A few hours away from his sister yet somehow worlds apart, Jack passed his spare time in Charleston writing notes and letters to family and friends on the war situation, wondering if and when he would get to enter the fray. At times he turned more philosophical, as when he mused to sister Kick on the meaning of the fall of Singapore, Britain’s supposedly impregnable base in Southeast Asia. “After reading the papers, I would strongly advise against any voyages to England to marry any Englishman,” he wrote, referring to Kick’s great love Billy Cavendish. “For I have come to the reluctant conclusion that it has come time to write the obituary of the British Empire. Like all good things, it had to come to an end sometime, and it was good while it lasted. You may not agree with this, but I imagine that the day before Rome fell, not many people would have believed that it could ever fall. And yet, Rome was ready for its fall years before it finally fell, though people, looking only at it through the rosy tinted glasses of its previous history, couldn’t and wouldn’t see it.” France, too, he went on, had become a second-rate power long before her crushing defeat in 1940, and Britain was on the “toboggan” of irreversible decline.50

He received a boost from a letter his father had received from former paramour Clare Boothe Luce, which Joe then forwarded to Jack. Luce, who had met with Jack some weeks before, worried that the elder Kennedy’s gloomy worldview was rubbing off on his children, especially his “darlyn” second son. Jack, she wrote, “has everything a boy needs to be a great success in the world, and one of the things that gives me comfort is the thought that no set of circumstances can lick a boy like Jack…and surely there are a lot of Jacks left in America, so we will be saved.” At the same time, however, “he is vaguely unhappy about your pessimism. It alarms him (‘so unlike Dad’) and dispirits him, and I do think that you…and I have no right to add the burden of doubt to the other burdens that he, and a million like him, must carry from here on out.” Luce went on to summarize the geopolitical situation and to call on Americans to grab hold of the challenge before them, and to fight to the utmost.51

Her analysis even made its way into a draft article (never published) that Jack pecked out on his typewriter in mid-February. Emphasizing the grave situation confronting the United States, he exhorted his compatriots to fight, for this war was “a serious and long business” that could not be run as a political battle. If Japanese forces prevailed against Singapore and the Dutch East Indies, “the Indian Ocean would become a Jap lake, and the Japanese position would approach invincibility.” And if, in the meantime, the Germans pushed through to the Persian Gulf via Turkey, “the first phase of the war would be ended in defeat. The situation facing the Allies then would be a question of gloomy alternatives. Churchill would be thrown out of office on the recoil of these double defeats and undoubtedly appeasement forces would be busy in Britain. The tremendous strength of the German-Japanese position would make Britain feel that providing she could be given suitable guarantees in regard to the empire, peace would be preferable.”

Thus, the stakes could hardly be higher, but Jack warned that the American people “might not be willing to make [the necessary] sacrifices for victory. The fundamental isolationism of [the] American character, the feeling of invulnerability bred in their bones by centuries of security behind the broad expanse of the Atlantic and the Pacific Oceans; this feeling, strengthened by the presence of a large army and navy, and air force, might cause it to prefer peace, however fitful.” It was a concise summary of his father’s philosophy, but Jack said it must be resisted, even if the outcome was gravely in doubt. He concluded, “We are embarked on a war that will bring either certain defeat or such blood, such sweat, and such tears that no one in America from the White House to the man in the street has ever imagined.”52

Much to his consternation, Jack’s back problems grew more severe that spring of 1942, prompting a Navy doctor at the South Carolina base to declare him unfit for duty. The pain was not constant but would come and go, though with sufficient frequency that in May he received authorization to travel to the naval hospital in Chelsea, Massachusetts, for further evaluation and treatment. While there, he also met with specialists at Boston’s Lahey Clinic. Surgery was discussed, but everyone understood that it could bring an end to Jack’s military career. Besides, the Navy doctors were not convinced an operation was necessary. They found no ruptured disk and surmised that tight muscles in the legs and “abnormal posture consequent thereto” were responsible for the pain. Instead of going under the knife, Jack would be prescribed a regimen of exercise and massage.53

Ironically, many people in this period remarked on his robust physical appearance. “You can’t believe how well he looks,” Rose Kennedy wrote to Joe Junior. “You can really see that his face has filled out. Instead of being lean, it has now become fat.” Quite possibly, this was on account of the steroid therapy Jack appears to have begun some time before, in order to deal with his ulcerative colitis. Still in an experimental stage, with little understanding of proper dosage or possible side effects, corticosteroids may have worked as desired on the colitis, but at the possible price of back and adrenal problems. In 1947, Jack would be officially diagnosed with Addison’s disease, an illness of the adrenal glands characterized by a lack of the hormones necessary to regulate blood, potassium, and sugar; it’s possible that his use of the steroids contributed to the disease.54

On June 24, en route back to South Carolina from Boston, he made a late-night stop in Washington, D.C., in hopes of seeing Inga. He called her shortly after 1:00 A.M. and asked if he could come over. She refused but, according to the FBI, was affectionate in words and tone. She also declined to see him off at the airport later in the day, but promised to stay in touch. Jack’s feelings for her had not diminished, and he called Kick frequently to muse aloud over what might have been. Yet his well-honed ability to compartmentalize had not disappeared, for to others in the family he showed his usual devil-may-care self. His clever wit, as well as his contemplative side, came out in a letter to his mother, one whose playful opening sentence suggests he did not yet know the full seriousness of Rosemary’s condition:

Thank you for your latest chapter of the “9 little Kennedys and how they grew” by Rose of Old Boston. Never in history have so many owed so much to such a one—or is that quite correct? If you would look into that little book of yours under Churchill, Winston—I imagine you can check it.

They want me to conduct a Bible class here every other Sunday for about ½ hour with the sailors. Would you say that is un-Catholic? I have a feeling that dogma might say it was—but don’t good works come under our obligations to the Catholic church? We’re not a completely ritualistic, formalistic, hierarchical structure in which the Word, the truth, must only come down from the very top—a structure that allows for no individual interpretation—or are we?55

The letter was one sign among several that Jack had begun asking probing questions about his religious faith and his church. According to John B. White of the Times-Herald, Kick Kennedy confided to him in early May that Jack had experienced a crisis of faith and seemed on the verge of renouncing Catholicism. Perhaps his awareness—however incomplete—of Rosemary’s situation disillusioned him, and perhaps his subsequent breakup with Inga, in which Catholic dogma certainly played a role (she was married, and a Protestant), also contributed. Or perhaps his questioning mostly reflected something more ordinary: a grown person’s effort to make sense of the teachings inculcated in him as a child. Most people of faith will go through such phases from time to time—belief and doubt, after all, go together in intelligent minds. Whatever the case, Jack did not abandon his Christian faith or his Catholicism that spring—he continued to attend Mass faithfully, and even in the White House he got on his knees to pray before bed—but he would continue throughout his life to question aspects of organized religion. The black-and-white world of his mother he could never quite recognize; he saw too many shades of gray.56

One day around this time, passing a church, he said to Chuck Spalding, “How do you come out on all this?” Spalding, who had been raised a Catholic, responded that he’d never taken the time to figure it all out; if he did, he guessed he would conclude by saying, “I don’t know.” Jack replied that he would say the same thing.57

Jack’s serious side also came out in a stirring speech he delivered in Charleston during an induction ceremony for new recruits, timed to coincide with a July 4 Independence Day celebration. (Why he was tapped to give it is not clear.) “For What We Fight,” he titled the address, and he began by praising the Founding Fathers and the Declaration of Independence. “Some may argue that the ideals for which we fight now, those embodied in the Atlantic Charter and the Four Freedoms, are…impossible to achieve,” Jack allowed, pointing to a world aflame with war and misery. But he insisted on the need to hold to these ideals, come what may. “A world which casts away all morality and principle—all hopeless idealism, if you will—is not a world worth living in. It is only by striving upward that we move forward.”