, “I won’t need it. You can pay me after you get out of college. You then would not have to borrow from that old Prick Uncle Ike [Lem’s uncle]. Let me know about this, and wether [sic] you need it, because I won’t be needing it.”22

The reunion of the three ex-Muckers was a happy one, and soon they were enjoying weekends in New York City, ninety minutes away by train. About his studies, however, Jack remained as lackadaisical as ever, if not more so. He barely cracked open his books. Princeton as an institution disappointed him—it seemed dismayingly similar to Choate in his mind, a kind of overgrown boarding school more than a university, palpably insular and oppressively Protestant. “I think he was a little disenchanted with the country-club atmosphere of Princeton,” a friend recalled. Nor did it help that he soon fell ill again. He could drag himself to class, but barely, and the jaundice from London returned—his complexion, an observer noted, took on a yellowish-brown hue, “as though he’d been sunbathing.”23 Already on November 11, barely two weeks after Jack’s arrival, his father wrote him an affectionate letter, suggesting that they monitor his health until Thanksgiving and then make a determination about whether he could remain in school: “After all, the only consideration I have in the whole matter is your happiness, and I don’t want you to lose a year of your college life (which ordinarily brings great pleasure to a boy) by wrestling with a bad physical condition and a jam in your studies. A year is important, but it isn’t so important if it’s going to leave a mark for the rest of your life….You know I really think you are a pretty good guy and my only interest is in doing what is best for you.”24

III

Thanksgiving came and went and Jack did not improve. He was sent to Peter Bent Brigham Hospital, in Boston, for tests and observation. (TELL US WHAT TIME TO ARRIVE FOR THE FUNERAL, Billings and Horton cabled him on December 10.) The doctors there were mystified, however, which prompted the university physician to write to the dean: “You are probably familiar with the interesting case of John Fitzgerald Kennedy, [class of] ’39. We have been in touch with his doctors ever since he came here and it now appears advisable for him to withdraw from the university for the purpose of having such examinations and treatment as his condition may require in the hope that he will improve sufficiently to return as a Freshman next fall.”25

And thus ended Jack Kennedy’s tenure as a Princeton man, six weeks after it began. He would not return. The prospect of being laid up in Boston seemed dreadful, but he couldn’t quibble with his father’s argument that it was imperative “to arrive at a definite conclusion regardless of how much time it takes because we must settle this matter once and for all on this occasion.” The physicians got to work. “They are doing quite a number of things,” the young patient wrote his parents from his hospital bed, “but I am rather a difficult subject.”26 A flood of letters to Billings followed—witty, obscene, uninhibited, gossipy, unflappable, and suffused with a striking vitality that his mother had noticed in his language ever since he was a small child.

January 18, 1936: “My blood count this morning was 3500. When I came it was 6,000. At 1500 you die. They call me ‘2,000 to go Kennedy.’ ”27

January [undated]: “[It is] the most harrowing experience of my storm-tossed career. They came in this morning with a gigantic rubber tube. Old stuff, I said, and I rolled over thinking it would be stuffed up my arse. I didn’t know whether they thought my face was my ass or what but anyway they shoved it up my nose and down into my stomach. Then they poured alcohol down the tube, me meanwhile going crazy as I couldn’t taste the stuff and you know what a good stiff drink does to me.”28

January 27: “They haven’t told me anything, except that I have leukemia, and agranalecencytosis [presumably he meant agranulocytosis, a rare blood disorder]. Took a peak [sic] at my chart yesterday and could see that they were mentally measuring me for a coffin. Eat, drink, and make Olive [Cawley], as tomorrow or next week we attend my funeral.”29

January 27: “Flash! Got the hottest neck ever out of Hanson Saturday night. She is pretty good so am looking forward to bigger and better ones. Also got a good one last night from J. so am doing you proud. Gave up Bunny Day, I must admit, as a failure.” (In an earlier letter he had boasted that he would soon “climb” her “frame.”)30

Though playful in these missives, Jack could be cruel toward Lem in a way that betrayed his sense of entitlement. “I don’t know why you and Rip are so unpopular with girls,” he scoffed in one, signing off with one of his nicknames: “You’re certainly not ugly looking exactly. I guess they’re [sic] is just something about you that makes girls dislike you on sight. I was figuring it out this morning….It certainly is too bad. I guess you are just not cut out to be a ladies man. Mr. Niehans even has a girl, and so has Ike England. Frankly, my son, I’m stumped. Well send me my belt you prick right away, Regards, Ken.”31

Yet there was a tenderness in the letters, too, a vulnerability that Jack hated to reveal but that Billings undoubtedly picked up on, however couched it was in Kennedy’s devil-may-care personal style. Still smitten with Olive Cawley, who had been named the first Peanut Festival Queen in Montclair, New Jersey, and was about to embark on a modeling career in New York, he asked Lem for help: “Am coming to you for advice on the Cawley situation—should I ask her after this deliberate slight?” (Olive had not replied to his most recent letter.) “It’s your roomie who is asking and he’s also asking you to leave my writing paper alone. That writing paper was a present from one of my feminine admirers, a woman who worships the very air I breathe,” he said of Mrs. Billings, “but who unfortunately has a son with bad breath.” The barb no doubt stung the easily wounded Billings, but he always sensed his friend’s underlying devotion to him. Rip Horton saw this side of Jack, too. “[He] was very light, very witty, a particularly loyal good friend who cherished old friendships very, very much,” Rip subsequently said. Sometimes, Horton added, Jack went to greater lengths to maintain the relationships than the friends did.32

Lem offered his own assessment: “I think it’s interesting,” he told an interviewer, “because I, frankly, haven’t had another friend whom I’ve known as long as Jack Kennedy….There must have been something about him that kept people wanting him to be their friend through all the years. Much more interesting is why Jack wanted to keep all these friends, since his mind and interests did grow, let’s face it, at a much faster clip than any of his contemporaries.”33

When Billings forfeited his scholarship at Princeton due to poor grades, Jack was quick to offer his sermonizing take. “It’s too damn bad about losing your scholarship,” he lectured, “but here is my advice. You have been a damn fool—spending money you didn’t have, taking week-ends you shouldn’t have, and generally fooling around.” Jack did not deny that he was partly to blame, but he admonished his friend that only hard work could salvage the situation. “If you decide to go on a vacation you can come [to Palm Beach] as we have plenty of room. However, you have been a terrific ass, and unless you come around now, you haven’t a chance. If you do good work now, maybe you can get the scholarship back.”34

The exhortation worked; Lem put in the necessary effort to reclaim the scholarship.

Beyond the misdiagnosis of leukemia, the Boston doctors reached no conclusions, and in February 1936 Jack was dispatched to Palm Beach to convalesce. His father was there, still waiting to be tapped for a major job within the Roosevelt administration. He had concluded a successful tenure as head of the Securities and Exchange Commission and hoped now to get a bigger role—a cabinet position, certainly, and ideally Treasury secretary. Roosevelt’s shift to the left in 1935—he created the Works Progress Administration, a massive employment and infrastructure program, and signed into law the Social Security Act—did not concern Kennedy, or if it did he refrained from saying so. On the contrary, he paid Arthur Krock of The New York Times $5,000 to gather together scattered notes into a short book with a snappy title, I’m for Roosevelt, that offered a rich man’s fawning endorsement of the New Deal and a second FDR term and would be published under Kennedy’s name in time for the 1936 presidential election. Businessmen should be grateful to Roosevelt for saving capitalism, the book argued, and it credited the president for every economic advancement since 1933.35

To head off complaints that the book was a mere attempt at gaining a senior post in Washington, Kennedy included a humble and disingenuous disclaimer at the outset: “I have no political ambitions for myself or my children and I put down these few thoughts about our President, conscious only of my concern as a father for the future of his family and my anxiety as a citizen that the facts about the President’s philosophy be not lost in a fog of unworthy emotion.”36

Barely had Jack arrived in Florida when his father determined that he needed fresh air and physical labor to build up his strength. (Jack had other ideas: “The girls are few and far between,” he lamented to Billings early on, “but speaking of between, I expect I shall get laid shortly.”) On Krock’s recommendation, he arranged for his son to travel to the Jay Six Cattle Ranch, in Benson, Arizona, for several weeks of hard work in warm weather. It was a dramatic change for the East Coast urbanite, but the labor—making adobe bricks, rounding up cattle, fixing fences—seemed to have its desired effect.37 Jack’s health improved dramatically, and he soon found time for extracurricular adventures across the border in Nogales. “Got a fuck and suck in a Mexican hoar-house [sic] for 65¢, so am feeling fit and very clean,” he reported to Billings in a letter entitled “Travels in a Mexican Whore-house with Your Roomie.” He enthused, “What a thing of beauty my body has become with the open air, riding horses and Mexicans.”38

One detects more than a bit of artistic license in these carnal boasts as our protagonist works to project an image of macho health—vigorous, outdoorsy, athletic, virile—that stands in contrast with the more fragile reality. “I think he was making it up,” one college friend later said of the sexual bragging of this period in the mid-1930s. “That was the masculine ethic. And I think he made up three-quarters of it. And I don’t hold it against him.” Jack was telling his friends, telling himself, what kind of man he sought to be and could be. He projected an image of himself as a lothario well before he actually became one.39

Before returning to the East Coast, Jack headed for Hollywood, where he claimed he met and bedded a gorgeous movie extra. “The best looking thing that I have seen,” he bragged to Lem. “I will show you her picture when I get in.”40 There followed a summer in Hyannis Port filled with fun and frolic with the rest of the Kennedy clan—Joe Junior, 21, Rosemary, 17, Kathleen, 16, Eunice, 15, Pat, 12, Bobby, 10, Jean, 8, and Teddy, 4—and a stream of visitors, who as always looked with astonishment at the packed event schedule and manic family energy. Relatives came, too, including the three children of Rose’s sister Agnes and her husband, Joseph Gargan: Mary Jo, Joey, and Ann. (Agnes would die suddenly of an embolism in September, at age forty-three; in subsequent years, the Gargan kids would spend their summers on the Cape, effectively raising the size of Joe and Rose’s brood to an even dozen.) If Jack did not hold quite the esteem in his younger siblings’ eyes that the mature and responsible Joe Junior did, he had their affection for his witty individualism and for the attention he paid to them—not least Rosemary. As Eunice remembered, he quietly made sure his mentally challenged sister was not left out at parties: “Jack would take her to a dance at the club, and would dance with her and kid with her and would make sure a few of his close pals cut in, so she felt popular. He’d bring her home at midnight. Then he’d go back to the dance.”41

Much time was spent on the water that summer, in innumerable sailing competitions. Together Joe Junior and Jack raced from Edgartown, on Martha’s Vineyard, to Nantucket and back to Hyannis Port. At the end of August, Jack won a major solo race, the 1936 Atlantic Coast Championships, with a margin of victory—four minutes—that astonished other sailors. No doubt it helped that the ever competitive Joseph P. Kennedy employed a Scandinavian maintenance expert that summer to look after the family’s boats in order to make sure each was in tip-top racing shape.

Jack also found time to do something else: reapply to Harvard. He preferred it over the smaller, more cloistered Princeton, he had decided, and it was where his father always wanted him to go. Young Joe, too, urged him to join him in Cambridge. Now entering his third year, Joe had experienced disappointments at Harvard—he’d been passed over by the elite final clubs and had yet to find glory on the football field—but he liked his courses in government and had a coterie of friends who appreciated his endless energy and ebullience. Women were a preoccupation and, following his father’s example, he played the field with abandon, preferring showgirls over coeds. (The former were less likely to latch on, he said, less likely to make demands.) On one occasion he escorted to a Harvard dance the budding film star Katharine Hepburn, who accepted his invitation on the condition that her mother also join.42

Jack wrote from Hyannis Port on July 6:

Gentlemen, I am writing in regard to my entering Harvard this fall, in the class of 1940. I presented an application to enter Harvard…last year to enter with the class of 1939 which was accepted. My plans changed, and I decided to go abroad to the London School of Economics for a year….After my return from [Florida] I went out to Arizona returning a week ago. After seeing my physician who said he thought it would be perfectly all right for me to attend college next year, I decided to present my application to Harvard. If there is any other information desired, I should be glad to communicate with you or go to Boston to discuss the matter.43

To be on the safe side, Jack submitted a similar letter to Princeton. But within three days Harvard’s dean of freshmen replied with the good news: he was in.44 In his roundabout way, Jack had had what in today’s parlance would be referred to as a gap year between high school and college, and he arrived in Cambridge in August a year older than most freshmen and two years older than a few. He stood six feet tall and weighed 149 pounds, and felt as good as he had in years.

IV

The Harvard that Jack Kennedy entered in the fall of 1936 was still what it had been when his father matriculated three decades before, and when his great-grandfather Patrick Kennedy stepped ashore in nearby East Boston sixty years before that: the oldest, most richly endowed, and most prestigious university in the nation. Jack’s arrival coincided with the institution’s three hundredth anniversary and all the attendant celebrations. (On September 18, fifteen thousand alumni, including Franklin Roosevelt, joined delegates from five hundred universities around the world for a day of speeches and celebration in Harvard Yard.)45 But there was scant evidence of smug self-satisfaction that fall in the presidential office of James B. Conant. Since becoming Harvard’s leader three years before, Conant, a gaunt and bespectacled chemist whose descendants arrived in the Massachusetts Bay Colony in 1637 but whose father was a lowly photoengraver from Dorchester, had set about making the institution more meritocratic, more academics-focused. His predecessor, the aristocratic and conservative A. Lawrence Lowell, had taken office in 1909, soon after Joe Senior matriculated, and over the next quarter century had done much to enhance Harvard’s architectural glories as well as its already robust reputation for exclusion: he set quotas on Jewish admissions, kept the small number of black freshmen out of Harvard dorms, and refused Marie Curie an honorary doctorate on account of her sex. When a senior professor was revealed to be a homosexual, Lowell not only demanded his prompt resignation but urged him to use a gun to “destroy himself.”46

Conant was no strict egalitarian, but he recognized that Harvard needed to change, needed to prioritize scholarly over social distinction. Rival institutions in the Midwest and California were on the rise, and it was no longer unheard of (if still rare) for major professors to turn down chairs at Harvard. Standards of faculty promotion were too lax, Conant determined, and the college was filled with “mediocre men” who were not doing first-rate original research. He set about toughening hiring and tenure standards for faculty and redressing what he saw as the “exclusively eastern orientation” of the student body (some 90 percent of the students came from states along the Eastern Seaboard) by offering Harvard National Scholarships to notably talented applicants from the Midwest and Far West who might not otherwise be able to afford the annual tuition of $400 or the additional $700 for room and board. “Many boys without financial resources are potentially future leaders of the professions, of business, and of public affairs,” Conant declared. “The country needs their talents and character.” Much to the delight of Irish, Italian, and Jewish day students from middle- or lower-class backgrounds who commuted by subway from their homes in greater Boston, he set aside the ground floor of Dudley House so that these boys would have somewhere to eat their brown-bag lunches.47

The journalist Theodore H. White, class of 1938 and one of the commuters, thrilled at Conant’s reforms. “Excellence was his goal as he began shaking up both faculty and student body,” White would recall in his captivating memoir In Search of History, before quoting approvingly from the president’s address to the freshmen in August 1934: “ ‘If you call everyone to the right of you a Bourbon and everyone to the left of you a Communist, you’ll get nothing out of Harvard,’ he said to us. And he went on to explain that what we would get out of Harvard was what we could take from it ourselves; Harvard was open, so—go seek.”48

All the same, college life went on much as it had before. Students continued, as always, to subcategorize themselves—no less under Conant than under his predecessors—and the hierarchies of privilege remained firmly in place. Theodore White identified three categories: white men, gray men, and meatballs. The white men were the “white shoe” prep school grads of prominent name—White’s own class contained two Roosevelts, a Hearst, a Rockefeller, a Morgan, a Saltonstall, and, a tad apart, a certain Joseph Kennedy Jr.—many of whom adhered to the timeworn maxim of the Harvard gentleman: “Three C’s and a D, and keep out of the newspapers.” The gray men were the products of public schools, “sturdy sons of the middle class.” They played football and baseball and hockey, edited the Crimson and the Lampoon, and ran for student government. (Among the gray men in White’s year was Caspar Weinberger, later to be Ronald Reagan’s secretary of defense.) At the bottom of White’s classification was his own group, the meatballs—scholarship boys and day students, many of them Italian, Jewish, or Irish. “We were at Harvard not to enjoy the games, the girls, the burlesque shows of the Old Howard, the companionship, the elms, the turning leaves of fall, the grassy banks of the Charles,” White wrote. “We had come to get the Harvard badge, which says ‘Veritas,’ but really means a job somewhere in the future, in some bureaucracy, in some institution, in some school, laboratory, university, or law firm.”49 For these students, social life at Harvard was a closed book—they emerged from the subway station in Harvard Square in the morning, went to class, and were whisked away on the evening train.

Within the groups could be found further distinctions. In Anton Myrer’s novel The Last Convertible, set in the same period, the blandly lovable narrator, George Virdon, a solidly middle-class product of a public high school who is at Harvard only because of a scholarship, describes the particular snobbery of the “St. Grotlesex” men—that is, the graduates of St. Mark’s, St. Paul’s, Groton, and Middlesex—who “by and large kept to themselves, dined and hung out at their exclusive final clubs, took a very casual attitude toward classes and grades, and very nearly constituted a college within the college. A Groton man sat next to me in a course on the Hapsburg Empire and never said a single word to me. Not one. It wasn’t that he cut me, exactly—I don’t think he ever even saw me. Some, like me, can accept it with equanimity and go their way. For others…it eats away at the vitals like acid: they may suppress it, but they never get over it.”50

A few students defied categorization. For White, the outstanding example in his class was the brilliant Arthur M. Schlesinger Jr., whose father was on the faculty in history and who somehow mingled with the meatballs as easily as with the gray and white men. With his intellectual precocity and ravenous curiosity, Schlesinger asked only that people be interesting. “How could one not be friendly to dear Teddy White, himself the most loyal and sentimental of old friends?” Schlesinger wrote in his own memoirs of his friend’s description.51

Jack Kennedy likewise would skirt White’s taxonomy when he arrived at Harvard two years later. According to family wealth and academic pedigree, Kennedy should have been in the top group, but his private school, though prestigious, was not “St. Grotlesex.” (In Myrer’s formulation, the men from larger prep schools such as Andover, Milton, Exeter, and Choate were “better mixers” than those from St. Grotlesex, though they still tended to separate themselves from the groups below them.) More important, Kennedy was an Irish Catholic in what was still a bastion of WASP privilege. He, too, was a kind of outsider, and it generated in him a palpable detachment, an aloofness resulting from his uncertainty about where he really belonged. It also made him more accepting of other outsiders, of whatever stripe, made him inclined to take people for who they were. At Choate he had moved easily among boys from different backgrounds; his best friend, Lem Billings, was a middle-class scholarship student from Pittsburgh. At Harvard as well, Kennedy’s circle of acquaintances would be wide, even if made up mostly of gray men and white men. His best friend would be Torbert “Torby” Macdonald, himself a hybrid: a middle-class Irish Catholic from suburban Boston who had gone to Andover and who commuted from home his freshman year.

V

Undistinguished though Jack Kennedy’s freshman-year academic performance was, his father, himself an academic mediocrity during his Harvard days, was pleased with what he saw. “I am impressed with the almost complete turnaround you have made in yourself in the last year,” he wrote to his son in February 1937, brushing aside Rose’s concerns that the boy was spending too much time in nightclubs. “You know I always felt that you had great possibilities and I think you are now starting to avail yourself of them.” Kennedy encouraged his sons’ skirt chasing and gallivanting about town, and welcomed their determined pursuit of athletic success. Schoolwork had its place, too, he believed, but mostly as a means to an end—power and social status. Jack was taking full advantage of his extracurricular opportunities, as he should. Moreover, he was doing so at Harvard, where Joe Senior had always wanted him to be. “Got a letter from J.P. purring on my shoulder,” Jack wrote to Lem soon after. “He is really worshipping at my feet these days.”66

At the same time, Mr. and Mrs. Kennedy urged their older children to broaden their horizons, to learn about the world. Over Christmas break in Palm Beach, Joe Senior expressed fears that a European war was coming and urged his second son to tour the Continent while he still could. “You ought to plan on seeing Europe before the shooting starts,” he told him.67 Jack, who had intended to spend the summer of 1937 racing his sailboat off Cape Cod, quickly warmed to the idea. At Harvard he had developed a particular interest in European history (during his four years he would take courses from prominent historians such as Roger Bigelow Merriman and William L. Langer), and he wanted to see the Continent up close. He would take his car, he determined, and would bring along a friend. Inevitably, the friend turned out to be Lem Billings. Joe Kennedy arranged with Mrs. Billings that he would pay Lem’s fare, on the understanding that Lem would pay back at least a portion of the amount after his graduation from Princeton.

They set off from New York on June 30, 1937, aboard the SS Washington. Also making the trip was Jack’s Ford, a convertible with a fold-down top that he bought on installment (with help from his father) early in his freshman year. More important for posterity, Jack also packed a small leather-bound notebook given him by Kick and bearing the title “My Trip Abroad,” in which he jotted down notes as the mood struck him. His first entry was true to form: “Very smooth crossing. Looked pretty dull the first couple of days but investigation revealed some girls—chiefly Ann Reed. Had cock-tails with the Captain who knew Sir Thomas Lipton and thus grand-pa. The chief source of interest was General Hill and his rather mysterious daughter. He was a congressman, she might have been anything.”68

The two friends stayed up all night to be sure to catch a passing glimpse of Jack’s ancestral Ireland, but decided it had not been worth it, Lem remembered, as “it necessitated sleeping the entire next day.” Upon docking at Le Havre, they took off in the Ford, bound first for Mont-Saint-Michel and then for Rouen, where the cathedral impressed them mightily. From there they motored on to Beauvais, some fifty miles north of Paris, bunking for the night in a spartan little inn called La Cotelette. Thus was established a pattern they would follow for much of the trip: days spent seeing architectural treasures and historic landmarks, followed by nights in modest hotels—Lem’s budget would allow no more. “This is another side of Jack’s character,” a grateful Billings recalled. “He was perfectly happy to live at places for forty cents a night, and we ate frightful food…but he did it [because] that was the only way I could go with him.”69

Initially, Lem had the greater interest in the cathedrals and monuments, but Jack, too, was drawn in, albeit more by the historical dimensions than by the aesthetics. “Up at 12:00,” reads his diary entry for July 8. “Wrote letters had lunch got our money and the medicine for Billings ‘mal d’estomac’ after much trouble—Then to Soissons—saw the Chemin des Dames—one of the great scenes of fighting during the war. Also saw the cathedral that had been bombed—then to Rheims where we looked at the cathedral and to the Hotel Majesty (1.00 for room for 2)—My French improving a bit + Billings’ breath getting very French. Went to bed early—General feeling seems to be there will not be another war.”70

The next day, after arriving in Paris:

July 9—Rheims, Chateau-Thierry, and Paris. The general impression seems to be that Roosevelt—his type of government—would not succeed in a country like France, which seems to lack the ability of seeing a problem as a whole. They don’t like [Premier Léon] Blum as he takes away their money and gives it to someone else. That to a Frenchman is tres mauvais. The general impression also seems to be that there will not be a war in the near future and that France is much too well prepared for Germany. The permanence of the alliance of Germany and Italy is also questionable. From there [Rheims] we went to Chateau-Thierry picking up two French officers on the way. Arrived in Paris around eight. By mistake in French, invited one of the officers to dinner but succeeded in making him pay for it. Looked around and got a fairly cheap room for the night.71

The readiness of the French to exploit American tourists got under the boys’ skin, and they took to parking the car around the corner from a prospective hotel in order to keep the proprietor from getting ideas and squeezing a higher rate out of them. When the car lights needed fixing, Jack felt certain the repair shop had fleeced him. “Got another screwing—these French will rob at every turn,” he noted sourly.72 Still, he and Lem loved the City of Light, and stayed out late at Moulin Rouge and other nightspots. At Catholic Mass at Notre-Dame on July 13, the eve of Bastille Day, Jack secured a seat near the front (thanks to an assist from the U.S. embassy, where his father had contacts), in the same row as the French president, while the Episcopalian Billings sat in the far back. The next day they took in the Paris Exposition, where the modern aircraft on display transfixed Jack—this was the future of warfare, he intuited, the future of geopolitical power.73

All the while, Lem marveled at his ever inquisitive friend’s penchant for asking the locals for their views on Hitler and the German threat, on whether a war was coming and, if so, whether France could win. The responses varied, but a common theme was that the newly constructed Maginot Line (a string of concrete fortifications and weapon installations erected by the French government in the northeast in order to deter an invasion) would keep the country safe. Jack also picked up a copy of John Gunther’s book Inside Europe, which became his bedside reading as they pressed on southward, in the direction of the Spanish frontier.74

“Walls very high but beautiful inside,” Jack wrote after visiting Blois. “Saw Wall of the Conspirators where 1500 were hung and also the place where Charles XIII bumped his head and died. Finally thrown off the walls and continued to Chenonceau, built on the water, which is also very impressive….Drove through to Angouleme, thru Tours to Poitiers, both deserted towns, and spent the night for 10 francs each.” Here they found a less tourist-friendly atmosphere than they had expected, and experienced difficulty getting traveler’s checks cashed. “Very impressed by the little farms we have been driving thru,” Jack wrote. “America does not realize how fortunate they are. These people are satisfied with very little and they have very little as it is really a very conservative country, at least outside Paris.”75

VI

Even before leaving America’s shores, the two Ivy Leaguers had talked of visiting Spain, which was in the throes of a civil war between General Francisco Franco’s fascist rebels and a republican government in Madrid. It was a nonstarter, as they themselves knew—their passports were marked “Not good for travel in Spain.” Still, they made a vain attempt to cross the border just south of Saint-Jean-de-Luz; the police turned them back. They did get a glimpse of the border town of Irún, which had been bombed by the rebels, and in the ensuing days Jack took every chance to talk with refugees and take notes on what he heard. Their harrowing tales left their mark. In particular, he recoiled from a story of an imprisoned father, starving after being kept without food for a week, being brought a piece of meat and eating it, then being shown his son’s body with a piece of flesh cut out of it.76

The tales of barbarism offered by the refugees took on added credence for Jack and Lem when they attended a bullfight in Biarritz. “Very interesting but very cruel,” Jack wrote, “especially when the bull gored the horse. Believe all the atrocity stories now as these southerners, such as these French and the Spanish, are happiest at scenes of cruelty. They thought funniest sight was when horse ran out of the ring with his guts trailing.” Billings in his trip diary echoed the point, but later acknowledged that perhaps he and his friend couldn’t appreciate the finer aspects of the sport: “Of course, we didn’t understand this temperament at all, and were disgusted by it.”77

Then it was on to Italy, with stops in Toulouse, Carcassonne, Marseilles, Cannes, and Monte Carlo en route. Jack, reading Gunther, kept pondering the Spanish situation. “Not quite as positive about Franco victory,” he recorded from Toulouse. “Shows that you can easily be influenced by people around you if you know nothing, and how easy it is to believe what you want to believe.” But the ultimate outcome in Spain, he went on, depended in large part on what the outside powers, in particular Germany, Italy, and Russia, chose to do.78

Lem took notice of his friend’s ponderings and saw in them something new: while Jack on the trip was the same witty, fun-loving, and girl-crazy millionaire’s son he had always been, Billings told a later interviewer, he now showed a new seriousness of purpose and “more of an interest and more of a desire to think out the problems of the world and to record his ideas than he did two years before at Choate.” Harvard had had an effect, as had seeing the Old World up close. “What I’m trying to say,” Billings observed, “is that there was a noticeable change in Jack Kennedy in the summer of 1937.”79

The powers of observation were on display also in Mussolini’s Italy. Jack had no affinity for fascism, but he was struck by the lively atmosphere on the country’s streets and by the attractiveness of its people. “Fascism seems to treat them well,” he remarked after two days. In Milan, the two stayed in an inn owned by a Fascist veteran of the Abyssinian campaign, “which he said was easy to conquer but uncomfortable.” Pictures of Mussolini were everywhere, but Jack wondered, “How long can he last without money and is he liable to fight when he goes broke?” They took in Milan’s vast cathedral, and saw Da Vinci’s crumbling Last Supper at the Dominican monastery Santa Maria delle Grazie. Soon thereafter, Jack completed Inside Europe, observing that “Gunther seems to be more partial to Socialism and Communism and a bitter enemy of Fascism.” But the question remained: “What are the evils of Fascism as compared to Communism?”80

On August 5, the Americans and their convertible arrived in Rome. The first night, they snuck into the Colosseum, only to find a big crowd already there. “Very impressive by moonlight,” Jack noted, though he would soon decide that “the Italians are the noisiest race in existence. They have to be in on everything, even if it’s only Billings blowing his nose.” While in the Italian capital, the two boys attended a “fantastic” Mussolini rally, witnessing firsthand Il Duce’s strutting style, and visited the Vatican, where through Joe Kennedy’s connections they met senior Church leaders, including Cardinal Eugenio Pacelli, whom they had earlier heard preach at Notre-Dame, in Paris.81

Jack also talked his way into a meeting with Arnaldo Cortesi, the New York Times correspondent in the city, in order to learn more about European geopolitical developments. Cortesi told him war was unlikely, given that “if anyone had really wanted war there had been plenty of excuses for it….Said Europe was too well prepared for war now—in contrast to 1914.” Jack came away energized by the encounter and scribbled notes about the nature of fascism, the relationship to socialism, and the possibility of a major military clash. “Would Fascism be possible in a country with the economic distribution of wealth as in the US? Could there be any permanence in an alliance of Germany and Italy—or are their interests too much in conflict?”82

There followed the obligatory visits to Florence, which disappointed Jack (though he was awed by Michelangelo’s David), and Venice, where they met up with American friends, including Al Lerner, from Choate days, who was now also in Jack’s year at Harvard. Photos survive of the suntanned Jack and Lem with the pigeons in Piazza San Marco, and there’s also this cryptic entry in Jack’s diary for August 15, concerning a date he had with a girl on which his pal tagged along for a ride on a gondola: “Billings managed to make a gay threesome. Billings objects to this most unjust statement.”83

VII

Only one significant destination remained on the great summer odyssey of 1937: Hitler’s Germany. In hindsight, with our knowledge of the ghastly conflagration that was to come, it looms as the most important part of the trip, but even at the time, Jack Kennedy gave it pride of place on the itinerary. He understood, as perhaps did Lem, that Europe’s future as well as the world’s rested in large measure on the German leader’s ambitions. The previous March, Hitler had unabashedly flouted the Versailles Treaty by sending troops into the Rhineland, which had been designated a demilitarized zone. The Western powers stood by. In August 1936 he ordered compulsory two-year military service, and that November he intervened with German air power on the side of fellow fascist Franco in the Spanish Civil War. Again the Western governments did little. All the while, Hitler engaged in intimidation of his country’s neighbors, especially those with German-speaking populations along the borders of the Reich, and set his sights on bringing Austria, the land of his birth, into the German fold.

Departing Italy on August 16, the boys motored their way north, through the Brenner Pass and thence to Germany by way of Austria and a youth hostel in Innsbruck. Upon arrival in Munich, the cradle of National Socialism, where Hitler had gotten his start with his failed Beer Hall Putsch of 1923 and where the buildings were now festooned with Nazi flags and pictures of the Führer, Jack recorded his view that the German dictator “seems as popular here as Mussolini was in Italy, although propaganda seems to be his strongest weapon.”84

The vibe in Bavaria felt wrong from the start, ominously so, in the boys’ minds. Both experienced a sense of foreboding as the days passed. “We had a terrible feeling about Germany and all the ‘Heil Hitler’ stuff,” Lem remembered. He and Jack found the Germans arrogant beyond measure, eager to show these Americans how superior they were. “Got up late and none too spry,” Jack scribbled in his diary early on. “Had a talk with the proprietor who is quite the Hitler fan. There is no doubt about it that these dictators are more popular in the country than outside due to their effective propaganda.” To Jack, it seemed doubtful that the Nazi regime had any real answer for the country’s core problems: too few resources for too large a population, and too many rival powers working—singly and in coordination—to keep German ambitions in check.85

Jack’s skepticism stood in contrast with the assessment offered by his brother Joe three years before, in 1934, when he visited Germany during his LSE year and was swept up in the Nazi mania. Hitler’s murderous intentions were then less obvious to outsiders, and one could make allowances as well for Joe’s tender age (he had yet to turn nineteen), but his words are nonetheless jarring, especially given that he had already then decided on a political career. He wrote to his father:

Hitler came in [to power]. He saw the need of a common enemy. Someone of whom to make the goat. Someone, by whose riddance the Germans would feel they had cast out the cause of their predicament. It was excellent psychology, and it was too bad that it had to be done to the Jews. This dislike of the Jews, however, was well-founded. They were at the heads of all big business, in law, etc. It’s all to their credit for them to get so far, but their methods had been quite unscrupulous….As far as the brutality is concerned, it must have been necessary to use some, to secure the wholehearted support of the people, which was necessary to put through this present program.

“As you know,” Joe Junior continued, “[Hitler] has passed the sterilization law which I think is a great thing. I don’t know how the Church feels about it, but it will do away with many of the disgusting specimens of men which inhabit this earth.” Overall, he summarized, the Nazi program had created “a remarkable spirit which can do tremendous good or harm, whose fate rests with one man alone.”^*2, 86

Having had their fill of Munich, Jack and Lem drove on to Nuremberg. The quality of the German roads awed them—especially the new autobahns, the world’s first interstate highways—and Jack insisted on picking up hitchhikers and quizzing them on the state of affairs and their views of the Nazi regime. In Nuremberg they learned that Hitler would be holding a rally in the city three days hence; they contemplated staying around for it (and later regretted not doing so) but once again found the haughtiness of the people hard to take. They hit the road again—“Started out as usual except this time we had the added attraction of being spitten on,” as Jack laconically put it in his diary, without further details—and made their way for England via Holland, Belgium, and finally the port of Calais.87

Time was now of the essence, as Jack wanted desperately to get to London to see Joe Junior and Kick before they returned to America. He made it in time, shopping with Kick rather than joining his brother on a visit with Harold Laski. He also met with his mother in Southampton, dutifully complimenting her on her latest Parisian fashion purchases and helping himself to what Lem in his diary referred to as a “mix of tomato juice & plenty of chocolate.”88 Back in London, he developed a bad case of hives, perhaps from the chocolates, prompting a frantic search by Billings for a doctor who would pinpoint the problem. One physician after another was stumped, until suddenly one morning the hives disappeared as fast as they had arrived. Soon after, the two young men embarked on the journey home to the United States, with a stop in Scotland on the way.

It’s tempting in hindsight to attach weighty importance to lengthy jaunts like the one Jack Kennedy and Lem Billings had in the summer of 1937. To do so isn’t always wise. The two were in most respects the same young men after the two-and-a-half-month trip that they had been before. Still, the adventure left an impression. In Jack’s case, his international sensibility, encouraged by his mother from the time he was a young boy, deepened, and one is struck as well by the increasingly sophisticated nature of his queries as the journey progressed, until by the end they were as serious-minded, if not yet as well developed, as those of professional journalists and diplomats. His determination to form independent judgments rather than simply echo his father’s assessments or give in to lazy isolationist clichés about “foreigners” grew stronger. Most portentously, one sees in the young Kennedy that summer an emerging capacity and willingness to view world affairs in contextual, dispassionate terms—a contrast with his father, who tended always to view the outside world mostly in terms of what it meant for himself and his family.89

As it happened, this tendency on the part of Joseph P. Kennedy to personalize all public policy issues would soon land him in a heap of trouble, and in time cause a further separation in the worldviews of father and son.

II

The wire came from Harvard, where the spring semester was now in full swing. Joe Junior, having failed in his final attempt to win a letter in football, was hard at work on a senior thesis on American organizations and the Spanish Civil War, and he looked forward to graduating in May. Jack was halfway through sophomore year. His Old World sojourn with Lem Billings the previous summer had matured him and deepened his interest in European politics and history, but that fall Jack, like many Harvard sophomores then and since, had attached primary importance to two nonacademic rituals of second year: the move into the college “house” where he would live for the next three years, and the attempt to gain admission into one of Harvard’s elite final clubs.

The house system was in fact quite new, the result of philanthropist Edward Harkness’s vision of creating at Harvard something akin to the residential colleges at Oxford and Cambridge. President A. Lawrence Lowell liked the idea and persuaded Harkness to part with $13 million to make it happen. Under the resulting plan, undergraduates spent their final three years at the university living not in traditional dormitories but in houses, seven of which were newly built neo-Georgian “river houses” overlooking Boston from the banks of the Charles, with masters, resident tutors, common rooms, libraries, and dining halls (which had table service and printed menus, and to which students wore jackets and neckties). Their names evoked Harvard’s history—Dunster, Eliot, Kirkland, and Leverett honored former presidents, while Adams, Lowell, and Winthrop recognized families long involved with the college.17

At Winthrop House, Jack roomed with Torby Macdonald, his good friend from freshman year. For their valet they hired, on a part-time basis, George Taylor, a cheerful, cigar-chomping African American whose calling card read “The Gentlemen’s Gentleman” and who also worked in the same capacity for Joe Junior. Taylor soon found himself picking up after Jack, who maintained his sloppy ways and left clothes strewn all over the floor. “One time he was changing his clothes to go out,” Macdonald remembered, “heaving his things into a heap in the middle of the floor. I told him to watch the way he was throwing things around our room because it was getting to look like a rummage sale. ‘Don’t get too sanctimonious,’ Jack countered. ‘Whose stuff do you think I’m throwing mine on top of?’ ”18

Torby soon figured out Jack’s system of dressing: he would simply put on whatever articles of clothing he spotted first upon getting up in the morning. More often than not it would be a baggy tweed jacket, wrinkled khakis, unmatched socks, and scuffed shoes. This disheveled manner of dress would remain a hallmark well into adulthood.19

Macdonald would in short order become, in historian Herbert Parmet’s words, “Harvard’s counterpart to Lem Billings”—or, more accurately, the number-two man behind Lem in Jack’s pantheon of friendships. Like Jack a second son who had to fight for recognition within his Irish Catholic family, Torby hailed from Malden, Massachusetts, where his parents were schoolteachers and his father also coached the high school football team. A stellar athlete who excelled in football, baseball, and hockey during his school days at Andover, Torby found success on the playing fields of Harvard as well. (He showed his talent early, posting fourth-quarter runs of sixty and twenty yards in the freshman game against Yale, and would find an honored place in the school’s football hall of fame.) What drew him and Jack together, however, was their shared sense of humor and their irreverence. They showed a proclivity for matching wits in a rapid-fire and wickedly humorous way that their Winthrop mates found irresistible. “Torby Macdonald was [Jack’s] foil,” one of these friends recalled, “because Torby was a very brilliant person, and Torby and he would have a dialogue with a laugh a second for four or five minutes at a time, and the rest of us would just sit there and enjoy it.”20

Most of all, Jack and Torby shared a similar outlook on life and a sense of trust. Born a mere eight days apart, they simply clicked. Friends could see it, as could family members—including Kick, with whom Torby promptly fell head over heels in love. Torby appreciated Jack’s unpretentiousness and his disinclination to flaunt his family name, while Jack valued Torby’s steadfastness and good cheer—and his status as an emerging Crimson football star. Yet any friendship with Jack Kennedy had limits, as Lem Billings had long since learned. When Macdonald, on one occasion, overheard Joe Junior lambasting his brother, he intervened on Jack’s side, only to learn that, among the Kennedys, family always came first: “Jack whirled on me and told me off in no uncertain terms for butting into a family affair. I never did it again.”21

Jack and Torby’s Catholicism greatly lengthened the odds that either of them would be chosen for a final club. Long the center of Harvard social life, final clubs had changed little since Joe Senior’s day—they were places where gentlemen took their meals, drank, and socialized. As before, clubmen were invited to the leading debutante parties on Beacon Hill and in Brookline; as before, they defined the social hierarchy of the college. Despite intense and continuous effort, Joe Senior had failed in his quest to get membership, as had Joe Junior, who had had to content himself with admission into the Hasty Pudding Institute, the university’s famed theatrical society (to which Jack was also accepted). Joe Senior and Joe Junior had both been stung by their failure, and it looked likely that Jack would suffer the same fate. Classmate Jimmy Rousmanière later said:

There are eight final clubs at Harvard. Each of them elects ten to fifteen in a class, so there’s only a hundred members accepted out of a class of a thousand….All of October of the sophomore year is sort of rushing season, and you get invited around every night for three weeks. They would invite perhaps a hundred people and finally find 15 that probably would like to join a particular club, and be acceptable—and I don’t think Jack Kennedy’s name ever got on that 15 list! The power of the Boston alumni was still so great—and they didn’t like Joe Kennedy or Honey Fitzgerald.22

But Jack had a couple of things going for him. To begin with, he had won kudos and a measure of renown for his chairmanship of the Freshman Smoker the previous spring. A rousing success, the event was still being talked about six months afterwards. In addition, Jack possessed a subtle social intelligence that his father and brother lacked, and he used his likability to excellent effect. Though no less determined than Joe Junior to win admission into a final club, he wore his ambition more lightly, and exuded more charm. He was also politically shrewder, and showed it by focusing his effort on the Spee Club, whose president, Ralph Pope, had expressed opposition to the anti-Catholic bias prevalent within Harvard institutions.23

Two years earlier, the Spee leaders had taken a pass on Joe Junior, whom they considered too pushy, and they now said no to Torby Macdonald, who, with his fondness for drink, seemed likely to solidify rather than weaken Irish Catholic stereotypes, and whose family was poor to boot. They might have rejected Jack as well had not two eminently viable friends, the blue-blooded Rousmanière and William C. Coleman Jr., the Episcopalian son of a Republican judge in Baltimore, made a pact that they would join only as a package with Jack. Pope took notice, and he liked what he saw in the younger Kennedy. “By the time you could say something,” Pope remembered, “he had a question or a remark about it, which went right to the heart. You never had to fool around or wonder, ‘What the hell does he mean?’ ” Pope signed off, “just for that reason—that we needed somebody with some sense in the place. We were a bunch of lightweights.” He said to the delighted trio, “O.K., if you guys want this three-man deal, we want it too. We’ll take you all.”24

Jack had achieved what was previously unachievable for a Kennedy: admission into the inner sanctum of establishment power, a Harvard final club.

III

The Spee’s handsome Georgian building, at 76 Mount Auburn Street, became Jack Kennedy’s second home for the remainder of his time at Harvard, his refuge, his place away from parental and professorial supervision and, when he so chose, from his roommate and his brother. He took many of his meals and did much of his socializing within the club’s ivy-covered walls and in short order was made assistant treasurer of the club and elected to its board of governors. From the club’s high-ceilinged, dark-paneled library, with its Hogarth prints, he wrote letters on the club’s stationery to family and friends and read for his courses. Intellectually, too, the Spee helped shape him, as mealtimes were an opportunity for wide-ranging discussion among self-confident young men able to discourse openly, freed from the masters and tutors of their Harvard houses. Contrary to Ralph Pope’s “lightweights” lament, the club was not without meritorious distinction, counting among its members Blair Clark, the head of The Harvard Crimson, the college newspaper, as well as Cleveland Amory, another Crimson editor. “The Spee had a damn good membership in those days,” recalled a member of the rival A.D. Club.25

Ironically, some contemporaries were of the view that the glory days of the final clubs were over. To them, the old Harvard of stark social stratification, clubmen, and “gentleman’s C’s” was fading away, on account of the new house plan as well as President Conant’s emphasis on scholarly rather than social distinction. Arthur Schlesinger Jr., two years ahead of Jack in the class of 1938, predicted in The Harvard Advocate, the undergraduate literary magazine, that the house plan, together with the influx of midwestern students and public school graduates, would transform the social dimensions of the university and effectively kill the final clubs, or at least banish them to the margins of Harvard life. “With a wave of Harkness’s hand,” Schlesinger wrote, “their chief excuse for existence—the pleasant living they provided—vanished,” for the houses provided facilities that were superior in all respects: comfort, convenience, and overall magnitude. “The clubs will probably persist,” he went on, “vain and exclusive little organisms, sustained by sons who join the clubs of their fathers, looking from within like the distillations of the best in Harvard life but from without like fragile soda water bubbles; yet the day is in sight when they will stop being very important even to the five per cent who now turn to them for refuge.”26

Decades later, Schlesinger would ruefully admit that his prediction had left out one key element: “the power of snobbery.”27 The university was becoming less homogeneous, more democratic, but the clubs remained in place and kept their standing atop the social order. Jack Kennedy was a proud clubman, certainly, thrilled with his new status and seemingly content with a gentleman’s C average in his coursework. He did pull off a B in sophomore year in Professor Bruce Hopper’s government class, New Factors in International Relations: Asia, but managed only a C in Modern Government, co-taught by William Y. Elliott and Arthur Holcombe, and in Introduction to Art History, with Wilhelm Koehler. He declared government as his concentration, and his main reading showed a tilt toward politics, history, and economics, with a list that included, among other books, Guy Stanton Ford’s Dictatorship in the Modern World, Gilbert Seldes’s Sawdust Caesar, Calvin Hoover’s Germany Enters the Third Reich, Herman Finer’s Mussolini’s Italy, Marx and Engels’s Communist Manifesto, Lenin’s State and Revolution, and Charles Beard’s The Economic Basis of Politics.28

In an English course on public speaking taught by Frederick Clifton Packard Jr., Jack earned a C. In a fascinating voice recording from that class uncovered by Harvard archivists in 2017, we hear the familiar voice and speech pattern, but with a more pronounced Boston accent, speaking in confident tones about Supreme Court justice Hugo Black and the recent revelation that Black had been a member of the Ku Klux Klan for almost two years in the 1920s. “Whether Mr. Black’s appointment to the Court was the correct one is hard to say,” the twenty-year-old declares early on. “It was evidently done in the heat of presidential anger at the conservative element who did not back Mr. Roosevelt’s court plan….He evidently had his reasons and he went forward as he saw them.”29

The grades don’t tell the full story, of course. They seldom do. Surely it reveals something about Jack Kennedy’s interests and aspirations that he chose for his topic in the class the Hugo Black controversy, whereas most of his classmates—at least those also captured on the recording—selected more mundane topics, such as sourdough bread, book collecting, and how to find a wife. Payson Wild, the acting master of Winthrop House and Jack’s instructor in Elements of International Law, remembered him as one who “really did have the ability to think deeply and in theoretical terms,” and to ponder big questions such as “Why do people obey?” In their one-on-one tutorials, Wild was impressed with the young man’s thoughtful and substantive analysis of the Aristotelian and Platonic political theories, and with how quickly he grasped the essentials of Hobbes, Locke, and Rousseau and the social contract theory of the state. Wild felt certain that Jack “had basically the deep interest, that there was in him a basis for all the pragmatic interests and concerns that he showed later on, which he had to show.”30

Wild also tutored Joe Junior, finding him less substantial intellectually than his brother. His mind was less creative. But Joe seemed already then to be the gregarious would-be politician: “He would call out under my window, ‘Hi, Dr. Wild. I’m coming.’ But Jack would never do that. He’d come up in a much quieter way.”31

Notwithstanding his growing interest in political matters, Jack steered mostly clear of the debates then roiling Harvard about the New Deal and Roosevelt’s activist government. Perhaps in part because the president was an unpopular man in the Yard—when he drove through Harvard Square during the 1936 campaign, FDR was booed lustily by students whose wealthy parents hated his liberal policies—Jack appears to have shunned altogether the Young Democrats and the Harvard Liberal Union, and there’s no evidence that he ever spoke out publicly in favor of Roosevelt’s reforms.32 The president, it seems, did not stir anything in him emotionally, either then or later. Still, Jack was proud of his father’s service in the administration, and he backed the comprehensive governmental effort to help the mass of Americans suffering extreme hardship in the Depression. He endorsed, one close friend recalled, “what the New Deal was trying to accomplish and that that was what government should do where it could.”33 This was Joe Senior’s view, too: unlike many Wall Street financiers, the elder Kennedy believed strongly in the state’s role in lifting up the downtrodden.

That autumn of 1937, the brothers were honored to host their father as the featured speaker in the Winthrop House Thursday evening lecture series. Late in arriving to the hall on account of sports practice, the two, according to head waitress Deedee de Pinto, hung back, not wanting to cause a stir. “Then the housemaster said, ‘Go on, boys, say hello to your father.’ They went up and both boys kissed him,” with no evident hesitation about showing such affection in public. John Kenneth Galbraith, then a Winthrop tutor, remembered “an absolutely wonderful talk, filled with anecdotes about [Kennedy’s] days in the unregulated stock market, telling what he personally knew of bucket shops, wire houses and pools,” and concluding with his role in “leading the raid as SEC policeman” that shored up the foundation of the capitalist system. Throughout, Galbraith was struck by the self-assurance, showmanship, and physical vitality that emanated from the lectern, and he concluded, “Kennedy was so ebullient and so successful in his presentation that even if his son had not become President, I would have remembered that night.”34

Jack’s health, meanwhile, continued to be better than it had been during his prep school years and his Princeton interlude but less good than it should have been. He went on suffering bouts of vague maladies. There were periodic trips to the infirmary and more than occasional missed classes. During fall football season, in which he suited up for the junior varsity team but saw little playing time, he suffered a debilitating back injury, though it did not prevent him from swimming that winter for Harvard against Penn, Columbia, Princeton, and Dartmouth.35 In February 1938, he paid a brief return visit to the Mayo Clinic, in Minnesota, to undergo tests relating to ongoing stomach and colon problems, and at the end of the month he found himself in the Harvard infirmary with a bad case of the flu. An intestinal infection followed in March that compelled a stay of several days in New England Baptist Hospital. His weight dropped through the spring, in spite of the ice cream machine his friends installed for him at the Spee Club.36

All the while, the astonishing Kennedy energy and vitality kept him going. Torby Macdonald marveled at the ceaseless activity, not least when it came to women. They gravitated toward Jack more than ever, drawn in by his winning smile and wry sense of humor, and by a lighthearted, peppery flirtatiousness that never seemed to cross the line into vulgarity or predatory encroachment. His relationship with Olive Cawley having sputtered to an end with his failed pursuit of her virginity, he now made up for lost time.37 Housemates would watch in wonderment as one or another Boston waitress came calling at Winthrop House. Or they’d see him zoom by on Memorial Drive or Garden Street in his Ford convertible, accompanied by a young woman from Radcliffe or Wellesley or Mount Holyoke or another of the women’s colleges in the area—seemingly a different girl each time.

His success with the opposite sex bemused him, at least in the early going. After all, he said to Billings, he wasn’t much better looking than other guys. The explanation, he went on, had to be in his personality. Billings, when asked by an interviewer long afterwards, saw a combination of factors: “Whenever he was home, there was always a girl around—usually it was a different girl each time. Almost, without exception, every girl he showed any interest in became very fond of him. I think the reason for this was that he was not only attractive but also he had tremendous interest in girls. They really liked him and he was very, very successful. This was important to him because he wanted to be successful in this area. He really enjoyed girls.”38 Like father, like son, in other words—and like older brother.

When Boston seemed too confining, Kennedy and Macdonald would drive to Smith or Vassar for double dates, taking turns behind the wheel. (Whenever Torby drove, Jack would snooze, astonishing his friend with his ability to fall asleep almost at will.) Or Jack would take a weekend jaunt to New York City, where he’d meet up with Lem Billings and Rip Horton and head to the fashionable Stork Club, on East Fifty-third Street. “In those days, that was the place to go,” Billings later said, “and the Stork Club was very anxious to attract young people. They particularly encouraged young models and pretty girls to come there, and they made things easier for the boys who brought pretty girls….There were presents for the girls and champagne. Of course we were very careful never to have more than one drink each while we were there—we couldn’t spend any more than that. Jack didn’t mind spending on the same basis as I did. Jack wasn’t much of a drinker, so it wasn’t any hardship to take one drink. He liked to dance very much.”39

“Jack certainly never made anyone conscious of his wealth,” Macdonald related. “In fact there were times when he had a disconcerting lack of consciousness about it himself. Once we double-dated a couple of girls and dined in a rather expensive Boston restaurant. When the bill came it amounted to something like $12. Jack dug into his pockets and came up with exactly nothing. I checked my wallet and found eight one-dollar bills. We had to borrow from the girls to get out of the place.”40

If not in his spending habits, Jack Kennedy’s sense of entitlement manifested itself in other ways. He was a notoriously reckless driver, with a fondness for putting the pedal to the floor and maneuvering quickly even in tight spaces. On one occasion in Allston, across the river from Cambridge, near the gray-arcaded horseshoe of Harvard Stadium, he got into a row with a woman after he backed into her car. Subsequently, he told Lem, the woman reported him to the police, “saying I had leered at her after bumping her four or five times, which story has some truth although I didn’t know I was leering.” Instead of taking the heat, Jack pretended he had loaned the car to Billings and urged him to agree. “Tell [the officer] you come from Florida if he asks for your license—also you’re sorry and you realize you should not have done it, etc….You write him a gracious letter and admit it,” he instructed. Lem, dutiful as always, went along.41

IV

Jack studied hard for his finals in the spring semester, hoping, he told friends, to finish with a flourish and make the dean’s list. He must have known it was a nonstarter—he simply had too much ground to make up in too many classes. He did find success outside the classroom, teaming up with brother Joe to carry Harvard to victory in the McMillan Cup sailing race, off Cape Cod, defeating nine other college teams in the process. Soon after that, the brothers joined their ambassador father, who had returned from London to attend Joe Junior’s graduation, on his voyage back to England. That summer, Joe Junior was to serve as secretary to his father while Jack would watch and learn and chip in as needed until the start of fall semester.42

The home visit had been a frustrating one for the ambassador. He had hoped to not only attend his firstborn’s graduation from Harvard but receive an honorary degree from the university. Friends had lobbied hard on his behalf but were turned down, on the grounds that an ambassadorship was an insufficient mark of distinction. The rejection stung all the more because two years prior, Kennedy had failed in his bid for a place on the Harvard Board of Overseers, running tenth among a dozen candidates. (Only the top five won a seat.) Associates tried in vain to console him by saying it was an honor merely to get on the ballot; he angrily insisted that only anti-Catholic bias could have caused the result. Now, with the refusal of an honorary degree, he felt doubly aggrieved, especially after The New York Times, quoting “authoritative sources,” indicated the bestowal would be forthcoming. To save face, Kennedy felt compelled to “refuse” what had not been offered to him and further announced he would miss Joe’s commencement in order to spend time in Hyannis Port with his ailing son Jack who, if he’d taken ill, certainly didn’t show it in the McMillan Cup. His petulance provoked mockery in the White House. “Can you imagine Joe Kennedy declining an honorary degree from Harvard?” Franklin Roosevelt chortled upon hearing the news.43

“It was a terrible blow to him,” Rose Kennedy later acknowledged. “After all those expectations had been built up, it was hard to accept that he wasn’t even in the running….Suddenly he felt as if he were once again standing in front of the Porcellian Club, knowing he’d never be admitted.”44

No wonder he looked forward to being back in Britain. There the press praised his every move, there the political leaders seemed more enamored of his performance than the Roosevelt administration at home was. From the start, Kennedy had won plaudits in London for his forthright and gregarious style and his close associations with Neville Chamberlain’s year-old Conservative government. Though Chamberlain held a low opinion of the United States and its president—he viewed FDR as an untrustworthy dilettante who was overly fearful of his own electorate—he and Kennedy (who had first met earlier in the decade) hit it off immediately, with the American giving full support to the prime minister’s efforts to head off a European war by whatever means necessary.45 Like Kennedy a self-made businessman who fancied himself a pragmatist, the prim, austere, silver-haired Chamberlain shared with the American a pessimistic worldview and a tendency to see the world in economic terms—Hitler, he believed, wanted primarily to have equal economic participation in Europe, and would cease his aggressive behavior once he had it. For both men, peace was a precondition for commerce and trade and thus for prosperity. For both, Communism represented a far greater danger than fascism. Kennedy soon became more than a mere ambassador: he became a trusted colleague to Chamberlain and Foreign Secretary Halifax, a man with whom they could confide freely and openly.46

An early letter to Arthur Krock bespoke Kennedy’s enthusiasm for the prime minister. “Chamberlain’s speech last Thursday was a masterpiece,” he enthused. “I sat spellbound in the diplomatic gallery and heard it all. It impressed me as a combination of high morals and politics such as I have never witnessed….All this means, as I size it up, that there will be no war if Chamberlain stays in power with strong public backing, which he seems to be acquiring by the day.”47

Kennedy also paid visits to Lord and Lady Astor at their palatial country estate at Cliveden, on the Thames in Buckinghamshire, which became known to critics as a favored meeting ground of Tory aristocrats determined to keep Britain out of war, through concessions to Germany if necessary. The “Cliveden Set,” left-wing journalist Claud Cockburn dubbed them, and though it would be too much to say that Kennedy was a dupe of the group—his basic outlook on world affairs had been formed long before his first visit to Cliveden—the discussions around the Astors’ dining table were intoxicating and gave him additional fodder for his claims. The American-born Lady Astor, originally from Virginia and now in her early sixties, radiated charm and glamour and fierce intelligence, as well as a pugnacious insistence on defending Hitler’s Germany against criticism and on the need for a strong Germany to act as a counterweight to Stalin’s Russia. The first woman to sit in the House of Commons, she was also known as one of the leading hostesses in all of Britain, with a knack for befriending the leading lights of the moment, such as T. E. Lawrence, George Bernard Shaw, and Mahatma Gandhi. She took to Ambassador Kennedy immediately, and he to her. They were kindred spirits, ebullient and forthright, whose conservative views, it may be said, came naturally to them; after all, they had a lot to conserve.48

“The march of events in Austria made my first days here more exciting than they might otherwise have been, but I am unable to see that the Central European developments affect our country or my job,” Kennedy wrote to Krock, summarizing his noninterventionist stance. Economics, he went on, were determinative: “The more I talk with people…the more convinced I am in my own mind that the economic situation in Europe, and that includes Great Britain, is the key to the whole situation. All of the playing house they are doing on the political fronts is not putting people back to work and is not getting at the root of the situation. An unemployed man with a hungry family is the same fellow whether the swastika or some other flag floats above his head.”49

In his first major speech as ambassador, weeks in preparation and delivered before the Pilgrims Society on March 18—mere days after the German annexation of Austria—Kennedy pleased his audience by pronouncing false the idea that the United States would never fight a war unless its home territory was directly threatened. His listeners were quiet, however, when he said “the great majority” of Americans, “appalled by the prospect of war,” were opposed to entering any kind of “entangling alliances.” And they were positively glum when he predicted that his country might well remain neutral in the event of a general war. Unbeknownst to the audience, Kennedy’s original wording, rejected by the State Department, had been still more provocative: the United States, that version read, had “no plan to seek or offer assistance in the event that war—and I mean, of course, a war of major scope—should break out in the world.”50

In retrospect, with our awareness of what lay in store, the words seem naive, shortsighted, stingy. It bears remembering, however, that at the time, in the late winter of 1938, Kennedy’s speech was fully in line with majority opinion in the United States. Most Americans embraced some form of “isolationism,” the key elements of which were an aversion to war and deep opposition to alliances with other nations. A 1937 Gallup poll found that nearly two-thirds of respondents thought American participation in the First World War had been a mistake. (Kennedy had held firmly to this view, it will be recalled, even at the time of U.S. entry in 1917; he never wavered from it.) Americans, this perspective held, had been tricked into intervening by clever British propaganda and by the machinations of U.S. arms merchants and bankers. Only a small minority of isolationists were actually sympathetic to fascism, and some were prepared to work with other nations to help China in its war against Japan. Some favored robust U.S. involvement in the Western Hemisphere to protect the nation against great-power threats. (In this sense the term was somewhat of a misnomer.) But all questioned whether the United States should be compelled to do what Europeans themselves appeared unwilling to do: block Nazi Germany. Isolationist sentiment tended to be strongest in the nation’s heartland and among those of Irish or German ancestry, but it was a nationwide phenomenon that cut across ethnic, socioeconomic, party, and sectional lines, and was given voice by Time magazine and by the Hearst newspapers.51

The Harvard diplomatic historian William L. Langer, with whom Jack took a course, marveled at the shift in popular attitudes since 1917, when so many people had bought Woodrow Wilson’s argument that the United States had a duty to make the world “safe for democracy.” Langer said, in a book he wrote with S. Everett Gleason, “Americans, having once believed, erroneously, that war would settle everything, were now disposed to endorse the reverse fallacy that war could settle nothing.”52 The British philosopher and historian of ideas Isaiah Berlin made the same point differently: the United States of the 1930s, he wrote, was where “a great social experiment [the New Deal] was conducted with an isolationist disregard of the outside world.”53

Popular culture reflected the national mood. Ernest Hemingway, for example, argued in Esquire in mid-decade, “They wrote in the old days that it is sweet and fitting to die for one’s country. But in modern war there is nothing sweet nor fitting in your dying. You will die like a dog for no good reason….Of the hell broth that is brewing in Europe we have no need to drink. Europe has always fought, the intervals of peace are only Armistices. We were fools to be sucked in once on a European war and we should never be sucked in again.”54 A similar theme was expounded in Dalton Trumbo’s Johnny Got His Gun and William March’s Company K, as well as in Lewis Milestone’s hugely popular film adaptation of Erich Maria Remarque’s novel All Quiet on the Western Front. The journalist and historian Walter Millis added seeming heft to the claim that involvement in World War I had been pointless with his 1935 bestseller Road to War: America, 1914–1917.55 Efforts to push back against this narrative, including by such luminaries as Walter Lippmann—Americans, he wrote, were being “duped by a falsification of history…miseducated by a swarm of innocent but ignorant historians, by reckless demagogues”—were only partly successful.56

Kennedy also found support for his views in the writings of the well-known historian Charles A. Beard, who in a series of books and articles pushed the argument that the United States should steer clear of any involvement in Europe’s looming crisis. A single lengthy sentence in The Open Door at Home, published in 1934, captured the essence:

By cultivating its own garden, by setting an example of national self-restraint (which is certainly easier than restraining fifty other nations in an international conference, or beating them in war), by making no commitments that cannot be readily enforced by arms, by adopting toward other nations a policy of fair and open commodity exchange, by refraining from giving them any moral advice on any subject, and by providing a military and naval machine as adequate as possible to the defense of this policy, the United States may realize maximum security, attain minimum dependence upon governments and conditions beyond its control, and develop its own resources to the utmost.57

Joe Kennedy would not have changed a word.

Franklin Roosevelt, consummate politician that he was, had no desire to get ahead of public opinion. By heritage and upbringing a thoroughgoing internationalist, Roosevelt as a young man had thrilled at cousin Theodore’s Cuban exploits and relished debating global issues with his Harvard classmates. As assistant secretary of the Navy from 1913 to 1920, and as James M. Cox’s running mate on the losing Democratic presidential ticket in 1920, he championed robust U.S. involvement in world affairs. Membership in the League of Nations, Roosevelt argued, sounding at times more Wilsonian than Wilson himself, was critical to the nation’s security and to world peace. It dismayed him that the Senate determined otherwise and rejected League membership. Gradually, however, during the second half of the 1920s, Roosevelt’s internationalism faded, at least in terms of public expression. His eyes now on the White House, he shifted his position to align with popular sentiment and, in the 1932 election, assured voters that he opposed American membership in the organization. In his reelection campaign four years later, he went further: “We shun political commitments which might entangle us in foreign wars….We seek to isolate ourselves completely from war.”58

It came as no surprise, then, that in mid-decade the president signed a series of neutrality acts by which Congress outlawed the kinds of contacts that had compromised American neutrality during World War I. The Neutrality Act of 1935 banned the export of weapons and ammunition to either side in a military conflict, and also empowered the president to warn American citizens against traveling on ships flying belligerent flags. The Neutrality Act of 1936 renewed these provisions and also outlawed loans to belligerents; such arrangements, lawmakers argued, could give the United States a large monetary interest in a conflict’s outcome. And in 1937, with global tensions ratcheting up and the Spanish Civil War raging, Congress passed a still more stringent Neutrality Act, this one introducing a cash-and-carry principle: warring nations wishing to trade with the United States would have to pay cash for their nonmilitary purchases and carry the goods from American ports on their own ships.59

By the end of 1937 FDR had begun to signal a tougher line. In a major speech in Chicago that October, he called for an “international quarantine” against the “epidemic of world lawlessness” and warned that U.S. national security was at stake. But he still moved gingerly. When the quarantine notion elicited condemnation in Congress and from some quarters of the press, he backed off. (Isolationist lawmakers had threatened him with impeachment.) Neither Roosevelt nor Secretary of State Cordell Hull, a courtly Tennessean and former congressman, objected to the thrust of Kennedy’s draft Pilgrims Society speech; they merely found its tone too rigid, especially at a time when U.S. journalists were clamoring for a firmer American response to “the German rape of Austria.”60

Nor did the White House at this point object to Kennedy’s supportive assessment of Chamberlain’s strategy vis-à-vis Germany. Here, too, hindsight can distort. Time would reveal the British prime minister’s shortcomings—his limited imagination, his tendency toward wishful thinking, his smug and hubristic self-confidence, his hunger for flattery and sensitivity to criticism, his distrust of public opinion, his stubborn belief that Hitler was amenable to individual persuasion and judicious concession. But it is well to remember that Chamberlain was no foreign policy naïf: he disliked Hitler and all that Nazi ideology represented, and he had been among the first, in 1934, to push for British rearmament, albeit in limited form. It should be borne in mind, moreover, that here, in the early months of 1938, the policy of appeasement—in essence, making concessions to Germany and to a lesser extent Italy in order to avert the outbreak of war—had broad support in British officialdom.

At the core of the policy was the belief, widely held among British analysts, including those on the left, that Germany had legitimate grievances with the harshly punitive Versailles Treaty of 1919. A modest redrawing of frontiers on the Continent was justifiable, these observers held, especially if this involved bringing adjacent German-speaking minorities within the Reich. (Even Winston Churchill, certainly no fan of Chamberlain’s approach, was willing to consider adjustments to the borders of Czechoslovakia, a view he was later happy to keep hidden.) In addition, the appeasement policy flowed from a conviction that Britain in 1937–38 had a weak hand, with commitments that massively exceeded its resources as it strove to protect far-flung interests in East Asia, Africa, the Mediterranean, and continental Europe, and with allies who were not dependable. A rearmament program was under way, but in piecemeal fashion (mostly in the development and production of fighter planes) as policymakers fretted that the soaring costs associated with it could not be sustained without wrecking a fragile national economy hit hard by the world economic crisis that followed the U.S. stock market crash in 1929. Civil defense efforts were also behind schedule, with a mere sixty fire pumps in place for the whole of London.

The public, meanwhile, recalling the horrors of the Somme and Passchendaele and influenced by a wave of anti-war memoirs and literature in the 1920s, shuddered at the thought of a return to the carnage and registered its opposition to military conscription and to policies likely to lead to war. The dominions also counseled peace. And if all that was not enough to condition Chamberlain’s approach, the Chiefs of Staff told him that Britain was in no condition to fight in 1938—the rearmament program needed more time. Alliance blocs could be pursued in the interval, certainly, but, given their role in the outbreak of war in 1914, did it really make sense to tie oneself to one of them?61

Roosevelt got all of this, and he saw value as well in Kennedy’s being able to use his close ties to Chamberlain to get valuable intelligence on British thinking at the highest levels. What got under FDR’s skin was something else: his ambassador’s tendency, evident from his first days in the post, to go it alone and do end runs around the State Department, to speak his mind too much and to write letters directly to prominent U.S. financiers, journalists, and select members of Congress. Discretion seemed a foreign concept to him, just as the skeptics had feared. As a diplomat, Kennedy was supposed to be the eyes and ears of his government, but he seemingly could not resist also being the mouth, peppering the letters with sharp views on policy. He marked them “Private and Confidential,” as if this guaranteed they would in all cases be read only by the recipient. Inevitably, word got around, leading to speculation that Kennedy was intent on using his position to advance his own career, specifically with an eye toward the 1940 Democratic presidential nomination.

“Will Joe Kennedy Run for President?” asked a May 21, 1938, article in Liberty magazine by the respected correspondent Ernest Lindley. Variations of the question were heard often in the press that spring. That Roosevelt had yet to announce his own plans for 1940 only added to the intrigue. Arthur Krock, who had drafted Kennedy’s pro-Roosevelt campaign book in 1936 and was widely known to be an unofficial publicist for the family (he may indeed have been on retainer to Kennedy, without acknowledgment to his readers or to his bosses at The New York Times), could hardly contain his enthusiasm in his column: “Here is Kennedy back again, the rage of London, the best copy in the British press, his counsel steadily sought by statesmen of the country to which he is accredited, his influence manifest and powerful in all matters in which the United States has an interest in Great Britain….Here he is back again, undazzled by such a taking up socially and officially as no American perhaps has known abroad since Franklin’s day.”62

Interior secretary Harold Ickes, whose dislike of the ambassador ran deep, speculated in his diary on the Kennedy-Krock effort: “I have been told that Krock is going to take some time off to devote himself to spreading the Kennedy-for-President gospel. There is probably no doubt that Kennedy is spending a great deal of money to further his Presidential ambitions. He has plenty of it and he is willing to spend it freely. Neither is there any doubt that he is making a good deal of headway in conservative quarters.”63

Roosevelt, annoyed by the burst of speculation and by the brazen opportunism it seemed to signify, rejected the option of recalling Kennedy—that would accomplish little except to give the nation’s most prominent Irish Catholic two years at home in the United States to cause mischief before the election. It could also alienate the Irish American electorate in key Northern states in the lead-up to the vote. Far better to keep Kennedy overseas but to clip his wings. Accordingly, Roosevelt allowed his press secretary, Steve Early, to leak copies of Kennedy’s “Private and Confidential” letters to the Chicago Tribune, which ran the story on June 23 under the headline “Kennedy’s 1940 Ambitions Open Roosevelt Rift.” The ambassador, furious at what he saw as presidential backstabbing, immediately denied any claims on high political office. When he complained to FDR about the leak, the president artfully pretended innocence.64

“In this way he assuaged my feelings and I left again for London,” Kennedy later wrote of the exchange, “but deep within me I knew that something had happened.”65

II

If Ambassador Kennedy had hoped to be able to ride out the European crisis in the Mediterranean idyll, it was not to be. By mid-August 1938 Adolf Hitler seemed poised to plunge the Continent into war by marching on Czechoslovakia. Whereas the Austrians (or at least the dominant Nazi Party) had acquiesced to the German takeover, the Czechs resisted. They had a security treaty with France and another with the Soviet Union, and they were determined to make a stand. Already the previous spring, Hitler and his generals had discussed plans for an attack; now he ordered the army to prepare for an October invasion. All the while, German propaganda trumpeted the complaints of Sudeten Germans and the urgent need to bring them into the fatherland. Under pressure from the State Department, Kennedy cut short his holiday and returned to London on August 29. Jack flew with him and thereby got a front-row seat as the Chamberlain government hemmed and hawed in fashioning a response.

All around him Jack could see signs of mounting British trepidation—and attempts at preparation. How things had changed, he thought, since the family’s departure for the French Riviera just a month before. Air-raid shelters had been hastily dug in Hyde Park, anti-aircraft guns were going into place along the Embankment, and there were sandbags ringing crucial London buildings to protect basement windows. Office windows above were crisscrossed with white tape. The first evacuees from British cities were gathered up and transported to the countryside. The Royal Air Force was put on full alert, and the Royal Navy mobilized. It seemed impressive on initial glance, but to Jack it amounted to a sad pretense of readiness. Sandbags and white tape—was that really what Britain had to offer?16

In a draft of a speech intended for an audience in Aberdeen, Scotland, Ambassador Kennedy asked whether his listeners could conceive of “any dispute or controversy existing in the world which is worth the life of your son, or of anyone else’s son? Perhaps I am not well informed of the terrifically vital force underlying all the unrest in the world, but for the life of me I cannot see anything involved which could remotely be considered worth shedding life for.” It was a perfect encapsulation of Kennedy’s political philosophy, and it brought a swift reply from Cordell Hull’s State Department: the section must be expunged. No American representative could issue such an open invitation to Nazi aggression. “The young man needs his wrists slapped rather hard,” a dismayed FDR muttered upon seeing the draft, an odd wording, since Kennedy was only six years his junior. The president privately parodied Joe by remarking, “I can’t for the life of me understand why anybody would want to go to war to save the Czechs.” But Roosevelt would do no more than grouse, and indeed hoped himself that some means could be found to preserve the peace.17

Neville Chamberlain desperately sought the same thing. His mistrust of Hitler had grown over the summer, but he stubbornly clung to the belief that the Führer had limited objectives and would be open to compromise. To believe otherwise was to believe that the German leader actually wanted war, and this seemed to the prime minister’s rational mind impossible, given especially the epic catastrophe that was the First World War. In this sense the prime minister was not merely “buying time,” as some historians have claimed, not merely putting off the day of reckoning until British capabilities had improved—he aimed to avoid war altogether. And certainly, he insisted, Czechoslovakia was not worth the price of a major military conflict. In a radio address to the British people, Chamberlain uttered words that tracked closely with Kennedy’s prohibited Aberdeen remarks: “How horrible, fantastic, incredible it is that we should be digging trenches and trying on gas-masks here because of a quarrel in a far away country between people of whom we know nothing.”18

The Paris government, under Prime Minister Édouard Daladier, a former history teacher from Provence who led the Radical Party (a centrist party despite its name), felt the same, even if it could not claim that Czechoslovakia was “far away.” In the French view, Czechoslovakia’s boundaries had been arbitrarily drawn up after World War I and lacked historical validity, and in any event France did not have the military capacity to defend the Czechs against German assault. When Soviet leader Joseph Stalin signaled that if the French and the British defended the Czechs he would help them, the response came quickly: Thanks, but no thanks.19

The solution, devised in London and enthusiastically backed by Joseph Kennedy—who was a fixture at 10 Downing Street and in the Foreign Office through much of September—was to appeal to Hitler’s civilized judgment by agreeing to the transfer of the Sudetenland to Germany, thereby depriving him of the motive for additional revision of the Versailles peace settlement. Or so the argument went. On September 15, three days after Hitler denounced the Czechs in a fiery, semi-hysterical speech at Nuremberg, Chamberlain met with the German leader at Berchtesgaden to talk terms. (Much to Hitler’s surprise, the Englishman had not insisted on a neutral site, or even a location on the Rhine, which would have cut the travel time in half.) He received a frosty reception but in effect affirmed his government’s unwillingness to oppose the breakup of Czechoslovakia. A second meeting, at Bad Godesberg on the twenty-second, yielded no agreement, whereupon Chamberlain returned to London and impressed upon the Cabinet his view that Hitler “would not deliberately deceive a man whom he respected with whom he had been in negotiation.” He also stressed the vital necessity of compelling the Czechs to submit, lest German bombers fill the skies over Britain, raining down their death and destruction.20

Kennedy encouraged the prime minister in this notion, his view influenced by a supposed expert he had befriended, the famed aviator and avowed isolationist Charles Lindbergh. More than a decade had passed since Lucky Lindy’s epic solo transatlantic flight, but he retained a hero status among many Americans—in name recognition, he ranked second only to Roosevelt. Germans, too, admired him deeply, and beginning in 1936 Lindbergh paid several visits to Germany to inspect the fledgling Luftwaffe up close, touring factories and military bases, including some that had never been seen by an American. His hosts carefully screened where he could go and what he could see, and he came away awed, both by the military buildup and by what he saw as the vitality and orderliness of the country. Subsequently, Hermann Göring, the Luftwaffe’s commander in chief, decorated Lindbergh with the Service Cross of the German Eagle, “by the order of the Führer.” When Lindbergh met Kennedy at the Astors’ home in May 1938, the two immediately hit it off, the normally reclusive flier finding in Kennedy someone witty and straightforward who shared his general take on things.21

Now he was back in London at Kennedy’s urgent request, landing on September 20. The next day at the U.S. embassy, he delivered a relentlessly alarmist oral report on the state of British and French air power vis-à-vis Germany’s. Kennedy asked him to commit his assessment to paper, which Lindbergh duly did the following day, a copy going also to 10 Downing Street at Kennedy’s directive. The Luftwaffe’s strength now exceeded that of the other European powers combined, the memo read; if unleashed over Britain, it could inflict sixty thousand casualties in a single day. French and British leaders must therefore resist war and “permit Germany’s eastward expansion,” lest they, too, be attacked: “For the first time in history, a nation has the power either to save or to ruin the great cities of Europe. Germany has such a preponderance of war planes that she can bomb any city in Europe with comparatively little resistance. England and France are too weak in the air to protect themselves.”22

In his diary entry for that day, Lindbergh summarized what he had told Kennedy. “The English are in no shape for war. They do not realize what they are confronted with. They have always before had a fleet between themselves and their enemy, and they can’t realize the change aviation has made. I am afraid this is the beginning of the end of England as a great power. She may be a ‘hornet’s nest’ but she is no longer a ‘lion’s den.’ ” Another entry continued the theme: “I cannot see the future for this country….Aviation has largely destroyed the security of the channel, and [Britain’s] superiority of manufacture is a thing of the past.”23

Lindbergh’s analysis, we now know, was grievously off. The Luftwaffe in late 1938 was far less formidable than he claimed, its capacity limited to supporting German ground forces in continental European operations. It had not yet developed a fleet of long-range four-engine bombers capable of doing real damage to more distant targets such as London. In late 1937, subordinates had informed Göring that no German bombers could “operate meaningfully” over England; at most, they could have a “nuisance effect.” The situation was little different ten months later.24

How much Lindbergh’s misapprehension influenced Chamberlain’s approach is hard to say. At most, it seems, it reinforced a strong inclination the prime minister already had.25 Yet so swiftly were events moving that it seemed war might result after all. On Friday, September 23, the Czech government ordered general mobilization; Hitler mocked the action and again demanded the handover of Sudeten territory. Hostilities seemed imminent as all over London people were being fitted for gas masks. (On Sunday the twenty-fifth, Joe Kennedy heard a van cruising slowly through Grosvenor Square with a loudspeaker, urging people not to delay in getting their masks.) If the Führer launched an invasion and France declared war in response, His Majesty’s Government would have to follow suit. British officialdom threatened to fracture, with Alfred Duff Cooper, First Lord of the Admiralty, and Conservative MP Winston Churchill urging a stiffening of the policy. As described by Joe Kennedy in a phone conversation with Cordell Hull, the split was between those in the Cabinet who advocated “peace at any price” and those who did not “want to take any more back talk from Hitler,” as they “would have to fight anyhow.”26

Chamberlain, firmly in the first group, on the twenty-ninth flew for a third meeting with Hitler, this one in Munich and with France’s Daladier and Italy’s Mussolini also present. In the early hours of the following day came the news: an agreement had been reached whereby Hitler would get the Sudetenland in exchange for a promise to stop there and respect the sovereignty of the remainder of Czechoslovakia. Chamberlain returned home to a hero’s welcome, announcing that he had achieved “peace for our time.” Because of the prime minister, editorial writers gushed, peace had been preserved, and thousands of young men would live. The Spectator nominated him for the Nobel Peace Prize. In Paris, Daladier was likewise greeted by cheering crowds. The Czechs had not been consulted.27

Only later would another effect become known: Hitler’s foes within his own military, believing him to be a deranged warmonger dragging the nation into a conflagration for which it was not prepared, had planned to move against him if Paris and London stood firm and the Führer launched an invasion of Czechoslovakia. Now they were rendered immobile by another easy and bloodless victory. The plot might well have come to nothing anyway, but a chance was lost. Not for five years would Hitler face another serious internal challenge to his rule.28

III

Jack Kennedy missed the denouement of the Czech crisis, having returned in early September for his junior year at Harvard.^* But he followed events closely from afar, devouring press accounts and radio reports whenever he could. (When Hitler delivered his Nuremberg address on September 12—the first one that Americans could follow live—Jack tuned in from the family home in Hyannis Port.) Though he didn’t yet know it, he would devote his senior thesis to these very developments, with particular focus on British decision-making in the years leading up to the Munich agreement.

Harvard friends indeed noticed a more serious-minded and diligent Jack Kennedy that autumn as he upped his game in the classroom, despite a heavy course load (he took six classes), and raised his average to a B. In Government 9a, with A. Chester Hanford, Jack impressed with his active and discerning participation in class and his capacity for independent thought, though Hanford found it curious that the grandson of Honey Fitz Fitzgerald showed so little interest in state and local politics as compared with national affairs and foreign relations.

Arthur Holcombe, an erudite senior member of the faculty who had been around long enough to teach both Joe Senior and Joe Junior and now had Jack as well, came away impressed by the young man. “He stood out among the group he lived with,” Holcombe later said. All of them saw a college education as “much more than studying things. They were interested in life. But Jack was more interested in ideas than most men who have the means of doing whatever they wish when they’re in college. He had a genuine interest in ideas, there’s no question about that.” In Holcombe’s Government 7 class, which focused on Congress, each student had to produce a research paper on an individual member of the House of Representatives, studying that lawmaker’s methods and assessing accomplishments and failures as objectively as possible. Holcombe assigned Jack the upstate New York Republican Bertrand Snell, known chiefly for representing the electric power interests in his district. The result, Holcombe found, was a “masterpiece,” based on “a very superior job of investigating,” though admittedly the young man had certain advantages: during Christmas vacation, “he goes down to Washington, meets some of his father’s friends, gets a further line on his congressman and on Congress.”29

Jack’s rooming arrangement at Winthrop House, meanwhile, had changed: he and Torby moved into a larger quad unit together with two football players, Charlie Houghton and Benjamin Smith (who would later fill Jack’s seat in the U.S. Senate when he was elected president), who were dismayed by Jack’s astonishing untidiness but otherwise found him to be a congenial and engaging roommate. “Jack was a very stimulating person to live with,” Houghton recalled. “Very argumentative in a nice way. He questioned everything. I think the depth of his curiosity was shown in that he’d challenge anything you said. He had the best sense of humor of all the Kennedys.”30

Donald Thurber, a fellow government major, likewise saw in Kennedy someone who was not content with the pat answer, who was willing to challenge assumptions and to ask, “What makes you think so?” “You got the impression that here was a mind that was learning from other people, and that longed to learn from other people—he would regard them as sources of information and knowledge to fill out his own.” Nor could Kennedy be considered a mere lothario intent on having a good time, Thurber continued. “I knew plenty of playboys. I could spot a playboy on the other side of the room. Jack didn’t fit into that mold at all—he was someone who played hard when he played, but his motivation was a serious one—you got the idea that he’d already decided life was a pretty serious proposition, even though it wouldn’t have to be, with lots of money and so on. But it was going to be a serious proposition.”31

To be sure, the desire for extracurricular fun had not dissipated. Kennedy wrote to Billings that fall about parties and sexual conquests, and about Harvard’s superiority over Princeton in football. “Dear Billings: Yours of the 19th received and horseshit noted. Numerous Harvard varsity men have been quoted as saying, ‘Four tough games in a row—Thank God we’re playing Princeton.’ ” He instructed Billings to get a date for the Harvard-Yale game on November 19, “as we’re going to have a party in Bronxville.” With the rest of the Kennedys overseas, the three family homes could be—and not infrequently were—perfect settings for myriad undergrad debaucheries.32

In personal appearance he remained as casual as ever, often showing up to class with wrinkled pants and mismatched socks, his tie askew. And he gave few outward signs of personal wealth, despite the fact that he had become, on his twenty-first birthday the previous spring, a millionaire, gaining access to a trust fund established for him by his father a decade before. (He also received on his birthday two $1,000 checks from his father, for meeting a challenge to refrain from picking up smoking or drinking; even afterwards, indeed to the end of his life, Jack seldom touched tobacco or alcohol, apart from the occasional cigar or daiquiri.) Jack showed limited interest in luxury goods, or in material possessions generally; with respect to those belongings he did have he was, like many children of privilege, nonchalant, losing golf clubs and tennis rackets and suitcases with abandon, much to his mother’s annoyance.33

He also fell in love, in a way he never had before. Her name was Frances Ann Cannon, a ravishingly beautiful North Carolina textile heiress and former Sarah Lawrence student who turned the heads of all the men in Winthrop House. Charlie Houghton took her out first and then Kennedy moved in, entranced by her looks, her sense of humor, her southern drawl, and her inquisitive mind and interest in politics. Soon her name started popping up in Kennedy’s letters to Billings, and friends wondered if she might be the one, especially after he followed her to Mardi Gras in New Orleans. There, at the Comus Ball, Cannon’s friend Jane Suydam (née Gaither Eustis) laid eyes on Jack for the first time. “He was standing there in the call-out section, very tanned, wearing white tie and tails,” she remembered. “He was unbelievably handsome. He had this remarkable animal pull. The impact on me was overwhelming.” Jack’s friends had somewhat the same reaction upon meeting Frances Ann. Rip Horton, for one, thought her the most beautiful girl Jack had ever dated and recalled thinking after one double date, “My God, why doesn’t Jack marry this girl?”34

Later Kennedy would contemplate that very thought, even though he surely knew the chances of a union were slim—his Catholicism was unacceptable to Ann’s family, as was her Protestantism to his. For the moment, though, his priorities were directed elsewhere—namely, to getting himself back to Europe as soon as possible. His family was there, and so was the geopolitical action, notwithstanding the lull following the Munich agreement. The summer of motoring around the Continent with Lem had fired Jack’s imagination, had made him hungry for more, so he asked his Harvard dean for permission to take a semester’s leave in the spring of 1939 in order to spend it in Europe. He pledged to take along a stack of books on political philosophy and to do groundwork—in consultation with his Winthrop House tutor, Bruce Hopper—on a senior thesis dealing with some aspect of diplomatic history and international law. The dean, impressed by Jack’s apparent seriousness of purpose, approved the request.

V

Then came Kristallnacht. In the late hours of November 9–10, following the fatal shooting of a German embassy official in Paris by a German Jewish refugee distraught over the deportation of his parents, a state-sanctioned pogrom was launched all over Germany—synagogues were set ablaze, apartments were wrecked and furniture demolished, Jewish men, women, and children were beaten, and some eight thousand Jewish shops and businesses were destroyed by rampaging Nazi hordes. The shattered glass of the shop windows gave a name to the horror: Crystal Night, or Night of Broken Glass. Nearly a hundred Jews were killed, by official figures (the true count was almost certainly higher), and thirty thousand Jewish men were arrested and sent to concentration camps, where they were viciously maltreated and let go only after promising to leave Germany. Hitler had approved the unleashing of the mobs at the urging of his propaganda minister, Joseph Goebbels, the hope being that it would speed up Jewish emigration. The German government then confiscated the insurance money due to the Jews for the property damage and imposed on them a gargantuan one-billion-mark fine for, as Hermann Göring put it, “their abominable crimes, etc.”44

Appeasers who previously had been able to avert their eyes from instances of anti-Jewish violence in Germany—there had been waves in 1933 and 1935, and another one after the takeover of Austria, earlier in 1938—now found that much harder to do. The savagery of the Nazi regime had been laid bare. Ambassador Kennedy, for one, was appalled by the images in the press, though seemingly as much because of the diplomatic implications as out of concern for the victims. “This last drive on the Jews in Germany has really made the most ardent hopers for peace very sick at heart,” he wrote to Charles Lindbergh on November 12. “It is more and more difficult for those seeking peaceful solutions to advocate any plan when the papers are filled with such horror. So much is lost when so much could be gained.”45

Joseph Kennedy’s attitude toward Jews is not easy to decipher, even at eight decades’ remove. He was not a hardcore anti-Semite in the way of, say, Henry Ford or the “radio priest” Father Charles Coughlin, attributing all evils to Jews and believing them genetically predisposed to being sinister and morally defective. Beginning in Hollywood in the 1920s and continuing through his career, Joe worked closely and effectively with Jews, often saying to them, “I’m an Irish Catholic; I know what it’s like to be discriminated against.” He admired and tried to emulate financier Bernard Baruch, interacting with him affectionately through the 1930s, and he tried repeatedly to convince Harvard to confer an honorary degree on Justice Louis Brandeis. In the early and mid-1930s he was on friendly terms with Felix Frankfurter and Henry Morgenthau. But Kennedy bought into anti-Semitic prejudices that were common (though by no means universal) among Americans of his station, and that were rife, for example, among the career officers in FDR’s State Department. It was a casual anti-Semitism, marked by indifference and lack of imagination, and it had deeply pernicious effects. Kennedy took for granted the social exclusion of Jews in elite America, in his America. At Harvard in the 1920s, President A. Lawrence Lowell had sought to maintain quotas on Jewish admissions. (Yale and Princeton were even more restrictive.) In Bronxville, the Kennedys resided in a community proud of its exclusion of Jewish residents. In tony Palm Beach, Jews were kept out of the most prestigious clubs, a situation that pertained also in Boston. On top of all that, Joe Kennedy had come of age in an Irish Roman Catholic milieu that distrusted Jews theologically, socially, and culturally.46

As his troubles deepened in late 1938, Kennedy grew more bitter, holding Jewish writers, columnists, and reporters responsible for the harsh press response to his Trafalgar Day speech—never mind that his non-Jewish press critics were far more numerous—and telling friends that the Jews of America were trying to manipulate the nation into war with Germany, a war likely to ensnare his sons. Roosevelt, he believed, was too much under the influence of Jewish advisers. In meetings with his German counterpart in London, Herbert Von Dirksen, Kennedy expressed admiration for Germany’s impressive growth under the Nazis and for the living standards now enjoyed by the German people. In one dispatch, dated June 13, Dirksen told superiors in Berlin that Kennedy “understood our Jewish policy completely; he was from Boston and there, in one golf club, and in other clubs, no Jews had been admitted for the past 50 years.” When Harvey Klemmer returned from a visit to Germany, he told Kennedy of the alarming actions he had witnessed, including Nazi storm troopers molesting Jews in the streets and painting swastikas on windows. In Klemmer’s recollection, Kennedy looked at him and replied, “Well, they brought it on themselves.”47

Yet there is little reason to doubt Kennedy’s later claim that the Kristallnacht violence genuinely pained him. In the days thereafter, he urged the Chamberlain government to embrace a large-scale Jewish rescue by facilitating the emigration of German Jews to territories in Africa and the Western Hemisphere, under the joint administration of the United States and Britain. The scheme, which never moved beyond the conceptual stage, would require an enormous number of transport ships as well as massive financial resources, but Kennedy insisted it could be done. The press took notice, perhaps with an assist from the ambassador’s publicity team. “What Mr. Kennedy has managed to do,” The New York Times reported, “is the talk of diplomatic circles in London at the moment.” But the moment did not last. The State Department, which had not been consulted and which was rife with anti-Semitic sentiments, took scant notice; American Jewish leaders kept their attention focused mostly on Palestine; and the White House, suspecting that Kennedy merely sought a means to reclaim the political momentum following his Trafalgar Day debacle, didn’t bother to respond.48

How Rose felt about Joe’s ambassadorial troubles, or about the deepening European and world tensions, is a mystery. Though she had a deep and abiding interest in history—and knew more of it than her husband did—her letters from this period are for the most part silent on politics. In the years to come, she would pen innumerable “round-robin” letters to her scattered children, some of them running multiple single-space typewritten pages in length. Lucid and well organized, they offered perceptive and sometimes witty observations about the goings-on within the Kennedy clan, but nary a word about the pressing affairs of the day. Her letters to Joe would be the same: several paragraphs detailing what the children were up to, then a throwaway sentence at the end noting that a speech he’d given had been well received in the press.

In her diary, she sometimes went further, though not by much. On September 15, with Chamberlain en route to the first meeting with Hitler, she recorded: “everyone ready to weep for joy and everyone confident the issues will be resolved.” She added her pride that “Joe has been on hand constantly and has aided [Chamberlain] by his presence. Feel that he has given great moral support.”49

Ever more marginalized within the administration, Joe drew sustenance from his family. Joe Junior, back in London after a tour of European cities—Prague, Warsaw, Leningrad, Stockholm, and Berlin—offered his father full support and expressed enthusiasm for what he had seen in Germany. “They are really a marvelous people,” Young Joe wrote to a friend, “and it is going to be an awful tough thing to keep them from getting what they want. Dad, as you know, got quite a lot of unfavorable comment in the U.S. press for his speech in trying to get along with the dictatorship. Makes me sore that all the rest of the people are trying to get everyone against the dictatorships. If we are not ready to fight them, we might as well get along with them.” Joe lauded his father for trying to find a means for Jews to get out of Germany, while privately agreeing with his claim that American Jews were trying to undermine U.S. neutrality.50

In a journal entry on November 21, Joe Junior wrote, “I don’t think [Dad] is too crazy about the job at this point and the other day spoke about quitting. He is afraid that they are trying to knock him off at home, and may make a monkey out of him in some diplomatic undertaking.” Another entry, from early December, continued the theme: “Dad is rather tired of his work. He claims that he would give it up in a minute if it wasn’t for the benefits that Jack and I are getting out of it and the things Eunice will get when she comes out next spring. He doesn’t like the idea of taking orders and working for hours trying to keep things out of his speeches which an ambassador shouldn’t say. He also doesn’t like the idea of sitting back and letting the Jewish columnists in America kick his head off. The papers have made up a pile of lies about him, and he can’t do anything about it but claims that he is going to let a few blasts when he gets back there in a few days.”51

The letter and diary entries are three examples of many that show Young Joe, twenty-three years old and a college graduate, remained in lockstep with his father’s worldview, unwilling or unable even to consider separating himself from the older man’s positions, however controversial. One looks in vain in Joe Junior’s writings from the period for any sign of independence, any indication that the ambassador had overstepped, had misread the geopolitical situation. It’s all one way: Dad knows best.

Jack, meanwhile, tried to direct his parents’ attention in a more positive way: the Broadway premiere of Cole Porter’s musical Leave It to Me!, starring Sophie Tucker and featuring several references to the Kennedys. (Upon learning that her husband has been named ambassador to the Soviet Union, Mrs. Leora Goodhue, played by Tucker, exclaims, “If only those sneaky Kennedys hadn’t grabbed London first!”) Jack attended on opening night and could hardly fail to hear the warning amid the levity: Ambassador Goodhue is recalled to Washington when he gives a speech calling for nations to get along. Still, Jack gave the performance a thumbs-up: “It’s pretty funny and jokes about us get by far the biggest laughs whatever that signifies,” he wrote to his parents.52 To his father he offered a half-hearted and convoluted endorsement of the Trafalgar Day address: “While it seemed to be unpopular with the Jews, etc., [it] was considered to be very good by everyone who wasn’t bitterly anti-fascist, although it is true that everyone is deadly set against collective security and don’t seem to have a very accurate conception of England’s position, due to the type of articles that have been written.”53

As it happened, father and son would spend the Christmas holidays together, in Palm Beach, while the rest of the Kennedys stayed behind in Europe, skiing in St. Moritz. In Florida the ambassador sat naked by the pool, lathered in cocoa butter, and took calls from associates around the country. A parade of visitors also stopped in, among them Arthur Krock, Walter Winchell, and “Colonel” Robert McCormick, editor and publisher of the staunchly isolationist Chicago Tribune. Far from walking back his endorsement of the Munich agreement, Joe crowed to Winchell that his decision to push Lindbergh’s grim analysis of Germany’s air strength on the British leadership had influenced Neville Chamberlain’s decision to work harder for a deal with Hitler.54

One wonders what went through Jack’s mind as he heard the elder Kennedy’s pontifications that holiday season. Very much his father’s son, he was at the same time more inclined than either Joe Senior or Joe Junior to keep an open mind on difficult international questions, to see both sides. He had a detachment and an ironic worldview that father and brother both lacked, and it inclined him toward a more noncommittal stance. At Harvard, meanwhile, his discussions inside and outside the classroom had given him a sense of why isolationism might prove untenable for the United States, why the appeasing of dictators might be both morally and strategically bankrupt and might only postpone the day of reckoning. Though isolationism was dominant among the students, the faculty were more mixed in their views. Jack’s Winthrop House tutor, Bruce Hopper, who would have considerable influence on his intellectual development in the year and a half to come, had little patience with the appeasers—on Armistice Day every November, Hopper, a charismatic and authoritative speaker, would don his World War I coat and lecture to students on the vital importance of collective security and of confronting international threats head-on. Democracy, Hopper would insist, had to be defended not just by enunciating principles but by standing up and fighting.55

Hopper introduced Jack to the flamboyant and brilliant British historian John Wheeler-Bennett, a cane-carrying, monocle-wearing expert on Germany (and, incongruously, on the U.S. Civil War) who was in the early stages of penning a book on the Czech crisis. A lecturer at the University of Virginia that fall, Wheeler-Bennett was a spellbinding public speaker, whom Harold Macmillan, who would later be prime minister during the Kennedy administration, once called “one of the best talkers” he’d ever met. At Hopper’s invitation, Wheeler-Bennett visited Cambridge and gave a talk on Munich and appeasement in Hopper’s Government 18 class. After the lecture, Jack introduced himself and asked for a one-on-one meeting, and Wheeler-Bennett remembered being impressed by the “most pleasing, open countenanced, blue-eyed young man.” The following afternoon, during a two-hour conversation along the Charles, with Winthrop and the other houses spread out next to them, golden and mellow in the late-day sun, the Briton impressed upon Jack the importance of considering “the imponderables of the human spirit” when assessing world affairs, and to consider carefully how one should balance principle with power in making policy. Jack, thrilled by the opportunity for sustained discussion with this erudite visitor, duly took down Wheeler-Bennett’s suggestions for books to read.56

As 1938 turned into 1939 and Jack Kennedy prepared to join his father in London after Harvard’s midyear exams, he knew what much of the rest of the world knew: that for a Europe in danger, Munich had provided but a breathing spell. The real crisis waited darkly in the wings.

II

By this point Jack Kennedy had arrived in Paris, where he hoped to serve a monthlong stint working at the U.S. embassy under Ambassador William C. Bullitt. Since departing the United States five weeks before, he had spent his time—apart from the excursion to Rome—in London, accompanying his father to lunches and dinners and other functions, all the while pining for Frances Ann Cannon.11 He met with the king and took tea with the twelve-year-old Princess Elizabeth. He also worked part-time in the embassy, handling correspondence and occasionally representing his father at minor local events. (Here he followed in his brother’s path, and also in that of John Quincy Adams, an aide during the ambassadorship of his father, John Adams, in the 1780s.) His letters show little evidence of father-son separation on the preferred strategy vis-à-vis Germany. If anything, Jack was the more sanguine, telling Lem Billings in late March, “Everyone thinks war is inevitable before the year is out. I personally don’t, though Dad does.”12

Now in Paris, spring had sprung, the daffodils and irises in the Jardin du Luxembourg bursting forth and the magnolias on the Champ de Mars in radiant bloom. The cafés were full. Jack thrilled at being there, and he took a liking to Bullitt, a wealthy Philadelphian and bon vivant who had been a cheerleader for the Bolshevik Revolution before turning rabidly anti-Communist during a stint as the first U.S. ambassador to the Soviet Union. Stylish and self-important, Bullitt was voted “most brilliant” in his Yale class of 1912, spoke fluent French and German, and made an immediate winning impression upon arriving in Paris in 1936—his hosts loved his flair and his linguistic prowess and considered him a man of superior judgment and taste. In short order he developed close ties to top French policymakers, even attending cabinet meetings, and—like Joe Kennedy in London—he kept the White House informed of the goings-on in the government. “Bullitt practically sleeps with the French cabinet,” the cantankerous interior secretary, Harold Ickes, noted in his diary.13 Initially supportive of appeasement—like Kennedy, he had been deeply influenced by Charles Lindbergh’s depiction of an invincible Luftwaffe—Bullitt did a one-eighty in the winter of 1939; by the time Jack arrived in Paris in late March, the ambassador was espousing a hard-line anti-German position. Hitler, he told Roosevelt, was a madman with boundless ambition.14

Whereas his father had developed a chilly relationship with Bullitt, largely on account of a deep mutual competitive jealousy, Jack was charmed by his host and delighted in his company. “Bullitt has turned out to be a hell of a guy,” he wrote to Billings. “Live like a king up there as Offie [Carmel Offie, Bullitt’s private secretary] + I are the only ones there + about 30 lackies.” The ambassador had “about 10 barrels of Munich beer in the cellar + and is always trying, unsuccessfully, to pour Champagne down my gullett.” By day, Jack helped modestly with basic clerical work but mostly spent his time reading incoming cables and memoranda, even though Offie considered some of them “none of his business.” Ever inquisitive, the young man asked questions about the functioning of the diplomatic process and about the meaning behind this or that missive, and he impressed both Bullitt and Offie with what would be a lifelong fascination with raw documentation. With his ready smile and insouciant manner, Jack masked how much knowledge he absorbed, and how swiftly.15

“Was at lunch today with the Lindberghs and they are the most attractive couple I’ve ever seen,” he confided to Billings in early April, without giving away what he thought of Charles Lindbergh’s pro-German sympathies or his gloomy analysis of the Anglo-French readiness for war (if he even knew about them). Anne Morrow Lindbergh, in particular, charmed him: “She takes a rotten picture and is really as pretty as hell and terribly nice.” Her husband didn’t return the compliment, writing in his diary of the luncheon that there were “probably forty people there, including some of society’s greatest bores.”16

On April 28, Jack and the rest of the embassy staff tuned in to Hitler’s two-hour, twenty-minute speech to the Reichstag, which was occasioned by Franklin Roosevelt’s message two weeks before in which he asked for Hitler’s assurance that he would desist for the next twenty-five years from attacking a list of thirty nations. In exchange, FDR said, Washington would play its part on behalf of disarmament and equal access to world markets and raw materials. Hitler rejected the offer, his voice dripping with sarcasm, to the delight of his roaring audience, and he also took the opportunity to renounce Germany’s nonaggression pact with Poland and to renew German claims to the seaport of Danzig.^*1 “Just listened to Hitler’s speech which they consider bad,” Jack wrote to Billings right afterwards. He himself was less concerned, he went on, for if the German leader hoped to go after Danzig or all of Poland, “the time would have been a month ago before Poland and England signed up. That he didn’t shows a reluctance on his part so I still think it will be OK. The whole thing is damn interesting and if this letter wasn’t going on a German boat and if they weren’t opening mail could tell you some interesting stuff.”17

This was Jack’s pattern during that spring of 1939: he tended in his correspondence to underestimate both the German dictator’s bellicosity and, more generally, the seriousness of European tensions and the likelihood of war. He also seems to have misjudged the shift in the popular mood that had occurred in France and especially Britain during the seven months he had been back in the United States. The Munich agreement had created a split in British opinion that persisted into the new year, but little by little the appeasers found themselves losing the battle for public support. The fall of Prague on March 15 effectively killed the debate, giving the lie to Chamberlain’s twin claims, upon returning from Bavaria, that he had brought “peace for our time,” as well as “peace with honor.” Together with the final defeat of the Republican side in the Spanish Civil War, culminating in the fall of Madrid in late March, it created in a great many Britons the conviction that the fascists could be stopped only by military force. Sooner or later, the battle would come. Moreover, many felt, Britain was now more ready to fight than it had been the previous fall, its rearmament program having made significant strides in the interval. To some observers, war might even be something to look forward to, if it helped wash away the malaise they felt had permeated British and European society since the decade began.18

All this is no doubt more clear in hindsight than it was at the time, but even so, Jack’s failure to detect the transformation in popular attitudes is striking, especially given his own Anglophilia, evident from a young age but now given more opportunities for full expression. The upper-class British credo “Work hard, play hard, socialize hard” came naturally to him, he realized, and he admired the qualities often associated with “posh” Englishmen: cleverness, wit, irony, understatement, detachment, indirection, coolness under fire, self-possession. The actor David Niven was a modern archetype, while an earlier one was Queen Victoria’s Whig prime minister Lord Melbourne—at least as rendered by David Cecil in his absorbing, gossipy biography The Young Melbourne, which appeared in Britain in early 1939 and which Jack devoured that spring. In Cecil’s hands, Melbourne becomes for the young Kennedy a fascinating, altogether charming figure, indeed a kind of model for life: sophisticated and wittily idiosyncratic, poised and nonchalant, curious about people and what made them tick, skeptical of received wisdom and hostile to ideologues, susceptible to the pleasures of the flesh yet at the same time appealingly devoted to queen and country.19

“Life had taught him…always to relate thought to experience, to estimate theory in terms of its practical working,” Cecil wrote of Melbourne, a description that fit Jack’s vision of himself. And though more egalitarian than Melbourne, and more committed to an activist, democratic politics that would use established institutions and principles to benefit the common people (in British terms, a Tory position more than a Whig one), Jack certainly would have identified with Cecil’s description of the broader upper-class milieu: “The ideal was the Renaissance ideal of the whole man, whose aspiration is to make the most of every advantage, intellectual and sensual, that life has to offer.” Melbourne’s own assertion that “things are coming to a pretty pass when religion is allowed to invade the sphere of private life” would likewise have appealed to Jack for its skeptical urbanity.20

Of Melbourne’s carnal pursuits Cecil wrote, “His animal nature and his taste for women’s society united to make him amorous, and natural tendency had been encouraged by the tradition of his home. Already, we gather, he had sown some wild oats. Like the other young men of his circle he thought chastity a dangerous state, and he seems early to have taken practical steps to avoid incurring the risks attendant to it.” Jack, of course, knew all about this “tradition” from his own home.21

Cecil’s succinct summation of the young Melbourne worked equally well for the young Kennedy: “He was a skeptic in thought; in practice a hedonist.”22

Rose Kennedy, in explaining to a later interviewer the reasons for her second son’s (and, palpably, her own) affinity for things English, spoke of his “Boston accent which is very much akin to the British, and then he responded to the British love of culture and literature and all that sort of thing.”

Most of the people in government circles and most of the people who had big houses and who entertained over there, were people whose families had been in government, and they had not only interest in government, in history and in politics, but they had had them for generations and so they were probably more cultured than the people were here, where most, or many, had started in very humble beginnings. And I think Jack responded to all that because he did like literature, and he did appreciate it, and then he was interested in government, and of course, he did enjoy seeing all the beautiful homes, because they were connected more or less to history. If you went away for the weekend, you’d see a house that had been there for hundreds of years….There were different souvenirs of the years they had spent in government in those houses, and all those things Jack responded to, and so he did enjoy himself [there] as did we all, I think. And then of course it was more or less akin to Boston, because Boston is in a great part British, the people there are of British-Irish heritage, much more than they are in New York, for instance.23

III

In early May, Jack returned to London to attend a dinner party his parents were hosting for the king and queen, who were departing shortly on a royal visit to the United States and Canada. Then he headed off for Eastern Europe and the Middle East. His father helped arrange the itinerary and made the necessary contacts, and he received logistical help as well from Carmel Offie in the Paris embassy.24 “Am now in Warsaw,” Jack reported to Lem Billings early in the trip.

It’s been damn interesting and was up in Danzig for a couple of days. Danzig is completely nazified, much heiling of Hitler, etc. Talked with the Nazi heads and all the consuls up there. The situation up there is very complicated, but roughly here it is:

1st. The question of Danzig and the corridor are inseparable. They [the Germans] feel that both must be returned. If this is done then Poland is cut off completely from the sea. If [the Poles] return just Danzig…[the Germans] could thus control Polish trade, as by means of guns they could so dominate Gdynia that they could scare all the Jew merchants into shooting their trade thru Danzig. However, aside from the dollar + chits angle—which is only secondary—there is the question of principle. The Germans don’t give a good god damn what happens to Poland’s trade—and they told me frankly that the best thing for Poland would be to come into a customs union with Germany.

But the Poles had other ideas, Jack continued. “Poland is determined not to give up Danzig and you can take it as official that Poland will not give up Danzig and 2nd that she will not give Germany extra-territoriality rights in the corridor for the highways. She will offer compromises but never give it up. What Germany will do if she decides to go to war—will be to try to put Poland in the position of being aggressor—and then go to work. Poland has an army of 4,000,000 who are damn good—but poorly equipped.”25

From there Jack pushed on to Russia, which struck him as “crude, backward, and hopelessly bureaucratic.” His airplane en route had a broken window, which seemed to bother no one on board, and he had to sit on the floor. In Moscow he dined with Charles “Chip” Bohlen, the slim and handsome second secretary at the U.S. embassy—upon whom he made a favorable impression with his “charm and quick mind”—and he also visited Leningrad and the Crimea.26 Then it was on to Turkey (a steamer ship brought him to Istanbul), Greece, Egypt, Palestine, Lebanon, Bulgaria, Romania, and Yugoslavia.27 At each stop Jack penned for his father a detailed assessment of the local political situation. The historian James MacGregor Burns, who in the late 1950s saw these missives (regrettably, most were subsequently lost or stolen), remarked on their cool detachment and shrewd, balanced analysis—and poor spelling.28

We do have one of these evaluations, the report from Jerusalem, and a remarkable document it is. Subtle and penetrating, and free of any hint of anti-Semitism, the letter shows Kennedy’s growing maturation as a thinker—and, no doubt, his many years of accumulated knowledge as a reader of history and international affairs, often from a sickbed. In particular, we see his grasp of the complex nature of the Arab-Jewish conflict in Palestine, and his understanding of the role of history in shaping the current tensions. Behind the official assertions of the two sides, we read, “are fundamental objections which, while they are not stated publicly, are nevertheless far more important.”

On the Jewish side there is the desire for complete domination, with Jerusalem as the capital of their new land of milk and honey, with the right to colonize the Trans-Jordan. They feel that given sufficient opportunity they can cultivate the land and develop it as they have done in the Western portion. The Arab answer to this is incidentally that the Jews have had the benefit of capital, which had the Arabs possessed, equal miracles could have been performed by them. Though this is partly true, the economic set up of [Arab] agricultural progress with its absentee landlords and primitive methods of cultivation, could not under any circumstances probably have competed with the Jews.

There are hints, too, of Jack’s emerging anticolonialism (“After all,” he reminds his father, “Palestine was hardly Britain’s to give away”) and more than hints of his insistence on the need to pursue a realistic, pragmatic outcome, one resisting propaganda from either side. “It is useless to discuss which has the ‘fairer’ claim. The important thing is to try to work out a solution that will work.” For Jack, this could be achieved only through the creation of “two autonomous districts giving them both self-government to the extent that they do not interfere with each other and that British interest is safeguarded. Jerusalem, having the background that it has, should be an independent unit. Though this is a difficult solution yet, it is the only one that I think can work.”

Even then, the report concludes, it might well not be enough, especially given the deep splits within both groups:

There is the strongly orthodox Jewish group, unwilling to make any compromise, who wished to have a government expressing this attitude, there is the liberal Jewish element composed of the younger group who fear these reactionaries, and wish to establish a very liberal, almost communistic form of government, and there are the in-betweens who are willing to make a compromise….As for the Arabs, while most of them are heartily sick of the whole business which is playing hell with their economic life, yet so strong is the hold of the Mufti by reason of his religious grip and because of the strength of the new nationalism, that it is going to be extremely difficult to effect a solution without bringing him back.29

On his final night in Jerusalem, Jack received an up-close demonstration of the seriousness of the conflict when thirteen bombs exploded in the Jewish section; all of them, he reported to his father, were detonated by the Jews themselves. “The ironical part is that the Jewish terrorists bomb their own telephone lines and electric connections and the next day frantically phone the British to come and fix them up.” His Majesty’s representatives, Jack thought, responded with alacrity and skill; he felt his admiration for the British way of doing things deepen still further.30

IV

By June 1939 Jack was back in London, working by day in the embassy and hitting the parties and clubs by night, often in the company of sister Kick and a small entourage of British friends. He now saw in a way he had not before that Britain was girding for war. Some weeks earlier, the Chamberlain government had introduced conscription, and Anglo-French military staff talks had commenced to consider how best to wage a three-year war with Germany. The Oxford Union debating society’s famous King and Country resolution from 1933 (“This House will in no circumstances fight for its King and Country”) was overturned and expunged from the union’s minute book. Ordinary Britons dug air-raid shelters in their back gardens. Chamberlain and Halifax still hoped Hitler would back down, or at least agree to negotiate without threats. The signing by Germany and Italy, in May, of the bombastically named Pact of Steel undermined the Englishmen’s hopes of detaching Italy from Hitler’s clutches, and they saw no option but to reaffirm publicly that if Germany attacked Poland, the British government would honor the guarantee to come to Poland’s support. The French vowed likewise.

The irony was rich: after refusing the previous summer to make a guarantee to Czechoslovakia, a country ready to fight and holding alliances with France and the Soviet Union, Chamberlain and Daladier were now issuing one to a country that, as their own military leaders made clear to them, was geographically exposed and militarily ill-equipped and could not be effectively assisted in the event of a German invasion, with the result that she would likely hold out only a few weeks. Why would Hitler be deterred in such a situation?31

Joseph Kennedy thought the Anglo-French guarantee would do little except increase the likelihood of war—a war, moreover, that Germany would win, and that the United States should have no part of. He was adamant on this point, if anything more so than he had been the previous year. Increasingly, however, as spring turned into summer, Kennedy’s pessimism rubbed Britons—including many leading political figures—the wrong way. In June, at a dinner in London in honor of the visiting Walter Lippmann (whose book The Good Society Jack Kennedy was reading that summer, at the urging of Bruce Hopper), Winston Churchill heard the columnist recount a meeting he had had with Kennedy earlier that day. The Western powers stood no chance against the mighty German war machine, the ambassador had insisted, which meant that Britain had no option but to concede to Hitler control over Eastern and Central Europe. “All Englishmen in their hearts know this to be true,” Kennedy had declared, “but a small group of brilliant people has created a public feeling which makes it impossible for the government to take a sensible course.”

Churchill, who had sat glumly brooding through the meal up to that point, exploded in fury. Kennedy was a timorous and naive man, he charged, an Anglophobe on account of his Irish heritage, whom Roosevelt, in a lapse of judgment, had foolishly selected for this vitally important post, and who was an impediment to British-U.S. cooperation. The author and diplomat Harold Nicolson, also at the table that evening, marveled at the scene as Churchill sat hunched, “waving his whiskey and soda to mark his periods, stubbing his cigar with the other hand,” as he insisted that Britain would stoically endure whatever the Germans threw their way and repay the destruction with interest. Even should Germany prevail in the encounter, he went on, it would still have to tangle, sooner or later, with the most powerful nation of them all, the United States. “It will then be for you, for the Americans,” he told Lippmann, “to preserve and to maintain the great heritage of the English-speaking peoples.” Churchill then urged him to use his influential column to get his compatriots to “think imperially” and maintain their time-honored commitment to holding high “the torch of liberty.” Lippmann, who prided himself on not being swept off his feet easily, came away mesmerized by the Englishman’s colossal gift for language and oration and by his obvious leadership qualities, which Lippmann decided exceeded even those of the great and charismatic Theodore Roosevelt.32

What Joseph Kennedy never understood—it’s a key explanation for his failure as ambassador—was that for many Britons, fighting had become a matter of dignity, even as they were under no illusions as to the heavy price it would extract. The concept of honor in international affairs was foreign to Kennedy; all that mattered was survival. Because Munich had been about such self-preservation, he saw no reason for Chamberlain or anyone else to be ashamed of it, and he continued in mid-1939 to regard Hitler as a responsible statesman with whom one could do business. War would be catastrophic, which meant that realism consisted of doing whatever was necessary to keep the peace. Jack, on the other hand, though pragmatically inclined like his father, had a greater feel for the things of the spirit, for the intangibles that often moved people. He understood, from his avid childhood reading about the deeds and misdeeds of past leaders, that respect and credibility mattered greatly in human affairs; they always had and they always would. His professors Bruce Hopper and Payson Wild had further impressed this notion on him. More directly, Jack, upon his return to London, could see the change in the young Englishmen he and Joe Junior and Kick met with socially: many of them now spoke of going after the Germans with guns blazing, come what may.33

One of these friends was David Ormsby-Gore, 5th Baron Harlech, whom he met through Kick and who would be Britain’s ambassador to Washington during the Kennedy administration, remaining a close confidant until the end. Like Jack a second son who found sanctuary in books as a youngster, the slim and sharp-nosed Ormsby-Gore, who often wore a silk scarf tied insouciantly around his neck, was independent-minded and fun-loving, and blessed with a formidable intelligence. He was also extremely well connected, his father having been a member of Parliament for twenty-eight years and his mother being the granddaughter of Lord Salisbury, a prime minister under Queen Victoria and towering figure in the Conservative Party. In their early encounters, Jack seemed to Ormsby-Gore to be cut from the same cloth as him: fascinated by politics and statecraft, more an observer than a pontificator, and more a social animal than a sober student of world affairs. They soon developed a deep mutual affection. “He was very thin, wiry-thin with, I don’t know how to describe it, this energy exuding from him,” Ormsby-Gore remembered of his friend. Underneath the party persona, however, the young Englishman detected a more serious dimension, “because of course he was preparing his thesis—it was a longer than normal thesis.”34

It was true: Jack had indeed decided on a topic for his upcoming Harvard thesis project. Bruce Hopper had reminded him in their spring correspondence that, with his travels and his father’s position, he had an unmatched chance to study history in the making. Jack agreed. Partly on account of his intense discussions with his British friends the previous summer, he had developed a fascination with Great Britain’s policies, and in particular with how it had gotten itself into such a predicament. How had it squandered the advantages it held after the Great War, when the empire stood supreme and the Royal Navy patrolled the world’s seas? Where had the Chamberlain appeasement policy come from, and how would one assess its soundness? Shouldn’t the British have been more prepared for the rise of Hitler’s Germany?35

Jack had the thesis very much in mind when, in July, he left London and crossed the Channel again. He wanted to see Germany up close and to gauge the likelihood of war. This time he traveled with his Harvard roommate Torbert Macdonald, who had come over to Europe with the Harvard track team. Torby would have preferred to linger in London, for he was in love with Kick Kennedy and hoped to spend time with her. But at Jack’s insistence they made their way for Munich, where they met up with Byron “Whizzer” White, a former all-American halfback from Colorado and now a Rhodes Scholar at Oxford. (Much later, under President Kennedy, White would be appointed to the Supreme Court.) Before their departure, Jack and Torby had been warned by Ambassador Kennedy to keep their heads down and stay out of trouble, but at the tomb of the Nazi hoodlum-martyr Horst Wessel the three Americans were accosted by local storm troopers who heckled them and threw rocks at their car (presumably because it bore British license plates). “Our first thought was to lay into them,” Macdonald recalled, “but Jack, even though he was as sore as the rest of us, led us in a diplomatic retreat.” The incident left the three Americans shaken. “If this is the way these people feel,” Jack said, maybe war was inevitable.36

Some days later, having parted ways with White, Jack and Torby rented a car in Paris, intending to drive to the Riviera, where the Kennedy family had again rented a vacation villa near Cannes. Traveling at high speed south of Paris, Jack lost control of the vehicle—a jalopy that seemed to have a mind of its own and continually bucked to the right—and flipped it over. The car skidded on its roof for thirty feet, and the luggage was strewn about the pavement. Upside down in the compartment, Jack turned to his friend and calmly remarked, “Well, pal, we didn’t make it, did we?”37

But eventually they did, meeting up with numerous Kennedys in the South. Kick was there, fueling Macdonald’s hopes, but she soon crushed them by making clear she was not interested in a romance. (She had fallen hard for William “Billy” Cavendish, the Protestant Marquess of Hartington and heir to the dukedom of Devonshire, and brother of Jack’s friend Andrew Cavendish.) That revelation sent the young men venturing north again, on August 12, bound once more for Germany. Rose noted in her diary that “they would like to go to Prague, but we are told no one is allowed to go there.”38 Undaunted, Jack headed for Vienna, while Torby split off to go to Budapest. Jack got into Prague with an assist from the U.S. embassy, but the diplomat responsible, George F. Kennan, was none too pleased to have to do it, recalling some years later:

In those days, as the German forces advanced like encroaching waves over all the borders of Bohemia, no trains were running, no planes were flying, no frontier stations existed. Yet in the midst of this confusion we received a telegram from the embassy in London, the sense of which was that our ambassador there, Mr. Joseph Kennedy, had chosen this time to send one of his young sons on a fact-finding tour around Europe, and it was up to us to find means of getting him across the border and through the German lines so that he could include in his itinerary a visit to Prague.

We were furious. Joe Kennedy was not exactly known as a friend of the career service, and many of us, from what we had heard about him, cordially reciprocated this lack of enthusiasm. His son had no official status and was, in our eyes, obviously an upstart and an ignoramus. The idea that there was anything he could learn or report about conditions in Europe which we didn’t already know and had not already reported seemed (and not without reason) wholly absurd. That busy people should have their time taken up arranging his tour struck us as outrageous. With that polite but weary punctiliousness that characterized diplomatic officials required to busy themselves with pesky compatriots who insist on visiting places they have no business to be, I arranged to get him through German lines, had him escorted to Prague…and with a feeling of “that’s that,” washed my hands of him.39

Kennan could be forgiven for his annoyance at having to play host to a college student at this moment in time, with tensions in Europe running close to the boiling point. Even so, his pomposity—never far below the surface with Kennan—got the better of him. His young guest was no ignoramus. Quite the contrary, Jack’s letters that spring and summer—to Billings, to his father, to others—reveal a penetrating and analytical mind at work, as well as a historical knowledge honed through immersion in books. Not all of the letters were carefully constructed—he often wrote in an emotive stream and showed a weakness for gossip and the crude put-down, suggesting he was not thinking as an aspiring politician with an eye to posterity—but invariably they contained telling insights about the local scene. The report to his father from Jerusalem in June was on par—in content if not in presentation—with what a veteran diplomat might produce.

V

History was on Jack Kennedy’s mind that summer as Europe’s crisis deepened. From Winston Churchill’s The World Crisis and from course readings at Harvard, he understood how easily miscalculation and stubborn pride could lead to a rupture among nations and a resort to arms. The current situation was not a replay of July 1914, he determined, not yet anyway, but certainly there were worrisome signs. In the final half of August, he hustled between German cities—Munich, Hamburg, Berlin—seeing in each place ample evidence of the fearsome Nazi disinformation machine at work, stoking tensions with the Poles over Danzig and the corridor. In Berlin he rendezvoused briefly with Joe Junior, who was on his own inspection tour of the Reich. Joe was now less enamored of the Nazi German state than he had been on previous visits, even as he held staunchly to his father’s worldview. “The anti-Polish campaign is beyond description,” Joe wrote. “Every edition of the newspapers has a more gruesome tale to tell of Polish outrages against the Germans, of planes being attacked and of German soldiers tortured.” The intent was obvious: when war came, “the Poles will be shown to be the aggressors, and it will be the duty of every German to stop them.” Newsreels showed the same thing, he added, with even young children brought forth to testify to the terrible deeds of the dastardly Poles.40

War might be close after all, Jack now sensed, a notion given credence by the secret message Alexander Kirk of the U.S. embassy in Berlin asked him to bring back to his father in London: Germany, the message read, would likely attack Poland within a week.41 But still Jack wondered: Would Hitler actually go through with it if it meant hostilities with Britain and France? This was indeed the question on all Germany watchers’ minds. Already months before, in early April 1939, Hitler had authorized a secret military directive for the destruction of Poland anytime after September 1 (but before the fall rains began in mid-September). The German leader doubted Western resolve, and he was not deterred when, over the early summer, Paris and London leaders reaffirmed their commitment to the Poles and the Poles themselves refused to yield on Danzig and the corridor. Britain and France, he still believed, would in the end refuse to fight. On August 19, the very day Jack arrived in Berlin, the first German formations began moving toward the Polish frontier; within four days, they were in place. Other units followed, leading ultimately to a massive attacking force of 1.5 million men. Meanwhile, weapons and soldiers were smuggled into Danzig so that the city, already Nazi-dominated, could be taken immediately upon the beginning of operations.42

Hitler wanted war in the summer of 1939, but he hoped it would be a local affair, involving only Germany and Poland. The obstinacy of Chamberlain and Daladier, and of Polish foreign minister Józef Beck, the key player in Warsaw, surprised and annoyed him and complicated his plans. With his generals warning him that Poland should not be attacked unless Germany could be assured of Russia’s neutrality, the Führer now launched one of the most astonishing about-face gambits in modern history (albeit one that took shape over several weeks), the news of which sent shockwaves around the world. In opposition to everything he had preached about the evils of Soviet Communism, he sent his obsequious foreign minister, Joachim von Ribbentrop, to Moscow on August 23 to negotiate a nonaggression pact with Joseph Stalin—who himself did a volte-face, having hammered for years on the absolute heinousness of fascism.43 In the early hours of the twenty-fourth the deal was signed, with a secret protocol splitting Poland and northeastern Europe between them. “All the isms,” a British midlevel official remarked, “are now wasms.” Hitler, overjoyed at what he saw as a triumph of colossal consequence, expected to hear of the swift collapse of the French and British governments, and he felt more certain that the Western powers would not fight for Poland. “Our enemies,” he had told his commanders the day before he dispatched Ribbentrop to Moscow, “are tiny little worms. I saw them at Munich. I’ll cook them a stew they’ll choke on.”44

Britain and France had made their own approaches to Stalin in the weeks prior, hoping that an entente between the three powers would be sufficient to constrain Germany once and for all. Had the effort succeeded, it might well have had the desired effect. But the plan was never as close to realization as some later observers claimed. On the Western side, the effort was desultory and late in coming—Chamberlain in particular could not shake his visceral suspicion of Communists in general and Stalin in particular, and, like most British officials, he held a low opinion of Soviet military effectiveness—while for Stalin there was logic, however ultimately misplaced, in casting his lot with the Germans, especially in view of his bottomless mistrust of British and French intentions. A ruthless practitioner of realpolitik (even if forced to justify his decisions with reference to Marxist-Leninist ideology, which, lucky for him, was an infinitely malleable doctrine), Stalin played with a Western alliance mostly, it seems, in order to pressure Berlin into making a deal that would bring concessions to his side. Specifically, he sought and received territory in eastern Poland, Bessarabia, and the Baltic states. In addition, the deal bought him time to build up the Red Army, which had been crippled by his recent paranoia-induced purges of senior officers, and to consolidate his defenses against the attack from the west that he had always feared.45

In London and Paris, officials had to pick themselves up off the floor after learning of the Nazi-Soviet pact. Even now, they hoped against hope that some means could be found to avoid the catastrophe and that Hitler would agree to negotiate.46 His willingness to meet on successive days with British ambassador Nevile Henderson, an arch-appeaser inclined to grasp at any straw, seemingly gave substance to this possibility. But not much substance. Neither Chamberlain nor Daladier was under any illusion about the fate that would soon befall Poland. When Joseph Kennedy encouraged Chamberlain to make more concessions to Berlin, the despondent prime minister shook his head. “I’ve done everything I can think of, Joe,” he said, “but it looks as if all my work is of no avail.”47

Kennedy, resigned to an imminent German attack, still hoped Britain would wriggle free of its commitment to the Poles. France would then assuredly follow suit, and a wider war would be averted. Certainly, the ambassador told American journalists on August 23, from a U.S. point of view one should hope for Chamberlain to abandon Poland and revert to the policy of appeasement. “I don’t see what we’ve got to gain if Britain goes to war,” he said. “I don’t care if Germany carves up Poland with British support. I’m for appeasement one hundred percent, and if one thousand percent is more than one hundred percent, I’m for it one thousand percent.” To which Ralph Barnes of the New York Herald Tribune responded, “Have you been telling this to Mr. Chamberlain?” Kennedy answered, “I’ve been telling him that every chance I had every day for more than a year.”48

VI

War came the following week. In the predawn hours of Friday, September 1, waves of Stukas, Messerschmitts, and Heinkels began bombing targets deep within Poland, and German armored columns crossed the frontier in overwhelming strength from the north, west, and (through Slovakia) south. Even now Chamberlain dithered, announcing to the House of Commons (with Joe Kennedy in the visitors’ box) that he would work with the French to get mediation through the good offices of Italy’s Mussolini. The chamber responded with stunned silence, then fury. Facing a revolt also within the Cabinet over the absence of a declaration of war, the prime minister at last agreed to issue an ultimatum to Hitler to withdraw; when, on the late morning of September 3, the appointed hour passed without a withdrawal, Chamberlain told the British people in a mournful, eloquent radio broadcast from 10 Downing Street that “this country is at war with Germany.” Even Chamberlain’s detractors found it a moving, resolute declaration. All over the nation, people gathered anxiously around their radio sets to hear the announcement, then stood up when the national anthem was played at the end, whereupon in London the first prolonged air-raid alarm sounded, causing widespread chaos.49

In the House of Commons early that afternoon, with Jack, Kick, and Joe Junior present in the visitors’ gallery along with their mother, Chamberlain spoke in sepulchral tones: “Everything I have worked for, everything that I have hoped for, everything that I have believed in during my public life, has crashed into ruins. There is only one thing left for me to do: that is devote what strength and power I have to forwarding the victory of the cause for which we have sacrificed so much.”50

Mrs. Kennedy was deeply stirred, as her husband had been by the earlier radio address. After the speech, the ambassador called 10 Downing Street. “Neville, I have just listened to the broadcast. It was terrifically moving….I feel deeply our failure to save a world war.” Chamberlain thanked Kennedy for reaching out and for his unfaltering support. “We did the best we could have done but it looks as though we have failed….Thanks, Joe, my best to you always and my deep gratitude for your constant help—Goodbye—Goodbye.”51

In his diary that day, Joe stayed on the theme, writing that the broadcast was so touching it almost made him cry. “I had participated very closely in this struggle and I saw my hopes crash too.” But the British leader could hold his head high: “It is a terrible thing to contemplate, but the war will prove to the world what a great service Chamberlain did to the world and especially for England.” By rejecting war at the time of Munich, eleven months earlier, Joe wrote, Chamberlain had given British officialdom a precious year to rearm and to line up popular support.52

Jack, however, found greater power in another speech on that extraordinary September day. Winston Churchill, now joining the Cabinet as First Lord of the Admiralty, rose slowly from the backbenches after Chamberlain had spoken. His remarks ran a mere four minutes, but they left the young American—and many others in the hall—spellbound. No one should underestimate the size of the challenge ahead, Churchill declared gravely, or fault the prime minister for his sadness at the failure to avert war, but a generation of Britons stood ready to prove themselves equal to the task.

This is not a question of fighting for Danzig or fighting for Poland. We are fighting to save the whole world from the pestilence of Nazi tyranny and in defense of all that is most sacred to man. This is no war of domination or imperial aggrandizement or material gain; no war to shut any country out of its sunlight and means of progress. It is a war, viewed in its inherent quality, to establish, on impregnable rocks, the rights of the individual, and it is a war to establish and revive the stature of man….We are sure that these liberties will be in hands which will not abuse them, which will use them for no class or party interests, which will cherish and guard them, and we look forward to the day, surely and confidently we look forward to the day, when our liberties and rights will be restored to us, and when we shall be able to share them with the peoples to whom such blessings are unknown.53

The drama played out differently in Berlin. The world war that Hitler had insisted would not materialize suddenly seemed a reality. Early that morning of September 3, Hitler’s chief interpreter, Paul Schmidt, had arrived at the Reich Chancellery with the text of the British ultimatum. Ushered into the presence of Hitler and Ribbentrop, Schmidt read it to them slowly, taking care to enunciate each word. “When I finished,” he wrote in his memoirs, “there was complete silence. Hitler sat immobilized, gazing before him.” Some moments passed, the quietude deafening, whereupon the Führer turned to Ribbentrop and said sharply, “What now?” Other subordinates, including press chief Otto Dietrich, likewise would recall Hitler’s stunned reaction to the ultimatum. When propaganda minister Joseph Goebbels arrived at the chancellery later in the day, he found Hitler furious with the British yet determined to fight. There would be no thought of pulling troops back from Poland. That evening, after the French had followed Britain’s lead and declared war, the German leader reiterated his belief that the threats by the two Western powers were empty; neither would wage a real military campaign.54

In Washington, the Roosevelt administration followed developments closely through near-constant communication with embassy staff in Berlin, Warsaw, Paris, and London. In the early morning of September 3, Washington time, soon after Britain’s declaration of war, President Roosevelt took a call from Joe Kennedy, who had given in to hopelessness and said a new dark age had descended on Europe, which meant “it’s the end of the world…the end of everything.” The president replied with soothing words.55 That night, FDR delivered a fireside chat in which he told the nation that while the United States would remain neutral in the new European struggle, he could not ask that every American remain neutral in judgment as well—a deliberate revision of Woodrow Wilson’s plea in 1914 that Americans be impartial in both thought and deed.

In London that evening, nerves were on edge as residents expected German bombers to arrive in the skies at any moment. A nightly blackout had been imposed, and a haunting quiet fell over the city. Most residents stayed inside their homes, listening to the BBC on the radio behind blackout blinds. “It is an eerie experience walking through a darkened London,” Kick Kennedy wrote of the blackout’s effects. “You literally feel your way, and with groping finger make sudden contact with a lamppost against which leans a steel helmeted figure with his gas mask slung at his side. You cross the road in obedience to little green crosses winking in the murk above your head. You pause to watch the few cars, which with blackened lamps, move through the streets….Gone are the gaily-lit hotels and nightclubs; now in their place are somber buildings surrounded by sandbags.”56

At 2:30 A.M., an aide called Ambassador Kennedy with stunning news: The British liner SS Athenia, bound for Canada and carrying thirteen hundred passengers, including three hundred Americans, had been torpedoed by a German submarine, seventeen hours after Britain’s declaration of war. The unarmed ship, ripped by explosions, was sinking somewhere west of the Hebrides. Jolted awake, Kennedy ordered that a list of the passengers be produced as quickly as possible. (Due to incomplete manifests, it would take weeks to get the final numbers and to determine that 112 passengers had perished, including twenty-eight Americans.) Before dawn, he walked down the hall and woke up Jack. In short order the youth hurried off to Scotland, accompanied by Eddie Moore. Many of the rescued passengers were being brought to Glasgow, and the ambassador wanted Jack to be present as his representative. With the regular embassy staff now overloaded with work, he had no one else to send.

The crowd that greeted Jack Kennedy at the Beresford Hotel demanded answers about what had occurred, as well as protection once they resumed their transatlantic voyage. “We want a convoy!” they hollered at him as soon as he arrived. “We refuse to go without a convoy!” Some shook their fists. According to the London Evening News, the young American showed a “boyish charm and natural kindliness,” as well as the “wisdom and sympathy of a man twice his age,” as he did his best to field questions and express understanding. Citing Roosevelt’s claim that convoys were unnecessary because Germany would not attack an American vessel, Jack told the passengers they should not expect protection on their homeward journey, which prompted shouts of “What about the submarines? You can’t trust the German Navy! You can’t trust the German Government!” Jack held his ground and kept his composure as he strove to be heard above the din. “You will be safe on a ship flying the American flag under international law,” he insisted. “A neutral ship is safe.”^*2 The most he could do, he went on, was to pass on their concerns to his father. This seemed to defuse the tension and calm the room. While in Glasgow, Jack also visited injured Americans in area hospitals, garnering respect for his calmly authoritative, courteous, and accessible demeanor. An “Ambassador of Mercy,” one journalist dubbed him.57

He was touched by what he saw. “The natural shock of the people would make the trip to America alone unbearable…because of the feeling that they will have that the United States exposed them to this unnecessarily,” he wrote to his father in arguing for a convoy to accompany whatever ship or ships brought the Athenia survivors back to U.S. shores.58

Once back in London, Jack was put in charge of the repatriation of the survivors. The work kept him in England longer than planned—the USS Orizaba left Glasgow on September 19, bound for New York, with some four hundred Athenia survivors on board—and he wrote to Harvard for permission to enroll for the fall semester late. The permission was granted. Jack expected to return to the university on September 29, but to his surprise he found a last-minute seat aboard a Pan American Dixie Clipper, the four-engine “flying boat” that had just commenced transatlantic passenger service that summer. He flew from Foynes, Ireland, on September 20, via Newfoundland, the aircraft swooping down, like an enormous metallic duck, at Port Washington, New York, the following day. According to The Boston Globe, Jack was “the general favorite with all on the Dixie, not because he was Ambassador Kennedy’s son but because he was himself, bright and helpful and interesting.”59

It had been an astonishing seven months overseas, more consequential than he ever could have anticipated, more eventful, surely, than the experience of any Harvard junior that year—or perhaps any year. He had received communion from the pope and taken tea with Princess Elizabeth; had read high-level diplomatic dispatches in London and Paris; had been accosted by Nazi toughs in Munich; had flipped his car south of Paris and survived; had paid visits to Poland and Russia; had darted south to Turkey, North Africa, and the Middle East; had traveled behind German lines in occupied Czechoslovakia and crisscrossed Germany in the immediate lead-up to war, before carrying a top-secret message back to London; had been present in the House of Commons for the historic session on September 3; and, to top it off, had made his debut as a public figure in response to the sinking of an ocean liner on the first day of Britain’s war.

It was the kind of exposure and training that no future president since John Quincy Adams had enjoyed at so young an age. And the experience left its mark, cultivating in him an intensified passion for foreign policy and world affairs that he never abandoned, and completing his transition to adulthood.60

Now he was back at Winthrop House, a college student once more, twenty-two years old and focused on the principal task ahead: taking all he had experienced and learned on his grand overseas adventure and turning it into a worthy senior thesis. No one yet knew it, but here, too, John Fitzgerald Kennedy, with a generous assist from his father, would do something extraordinary and put his name before the public once again.

II

That would come later. At the time of publication, Jack was pleased with his effort, and said so to his father.9 Joe, in turn, felt paternal pride at seeing his second son writing for The Harvard Crimson and personal satisfaction that the line of argument so closely matched his own. It was a tonic that, frankly, he needed, for the fall of 1939 was in other respects a miserable time for him. He toiled alone in London, having sent most of his family back to America at the outbreak of hostilities. (Rosemary stayed behind at her Assumption Convent School, reestablished at Belmont House, in Hertfordshire, thirty miles northwest of London, after the start of the war.) The dinner invitations that had come thick and fast during his and Rose’s first year in England now were few and far between; many evenings he spent by himself. The solitude weighed on him, made him morose, rendered his charcoal worldview darker still.

“I haven’t changed my opinion at all about this situation,” he wrote his two eldest sons on October 13. “I think that it will be a catastrophe financially, economically, and socially for every nation in the world if the war continues and the longer it goes on, the more difficult it will be to make any decent rearrangement.” To Arthur Krock he expressed even deeper distress: “One couldn’t be more pessimistic than I am as to the future outlook for the world if this war continues any length of time.”10

All around him Kennedy could see preparations for a war he hated: parks bristling with anti-aircraft guns and big black arrows pointing in the direction of air-raid shelters. His formerly close relationship with Neville Chamberlain’s government was fast fraying, on account of the changed circumstances: Britain was at war and ruling out early negotiations with Hitler, while Kennedy remained steadfast that Germany would win and that America must not intervene. Britain’s glory days had long since passed, he felt certain, and he told Roosevelt he saw “signs of decay, if not decadence, here, both in men and institutions….Democracy as we now conceive it in the United States will not exist in France and England after the war, regardless of which side wins or loses.” Consequently, “we [in America] should curb our sentiments and our sentimentality and look to our own vital interests.”11 Invariably, these assessments got back to 10 Downing Street and to the Foreign Office, which in September began keeping a “Kennedy dossier” on him.

The file, which remained classified for the next several decades, contains various explanations for the ambassador’s gloom: his Irish American heritage, which made him delight in “seeing the lion’s tail twisted”; his innately pessimistic worldview; his acceptance, thanks to the reports of Charles Lindbergh and Joe Junior, of the notion of German air superiority; and his laser-like focus on “the financial side of things,” which rendered him unable, “poor man, [to] see the imponderabilia which, in a war like this, will be decisive.” William Hillman, a U.S. journalist and friend of Kennedy’s, told a Foreign Office contact that Kennedy was “a professing Catholic who loathed Hitler and Hitlerism almost, though perhaps not quite, as much as he loathed Bolshevism, but he was also a self-made man who had known poverty and who did not want to know it again.” Hillman got the poverty bit wrong, but on the whole his assessment rang true. The prospect of “bankruptcy and defeat” had become obsessions in the ambassador’s mind, he said, which had the effect of making him immune to reason.12

III

In Cambridge, Jack was beginning to second-guess his “Peace in Our Time” editorial. The national debate over the neutrality legislation influenced his thinking, as did his discussions with his fellow undergraduates in the classroom, as well as his one-on-one conversations with professors. (He took four courses, all in government: Elements of International Law, Modern Imperialism, Principles of Politics, and Comparative Politics.) Though he was not ready to renounce the editorial—not yet—and he remained partial to his father’s overarching philosophy, Jack backed off his certitude and acknowledged the merits in the interventionist arguments by President Conant and others. He foreswore penning more Crimson pieces.31

It marked a reversion, in a way, to the old Jack, clinical and observant rather than mixing it up in the arena. The editorial was out of character for him, something to expect from his more strident and doctrinaire older brother. Looking back decades afterwards, Arthur Holcombe remarked of Jack that “the style of the man was formed while he was quite young….He was never a crusader, as some men are. You can pick some crusaders out of a class, while they’re still undergraduates; they have that commitment to act upon an idea, which to them is decisive of their behavior. That wasn’t the challenge to which [Jack] responded.” The issue was not lack of talent, the professor went on, for Jack had it in abundance; rather, it was a lack of direction, hardly unusual even among upperclassmen at Harvard. “Everybody knew that he was going to make a great success of whatever he turned his attention to,” Holcombe said, no doubt with the benefit of hindsight.32

For now, however, Jack kept his focus on his courses, on laying the groundwork for his thesis, and on his pursuit of women—not necessarily in that order. Frances Ann Cannon, his infatuation of junior year, remained the chief object of his affections. To his sister Kick he had revealed that he intended to ask Cannon to marry him. “Jack is taking out Frances Ann this weekend so we can all hardly wait,” Kick wrote to her father. How much his parents knew of his plan is not clear; in her memoirs, forty years later, Rose would say merely that Frances Ann was “an attractive girl in whom Jack seemed to be quite interested at that time and evidently she was interested in him, too. At least Kick seemed to be implying that some ‘announcement’ was in the offing.” Jack’s former roommate Charlie Houghton also had his eye on Miss Cannon, and he had the advantage of being a Protestant. In any event, neither suitor won his prize: when Jack and Charlie showed up together on the doorstep of Frances Ann’s apartment one evening, she introduced them to her new fiancé, an aspiring writer named John Hersey. The two Harvard men beat a hasty retreat.33

The rejection stung Jack deeply. To friends he would claim it was he who broke off the relationship, but his closest confidants—Kick, Torby Macdonald, Lem Billings—knew better.^*1 As if to compensate, he resumed playing the field more energetically than ever, and with his usual knack, astounding his Winthrop House mates with the ease with which he seemed to score date after date with woman after woman. One frequent companion was Charlotte McDonnell, a friend of Kick’s from her Catholic girls’ school; on other occasions it would be models and actresses, few of whom would get a second call and none of whom he introduced to his family. “I went to N.Y. last weekend for Thanksgiving,” he reported to Billings in late November, “—and had quite a time. Met that model Georgia Carrol[l] who is really something—and met some other good stuff.”34

McDonnell was under no illusions about her prospects. “I went out with Jack lots of times,” she remembered, “but he was never in love with me. He liked to think he was, when things were going bad and he didn’t have anyone else, but he really wasn’t. He’d come down and talk to his friends. He’d talk to Lem and he’d talk to Torby and he’d say, ‘Hey, what would you think if I married Charlotte?’ And they’d have a big pow-wow. But when it comes down to the nitty-gritty, did he ever ask me to marry him? No, he did not….We just had a good time together.”35

Just as Jack’s general disregard for women’s feelings stayed the same, his cavalier attitude toward material possessions also had not changed. Suits would be left behind on trips, driver’s licenses would disappear, library books would go missing. When another in a long line of wristwatches somehow vanished, Paul Murphy, who oversaw Joe Senior’s New York office and often paid the family’s bills, intervened on Mrs. Kennedy’s behalf:

She is very much disturbed about the loss of your wristwatch as she feels that you have lost altogether too many watches. She wants you to know she has had her gold wristwatch since she was twenty-one. She would like to have you buy an inexpensive but reliable watch to replace the one you have lost. If you can keep the new watch for about five years, she will then buy you a better one with the money received from the insurance company. Your mother has talked with your father about the above suggestion and he has agreed to it. And he has asked me to advise you that he does not want your mother annoyed with any arguments.36

In the classroom, Jack stayed on the upward trajectory he had started in his junior year. His travels overseas, often solo, had deepened both his knowledge and his engagement with global politics in all its dimensions, and he also brought to bear his broad understanding of contemporary international history, cultivated during a lifetime of serious reading. He had grown more mature, more focused, a point noted by his closest professorial contacts, Payson Wild and Bruce Hopper, who now directed him in what was assuredly the most intensive period of academic study he would ever undertake. Jack’s notes from his classes in the fall of 1939 support this notion, as he delved deeply into the twentieth-century “isms”—communism, socialism, fascism, capitalism, nationalism, totalitarianism, imperialism, militarism.

Fascism, Jack recorded, was largely pragmatic in nature, “a system built up by trial & error, by experiment and practice. Whatever survives the test of experience is valid, the rest is discarded.” Thus, both Mussolini in Italy and Hitler in Germany felt free to reverse themselves as situations warranted, whereas Stalin in Russia felt obliged to pay “at least lip service to the doctrines of Marx.” Yet the similarities between Marxism (as practiced in the Soviet Union) and fascism were obvious, not least in their brutally anti-democratic nature and their de facto one-party rule. “The [Communist] may insist that he is truely Dem. in wishing the collective rule of the people to triumph but in practice his [state] is as totalitarian & intolerant to opposition as the Fascist [state].” In practice, Jack’s notes read, “both the Soviet and Fascism system are coming closer and closer together upon the assault upon priv. capitalism. Both represent an attack on individualism, on the sense of personal dignity & freedom which is the heritage of the 19th century in the West. Both subordinate the individual to the collectivity.”37

In a case study for Wild’s international law class, Jack examined the rights and responsibilities of neutrals in wartime, through an analysis of four different scenarios. Drawing upon a range of published sources as well as a close reading of the Hague Convention of 1907, he offered nuanced and tightly argued analyses of each situation, in clear and succinct prose. With respect to neutral pilots guiding ships of belligerent nations through neutral waters, for example, he concluded that existing international law was not altogether clear but that the best interpretation nevertheless presented itself: “If they are employees of the state, it is a breach of state A’s neutrality to allow its licensed pilots to pilot the vessels of state Y to a point ten miles beyond in the high seas unless there are conditions of distress. If they are merely private individuals licensed by the state, it is not a breach of state A’s neutrality.”38

Most interesting of all, in that it seemed to disavow entirely the thrust of his Crimson editorial and to anticipate arguments in his senior thesis, was a thirty-five-page investigation of British policy toward the League of Nations in the two decades that had passed since the organization’s founding, in 1919. From the start, Jack asserted, collective security foundered on the unwillingness of the great powers to surrender national sovereignty to the decisions of the League. Even so, Britain “could have made herself the champion of small nations by standing for international law and a League policy” but refused to do so, on account of her fear of Soviet Communism and her lack of support from a standoffish United States. The Nazi threat, meanwhile, was consistently and grievously minimized as British policymakers somehow assumed that once Hitler’s territorial grievances were addressed, his power would collapse or at least be contained. “They seem to entertain the notion that when there are four Caesars in power at the same time, not one of them will ultimately succeed in conquering the world,” he wrote. “The danger lies in having one Caesar who stops only when defeated by a world coalition.”

A throwaway aside in the paper’s conclusion revealed a starkly different take on U.S. participation in the First World War than either his father’s or his older brother’s take—or, for that matter, those of most members of the class of 1940. “This is not the place to speak of America’s entry into the World War except to remark that American participation did not fail to save democracy. Had she not joined, democratic England and France would be powerless and the United States would in no way claim isolation for herself today. There is reason to believe that continued American participation in international efforts for peace and the establishment of law and order would have borne much fruit.”39

VI

The ambassador was delighted to get this news. He had long wanted his sons to become published authors. It would add luster to their résumés and enhance their reputations, as he himself had found with his slim, ghostwritten campaign volume for FDR’s reelection in 1936. “You would be surprised how a book that really makes the grade with high-class people stands you in good stead for years to come,” he wrote to Jack.70 Over the previous months Kennedy had worked tirelessly to push Joe Junior’s writings on publishers, both in the United States and in Britain, suggesting that they bring out a book-length collection of Joe’s travel letters. He even tapped his speechwriter Harvey Klemmer to help polish the material. Still, the editors politely declined. Though Joe Junior’s serious demeanor gave the impression of gravitas, his ideas as expressed on the page were at times banal and sophomoric (“Does it ever occur to people that there are happy people in Italy and Germany?”), his prose earnest and wooden. Even magazine and newspaper editors rebuffed the father’s entreaties on his oldest son’s behalf (though Young Joe did get one short piece placed in The Atlantic Monthly71). Now, with Krock’s enthusiasm for Jack’s manuscript, the second son might get his name on a dust jacket first.

Krock’s faith in the study’s publication potential was genuine, but he also had an ulterior motive: he had long seen Joe Kennedy as a man of destiny, someone to whom he ought to hitch his wagon, someone who might succeed Franklin Roosevelt—a man Krock detested—as president of the United States. Well aware of the ambassador’s ambitions for his sons, Krock wanted to please him by helping out. He also saw great potential commercial success in a memoir by Joe Kennedy focused on his ambassadorship—when he sent Jack’s thesis to Gertrude Algase’s literary agency in New York, he told Algase he had in mind a twofer: a book by the father as well as one by the son.72

The ambassador intended to give his son a thorough critique of the thesis well in advance of the revision, but real life intervened. On April 9 the Phony War came to an abrupt and violent end as the Nazis invaded Denmark and Norway, mostly in order to secure the route by which high-grade Swedish iron ore reached Germany. In the days prior, the Royal Navy had begun mining Norwegian waters in order to force freighters bound for Germany into the open sea, where they could be subject to the British blockade. But the Allies were unprepared for the bold German preemptive stroke. Nine Wehrmacht divisions, backed by the Luftwaffe, knocked out the Danes in a single day and seized control of all the southern ports and airfields in Norway. There followed two weeks of skirmishing in central Norway between German and Allied forces, with the Germans prevailing and forcing a British and French withdrawal. By late spring the whole of Norway was under German control.

Churchill had been chiefly responsible for the planning and execution of the Norwegian operation, and Joe Kennedy expected him to suffer the consequences. “Mr. Churchill’s sun has been caused to set very rapidly by the situation in Norway which some people are already characterizing as the second Gallipoli,” Kennedy cabled to FDR and Cordell Hull in late April.73 Such was the irony, however, that the Scandinavian disaster elevated Churchill’s position at the expense of Neville Chamberlain. Many in Parliament blamed the prime minister for the outcome, and on May 7 thirty-three Conservatives voted against Chamberlain’s government following a debate on the operation. One of them, Leo Amery, offered a stinging rebuke of Chamberlain that he ended by quoting Cromwell’s dismissal of the Long Parliament, in 1653: “Depart, I say, and let us be done with you. In the name of God, go!” Shaken to the core, a downcast Chamberlain departed the chamber, shouts of “Go! Go! Go!” ringing in his ear.74

King George and many Tory grandees wanted Lord Halifax to take the helm. In their eyes he was the natural choice, whereas Churchill was an unscrupulous and volatile maverick with a checkered political past. But Halifax, who had a deeply imbued sense of public service, believed Churchill would make a stronger war leader and refused the appointment. Chamberlain, hoping to the end to survive in power, recognized the game was up when the Labour Party refused to back him—on May 10, he advised the king to send for the sixty-five-year-old Churchill. The king, after one more failed attempt to get Halifax to take the post, agreed.

“We have before us an ordeal of the most grievous kind,” Churchill declared that day, in his first speech to the House of Commons as prime minister. “We have before us many, many long months of struggle and of suffering. You ask, what is our policy? I can say: It is to wage war, by sea, land and air, with all our might and with all the strength that God can give us; to wage war against a monstrous tyranny, never surpassed in the dark, lamentable catalogue of human crime. That is our policy. You ask, what is our aim? I can answer in one word: It is victory, victory at all costs, victory in spite of all terror, victory, however long and hard the road may be; for without victory, there is no survival.”75

What a time to take power! Early on the day of Churchill’s appointment, May 10, Germany launched a massive offensive in the west, with attacks on the Netherlands, Belgium, and Luxembourg. The British and French generals responded by moving their forces toward the Dyle River, in Belgium, expecting to receive the weight of the German thrust there. Instead, on the thirteenth, the first German units in Army Group A, under Gerd von Rundstedt, broke through the tightly forested and ill-defended Ardennes near Sedan, on the Meuse River, past the western terminus of the vaunted Maginot Line. A two-day battle ensued, whereupon the victorious Germans dashed into the open countryside and curved west. As historian A. J. P. Taylor would write, “When they ran out of petrol, they filled up at the local pump without paying. They occasionally stopped to milk a French cow.” On May 20, the 2nd Panzer Division, under Heinz Guderian, covered sixty miles and reached the Channel coast near Abbeville. The lines of communication between the Allied front lines in Belgium and the rear areas had been completely cut.76

The world looked on in stunned disbelief. How could this have happened? The total strength of the German military, on the one hand, and the French, British, Belgian, and Dutch forces, on the other, were after all roughly comparable. The French had more wheeled vehicles and tanks, and arguably the edge in the quality of their tanks and artillery. Even in the air, France and its allies had a comparable number of bombers and fighters to the Germans. To top it all off, the signs were abundant in the lead-up to the attack that Hitler was massing troops for an assault through the Ardennes forest. Yet now, less than a week in, the battle had the makings of a rout. In tactics and leadership, the Germans had shown themselves superior. The French general staff didn’t even fully grasp what was happening to them as radio communications broke down between General Maurice Gamelin, the overall commander, and his officers at the front.77

It got worse from there. In the north, masses of French and British troops were soon trapped in the coastal area of Calais and Dunkirk—300,000 men were pinned against the sea. They appeared to be doomed, until Hitler astonished his generals by ordering Guderian to halt (probably in a mistaken belief that Britain would wish to sue for peace). The British Expeditionary Force, and many French units, too, were able to escape from the Dunkirk beaches thanks to the heroic efforts of an armada of ships—some of them crewed by naval personnel, some manned by their civilian owners and crew—though despite later mythology, it was hardly an Allied victory.78 In the east, the Wehrmacht captured the fortresses along the Maginot Line in short order; in the center, the Allies fell back in confusion. On June 17, with the French war effort collapsing wholesale, and with German armies south of Dijon and pressing down the coastline, Prime Minister Paul Reynaud—who had succeeded Daladier three months before—resigned. From there the end came quickly. On June 22, France capitulated at Compiègne, in the same railway car used for the signing of the armistice in November 1918. In the earlier war, Germany had sacrificed a million of its soldiers over four years in a vain effort to defeat France; this time it had succeeded in six short weeks, at the cost of a mere 27,000 German lives. A jubilant Hitler, visiting Paris for the first and only time in his life, posed like a tourist before the cameras next to the Eiffel Tower.

In London, Joseph Kennedy despaired at the developments. “The situation is terrible,” he wrote to Rose on May 20. “I think the jig is up. The situation is more than critical. It means a terrible finish for the Allies.” Disappointed to see Neville Chamberlain’s government give way to one headed by Winston Churchill, the ambassador implored President Roosevelt to sue for peace on behalf of the Allies. “I saw Halifax last night,” he cabled Cordell Hull on May 24. “The situation according to the people who know is very very grim. The mass of the people just never seem to realize that England can be beaten or that the worst can happen to them….I do not underestimate the courage or guts of these people but…it is going to take more than guts to hold off the systematic air attacks of the Germans coupled with terrific air superiority in numbers….[Halifax] is definitely of the opinion that if anybody is able to save a debacle on the part of the Allies if it arrives at that point it is the President. Halifax still believes that that influence is one that the Germans still fear.”79

FDR refused the suggestion, but his ambassador had not exaggerated the sense of imminent doom on the part of Halifax and other senior British officials, and among London’s upper classes in general. “A miracle may save us,” Alexander Cadogan, the head of the Foreign Office, confided in his diary on May 21, “otherwise we’re done.” On May 25, the day after Kennedy sent his cable, the War Cabinet commenced an extraordinary three-day debate, unknown to anyone outside this tight circle, over whether to seek a negotiated settlement with Hitler, by way of Italian mediation. Halifax argued in favor: even as he conceded that the chances of gaining an agreement that preserved Britain’s independence and freedom of maneuver were slim, every political alternative, he said, should be pursued. Churchill stood in firm opposition—“peace and security could never be achieved in a German-dominated Europe,” he insisted. But the new prime minister had to move gingerly, his hold on power in these early weeks more tenuous than we tend to remember. He knew he could scarcely afford a Halifax resignation. Bit by bit, through cajolery and rhetorical flourish, Churchill won his colleagues over, and by May 28 there was agreement: Britain would fight on, alone if necessary.80

One can’t help but wonder: What if Churchill had lost the debate? What if the War Cabinet had chosen differently in those indigo days of May 1940 and Britain had sued for peace? What would have been the effect on the war, on the course of the twentieth century, on America’s standing in the world? And what would it have meant for Joe Kennedy and his family?

A few days later, Kennedy was ushered into a meeting with the prime minister, who told him that England stood next on Hitler’s list and that therefore the United States must provide more aid. “The president can’t do anything with Congress lined up against him,” Kennedy replied, “and Congress won’t act unless it feels that the American people are behind it.” The argument had always worked with Chamberlain, but Churchill barreled ahead. “The American people will want to come in when they see well-known places in England bombed,” he assured his guest. “After all, Hitler will not win this war until he conquers us, and he is not going to do that. We’ll hold out until after your election and then I’ll expect you to come in. I’ll fight them from Canada. I’ll never give up the fleet.”81

Nonetheless, another rejection soon followed, this one from Harcourt Brace. Publisher Alfred Harcourt, who like Harper saw only the original thesis, not the revised manuscript, conceded that “the boy has written a much better than average thesis,” but he questioned whether the subject matter would resonate with American readers. His chief editor agreed: the European situation was simply moving too fast to proceed with publication. Sensing a pattern with the established presses, agent Gertrude Algase changed tack and tried upstart Wilfred Funk, who had recently created a small imprint bearing his own name. Algase sent Funk the revised version and got back word immediately: he would publish. The author was Joseph P. Kennedy’s son, after all, and Algase had hinted that Henry Luce would read the manuscript and perhaps pen a foreword. Funk secured the book, paying its author an advance of $225 ($250 minus the 10 percent agent’s commission).86

A shrewd decision it was. Advance sales exceeded expectations by a wide margin, and Wilfred Funk realized he would at least recoup his investment. Whether the early interest “is just a flurry because of the youngster’s name and curiosity on the part of the book stores, we can’t tell,” Algase wrote candidly to Krock. “It probably is, and whether or not the book will renew its sale after the book shops have available copies I don’t know.” She added that the author himself left a winning impression: “Jack Kennedy is one of the nicest youngsters I’ve met, unaffected, cordial and hard-working in his own right. I’d like to watch him grow up and go places.”87

Algase would get her chance to see him “go places,” and could justifiably claim to have played a part in setting him on his way. For the book she helped shepherd into production would strike a chord among Americans and would signify for all to see that Jack Kennedy, age twenty-three and a freshly minted Harvard graduate, was his own man, not beholden to his father’s isolationist views. Indeed, he was willing to rebuke in print the core tenets of appeasement.

It was a message whose time had come. In ways not yet fully clear as Why England Slept hit the shelves in the middle of 1940, the fall of France had changed the calculus for millions of Americans, even the man in the White House. Adolf Hitler suddenly seemed poised to conquer all of Europe, including Great Britain, and meanwhile the Japanese threat grew steadily in East and Southeast Asia. Preparedness took on a whole new meaning, a whole new level of importance—could it be that the slim new volume by the ambassador’s handsome second son offered useful lessons?

II

History has little to say on how the hypercompetitive Joe Junior felt about another development that summer of 1940: his brother’s sudden literary success. To his father he offered gracious words about Jack’s book, but to a friend’s father in California he was reportedly more measured, noting that Jack had benefited from professionals’ help.10 If indeed Joe struggled with being outshone in this way, one can see why. After all, it wasn’t supposed to be like this. All his life he had been the golden child, the one who had barely emerged from the womb when his grandfather predicted he would grow up to be president. He had always been the more diligent student, the stronger athlete, whereas Jack had been content to coast along, to goof off—when, that is, he wasn’t laid up in the infirmary. For years Joe had heard his father’s voice in his ear, urging him to write a book. He had tried his damnedest to make it happen, even risking life and limb to file lengthy reports from the Spanish Civil War with the thought that these might then be gathered into a volume. No book resulted, yet now here was his brother, snapping up a contract for a senior thesis that he’d dashed off in a few months from the comfort and safety of Cambridge, then spent a few days revising for publication. Maybe Jack had the better and timelier topic, but the whole thing still seemed unfair.

Jack’s book hit store shelves on July 24. The timing was sublime, coming one month after the fall of France, three weeks after the first German daytime aerial attacks against British land targets (the communities of Wick and Hull), and two weeks after the Luftwaffe started hitting convoy ships in the Channel. The American reading public suddenly clamored for information about the war and its origins, and Why England Slept was one of the first books to offer it. Shrewdly—and brazenly, given that he had been carrying on a long-term love affair with the man’s wife—Joe Kennedy had asked Henry Luce to pen a brief foreword, and the famed publisher agreed. (First Arthur Krock of The New York Times had assisted with revisions and now the legendary head of Time Inc. contributed an introductory essay: Jack did not lack for high-powered help.)11

More and more, Henry Luce was emerging as a leading exponent of American internationalism. Isolationism, as he saw it, might have been an acceptable strategy when the nation was weak; now that it had become a full-fledged member of the great-power club—and seemed destined, by dint of geography and demography, to become the most powerful of all—such a stance would no longer do. Instead, he believed, leaders in Washington must grab the mantle of world leadership. They must defend U.S. territory, to be sure, but they must also defend and promote democratic values far beyond America’s shores, indeed to all four corners of the globe. The nation’s security depended on it.12 A few months later, in early 1941, Luce would articulate his vision in what would become one of the most influential articles in the history of U.S. statecraft. “The American Century,” it would be titled, and it would be a kind of blueprint of grand strategy for a succession of administrations, Democratic as well as Republican, John F. Kennedy’s among them. Americans, Luce would write, must “accept wholeheartedly our duty and our opportunity as the most powerful and vital nation in the world and in consequence to exert upon the world the full impact of our influence, for such purposes as we see fit and by such means as we see fit.” Even now, in the middle months of 1940, as he sat down with Jack’s book, Luce was coming to this expansive assessment of the nation’s role in the world. At the Republican National Convention in Philadelphia in late June, he helped engineer the stunning victory of Wendell Willkie, a corporate executive and an avowed internationalist, to be the party’s standard-bearer in that fall’s presidential election.13

“When the manuscript, or rather the proofs, arrived, I was very impressed by it,” Luce remembered. “At this time, of course, it was after Munich and the hot war was on. England, as they said, stood alone and the popular tendency was to put all the blame on the so-called appeasers, namely, Mr. Chamberlain and the Tory appeasers, the Cliveden Set.” Why England Slept, however, showed that blame had to be spread across nearly all levels of British society. “What impressed me was, first, that he had done such a careful job of actually reviewing the facts, the facts such as attitudes and voting records, with regard to the crisis in Europe. And I was impressed by his careful scholarship, research, and also by his sense of personal involvement, responsibility in the great crisis that was at that time in flames. And that’s what made me very optimistic about the qualities of mind and of involvement in public affairs that was displayed in this book.”14

In his foreword, Luce lauded the young author’s penetrating analysis and his crucially important concluding message: that Americans must expend every effort to prepare for the likelihood of war. “I cannot recall a single man of my college generation who could have written such an adult book on such a vitally important subject during his Senior year at college,” he enthused.15 Though the essay excoriated the pro-appeasement position of observers such as his father, Jack responded with fulsome gratitude: “The foreword is wonderful, and makes the book far more timely. Especially is this true of the point about the similarity of Chamberlain’s ‘Peace in Our Time,’ and our ‘We Will Never Fight in Foreign Wars,’ and the parallel effect that they have had on our war efforts. I missed this and it was very vital. Also, I am very glad that you gave the background regarding the American responsibility for the present situation, as it is really vitally necessary for any understanding of the problem.”16

Luce’s endorsement no doubt helped sales, although they would have been healthy regardless. Within two days, the first allotment of thirty-five hundred copies had been snapped up, and Wilfred Funk quickly arranged for a second, larger printing. By year’s end Funk could claim sales in the United States and Britain totaling well into five figures—a remarkable result for what was after all a revised undergraduate thesis. The book made the New York Times’s “bestsellers of the week” list for Boston and was a Washington Post “Reader’s Choice” selection.17 The later claim that Joe Kennedy boosted sales by buying cartons of copies that he stored in his Cape Cod basement, though plausible enough in theory (it’s the kind of thing one would expect from him), lacks evidence; even if true, it would not have made much of a difference to a book that rode a wave of highly favorable reviews, in The New York Times, the San Francisco Chronicle, The Wall Street Journal, the New York Herald Tribune, the Minneapolis Tribune, and Time, among other publications. A few discordant notes aside—some critics felt Jack was too easy on Baldwin and Chamberlain, and that he left fuzzy what exactly should be the lesson for Americans—the young author won praise for the power and nuance of his argument and the wealth of evidence he marshaled in support of it.

Some reviewers noted the titular allusion to Churchill’s earlier collection of essays, While England Slept, but for the most part they missed the key philosophical difference between the two works: whereas Churchill stressed the role of individuals in shaping history, Kennedy was clinical, impersonal, placing heavy emphasis on structural determinants. (“Personalities,” he lamented in his introduction, “have always been more interesting to us than facts.”18)

No less a figure than the president of the United States offered his congratulations. In a letter addressed to “My dear Jack,” Franklin Roosevelt wrote that he found the book lucid and perceptive, “a great argument for acting and speaking from a position of strength at all times.” Former teachers also reached out, including one from the early years. “I wish now to congratulate little ‘Jackie’ Kennedy of the Devotion School, Brookline,” wrote Mrs. Roberts. “I must confess I am very proud of your success. You are indeed a splendid example of American youth, and your success so early, I am sure, warms your mother and daddy’s heart with pride.” The old Choate headmaster himself, George St. John, lauded Jack’s book for its “restrained, scholarly, and convincing” nature. “That could have been said of the book if it had been written ten or twenty years later in light of History. Coming to the people of America now, it is the work of a patriot, a prophet, and a missionary.”19

Inevitably, the favorable publicity and heavy sales figures rubbed some people the wrong way. One detects more than a little professional envy in the pompous response of famed British economist and professor Harold Laski, onetime teacher of Joe Junior and, briefly, Jack. It would have been easy “to repeat the eulogies Krock and Harry Luce have showered on your boy’s work,” Laski wrote Joe Kennedy, but “I choose the more difficult way of regretting deeply that you let him publish it.” Labeling the work “very immature,” Laski said it lacked any semblance of structure and dwelled “almost wholly on the surface of things.”20

The sounder British judgment was that by the distinguished military historian and theorist B. H. Liddell Hart, who praised Why England Slept for the “outstanding way it combines insight with balanced judgment—in a way that nothing that has yet been written here [in Britain] approaches. It is all the more impressive by comparison with other recent books which I have read, by both English and American writers, who were apt to get led astray by superficial appearances, so that they too often miss the wood for the trees, even if they do not go astray down some by-path.” Liddell Hart, whose own book The Defence of Britain had appeared the previous year and covered some of the same ground, did identify several errors of fact or interpretation Jack had committed, but his overall assessment was praiseful—and this from a scholar infinitely more expert on the topic than was Laski.21

The British reviewers were as a group highly complimentary, a fact that gave Jack special satisfaction—he was, after all, writing about their country. John Wheeler-Bennett (who, given his association with the book, should have turned down the assignment) was effusive, commending Jack in The New York Sun for writing not as “the ambassador’s son” but “forming his opinions for himself, sifting his evidence and finally evolving a political and psychological analysis of rare penetration, with an immensely appealing quality of freshness and breadth of understanding.” A tad overheated, maybe, but basically right. Another Englishman, Nigel Dennis, writing in The New Republic, was likewise impressed: “Mr. Kennedy’s is probably the first book that tries to distribute the blame for Britain’s inefficiency in diplomacy and military preparedness among the British people generally. This is a bold departure from the common rule, and the author believes that writers who refuse to take it are fooling their countrymen as well as themselves.” Dennis acknowledged that “a more exact distribution of blame” must await a larger study, but he found it hard to deny either the book’s general thesis or the import of the topic.22

And the contribution would endure. The British historian Hugh Brogan, writing near the end of the century, conceded some shortcomings—Jack drove home some assertions too repetitiously; the assessment of the Munich Crisis did not hold up all that well—but ringingly proclaimed that Why England Slept “will always have an honourable place in the small library which the controversy about British policy under Baldwin and Chamberlain has called into being.” Like the other books on Brogan’s select list—among them Churchill’s The Gathering Storm—Kennedy’s effort was not merely a contribution to historical understanding; it was also, Brogan maintained, a political intervention, in the way it roused its American readers to the great and vital task before them: to confront the reality of the Nazi threat and prepare to meet it, with eyes wide open.23

Of course, it is in biographical terms that Why England Slept really matters to us. We care about it because of what it tells us about John F. Kennedy, age twenty-three and just out of college. And because the book is substantially the same as the thesis, we can again recall Nigel Hamilton’s assessment of the latter: “Nothing else Jack would write in his life would so speak the man.” Two things in particular stand out. First, the book marked a significant early step by Jack toward a public career. To read the book is to see that its young author was clearly fascinated by the problems of democratic leadership in foreign affairs, and the dilemmas that confront policymakers who seek to do what is required of them while not alienating their temperamental constituents. It’s a theme Kennedy would return to in a later book, Profiles in Courage, and a conundrum he would confront to the end of his days. In 1940 he was not a candidate for political office, and the book could certainly have foreshadowed a career in, say, journalism, or academia, or the law. But no contemporaneous reader of the thesis or the book could doubt that here was a potential future politician—especially if that reader also happened to be aware of his lengthy earlier course paper on Congressman Bertrand Snell. Even less can a reader of a subsequent generation fail to see the author’s future implicit in line after line—in the need for an energetic leadership that will awaken and educate the people (the 1960 campaign), for example, and in the importance of “keep[ing] our armaments equal to our commitments” (the Berlin Crisis). The theme of the 1961 inaugural seems, in Brogan’s words, “to be foreshadowed in the observation about Britain in the 1930s, that ‘there was a great lack of young progressive and able leaders. Those who should have been taking over were members of the war generation, so large a portion of whom rested in Flanders Fields.’ ”24

Second, the book represented for Jack Kennedy a political emancipation from his father. He remained the devoted son, and would stay under his father’s influence in important respects (though not as much as many later authors and documentary filmmakers would have us believe), but he showed here a capacity for independent thought that is notable—and that the father, to his credit, did not discourage. As Stephen C. Schlesinger notes in the foreword to a recent reissue of the book, Why England Slept constituted “a studied rebuke to the whole idea of appeasement—and so, in part, to his own father’s views.” (That a young man who saw Hitler’s Europe up close would abandon the pro-appeasement position isn’t surprising; indeed, the oddity is that Joe Junior, who also traversed the Continent in the lead-up to war, stayed doggedly true to Joe Senior’s outlook.) When, in August, a reporter from the Boston Herald had the temerity to ask Jack if he was a “mouthpiece” for his famous father, he offered a biting reply: “I haven’t seen my father in six months, nor are we of the same opinion concerning certain British statesmen.” Six months was about how much time had elapsed since he started serious work on the thesis that became the book. With his book, Jack had staked out his own independent position on the most pressing international issue of the day: how to respond to the menace of German power. And his audience was no longer just his father or his thesis committee, but readers everywhere.25

III

Solicitations of all kinds now flowed thick and fast into his mailbox. Some correspondents urged him to write a follow-up volume, others that he pen a series of magazine articles, still others that he take his show on the road with a major lecture tour. A New York University professor of history, Geoffrey Brown, offered his help in getting Jack connected to a big-name publisher. But Bruce Hopper, Jack’s Harvard mentor, urged caution. “Because of your years, you will be the object of all kinds of offers,” Hopper wrote him in late summer. “Beware them all.”

Of course, there are some of your readers who will assume that you got your material from your father. I know you got your material by yourself, and wrote your thesis by yourself. In the end it doesn’t matter what anyone thinks. What does matter is that you protect yourself from the pressure to lend your name to this or that cause. The public is fickle, and, in the end, ungrateful. And the public ruins its idols, yes?

I can’t imagine you getting excited over public acclaim, so this word is really unnecessary. It is just that I know your mailbox must be full of laudatory reviews, letters of appreciation, and offers (maybe even from Hollywood!). Take them all in perspective, as reward for a job well done, and then try to forget them.26

Jack took Hopper’s advice to heart, more or less. He flirted with writing a second book, this one focused on America’s role in the collapse of peace between the wars, but soon shelved the idea. He rejected requests for shorter articles and turned down myriad speaking invitations, contenting himself with granting interviews, many conducted on the phone from the family home in Hyannis Port, in between touch football games and sailing outings. Charles “Chuck” Spalding, a tall and gangly new acquaintance who in time would become one of his closest friends, recalled, on his first visit to the home, seeing Jack seated in the living room, signing copies of the book, a stack of admiring letters strewn about—one of them, from the prime minister of some country or other, was on the floor under a damp bathing suit. (Like countless other visitors, Spalding marveled at the extraordinary energy in the home as family members buzzed all around, everyone “vitally involved” in everything. It was infectious. “Right then it seemed to me this was something special,” Spalding remembered. “It is a very startling thing to run into. You can go your whole life without finding that kind of excitement.”)27

Sooner or later, the interviewers got to the question of What next? Jack had a ready answer: he would enroll in Yale Law School. Some months before, he had asked Harvard to send his transcript to the admissions office in New Haven, and Yale responded promptly to say he was in.28 But though he had made noises to Hopper and others about being interested in international law, the idea of pursuing a legal education was half-formed at best, more a postgraduate plan that sounded good and sensible than something he had thought through. To friends like Lem Billings, Jack seemed much more inclined—whether he fully admitted it to himself or not—to a career in journalism or academia or politics. For that matter, for Jack as for many college graduates that summer, the darkening world situation made all plans fluid. Was war in the offing? Would there be conscription, as the Washington bigwigs seemed to hint? (The answer would be yes: a congressional bill that September authorized the first peacetime draft.) In Billings’s recollection, he and Jack Kennedy and their peers, regardless of their immediate employment status, were merely marking time, playing the waiting game.29

Health problems also reared up to complicate Jack’s planning. In addition to experiencing the ill-diagnosed gastrointestinal issues of old, he suffered from back pain. The cause was uncertain, but he speculated it was his college football injury flaring up. He also appears to have had a malady that his doctors at the Lahey Clinic, in Boston, and the Mayo Clinic, in Minnesota (to which he returned for tests in early September), kept carefully hidden—namely, venereal disease. The urologist at Lahey, whose report said the infection occurred in the spring of 1940, effectively treated the gonorrhea but could do little with the accompanying symptoms. Jack soon complained to his older brother about the painful urination and repeated the doctors’ grim word that the urethritis would be his occasional companion for the rest of his days. For the combination of ailments, the physicians at Lahey and Mayo recommended against the stress of full-time legal studies and in favor of quiet convalescence.30

And so, in the late summer of 1940, Jack scrapped his law school plans, at least for the time being, and set out for California.31 He wanted to get his health in order in the sunshine, he told friends and family, and vowed to keep productive by auditing classes at Stanford University. Joe Junior’s friend Tom Killefer had waxed lyrical about the country-club quality of Stanford, nestled among rolling hills thirty miles south of San Francisco, and had reminded Jack that, unlike most of the Ivy League, the school was coeducational, which meant the presence of some two thousand female students (who were forbidden from walking on the quad unless they wore silk stockings). Jack had all the information he needed and headed west. It was a lark more than anything else. He intended to study business but soon found that the topic bored him, and he drifted instead into classes on politics and international relations. Even more, he drifted into student hangouts on and around campus, often pulling up in his slick new Buick convertible coupe with red leather seats, purchased with earnings from Why England Slept.32

A minor celebrity on account of his book and being the son of Ambassador Kennedy, Jack made few male friends on the overwhelmingly Republican campus (it didn’t help that he insisted on wearing an FDR button everywhere he went, or that he didn’t smoke and seldom touched alcohol), but he was popular among the coeds, who were drawn by his casual appearance and tousled hair, and by—several later said—his undeniable magnetism and sex appeal. He fell especially hard for Harriet Price, a witty and strikingly beautiful member of the Pi Phi sorority who went by the nickname of Flip and was considered a campus queen. The two drove to Carmel and San Francisco together (taking breaks en route so that Jack could get out and stretch his sore back), attended Stanford football games, went to movies, and dined at L’Omelette and Dinah’s Shack. What they did not do was have sex: Flip rebuffed his every attempt, insisting that she would not exchange her virginity for anything but marriage. “I was wildly in love with him,” she recalled. “I think Jack was in love with me…but no, he wasn’t ready for marriage.”33

Ambassador Kennedy was a frequent topic of conversation. “He talked of his father’s infidelities,” Price remembered, and clearly “knew everything that was going on in the marriage….I think his father had a tremendous influence, I don’t think there’s any question about that, but not all to the good! It seemed to me that his father’s obvious rather low opinion of his wife and the way he treated her, that some of that rubbed off on Jack. He wasn’t mean or anything about his mother, but I think that denigration, that came from the father, rubbed off on the son. And that’s where all the womanizing and everything came from!”34

Price would have felt confirmed in her view if she’d seen some of the correspondence between father and son. The letters from this period (and later) make amply clear that the ambassador expected Joe and Jack to carry on sexually in the same way he did, and to view women as little more than objects to be conquered. “It strikes me that you and Joe must have done some great work over there when I wasn’t looking,” he says in one missive, a reference to a “beautiful blonde” from England who’d contacted him to express her gratitude for Jack’s help in getting her a residence permit in the United States. Jack, for his part, after a trip to the American South earlier in 1940, reports to his father that “an awful lot of people were down—three girls to every man—so I did better than usual—the girls—having a bit of a battle at first but finished up the week in a blaze of glory.”35

The West Coast interlude is notable for one additional reason. On October 29, three thousand miles away, a blindfolded secretary of war, Henry Stimson, facing a phalanx of news cameras, reached into a large glass bowl shortly after noon to select the first draft lottery slips. He handed each slip to President Roosevelt. The eighteenth one bore the serial number 2748. “The holder of 2748 for the Palo Alto area,” reported The Stanford Daily on its first page, “is Jack Kennedy, son of Joseph P. Kennedy, U.S. ambassador to the Court of St. James’s, and student at Stanford Business School. Young Kennedy is the author of a recent best-seller on the conditions of England before the outbreak of World War II.”36

Jack Kennedy, too sick for law school, had been drafted.

To his embarrassment, the news spread far beyond the campus newspaper. Jack’s close friend Rip Horton recalled being in a movie theater in New Jersey “just at the time the draft was being put into effect—drafting men into the Army….[Jack’s] picture was flashed on the screen and I remember getting quite a kick out of it, thinking of him being drafted into the service.” There followed teasing cables and letters to Jack from various friends, all of whom could see the incongruities: not merely that their sickly friend faced a call-up, but that his father was a vociferous opponent of U.S. intervention in foreign wars.37

IV

Though Jack didn’t mention it in his correspondence with friends, one other element factored into his thinking: the association of his surname with cowardice, courtesy of his father’s ostensible routine in wartime London. In recent months, some British observers had accused the ambassador of lacking grace under fire because of his habit of retreating most every evening from the city to his sixty-room rented mansion in Windsor rather than face the German air raids in central London: the Blitz had begun on September 7 and would last until May 10, 1941. (By October the Luftwaffe had ceased daytime operations in favor of night attacks alone.)38 “Jittery Joe,” the critics called him, and soon the accusation made its way into the press. “I thought my daffodils were yellow until I met Joe Kennedy,” one Foreign Office wit sneered, and even some Americans took notice: “Once the Blitz started,” Kennedy’s aide Harvey Klemmer recalled, “he went to the country almost every night. He kept saying he had nine kids to look after, this big family he was responsible for. He took off every night before it got dark.”39

The “Jittery Joe” charge was largely bogus. By all accounts, Kennedy showed scant fear when the German bombs fell close to him, including at least once near his country home. Henry Luce remembered speaking with him on the transatlantic phone on one occasion when aerial attacks could be heard in the background; Kennedy spoke calmly and conveyed no special concern.40 What really lay behind the cowardice claim, one suspects, was British annoyance at the ambassador’s unyielding bearishness. He still believed—as did, it should be noted, a great many other informed observers on both sides of the Atlantic—that Britain faced ultimate, inevitable defeat against the Germans and should therefore seek to make peace with them.41 He failed to realize that this defeatism, and in particular his willingness to express it so openly, only served to reduce his already plummeting influence with policymakers. Winston Churchill didn’t trust him, and neither did the Foreign Office. His own government in Washington kept him out of all high-stakes bilateral negotiations, including the destroyers-for-bases agreement, sealed in early September, in which fifty aging U.S. destroyers were transferred to the Royal Navy in exchange for access to air and naval bases in British colonies. The isolation left Kennedy angry and humiliated in equal measure.^*1

“The people here keep saying their chin is up and that they can’t be beaten,” he vented in a letter to Jack in September, “but the people who have had any experience with these bombings don’t like it at all….The only thing I am afraid of is that I won’t be able to live long enough to tell all that I see and feel about this crisis. When I hear these mental midgets (USA) talking about my desire for appeasement and being critical of it, my blood fairly boils. What is this war going to prove? And what is it going to do to civilization? The answer to the first question is nothing; and to the second I shudder even to think about it.”42

Having long since grasped that he remained in London only because Franklin Roosevelt wanted to keep him from inserting himself into the hotly contested presidential campaign back home (FDR and Willkie were neck and neck in the polls), Kennedy in October took the risky step of demanding to be recalled. If the State Department did not do so, he added, aide Eddie Moore would release to the press a document containing a full and frank expression of Kennedy’s views. The ensuing hoopla, the ambassador implied, could be enough to swing the election to Willkie. It was naked blackmail, and it worked: Kennedy was summoned to Washington in late October, with instructions to make no public comment of any kind until he had met with the president. Before departure he called on the king and queen and visited Neville Chamberlain, dying of throat cancer, who whispered to him, “This is goodbye. We will never see each other again.”43

Thus came to an end, for all practical purposes, the great adventure known as “Joseph P. Kennedy, Ambassador.” He was, it must be said, miscast for the role, as some had suspected from the start. He lacked the successful diplomat’s skill at discretion, lacked a sense of history, lacked a subtle understanding of people and their motivations, lacked a feel for the abstractions of world politics. Cynical and pessimistic by nature, he tended to view political matters, including foreign affairs, mostly according to what they meant for him personally and for his family; if the same could be said for many people in this world, with Kennedy it was more extreme, more unfiltered, and left him without a broad sense of responsibility to a shared cause. Though no champion of Nazi Germany, he tolerated Hitler far longer than did most other appeasers, including Chamberlain—through the invasion of Poland, through the fall of France, through even the Blitz and the end of his ambassadorship. Some part of him even lamented the stoic fortitude of his British hosts, since the longer they endured, the greater the likelihood of a U.S. military intervention.44

For all that, Kennedy’s tenure in London was not without successes. He won deserved praise, for example, for reorganizing embassy operations to make them more efficient and productive. He was affable, vigorous, and hardworking, and his early dispatches to Washington showed that he could be an insightful observer of the British political scene. (Even seasoned State Department experts appreciated his missives, which drew on his close contacts with Chamberlain and Halifax in particular.) In bilateral trade talks he was in his element, and he proved adept at negotiating trade issues with skill and finesse. If Europe had remained in a state of peace during his ambassadorship, Kennedy might have departed triumphantly, his political future still rosy at age fifty-two; instead he left under the darkest of clouds, his prospects for high elected office shattered forever.45

His sons, though, were a different story. They still had the future open to them, even if their father’s troubles added a layer of uncertainty. Franklin Roosevelt shrewdly played to this notion at a White House dinner on the evening of October 27, nine days before the election. Since Kennedy’s return earlier that day, the speculation had been intense: would he endorse Wendell Willkie, come out for the president, or stay quietly neutral? Henry and Clare Boothe Luce and top GOP leaders urged him to declare for the internationalist Republican; Rose Kennedy argued with equal fervor that he would be condemned as an ingrate if he turned against the president now. Joe suspected she was right, and moreover he saw Willkie as barely distinguishable from Roosevelt on the pressing issues of world affairs. (To frustrated isolationists, the two candidates were the “Willkievelt twins,” whose repeated proclamations that they would keep America’s boys out of foreign wars were not to be trusted.) That evening, with Mrs. Kennedy and several others present, Roosevelt mixed charm and not-so-veiled threats. “I stand in awe of your relationship with your children,” he said, after nodding in sympathetic support as Kennedy went through his list of grievances. “For a busy man as you are, it’s a rare achievement. And I for one will do all I can to help you if your boys should ever run for political office.” According to FDR’s son James, the president then pivoted, warning that if Kennedy endorsed Willkie, he would become an outcast, his sons’ prospective political careers scuttled before they could even begin. Two days later, in an evening address on CBS Radio, Kennedy endorsed Roosevelt for another term. One week after that, Roosevelt won a decisive victory, though with lower margins than in 1932 or 1936.46

The story of Joseph Kennedy as diplomat still had one more sorry chapter. Three days after the election, he sat for a ninety-minute interview in Boston with Louis Lyons of The Boston Globe and two reporters from the St. Louis Post-Dispatch. Accustomed to the British system, where journalists typically took care to shape an interviewee’s remarks to fit within the strict borders of acceptable discourse, and assuming—he subsequently said—that his most provocative comments were off the record, Joe launched in. “Democracy is all finished in England,” he declared, and “it may be here,” too. If the United States entered the war, “everything we hold dear would be gone.” Warming up, he said he supported FDR because he was the only man who could control the “have-nots” who “haven’t any stake of ownership.” He tossed in inappropriate remarks about the queen (she had “more brains than the Cabinet” and would be the one to salvage a deal with Hitler in the end) and reminded the reporters that Charles Lindbergh’s views had a lot to commend them. To the question of whether America would refuse to trade with the Nazis if Hitler won the war, Kennedy shot back, “That’s nonsensical.”47

The story ran in the Globe on November 10, 1940, right beside the announcement of Neville Chamberlain’s death. The uproar was instantaneous, in Europe as well as in the United States. Only the Berlin Börsen-Zeitung editorialized in support. Kennedy pressured the Globe’s executives to repudiate Lyons’s story, but the damage was done.48 Kennedy officially resigned his post and retreated to Palm Beach, as convinced as ever of the correctness of his geopolitical views and resentful of the ostracism he had suffered. As he often did when feeling aggrieved, he pointed the finger at American Jews for what he saw as their outsize power in Washington and their nefarious schemes to get America into the war. He longed for some means of hitting back at his critics, and asked Jack to outline an article for him; the resulting pair of documents, belatedly and rapidly produced, one of them nine pages in length, are remarkable for what they show of Jack’s sharpening political skills and his changing relationship with his father—it was now a more complex and dynamic bond than the one Joe had with Joe Junior. Jack was his own man in a way his brother would never be.49

Jack urged his father to avoid going nasty—the high road was the only road worth traveling in this instance, not least because journalists had endless opportunities to strike back. This meant being calm and judicious and avoiding any hint of defensiveness. “I don’t mean you should change your ideas or be all things to all men, but I do mean that you should express your views in such a way that it will be difficult to indict you as an appeaser unless they indict themselves as war mongers.” Here Jack hit upon one of his main themes: the “appeaser” label was an albatross from which his father needed to free himself. And he needed also to disabuse critics of the notion that he saw little to worry about in Hitler and the other dictators of the world:

I would think that your best angle would be that of course you do not believe this, you with your background cannot stand the idea personally of dictatorships—you hate them—you have achieved the abundant life under a democratic capitalist system—you wish to preserve it. But you believe that you can preserve it by keeping out of Europe’s wars etc. It’s not that you hate dictatorships less [than the interventionists do]—but that you love America more….The point that I am trying to get at is that it is important that you stress how much you dislike the idea of dealing with dictatorships, how you wouldn’t trust their word a minute—how you have no confidence in them.50

The accompanying draft article, sketched out by the son on the father’s behalf, flowed from these judgments. “On November 6, the day after the election, I resigned from a post that I have held for nearly three years,” Jack began, before laying out the older man’s explanation for his belief in appeasement and his grim analysis of the geopolitical situation: “My views are not pleasant. I am gloomy and I have been gloomy since September, 1938. It may be unpleasant for Americans to hear my views but let me note that Winston Churchill was considered distinctly unpleasant to have around during the years from 1935 to 1939. It was felt he was a gloom monger,” Jack wrote, neatly attempting to tie his father to the Briton’s coattails. And so on the piece went, for several pages and in clear and economical prose, stressing Joe Kennedy’s faith in open diplomacy and his determination to do his level best to aid President Roosevelt in keeping the United States out of the war.51

A striking feature of the cover memo is the almost complete lack of deference. Twenty-three-year-old Jack is writing as an equal, as though addressing a colleague or friend trapped in a fraught situation. Upon mailing the items, he evidently felt the urge to say more, and so, on board a United Airlines flight from San Francisco to Los Angeles, he penned a nine-page “supplementary note,” this one hammering a simple point: the United States had no choice but to come to Britain’s aid. The isolationists in America had done grievous damage, Jack argued, for they failed to see that “if England is forced to give in by summer [1941] due to our failure to give her adequate supplies, we will have failed to meet our emergency, as England did before us. As England failed from September 1938 to September 1939 to take advantage of her year of respite due to her feeling that there would be no war in 1939, we will have failed just as greatly.” The simple reality, he went on, was that a British defeat would leave the United States “alone in a strained and hostile world,” spending huge amounts on defense and leaving voters to wonder “why we were so stupid as to not have given Britain all possible aid.”

Having thus admonished his father, Jack added a plea: “Of course, I do not mean you should advocate war, but you might explain with some vigour your ideas on how vital it is for us to supply England. You might work in how hard it is for a democracy to get things done unless it is scared and how difficult it is to get scared when there is no immediate menace—We should see that our immediate menace is not invasion, but that England may fall—through lack of our support.” History would not look kindly upon an America that followed Chamberlain’s lead, and in the future, “as we look back, we may be shocked at our present lack of vigour.” Jack loyally acknowledged that the picture of his father in the popular imagination was wrong—the older man did not oppose all assistance to Britain. But he warned that perception was reality: in the common view “you are [an] appeaser + against aid—This you have to nip.”52

Soon thereafter, following some hobnobbing in Hollywood (at one party he chatted up Clark Gable and Spencer Tracy, and he roomed for a few days with aspiring actor Robert Stack) and an academic conference in Riverside at which he served as rapporteur, Jack Kennedy left California behind.^*2 He missed his East Coast social life, missed his family. For a time he exchanged love letters with Harriet Price; as the weeks passed the letters grew more infrequent, then they ceased altogether. In one of her last notes, Harriet referred to Jack’s fatalistic view of life when she informed him that she’d almost been killed in a car accident—she was thrown out of the car yet somehow emerged unscathed. “But as you say, ‘That’s the way it goes.’ ”53

V

Dr. Sara Jordan of the Lahey Clinic, in Boston, took one look at Jack Kennedy and was aghast. It was the morning of December 9, 1940, and he had arrived in her office for an examination. The sojourn in the California sunshine, she could see, far from restoring the young man to robust good health, seemed to have had the opposite effect, as he now weighed less than before he went. He looked emaciated and drawn. Jordan insisted that Jack return to Boston after Christmas for further tests at New England Baptist Hospital and urged him to avoid any further full-time studies until fall 1941. He did as instructed, spending part of January 1941 in confinement in the hospital. From his bed there he penned a short article—his first publication since his book appeared—for the New York Journal-American, under the headline “Irish Bases Are Vital to Britain.”

Much to Jack’s satisfaction, his father had taken the advice in his December letters to heart, at least partially. When, in December, the Roosevelt administration called on Congress to pass a “Lend-Lease” bill—the United States would lend or lease military goods to the British, much as one lends a garden hose to a neighbor to fight a fire, out of compassion as well as enlightened self-interest—Joe Kennedy expressed opposition. It would be a giant step toward war, he declared. Some in the administration worried that Kennedy might go further, deploying his bottomless resources to try to thwart the plan. As the days passed, however, he shifted ground until, in a highly anticipated address on NBC Radio on January 18, he dropped his opposition. On the twenty-first, one day after Franklin Roosevelt’s third inauguration, Kennedy crushed the hopes of Capitol Hill isolationists by offering not a peep of dissent to Lend-Lease when he appeared before a congressional committee considering the bill.54

Admittedly, more than Jack’s advocacy was at work. For one thing, the elder Kennedy hoped against hope to be appointed to another high-level post in the administration, and thought it prudent to go along with the president’s wishes. For another, now that he was back on American soil, he better understood that his isolationist cause was faltering. The weight of public opinion strongly backed Lend-Lease, backed aid for Britain. Against his predictions, the British were holding on, but they were desperate for more help, and Kennedy could see that most Americans wanted to give it. They were buying the administration’s arguments, he perceived, and he saw as well the growing influence of radio correspondents such as Edward R. Murrow, whose rich, low-key, nicotine-scorched reports from wartime London kept Americans spellbound. (“This…is London,” he would begin each broadcast, a distinctive hesitation suggested by his old high school teacher.) Murrow was resolutely pro-British, and there is no doubt his broadcasts bolstered the interventionist side in the U.S. debate by stressing Winston Churchill’s greatness and England’s bravery. More than that, though, correspondents like Murrow, speaking through the blaring of sirens, the whine of aircraft, and the roar of bomb bursts, brought the war home to Americans in a uniquely powerful way, one that made them feel closely connected to sufferers an ocean away. As the writer Archibald MacLeish said of Murrow’s reports, “Without rhetoric, without dramatics, without more emotion than needed be, you destroyed the superstition of distance and of time.”55

Joe Junior, meanwhile, argued the isolationist position more strongly than ever. Intensely stubborn by nature, he could also be tone-deaf in framing his arguments, and combative to the point of recklessness. Through the winter of 1941 he railed against the Lend-Lease measure, and he didn’t let up even after Congress approved the bill by comfortable margins, in early March, thereby granting the executive branch extraordinary new powers. (The president alone would decide what to lend and to whom.) In a Ford Hall Forum in Boston on January 6, Joe insisted that the United States could not afford to bolster a doomed Britain and should instead prepare to implement a bartering system with Germany. Better to accede to Nazi domination of Europe, he went on, than to leap into a war that would strain the American economy beyond the breaking point and let loose the forces of radicalism. Late that month, Joe told another Boston audience that America should even resist sending food convoys if doing so risked pulling the nation into the war. He stuck to that position in the weeks thereafter.56

Jack thought his pugnacious brother foolhardy to speak so dogmatically on the issue, not to mention wrong on the merits. But Joe was also his sibling, so there could be no question of denouncing him. Jack contented himself during these weeks with quietly endorsing the administration’s policy and thinking about what he should do next. Planning too far ahead was pointless, he believed, as war clouds threatened both in the west and in the east. In March, he again asked Harvard to send his transcript to Yale Law School, but he seemed no more committed to the prospect of legal studies than he had been the year before, and apparently did not submit a new application. His health stabilized, he indulged his interest in travel, visiting first Bermuda and then South America, where his mother and Eunice were already touring. Jack flew from Miami to join them in Rio de Janeiro, then moved on without them to Argentina. The pro-Nazi mood in Buenos Aires stunned him, as did the palpable undercurrent of anti-Americanism. From there it was on to Uruguay and Chile by plane, then, on June 10, by cruise ship from Valparaíso back to the States, with stops in Peru, Ecuador, and Colombia, followed by passage through the Panama Canal.57

Throughout the trip there had been ominous signs that world tensions were ratcheting up still further. In the Far East, the Japanese were pushing deeper into China and strengthening their hold on Southeast Asia. In the Atlantic, meanwhile, British shipping losses to the German U-boats rose to perilous heights that spring, prompting pleas from Churchill and top White House aides for U.S. convoys. In a major speech on May 27, FDR did not call for convoys—he feared moving too far ahead of public opinion—but he left little doubt that he thought developments in the Atlantic could bring the United States into the war at almost any moment. Announcing an unlimited state of emergency, the president warned of Hitler’s global ambitions and pointed to the threats to island outposts such as Iceland, Greenland, and the Azores, from which the Nazis could launch aerial attacks on North and South America. Behind the scenes, U.S. negotiators worked to bring Iceland under American protection, and in June Roosevelt extended the U.S. defense perimeter well out into the North Atlantic.58

Then, on June 22, Hitler launched his boldest move of the war. Tossing out his August 1939 pact with Stalin, he ordered a massive assault on the Soviet Union, involving 3.2 million men, 3,600 tanks, and 600,000 motorized vehicles along a front that stretched for two thousand miles. Supporting aircraft numbered 2,500, and there was a throwback to the battles of old: 625,000 horses used for transport.59 It was the largest land operation in history. For the Western Allies the invasion, code-named Operation Barbarossa, had one salutary effect in the short term: it eased the pressure on Great Britain. It also served to draw London and Washington officials closer together and to bring the United States nearer to active participation in the Battle of the Atlantic. Roosevelt, convinced that Soviet survival was crucial to Nazi Germany’s defeat, pledged to provide Lend-Lease assistance to Stalin’s government, despite deep aversion among many in Washington to helping the Kremlin leader—who had systematically and ruthlessly purged dissidents, signed a pact with Hitler, and brutalized eastern Poland.

It was a stunning development, changing the whole complexion of the war. Earth-shattering events had passed in a blur. Jack, still on his cruise ship en route home, was pondering the implications when there arrived news of a more personal nature: his brother had volunteered for military service! It seemed unthinkable: through April and into May, Joe Junior had continued his strident anti-war and anti-administration rhetoric, insisting in an address at Temple Ohabei Shalom, in Brookline, on April 29 that it would be “perfectly feasible for the United States to exist as a nation, regardless of who wins the war.”60 American escorts for ships carrying Lend-Lease aid would be a terrible mistake, he had added, as it would inevitably lead to the sending of men. Yet mere weeks later, this co-founder of the Harvard Committee Against Military Intervention, this frequent admirer of Hitler’s Germany, this fervent proponent of America First principles, opted to forgo the final year of law school and sign up for the Naval Aviation Cadet Program of the U.S. Navy Reserve.

Joe Senior was dumbfounded. His firstborn not only had volunteered but had chosen the most dangerous branch of service, naval aviation. The Ambassador (as he was now often called, even as a private citizen) offered to pull strings and get Joe assigned to a desk job in the Office of Naval Intelligence, in Washington, but his son refused. For months it had infuriated him that people were questioning the Kennedys’ courage, were leveling snide accusations against his father. How dare they? What did they know about bravery? He would prove them wrong by becoming a Navy flier. Joe Senior, knowing better than to stand in his proud son’s way, gave his blessing. “My father, especially, approves of what I’m doing,” Joe told the press, in a revealing exaggeration. “He thinks I’m doing what I should be doing, and he’s glad for it.” In late June, Young Joe was inducted, along with FDR’s youngest child, John, and several other would-be aviators from Harvard. They became seamen second class, at a pay rate of $21 per month. Joe’s physical examination at Chelsea Naval Hospital, in Boston, showed him to be in sterling physical shape—he stood five feet eleven and weighed a robust 175 pounds, and without a single blemish on his health record.61

Jack knew what he must do: he had to follow suit. He promptly volunteered for the Army Officer Candidate School, but failed the physical on account of his bad back. He then tried the Navy, with the same result. He vowed to press on, and in Hyannis Port that summer he embarked on an exercise regimen to strengthen his back, in anticipation of his next attempt to enlist. How effective the workouts were, he couldn’t tell, but he felt good overall, free to enjoy his favorite place and time: the Cape in the summer. An early highlight was the Fourth of July weekend—always a time of special celebration in the Kennedy household, with a festively decorated porch and a long wooden table piled high with summer delicacies. The scene was frenetic as always, and filled with laughter. Jack and his siblings loved it, but on this holiday their father found himself worrying that his worst fears were coming true: a war he detested was drawing ever closer to America, and one son had already enlisted, with a second determined to join him. Fifteen-year-old Bobby was not too far behind, and Kick and Eunice were musing aloud about joining the Red Cross or even the Women’s Army Corps. If U.S. intervention came, Joe wondered, would there ever be another family gathering like this one?

There were more fun times in that sun-drenched Hyannis summer—the touch football games on the sloping lawn, the board games, the movie nights, the outings to Rexall’s for ice cream. Joe Junior was around a lot, commuting on weekends from his training base at Squantum, near Boston. Visitors came and went. Torby Macdonald showed up, which was unexceptional except that his letters to Jack, always playfully sarcastic, had of late taken on darker tones, the sarcasm more biting, more caustic, as though he resented Jack’s successes. The two also disagreed politically, with Torby espousing pro-appeasement and indeed even pro-German views.62 Lem Billings came, too, of course, as did John Hersey. Chuck Spalding, ever observant, marveled anew at the spectacle he had first encountered the summer before, one he found at once unique and quintessentially American. “It was a scene of endless competition, people drawing each other out and pushing each other to greater lengths. It was as simple as this: the Kennedys had a feeling of being heightened and it rubbed off on the people who came in contact with them. They were a unit.”63

That they were—an extraordinary constellation of eleven handsome and energetic people, close-knit and loving, protective of one another, living under one roof in the three-gabled house overlooking Nantucket Sound. But not for much longer. The patriarch was right to feel a sense of foreboding: that summer of 1941 would be the last time his family was all together.

III

IV

V

Already now, he went on, Americans should think about the attitudes they would adopt after the guns fell silent: “Weary of war, we may fall ready victims to post-war cynicism and disillusionment, as we did at the end of the last war.” It would be a dreadful mistake, for victory would be no less consequential for being incomplete. “Even if we may not win all for which we strive—even if we win only a small part—that small part will mean progress forward and that indeed makes our cause a worthy one.” Then a ringing finale: Americans must strive, like their forebears, to reach for that goal, to “renew that heritage” and maintain that idealism, even in the face of great odds. “The sacrifice is not too great,” the young ensign declared. “As young men, it is, after all, for our own future that we fight. And so with a firm confidence and belief in that future, let us go forward to victory.”58

Would he himself get to contribute to that good fight? It seemed doubtful, given his infirmities, but through the spring he persistently lobbied for combat service. In late July 1942, there finally came welcome news: he was being transferred to midshipmen’s school at Northwestern University, in suburban Chicago. On the way there, he stopped once more in Washington and called Inga. She again refused to sleep with him but agreed to meet the next day. His physical condition shocked her. In a phone call to a friend monitored by the FBI, she said, “He is going on active sea duty. Only you know, his back—he looks like a limping monkey from behind. He can’t walk at all. That’s ridiculous, sending him off to sea duty.”59

One wonders about the mood overall of the young men who reported on that first day of midshipmen’s training. The war news had been mostly grim since Pearl Harbor. In the months after the attack, the area of Japanese conquest spread like spilled ink on a map—Hong Kong and British Malaya fell in December 1941, followed by Singapore in February, then Burma and the Dutch East Indies (Indonesia), then the Philippines. The U.S. bases at Guam and Wake Island also succumbed.60 Meanwhile, China grew weaker and India appeared threatened, as did Australia. In the Atlantic, German submarines were sinking ships faster than the Allies could replace them (in the first months after America’s entry into the war, the U-boats sank 216 vessels, some so close to U.S. shores that people could see the glow of burning hulls), while on land the German forces resumed their advances in Russia and the British defense of Egypt faltered. By the spring of 1942, the Axis powers controlled more than a third of the world’s population and mineral resources. It seemed only a matter of time before the Wehrmacht would be at the gates of India, to be met there by ally Japan, advancing from the east. In June, Jack and his mates in Charleston cheered the epic U.S. naval victory against Japan in the Battle of Midway, but the decisive nature of that encounter would become clear only in time.61

Despite the Japanese advances in the Pacific, Roosevelt’s war strategy was “Europe First,” a commitment he affirmed in a conference with Winston Churchill in Washington a few weeks after Pearl Harbor. In the president’s view and those of his chief advisers, Germany represented a greater danger to the United States than did Japan. If Hitler conquered Stalin’s Soviet Union, they felt certain, he would pose an acute existential threat to U.S. security. American planners also worried that the USSR, suffering almost unimaginable losses in the face of the Wehrmacht’s ferocious power, might pursue a separate peace with Nazi Germany and consequently shred the Allied coalition. Washington must therefore work first with Britain and the Soviet Union to defeat the Germans, then confront an isolated Japan.

But there would still be plenty to do in the Far East in the short term, and it was the likely destination for Ensign Kennedy, given the heavy naval effort there—provided he could get through his training program. He pronounced himself less than impressed by the curriculum and the facilities. “This goddamn place is worse than Choate,” he informed Lem Billings, “and Lt. J. makes Jack Maher look like a good guy—well maybe not a good guy, but a better guy. But as F.D.R. always says, this thing is bigger than you or I—it’s global—so I’ll string along.” Jack added that he wanted to command one of the motor torpedo boats, or PTs (for “patrol torpedo”), as they were popularly known. “The requirements are very strict physically—you have to be young, healthy and unmarried—and as I am young and unmarried, I’m trying to get in. If I last we get command of a torpedo boat—and are sent abroad—where I don’t know.”62

Jack’s desire for a PT command likely owed something to the remarkable publicity a handful of torpedo boats in the Philippines had received in the United States after the Japanese invasion. The papers were full of tales of the heroic deeds of these small craft and their skippers, in particular Lieutenant Commander John Bulkeley, who had won a Congressional Medal of Honor for extracting General Douglas MacArthur from the fighting on the Bataan Peninsula, in the Philippines, in March and transporting him back through five hundred miles of Japanese-dominated waters to safety. Bulkeley, a self-aggrandizing but extremely skillful promoter of the PTs, had exaggerated mightily in selling their importance to FDR and the American public. Jack bought into the hoopla. His natural skepticism made him dubious that the lightly armed vessels were inflicting as much damage on the Japanese as Bulkeley claimed, but there was an undeniable swashbuckling quality to the PT missions that appealed to him. The boats had glamour, pure and simple. And if commanding a torpedo boat got him away from the tedium of office work or—he imagined—toiling as a subordinate on a destroyer or aircraft carrier, so much the better.

And there was, one imagines, one additional reason for his attraction: on a summer day the previous year, Jack had sailed his beloved sloop Victura from Hyannis Port across Nantucket Sound and into Edgartown, on Martha’s Vineyard. When he entered the harbor, he spied a sleek new type of vessel he had not seen before: a PT boat the Navy had brought from Newport and put on display. Mesmerized by her trim lines and powerful aura, Jack had the urge in that instant to hop on board, take the wheel, and open the throttles wide. Now perhaps he could get his opportunity.63

Then again, the chances of Jack Kennedy becoming a PT commander should have been vanishingly small, even leaving aside his bad back. The competition was fierce, with more than a thousand applicants for fifty slots. Yet Jack was tapped, thanks in large measure to an assist from his father, who invited Bulkeley to a leisurely lunch at the Plaza Hotel, in New York, and asked him if he had the power to get Jack into a torpedo boat. Bulkeley said he did, and promised to interview Jack when he returned to Northwestern. Joe expressed his thanks, adding that he hoped his son would be sent someplace that wasn’t “too deadly.” Jack performed well in the ensuing interview, impressing Bulkeley and Lieutenant Commander John Harllee with his obvious intelligence and leadership qualities, and with the fact that he had grown up around boats and was an expert sailor who had won a regatta for Harvard. Questions regarding his physical health did not come up.64

To Harllee’s mind there was nothing wrong with Joe Kennedy lobbying on his son’s behalf: “There’s a lot of people in America who use political influence to keep out of combat,” he told a later interviewer, “but Jack Kennedy used it to get into combat!”65

“He was in pain,” a roommate remembered, “he was in a lot of pain, he slept on that damn plywood board all the time and I don’t remember when he wasn’t in pain.” But Jack relished the training, most of it in Elco motor torpedo boats of the PT 103 class. Low and squat and measuring eighty feet in length, with a twenty-foot, eight-inch beam, the vessels had wooden hulls and were powered by three twelve-cylinder Packard engines, each with 1,350 horsepower, allowing a speed of forty-three knots. Each carried four twenty-one-inch torpedoes and four .50-caliber machine guns on two twin turrets, as well as depth charges, rocket launchers, and mine racks. A normal complement was two to three officers and nine men. Jack, comfortable on the sea from his many years of sailing off the Cape, loved handling the boats, and he loved their speed. Most of all, he cherished the freedom they brought. “This job on these boats is really the great spot of the Navy,” he crowed to Lem, “you are your own boss and it’s like sailing around in the old days.”67

Even the evident inadequacies in the training—the men received little instruction on the handling and use of torpedoes and virtually no nighttime training, though it was well known that the PT boats were too vulnerable to enemy aircraft to operate except under cover of darkness—didn’t deter him, and he impressed his mates with his seafaring skills and intelligence as well as his self-deprecating wit and lack of pretension. He was “receptive to everybody,” recalled Sim Efland, a roommate, and in no way “a stuck-up individual” with a superior attitude. “When I think of my association with Jack: he associated with people no matter who—and that was unusual. Here I was, a southerner, and all these other people from Harvard, Yale, and these other places would give me hell. Say, ‘We can’t understand what you’re talking about, you don’t talk like we do, you talk too slow,’ or something. Now Jack didn’t do that. He respected people. He was also a good analyst, I felt….I had a lot of respect for him.”68

Another roommate, Fred Rosen, likewise held Jack in high regard, notwithstanding one rocky episode in their Quonset hut. As Rosen recalled in an interview many years afterwards, Jack one evening observed casually that Jews were all “going into the Quartermaster Corps” in order to avoid combat. Rosen, who was Jewish, bristled. “They must be good at trigonometry, Jack,” he shot back. “Why?” “Because the navy’s navigators are drawn from the Quartermaster Corps.” An extended exchange followed, in which Rosen persuaded Jack to recant his anti-Semitic assertion. To Rosen, Jack’s casual, unthinking prejudice likely owed much to his father’s pontifications around the family dining table over the years, and he admired Jack all the more for his willingness to admit his error.69

At the end of the eight weeks, in late November, John Harllee, the senior instructor, graded Jack superior in boat handling, good in engineering, and “very willing and conscientious.” So impressed was Harllee that he selected Jack to be a PT instructor, which meant he would remain stateside for a minimum of six additional months instead of getting a combat assignment. (It’s possible there was more involved in the decision than Jack’s stellar performance: his father had made clear to Bulkeley and perhaps to Harllee his anxiety about seeing his sons in combat.) Far from being flattered or relieved at the news, Jack reacted angrily, insisting that he be sent overseas to one of the war zones. (He was being “shafted,” he said to his Navy pals, who promptly gave him the nickname “Shafty.”) Harllee refused to bend. “I told him that we needed people of his ability for instructors. I absolutely insisted that he remain, which made him extremely unhappy.”70

Jack did not give up. With the help of his grandfather Honey Fitz, he arranged a one-on-one meeting with Massachusetts senator David I. Walsh, the chairman of the Senate Naval Affairs Committee. Walsh liked what he saw—“Frankly, I have not met a young man of his age in a long time who has impressed me so favorably,” he wrote to Honey Fitz. “He has a fine personality, energetic and outstanding qualities of leadership, and with all a becoming modesty”—and urged the Navy Department to transfer Jack to a combat zone.71 The appeal evidently had an effect, for in January 1943 the young officer was detached from his Melville duties and ordered to take four boats to Jacksonville, Florida, and await further instructions on his next assignment. En route to Florida, one of the boats ran aground and Jack dove into the freezing water to clear a towrope that had become tangled in a propeller. He became ill and was laid up in Morehead City, North Carolina, with a temperature of 103, but soon recovered and rejoined his flotilla in Jacksonville. Expecting a combat assignment (“Am on my way to war,” he wrote to brother Bobby, who was in his final year of prep school), Jack learned, to his annoyance, that he was being sent not to a war theater but to patrol duty at the Panama Canal. He again turned to Senator Walsh, who again wrote on his behalf.72

How to explain this unrelenting determination to see military action? More than a few fellow draftees, after all, whatever their subsequent claims to the contrary, were quite content to wear the uniform in safer locales, far from enemy concentrations—locales like, well, Panama. Was it because he felt invincible, as young men often do? This seems unlikely, given his checkered health history and that, even this early in the war, he was writing sober letters about college chums who had been killed or were missing in action. Did he want a war record on which he could later run for political office? Again, maybe, though it seems far-fetched to believe that this calculation drove him, even if one folds in a perceived need to overcome any lingering “Kennedys are cowards” whispers arising from his father’s actions in London during the Blitz. No, the real answer seems more basic: Jack’s long immersion in world politics, through reading and writing and travel, together with the inspirational exhortations of people like James Forrestal, John Bulkeley, and Clare Boothe Luce, had convinced him that this was a crusade against totalitarianism, in which the future of Western civilization was at stake and in which all must do their part. Thus he applauded Lem Billings (who had been rejected by the Army and the Navy because of his poor eyesight) for getting himself close to combat as an ambulance driver in North Africa, and Rip Horton for contemplating switching from the Quartermaster Corps to a paratrooper role. And thus he cheered brother Joe’s efforts to become a Navy flier.73

Senator Walsh’s intervention did the trick. On March 6, 1943, Lieutenant John Fitzgerald Kennedy boarded the troop carrier Rochambeau on pier 34 in San Francisco, bound first for San Diego for a troop pickup and then for the New Hebrides, eleven hundred miles northeast of Australia. He was on his way to the war.