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.
On the beach in Hyannis Port, September 1931. From left: Bobby, Jack, Eunice, Jean, Joe, Rose, Pat (in front of Rose), Kick, Joe Junior, and Rosemary.
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.