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 and Jack, winter 1934.
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 bei
ng 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 a
nd 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
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