CHAPTER 2

Privileged Youth

Youth [is] not a time of life but a state of mind… a predominance of courage over timidity, of the appetite for adventure over the love of ease.

—Robert F. Kennedy (1966), borrowing from Samuel Ullman, “Youth” (1934)

AS HE GREW UP, Jack Kennedy came to understand that being the second son of one of America’s richest and most famous families set him apart from the many other privileged youths he knew. The Cabots, Lodges, and Saltonstalls were better-known Boston clans; the Carnegies, Rockefellers, and Vanderbilts were wealthier; and the Adamses, Roosevelts, and Tafts were more prominent as political dynasties. But the Kennedys were also a recognizable national force, a next generation ready to take on the world. And if Joe Kennedy were ever to become president, Life magazine said in 1938, his appealing children would have played a significant part. “His bouncing offspring make the most politically ingratiating family since Theodore Roosevelt’s.” They were a symbol of hope to the country’s millions of ethnics and its more established middle class who remained wedded to the belief—even in the worst of economic times—that anyone with exceptional talent and drive could still realize material opulence and public eminence exceeding the ordinary promise of American life.

JACK’S FIRST MEMORIES from 1922–23 were associated with the Naples Road house and attendance at the local public school, Edward Devotion. In 1924, Joe Jr., now nine, and Jack, age seven, were sent to a local private school, Dexter, where—unlike Devotion, which had shorter hours—they would be supervised from 8:15 in the morning until 4:45 in the afternoon. This schedule freed Rose to give more attention to Rosemary, whose retardation mandated home tutoring. The boy’s mother also saw Dexter as a guard against the mischief—the “state of quixotic disgrace,” she called it—for which Joe Jr. and Jack had an obvious affinity. To their father, Dexter, the successor to the discontinued lower school of the prestigious Noble and Greenough School, would bring his sons together with their Beacon Hill counterparts, the offspring of Social Register families such as the Storrows, Saltonstalls, and Bundys.

Jack’s first ten years were filled with memories of Grandpa Fitz taking him and Joe Jr. to Red Sox games, boating in Boston’s Public Garden, or on the campaign circuit around Boston in 1922, when the old man made a failed bid for governor. There were also the childhood illnesses from bronchitis, chicken pox, German measles, measles, mumps, scarlet fever, and whooping cough that confined him to bed, where he learned the pleasure of being read to by Rose or reading on his own about the adventures of Sinbad the Sailor, Peter Pan, and Black Beauty. His favorites were Billy Whiskers—the escapades of a billy goat that traveled the world and “which Jack found vastly interesting”—and Reddy Fox, one of various animals “mixed up in a series of simple, but… exciting adventures.” Jack was also drawn to the stories of adventure and chivalry in Sir Walter Scott’s Waverley novels, to biographies of prominent characters, and to histories, “so long as they had flair, action, and color,” Rose recalled. He read and reread King Arthur and the Round Table.

Young Jack regularly took morning walks with Rose and one or two of his siblings to the local shopping area, the five-and-ten, and the parish church, which Rose explained was not only for Sunday or special holidays but part of a good Catholic’s daily life. And there were the summers away from Boston, first at Cohasset, a Protestant enclave on the South Shore, where the family met a wall of social hostility in 1922, including Joe’s exclusion from membership in the town’s country club, then at the Cape Cod villages of Craigville Beach in 1924 and Hyannis Port, beginning in 1926, both more welcoming. Traveling to the Cape in Joe’s chauffeur-driven Rolls-Royce, the Kennedys rented a two-and-a-half-acre estate overlooking the Hyannis Port harbor. There, Jack learned to swim and enjoy the outdoor activities that became a constant in the family’s life.

“It was an easy, prosperous life, supervised by maids and nurses, with more and more younger sisters to boss and to play with,” Jack told his 1960 campaign biographer, James MacGregor Burns. When later asked if anything really bothered him as a child, Jack could only think of his competition with Joe. Their games and roughhousing on the front porch occasionally descended into hostilities that disrupted their strong mutual attachment. “He had a pugnacious personality,” Jack said about his brother. “Later on it smoothed out, but it was a problem in my boyhood.” A young woman Jack dated as a teenager remembered that whenever they were alone, Jack would talk about his brother. “He talked about him all the time: ‘Joe plays football better, Joe dances better, Joe is getting better grades.’ Joe just kind of overshadowed him in everything.”

Joe Jr., bigger and stronger than Jack, bullied him, and fights between the two—often fierce wrestling matches—terrified younger brother Bobby and their sisters. Jack particularly remembered a bicycle race Joe suggested. They sped around the block in opposite directions, meeting head-on in front of their house. Never willing to concede superiority to the other, neither backed off from a collision that left Joe unhurt and Jack nursing twenty-eight stitches. Joe Jr. patiently instructed all his younger siblings in the rules and techniques of various games, except for Jack. A football handoff became an opportunity to slam the ball into Jack’s stomach “and walk away laughing as his younger brother lay doubled up in pain.” Jack, who refused to be intimidated, developed a hit-and-run style of attack, provoking Joe into unsuccessful chases that turned Jack’s flight into a kind of triumph.

But for all the tensions, Jack thought Joe hung the moon. When Joe went to summer camp in 1926, the nine-year-old Jack briefly enjoyed his temporary elevation to eldest sibling. But as Joe Sr. noted, Jack was soon pining for his brother’s return and made his father promise that he could accompany Joe Jr. the following summer. Jack later remembered that there was no one he would “rather have spent an evening or played golf or in fact done anything [with].” Still, a rivalry remained. In November 1929, when Joe Jr. returned home for Thanksgiving from his first term at boarding school, Jack took special pleasure in recording his triumphs over his dominant brother. “When Joe came home he was telling me how strong he was and how tough,” Jack wrote their father. “The first thing he 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 threw him over on his neck.” Jack also crowed over the paddling the sixth formers (the seniors) at the school gave Joe, who “was all blisters…. What I wouldn’t have given to be a sixth former.”

The backdrop for all this was no longer Brookline. In September 1927, when Jack was ten, the family had moved to Riverdale, New York, a rural Bronx suburb of Manhattan. Joe had become a force in the film industry, and his ventures took him between New York and Los Angeles, so there were sensible business reasons for the relocation.

But Joe’s frustration with Boston’s social barriers had as much to do with the move to New York as convenience. Boston “was no place to bring up Irish Catholic children,” Joe later told a reporter. “I didn’t want them to go through what I had to go through when I was growing up there.” But unwilling to completely sever ties to the region that both he and Rose cherished, Joe bought the Hyannis Port estate they had been renting, ensuring that the family would continue to spend its summers on the Cape.

The move to New York was not without strain. Despite being transported in a private railway car and moving into a thirteen-room house previously owned by former Secretary of State Charles Evans Hughes in a lovely wooded area overlooking the Hudson River, Rose remembered the change as “a blow in the stomach. For months I would wake up in our new house in New York and feel a terrible sense of loss.” Her distance from familiar surroundings, friends, and family made for a painful transition. The ancestors in the North End tenements would have puzzled over her hardship. A second move in 1929 into a mansion on six acres in the village community of Bronxville, a few miles north of Riverdale, where the average per capita income of its few thousand residents was among the highest in the country, was more to Rose’s liking.

Jack had quickly settled into the private Riverdale Country Day School, where he excelled in his studies in the fourth and fifth grades. In the sixth grade, however, when Joe Jr. went to the Choate boarding school in Wallingford, Connecticut, Jack’s work suffered, falling to a “creditable” 75, a February 1930 report stated. Despite his undistinguished school record, or possibly because of it, Joe and Rose decided to send Jack to boarding school as well. But instead of Choate, Rose enrolled Jack in the Canterbury School in New Milford, Connecticut, an exclusive Catholic academy staffed by fourteen Catholic teachers for ninety-two students. Of the twenty-one students in the school’s 1930 graduating class going to college, seven went to Yale, seven to Princeton, and one to Harvard.

Although attending a boarding school marked Jack as a privileged child, he did not appreciate being sent so far away from home. (It would not be the last time Jack felt the burdens of privilege.) “It’s a pretty good place,” he wrote a relative, and “the swimming pool is great,” but he saw little else to recommend the school. He was “pretty homesick the first night” and at other times thereafter. The football team looked “pretty bad.” Worse, “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.” His attendance at chapel every morning and evening would make him “quite pius [sic] I guess when I get home,” he grudgingly told Rose. He also had his share of problems with his classes. English, math, and history were fine, but he struggled with science and especially Latin, which drove his average down to a 77. “In fact his average should be well in the 80’s,” the headmaster recorded. Jack admitted to his mother that he was “doing a little worrying about my studies because what he [the headmaster] said about me starting of[f] great and then going down sunk in.”

In the fall of 1930, when he was thirteen and a half, Jack was more interested in current events and sports than in any of his studies. Football, basketball, hockey, squash, skating, and sledding were Jack’s first priorities, but feeling closed off in the cloistered world of a Catholic academy made him increasingly eager to keep up with the state of the world. He wrote Joe from Canterbury: “Please send me the Litary [sic] Digest, because I did not know about the Market Slump until a long time after, or a paper. Please send me some golf balls.” A missionary’s talk one morning at mass about India impressed Jack as “one of the most interesting talks that I ever heard.” It was all an early manifestation of what his later associate Theodore C. Sorensen described as “a desire to enjoy the world and a desire to improve it; and these two desires, particularly in the years preceding 1953, had sometimes been in conflict.”

In 1930, however, pleasure seeking clearly stood first. In 1960, when Time journalist Hugh Sidey asked Jack, “What do you remember about the Great Depression?” he replied, “I have no first-hand knowledge of the depression. My family had one of the great fortunes of the world and it was worth more than ever then. We had bigger houses, more servants, we traveled more. About the only thing that I saw directly was when my father hired some extra gardeners just to give them a job so they could eat. I really did not learn about the depression until I read about it at Harvard.”

He was insulated by money but also by nurture. Charles Spalding, one of Jack’s close childhood friends, who spent weekends and holidays with the family, noted, “You watched these people go through their lives and just had a feeling that they existed outside the usual laws of nature; that there was no other group so handsome, so engaged. There was endless action… endless talk… 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. I remember thinking to myself that there couldn’t be another group quite like this one.”

If Jack understood that he was part of an unusual family, it also bred a certain arrogance. Joe Sr. could be abrupt and unfriendly, even disdainful of anyone he considered unworthy of his attention, especially those who did not show him proper regard. He saw some of this as payback for the humiliating slights inflicted on him for being an Irish Catholic.

Most victims of Joe’s disdain were not ready to forgive and forget. They saw Joe and the family as pretentious and demanding. At Cape Cod, for example, where renovations had turned the original cottage on the Kennedy property into a house with fourteen bedrooms, nine baths, a basement theater wired to show talking pictures, and an outdoor tennis court, Joe had a reputation as “opinionated,” “hard as nails,” and “an impossible man to work for.” The family was notorious for its casualness about paying its bills or carrying cash to meet obligations in a timely fashion. Shopkeepers and gas station attendants lost patience with giving the family credit and having to dun servants for payment. “We’re Kennedys,” a carful of kids told a gas station owner who refused to accept a promise to pay later for a fill-up. A call to the Kennedy compound brought a chauffeur with a can of gasoline to get the car back to the estate.

Jack came to his maturity with an almost studied indifference to money. He never carried much, if any, cash. Why would someone so well-off need currency to pay for anything? Everyone knew or should have known that he was good for his debts, be it a restaurant check, a clothing bill, or a hotel tab. He was always asking friends to pick up the bill, not because he expected them to pay but because his handlers, his father’s moneymen, would square accounts later. And they usually did, though occasionally some of Jack’s creditors would have to make embarrassing requests for payment of loans or debts that he had overlooked.

The self-indulgence of the Kennedy children was often on public display. Stepping off one of the Kennedy boats onto the Hyannis Port pier, the children would shed articles of clothing as they marched along, expecting “that someone else would pick up after them.” Kennedy maids particularly complained about Jack’s slovenliness: “the wet towels in a heap on the floor, the tangle of ties in one corner, the bureau drawers turned over and emptied in the middle of the bed in a hurried search for some wanted item.”

The children also had little sense of being confined to a place and time. One of Jack’s childhood friends remembered them this way: “They really didn’t have a real home with their own rooms where they had pictures on the walls or memorabilia on the shelves but would rather come home for holidays from their boarding schools and find whatever room was available…. ‘Which room do I have this time?’ ” Jack would ask his mother. He did not feel he had to live by the ordinary rules governing everyone else. He was always arriving late for meals and classes, setting his own pace, taking the less-traveled path; he was his father’s son. With the Kennedys, Jack’s friend recalled, “life speeded up.”

There was also a remarkable sense of loyalty. Joe taught his children, particularly Jack and Joe Jr., to rely on family unity as a shield against competitors and opponents. On a crossing to Europe in 1935, Joe called Jack away from a game of deck tennis to meet Lawrence Fisher, one of the brothers who had gained fame and fortune designing autos for General Motors. “Jack, I sent for you because I want you to meet Mr. Lawrence Fisher, one of the famous Fisher Body family. I wanted you to see what success brothers have who stick together.” It was a lesson that none of the Kennedy children ever forgot. Once, when Joe Jr. and Jack argued with each other and one of Jack’s friends tried to take his side, Jack turned on him angrily, saying, “Mind your own business! Keep out of it! I’m talking to Joe, not you!”

AFTER A YEAR at Canterbury School, Jack was not keen to return, wishing instead to follow Joe Jr. to Choate. Joe acquiesced to his son’s request, and in September 1931 Jack joined his brother at the storied New England academy. Joe and Rose were less interested in the distinctive education the boys would receive than in the chance to expose them to the country’s power brokers, or at least the sons of America’s most influential families. Choate was not quite on a par with the older, more elite prep schools of Andover, Exeter, St. Mark’s, or St. Paul’s, but it was distinctive enough—part of a wave of boys’ boarding schools founded in the 1880s and 1890s. Association with the best and the brightest, Joe and Rose believed, would ultimately come at Harvard, but the prelude to admission there was an education at a school like Choate. As Jack would soon learn, membership in the world of privilege carried lifelong responsibilities that would both attract and repel him.

An IQ of 119 and strong scores on the English and algebra parts of Jack’s Choate entrance exams had helped ease his admission, though the desire to have Jack Kennedy at the school was decidedly mutual. Choate, which had a keen interest in the sons of a family so wealthy and, by 1930, publicly visible, had in fact courted first Joe’s and then Jack’s attendance. Jack had actually failed the Latin part of Choate’s entrance exam in the spring of 1931, but the school was more than happy to let him retake the test after some summer tutoring. And even if he did not measure up on his next Latin test, Choate intended to enroll him in the fall term; the only question was whether he would start “a straight Third Form schedule,” which he did when he met the Latin requirement in October.

The difficult transition from teenager to young adult characterized Jack’s four years at Choate. Not the least of his difficulties was a series of medical problems that baffled his doctors and tested his patience. From the time he was three, not a year passed without one physical affliction or another. Three months before his third birthday, he came down with a virulent case of scarlet fever. A highly contagious and life-threatening illness for so small a child, he had to be hospitalized for two months, followed by two weeks in a Maine sanatorium. To get Jack proper care at the Boston medical center best prepared to treat the disease, Joe had to exert all his influence, including that of his father-in-law. With 600 local children suffering from scarlet fever and only 125 beds available at Boston City Hospital, arranging Jack’s admission was no small feat. But when it came to medical attention for his children, Joe was as aggressive as in any of his business dealings: He not only got Jack into the hospital but also ensured that one of the country’s leading authorities on contagious diseases would care for him. During the 1920s, Jack’s many childhood maladies included chicken pox and ear infections. They compelled him to spend a considerable amount of time in bed or at least indoors, convalescing.

At Canterbury in the fall of 1930, at age thirteen, he began to suffer from an undiagnosed illness that restricted his activities. Between October and December he lost nearly six pounds, felt “pretty tired,” and did not grow appropriately. One doctor attributed it to a lack of milk in his diet, but the diagnosis failed to explain why during a chapel service he felt “sick dizzy and weak. I just about fainted, and everything began to get black so I went out and then I fell and Mr. Hume [the headmaster] caught me. I am O.K. now,” he declared bravely in a letter to his father. In April 1931, he collapsed with abdominal pains, and the surgeon who examined him concluded that it was appendicitis and that an operation was necessary at the nearby Danbury Hospital. Later notes on Jack’s school attendance describe him as “probably very homesick during his time at Canterbury. He wrote a great deal of letters home. In May, he left school with appendicitis and did not return.” But having completed his year’s work with the help of a tutor at home, he was able to move on to Choate in the fall.

There, his medical problems became more pronounced. Several confinements in the infirmary marked his first year at the school. In November, “a mild cold” cost him two nights in the hospital, and when he went home for Thanksgiving, Joe remarked on how thin he looked. In January, he was confined again for “a cold,” which did not clear up quickly, turned in to “quite a cough,” and kept him in the infirmary for more than a week. Although administered regular doses of cod liver oil and enrolled in a bodybuilding class, his weight remained at only 117 pounds—less than robust for a fourteen-and-a-half-year-old boy—and he continued to suffer fatigue. In April, he had to return to the infirmary because of another cold, swollen glands, and what was described as an abnormal urine sample.

More puzzling medical problems punctuated Jack’s second year at Choate. In January and February 1933, “flu-like symptoms” plagued him, as well as almost constant pain in his knees. “Jack’s winter term sounded like a hospital report,” a fiftieth-anniversary remembrance of his attendance at the school recounted, “with correspondence flying back and forth between Rose Kennedy and Clara St. John [the headmaster’s wife]. Again, eyes, ears, teeth, knees, arches, from the top of his head to the tip of his toes, Jack needed attention.” X rays showed no pathology in his knees, and so his doctor attributed his difficulties to growing pains and recommended exercises and “built-up” shoes.

Matters got worse the following year. Over the summer of 1933, after he had turned sixteen, he gained no weight. It precluded him from playing football, but more important, it stimulated fresh concerns about his health, which now went into a sharp decline in January and February 1934. “We are still puzzled as to the cause of Jack’s trouble,” Clara St. John wrote Rose early in February. “He didn’t look at all well when he came back after Christmas, but apparently had improved steadily since then.” But at the end of January he became very sick and had to be rushed by ambulance to New Haven Hospital for observation. Mrs. St. John told Jack: hope with all my heart that the doctors will find out in the shortest possible order what is making the trouble, and will clear it out of the way even quicker than that.” His symptoms were a bad case of hives and weight loss; but the doctors now feared that he had life-threatening leukemia and began taking regular blood counts. “It seems that I was much sicker than I thought I was,” Jack wrote classmate LeMoyne Billings after he got out of the hospital, “and am supposed to be dead, so I am developing a limp and a hollow cough.” He complained that his rectum was “plenty red after the hospital. Yours would be red too if you had shoved every thing from rubber tubes to iron pipes up it. When I crap I don’t even feel it because it’s so big.” By March, Jack’s symptoms had largely disappeared, but his doctors remained uncertain about the cause of his difficulties.

In addition to his illnesses, Jack now struggled with normal adolescent problems about identity and sexuality, as well as having to live in the shadow of a highly successful and favored elder brother. By the time Jack arrived at Choate, Joe Jr. had established himself as, in the words of the headmaster’s wife, “one of the ‘big boys’ of the school on whom we are going to depend.” Rose had already signaled George St. John, the headmaster, that Jack was not Joe Jr.—unlike Joe Jr., Jack did not acclimate easily to either academic or social regimens. Mindful of their concern, the headmaster told Joe, “Jack sits at a nearby table in the Dining Hall where I look him in the eye three times a day, and he is fine.”

But Joe Jr.’s success on the playing fields and in the classroom took its toll on Jack. A tall, skinny boy of fourteen, whom his classmates called Rat Face because of his thin, narrow visage, Jack was too slight to gain distinction in athletics, which he badly wanted. When his brother won the school’s coveted Harvard Trophy at his graduation in 1933, an award to the student who best combined scholarship and sportsmanship, it confirmed in Jack the feeling that he could never win the degree of approval his parents—and, it seemed, everyone else—lavished on his elder brother. Jack told Billings that he believed he was as intelligent as his brother, and probably even as good an athlete, but he had little confidence that his family would ever see him as surpassing Joe Jr.

In addition to feeling too much in his brother’s shadow, Jack wrestled with the strains of uncommonly high parental expectations, pressures to live up to “Kennedy standards,” to stand out not just from the crowd but from the best of the best. The overt message, especially from his father, was “second best will never do.” Whether in athletics, academics, or social standing, there was an insistent demand that the Kennedy children, especially the boys, reach the top rung. The lesson Jack now learned was that privilege had its advantages and pleasures, but it also had its demands and drawbacks. As one Kennedy family biographer said: “[Joe] stressed to his children the importance of winning at any cost and the pleasures of coming in first. As his own heroes were not poets or artists but men of action, he took it for granted that his children too wanted public success…. All too often, his understanding about their desires… were fruits of his experience and his dreams, not necessarily theirs.”

Joe Jr., with a robust constitution, a temperament much like his father’s, and a readiness to follow his lead, was Joe’s favorite. Yet despite this and whatever Jack’s antagonism toward Joe, an understanding that his father would do anything for him, that his overpowering dad was motivated by an intense desire to ensure his well-being, established surpassing lifelong ties of affection. Jack also identified with Joe’s iconoclasm, with his talent for seeing opportunities conventional businessmen missed, making independent judgments at variance with prevailing wisdom, and setting social standards that ignored accepted rules for married life.

For all the love and attention he lavished on his second son, Joe resented the many medical problems that plagued Jack’s early life. “Jack was sick all the time,” one of his friends recalled, “and the old man could be an asshole around his kids.” In the late 1940s, during a visit to the Kennedys’ Palm Beach, Florida, home, the friend, Jack, and a date bade Joe good night before going out to a movie. Joe snidely told Jack’s girlfriend: “Why don’t you get a live one?” Angered by the unkind reference to Jack’s poor health, afterward the friend made a disparaging remark about Joe. But Jack defended his father: “Everybody wants to knock his jock off,” he said, “but he made the whole thing possible.”

It was typical of Jack to see the best in people and outwardly not take umbrage at Joe’s occasional hostility toward him for his physical limitations. But Joe’s hectoring did make Jack wonder whether the pressure was worth the many privileges his father’s wealth and status conferred on him. “We all have our fathers,” Jack said resignedly to a friend complaining about his parent. At a minimum, Joe’s allusion to Jack’s health problems struck a painful chord. Jack was self-conscious about his physical problems and worked hard to overcome and ignore them. One friend said, “[Jack’s] very frame as a light, thin person, his proneness to injury of all kinds, his back, his sickness, which he wouldn’t ever talk about… he was heartily ashamed of them, they were a mark of effeminacy, of weakness, which he wouldn’t acknowledge.” When this friend upbraided Jack for being too concerned about improving his appearance by getting a tan, Jack replied, “Well,… it’s not only that I want to look that way, but it makes me feel that way. It gives me confidence, it makes me feel healthy. It makes me feel strong, healthy, attractive.”

Within sharply delineated bounds, Jack rebelled against school and, indirectly, parental authority at Choate. His schoolwork continued to be uneven—strong in English and history, in which he had substantial interest, and mediocre at best in languages, which required the sort of routine discipline he found difficult to maintain. His low grades in Latin and French compelled him to attend summer session in 1932, at the end of his freshman year. Rose later remarked on how concerned they were about Jack’s health during his Choate years. But “what concerned us as much or more was his lack of diligence in his studies; or, let us say, lack of ‘fight’ in trying to do well in those subjects that didn’t happen to interest him…. Choate had a highly ‘structured’ set of rules, traditions, and expectations into which a boy was supposed to fit; and if he didn’t, there was little or no ‘permissiveness.’ Joe Jr. had no trouble at all operating within this system; it suited his temperament. But Jack couldn’t or wouldn’t conform. He did pretty much what he wanted, rather than what the school wanted of him.”

During his years at Choate, Jack remained more interested in contemporary affairs than in his classes. But although he “conspicuously failed to open his schoolbooks,” Choate’s headmaster recalled, he “was the best informed boy of his year.” One classmate remembered that Jack was able to answer between 50 and 60 percent of the questions on the popular radio quiz show Information, Please, while he himself could only get about 10 percent of them right. Jack’s limited grasp of the Great Depression suggests that he did not have much interest in economic affairs, but he became a regular subscriber to the New York Times, reading it, or at least glancing at it, every morning. He also began a lifelong fascination with the writings of Winston Churchill.

Although Jack’s academic work was good enough in his junior and senior years to allow him to graduate in the middle of his class, and although he enjoyed considerable popularity among his peers, winning designation from his senior classmates as the “most likely to succeed,” he still refused to fit in. “I’d like to take the responsibility for Jack’s constant lack of neatness about his room and person, since he lived with me for two years,” Jack’s housemaster wrote. “But in the matter of neatness… I must confess to failure.” Jack’s sloppiness was seen as symbolic of his disorderliness “in almost all of his organization projects. Jack studies at the last minute, keeps appointments late, has little sense of material value, and can seldom locate his possessions.”

In November 1933, Joe Sr. wrote George St. John: “I can’t tell you how unhappy I was in seeing and talking with Jack. He seems to lack entirely a sense of responsibility. His happy-go-lucky manner with a degree of indifference does not portend well for his future development.” Joe urged his eldest son to help in any way he could to encourage Jack’s commitment to his work. Joe worried that Jack might end up as a ne’er-do-well son ruined by an indulged childhood. “We have possibly contributed as much as anybody in spoiling him by having secretaries and maids following him to see that he does what he should do,” Joe told Choate’s assistant headmaster.

In his final year at Choate, Jack pushed the school’s rules to the limit. Organizing a Muckers Club, the headmaster’s term for Choate boys who defied the rules and did not meet their obligations to the school, Jack and several of his friends aimed to “put over festivities in our own little way and to buck the system more effectively.”

LeMoyne Billings and Ralph (Rip) Horton, Jack’s two closest friends, were “co-conspirators” in the “rebellion.” Jack and Billings had a natural affinity for each other. Both had more successful elder brothers who had set seemingly insurmountable standards at Choate for their younger siblings. Like Jack, Lem loved practical jokes and was irreverent about the school’s many rules regulating their daily lives. Billings, the son of a Pittsburgh physician, and Horton, the child of a wealthy New York dairy business family, deferred to Jack, who enjoyed higher social standing and, like his father, insisted on being the leader.

Although the Muckers represented no more than a small rebellion on Jack’s part, in the cloistered atmosphere of a rural private school, where such defiance took on a larger meaning, St. John responded angrily. He “let loose” at the thirteen club members in chapel, naming names and denouncing their corruption of the school’s morals and integrity. Privately, he described the Muckers as “a colossally selfish, pleasure loving, unperceptive group—in general opposed to the hardworking, solid people in the school, whether masters or boys.” He wired Joe Kennedy to come “for a conference with Jack and us which we think a necessity.” Choate English teacher Harold Tinker later admitted that St. John enjoyed the thought of humiliating Jack’s father: St. John was anti-Catholic—something he made quite clear at faculty meetings—and “resented having Catholics at his school,” especially any related to someone as rich and prominent as Joe Kennedy. But St. John also understood that the well-being of the school partly depended on giving no overt expression to his bias. Though Jack had no evidence that the headmaster would act on his anti-Catholicism, he nevertheless feared that St. John might expel him and destroy whatever approval he still enjoyed from his parents. The episode, however, blew over when Jack promised to disband the club and take his punishment of a delayed Easter vacation.

In acting as he had, Jack played out several impulses that dominated his early life. He tested the rules so boldly at Choate because he believed he could get away with it. As the son of a wealthy and prominent family—Joe had become the chairman of Franklin Roosevelt’s Securities and Exchange Commission in the summer of 1934—Jack felt some invulnerability to St. John’s strictures. But he also understood that the limits to what St. John would allow might be influenced by Jack’s own powers to ingratiate himself with both his elders and his peers. He was very well liked by most of the other boys at the school, as their willingness to vote him most likely to succeed demonstrates. St. John himself readily acknowledged that Jack had a winning way that endeared him to most everyone: “In any school he would have got away with some things, just on his smile. He was a very likeable person, very lovable.” Writing Joe in November 1933, St. John concluded that “the longer I live and work with him and the more I talk with him, the more confidence I have in him. I would be willing to bet anything that within two years you will be as proud of Jack as you are now of Joe.” In another letter that month, St. John went so far as to declare: “I never saw a boy with as many fine qualities as Jack has, that didn’t come out right… in the end.” The following February, during a health crisis Jack weathered, St. John told Joe, “Jack is one of the best people that ever lived—one of the most able and interesting. I could go on about Jack!” He may not have liked Catholics, but he certainly liked this Catholic, a testament to Jack’s remarkable charm.

In his limited rebellion at Choate, Jack was also playing out a trait Joe Sr. had consciously worked to instill in his children. Joe was not entirely blind to the fact that he was an overbearing, demanding, insistent character who dominated almost everyone and everything he touched. Because he sensed how destructive this could be to his offspring, especially the boys, he made a point of encouraging a measure of independence and even irreverence. Visitors to the Kennedy home who watched Joe’s interactions with Joe Jr. and Jack remembered how he would push them to argue their own point of view, make up their own minds, and never slavishly follow accepted wisdom. Lem Billings recalled that mealtime conversations at the Kennedys’ never consisted of small talk. Joe Sr. “never lectured. He would encourage them [the children] completely to disagree with him, and of course they did disagree with him. Mr. Kennedy is, I’d say, far right of his children, and yet he certainly didn’t try to influence them that way.”

And perhaps if Joe Sr. saw in his eldest son what could be, he saw in Jack more who he was. When St. John interrupted a conversation between him, Jack, and Joe 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 Mucker’s Club had been mine, you can be sure it wouldn’t have started with an M!” Joe’s irreverence was not lost on Jack, who inscribed a graduation photo to one of the other leading lights in the club, “To Boss Tweed from Honest Abe, may we room together at Sing Sing.”

When Joe Jr. graduated from Choate, his father sent him to study in England for a year with Harold Laski, a prominent socialist academic. Rose considered this “a little wild and even dangerous,” but Joe, convinced it would encourage greater independence and sharpen his son’s ability to argue the case for a more conservative outlook, ignored his wife’s concern. And when Joe Jr. returned after a summer trip to Russia with Laski and described the advantages of socialism over capitalism, Joe told Rose, “If I were their age I would probably believe what they believe, but I am of a different background and must voice my beliefs.” Joe made it clear that he cared much less about their different outlooks than that they had reached independent judgments.

St. John saw even more of this sort of constructed independence in Jack’s behavior. “Jack has a clever, individualist mind,” he told Joe. “It is a harder mind to put in harness than Joe [Jr.]’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.” The mature John Kennedy would fulfill St. John’s prediction.

DESPITE BEING SIXTY-FIFTH in a class of 110, Jack was assured a place at Harvard. In 1935, as the son of so prominent an alumnus, with an elder brother in good standing at the university, and Harry Hopkins, FDR’s welfare administrator, and Herbert Bayard Swope, the prominent journalist/editor, listed as nonacademic references, Jack had few doubts about his admission. But reluctant once more to be directly in Joe Jr.’s shadow, he chose to go to Princeton with Lem Billings and other Choate friends. Joe Sr. accepted his son’s decision as a welcome demonstration of Jack’s independence—though he may have smiled when the son who so wanted to diverge from his elder brother’s path asked to follow Joe Jr. in spending a year in England under Harold Laski’s tutelage.

In the conflict between self-indulgence and worldly interests, the former gave little ground to the latter in Jack’s eighteenth year. And in fact, in the summer and fall of 1935, when he traveled to Europe for the first time, Jack was less interested in studying with Laski at the London School of Economics than in making acquaintances and enjoying the social life in London. Rising European tensions over the Rhineland and Italy’s invasion of Ethiopia registered less on Jack as a significant moment in history than simply as reasons to go home.

In October, when one of Jack’s bouts of illness added to concerns about keeping him abroad, he returned to America, where he quickly seemed to recover and petitioned for late admission to Princeton’s fall term. When the university denied it, Joe arranged through a prominent Princeton alumnus for Jack’s enrollment at the beginning of November. He lasted only until December, when illness again interrupted his studies and sent him to Peter Bent Brigham Hospital in Boston. Recuperating from his still-undiagnosed maladies in Palm Beach, Florida, Jack accepted his father’s suggestion that he go to Arizona for two months beginning in April. There, the warm climate and relaxed pace at a ranch seemed to restore Jack’s health. With time to reflect, Jack changed his mind about college. Princeton’s cloistered environment and spartan living quarters in South Reunion Hall had disappointed him, so he decided to renew his application to Harvard in July 1936, receiving admission to the fall term within three days of applying.

During his first two years at Harvard, Jack largely continued the pattern he had established at Choate. His academic record was unimpressive: a B-minus in government the first year and a B in English the second were offset by grades of C and C-plus in French, history, and a second government course, his major interest. “Exam today,” he wrote Billings during his first finals period in January 1937, “so have to open my book & see what the fucking course is about.” When he got too far behind in his work, Jack occasionally relied on a tutoring service or an outside “cram school,” which charged a fee for bringing unprepared students up to speed for an exam. Jack’s freshman adviser predicted that he would probably do better in time, but in his sophomore year he had still not lived up to his talent or promise. “Though his mind is still undisciplined,” his tutor wrote, “and will probably never be very original, he has ability, I think, and gives promise of development.”

Jack’s classmates and teachers remember a charming, irreverent young man with a fine sense of humor and a passion for sports and the good life. He certainly showed no overt interest in the campus activism provoked by the Depression, FDR’s New Deal, and the challenges to democracy and capitalism from fascism, Nazism, and communism. There is no indication that he read any of the popular progressive journals of the day, such as The Nation, the New Republic, or New Masses, or gave much, if any, heed to the parades and protest demonstrations organized by students eager to have a say in public affairs. He had little use for doctrinaire advocates who “espoused their causes with a certitude which he could never quite understand.” Indeed, after only two months at Harvard, he privately vented his irritation with the political clichés he had been hearing in a whimsical letter to Billings. “You are certainly a large-sized prick to keep my hat,” he complained to Lem, “as I can’t find my other one and consequently am hatless. Please send it as I am sending yours…. Harvard has not made me grasping but you are getting a certain carefree communistic attitude + a share the wealth attitude that is rather worrying to we who are wealthy.”

His focus remained on the extracurricular and social activities he found more enjoyable, and stamped him as one of the many students at Harvard more interested in earning the social standing that attendance and graduation provided than in the book learning needed to advance a career. Although James Bryant Conant, Harvard’s president beginning in 1933, stressed the importance of “meritocracy,” a university focused more on the intellect and character of its students than on their social origins, social snobbery continued to dominate the undergraduate life of the university. Jack’s first two years on campus were a reflection of these mores. Football, swimming, and golf, and service on the Smoker and Annual Show committees occupied his freshman year, while junior varsity football, varsity swimming, the Spee and Yacht Clubs, and service on the business board of the Harvard Crimson filled his second year.

Jack put a premium on succeeding at these chosen activities. He was a fierce competitor. “He played for keeps,” the football coach recalled. “He did nothing half way.” Swim practice often occupied four hours a day sandwiched between classes. The athletic competitions gave him some gratifying moments: the freshman swim team went undefeated, and an intercollegiate championship in sailing for the boat he commanded sophomore year was a high point.

Yet, as at Choate, his brother continued to eclipse him. Joe Jr. was the best-known member of his class, and “Jack was bound to play second-fiddle,” a Harvard contemporary and later dean of admissions said. Whereas Joe was big enough and strong enough to play varsity football, Jack, at six feet and 150 pounds, was too slight to make more than the sophomore junior squad. Moreover, his fragile health undermined his success as a backstroke specialist, contributing to his failure to beat out a classmate for the starting assignment in the Yale swim meet.

His brother’s success in campus politics also reduced any hopes Jack may have had of making a mark in that area. Under an unstated family rule of primogeniture, the eldest son had first call on a political career. And Joe Jr. left no doubt that this was already his life’s ambition. Economist John Kenneth Galbraith, one of Joe’s tutors, remembered him as keenly interested in politics and public affairs and quick to cite his father as the source of his beliefs. “When I become President, I will take you up to the White House with me,” he liked to tell people. Joe’s quick rise to prominence on campus gave resonance to his boasts. He won elections as chairman of the Winthrop House committee, as a class representative to the student council, as an usher for Class Day, and as business manager of the class album. He also enjoyed prominence as an outspoken anti-interventionist in the emerging troubles abroad.

Although very much in his brother’s shadow during his freshman and sophomore years, Jack also gave indications that he had more than a passing interest in public issues. A failed bid for a student council seat suggested that he was not content to leave politics entirely to his father and brother or that he was focused solely on high jinks. Moreover, his academic work began to demonstrate a substantial engagement with political leadership and how influential men changed the world. Economics, English, history, and government courses formed the core of his first two-year curriculum. In March 1937, his freshman adviser noted that Jack “is planning to do work in Gov. He has already spent time abroad studying it. His father is in that work.” He read several books on recent international and political history, and more revealing, he wrote papers on King Francis I of France and Enlightenment philosopher Jean-Jacques Rousseau. His essays focused on the uses of political and intellectual power to alter human relations, Francis I being notable to Jack as someone who had made himself the “undisputed and absolute” ruler of France and the architect of the French Renaissance, and Rousseau was the author of works that Jack saw as “the seeds of the revolution that took place in 1789.”

JACK’S GREATEST SUCCESS in his first two years at Harvard was in winning friends and proving to be “a lady’s man.” He made a positive impression on almost everyone he met. “A gangling young man with a slightly snub nose and ‘a lot of flap in his reddish-brown hair,’ ” Jack etched himself in the memory of one classmate who saw him climbing the stairs of the Crimson building “with his long coltish stride.” One professor remembered “his bright young face which stood out in the class.” According to the master of John Winthrop House, who interviewed Jack and reviewed his request for a transfer there in 1937 from Weld Hall, he was a “good boy,” one of the “most popular at Weld,” and “one of [the] most popular men in his class.” John Kenneth Galbraith remembered Jack as “handsome… gregarious, given to various amusements, much devoted to social life and affectionately and diversely to women.”

“We are having one hell of a fine time,” Jack wrote Billings after arriving on campus and reconnecting with some Choate friends. “I am now known as ‘Play-boy,’ ” he wrote again in October. Jack was “very humorous, very bright, very unassuming,” said Torbert Macdonald, his closest Harvard friend, who became a star back on the football team. “Anytime you were with Jack Kennedy you would laugh,” another athlete friend recalled. Lem Billings agreed: “Jack was more fun than anyone I’ve ever known, and I think most people who knew him felt the same way about him.” His irreverence particularly endeared him to classmates, who shared a certain distaste for the social hierarchy of which they themselves were so much a part.

Jack’s discovery that girls liked him or that he had a talent for charming them gave him special satisfaction. As early as the summer of 1934, when he was seventeen, he had become aware that young women were attracted to him, reporting to Billings that the girl next door on the Cape had called from Cleveland to ask about his health. “I can’t help it,” he declared with evident self-pleasure. “It can’t be my good looks because I’m not much handsomer than anybody else. It must be my personality.”

His letters to Billings over the next few years, especially through his sophomore year at Harvard, contain numerous references to his sexual exploits. Some of this was adolescent bragging. “I had an enema given by a beautiful blonde,” he wrote Billings during a hospital stay in June 1934. “That, my sweet, is the height of cheap thrills.” “The nurses here are the dirtiest bunch of females I’ve ever seen,” he wrote a few days later. “One of them wanted to know if I would give her a work out last night…. I said yes but she was put off duty early.” During his first two years at Harvard, Jack had a series of conquests he graphically described to Billings. He worried that one of his weekend outings might mean “a bundle from heaven. Please keep all this under your skin and I wish now I had kept mine under my skin if you know what I mean. I would have less worries.” But it did not deter him. “I can now get my tail as often and as free as I want which is a step in the right direction,” he told Billings a few months later.

In rereading this correspondence years later, Billings categorized the letters as “dirty,” “very dirty,” or “not so dirty.” But he understood that there was more here than some adolescent rite of passage by a young man with a strong sexual appetite. “He was interested, very interested, in girls,” Billings remembered. But it was also “a form of being successful at something.” It was “important to him,” because it was an area in which he held an advantage over his brother and Billings and most of his other peers. At a wedding reception, Lem wrote Jack’s sister Kathleen, “brother John was right in his element as he found Dotty Burns & Missy Greer there—all anxious to hear about how Marlene Dietrich thinks he’s one of the most fascinating & attractive young men she’s ever met.”

When Billings told him that he was so successful with women only “because he was Joseph P. Kennedy’s son, since his father was pretty well known as a very rich man,” Jack was determined to prove him wrong. He insisted that they take out blind dates and change identities. “I was to be Jack Kennedy and he was LeMoyne Billings. He went so far as to get his father’s Rolls for the occasion. We had one very competitive night trying to see who would do better and I’m afraid, as I recall, he was satisfied with the results.”

A normal adolescent appetite and the competitive advantage over brother Joe and other rivals are only part of the explanation for Jack’s preoccupation with sexual conquests. Although it is impossible to know exactly how much Jack knew about Joe’s extramarital affairs, or when he first learned of them, it is clear that by the time he was at Harvard, Jack had a pretty good idea that his father, who was often away in New York, Hollywood, and Europe on business, was quite the man about town. Certainly by the time he was twenty-three, according to one girlfriend, Jack knew about his father’s infidelities. “He said his father went on these long trips, was gone so much of the time, and that he’d come back and give his mother some very lavish presents—a big Persian rug or some jewelry or something like that. Obviously, Jack knew everything that was going on in [his parents’] marriage.”

Stories about his grandfather Fitzgerald further buttressed Jack’s understanding of how elastic certain rules might be. At the very least, it is evident that Joe had no objection to Jack’s active social life and even facilitated it. In October 1936, Jack told Billings that he “went down to the Cape with five guys from school—EM [Edward Moore, Joe Sr.’s administrative assistant and confidant] got us some girls thru another guy—four of us had dates and one guy got fucked 3 times, another guy 3 times (the girl a virgin!) + myself twice—they were all on the football team + I think the coaches heard as they gave us all a hell of a bawling out.” This enthusiastic defiance of public standards of sexual behavior would be another link between father and son. Jack told “locker room stories about his father’s conquests.” Jack once described how Joe tried to get into bed one night with one of his sisters’ friends, whispering to her as he began removing his robe, “This is going to be something you’ll always remember.” Jack, with an amused smile, would tell female visitors to Palm Beach or Hyannis Port, “Be sure to lock the bedroom door. The Ambassador has a tendency to prowl late at night.”

Of course, Joe’s sexual escapades were an abuse of someone as devout and conventional as Rose. She took exception to even the slightest off-color story. Any acknowledgment of infidelity carried on under her roof before the eyes of her children was impossible. But Jack and his siblings were more sympathetic to Joe than to Rose in this family conflict. They not only accepted their father’s philandering at Palm Beach and Hyannis but facilitated it away from home. A Washington, D.C., socialite recounted the occasion in the 1940s when Joe Sr., Jack, and Robert Kennedy invited her to their table in a posh restaurant. The boys explained that Joe would be in town for a few days and “needed female companionship. They wondered whom I could suggest, and they were absolutely serious.” Similarly, when Joe visited Hollywood in the 1950s, his daughter Patricia, who was married to actor Peter Lawford, would ask the wife of a television producer to get the names and phone numbers of female stars her father might call.

Certainly the risk taking was part of the appeal for Jack. The fact that the football coaches gave him and his friends hell did not deter him from planning to go “down next week for a return performance.” In fact, in response to Jack’s “little party,” the coaches demoted him to the third team, which angered him but did not alter his social life. Nor did the possibility that he and his friends might have gotten one or more of the girls pregnant or contracted a sexually transmitted disease hold him back. “One guy is up at the doctor’s seeing if he has a dose,” he wrote Billings, “+ I feel none too secure myself.” Yet taking chances and breaking rules were partly what made life fun; and at age nineteen, he was enjoying himself too much to stop.

Jack’s easy conquests compounded the feeling that, like the member of a privileged aristocracy, of a libertine class, he was entitled to seek out and obtain what he craved, instantly, even gratefully, from the object of his immediate affection. Furthermore, there did not have to be a conflict between private fun and public good. David Cecil’s The Young Melbourne, a 1939 biography of Queen Victoria’s prime minister, depicted young British aristocrats performing heroic feats in the service of queen and country while privately practicing unrestrained sexual indulgence with no regard for the conventional standards of monogamous marriages or premarital courting. Jack would later say that it was one of his two favorite books.

One woman reporter remembered that Jack “didn’t have to lift a finger to attract women; they were drawn to him in battalions.” After Harvard, when he spent a term in the fall of 1940 at Stanford (where, unlike at Harvard, men and women attended classes together), he wrote Lem Billings: “Still can’t get use to the co-eds but am taking them in my stride. Expect to cut one out of the herd and brand her shortly, but am taking it very slow as do not want to be known as the beast of the East.”

But restraint was usually not the order of the day. He had so many women, he could not remember their names; “Hello, kid,” was his absentminded way of greeting a current amour. Stories are legion—no doubt, some the invention of imagination, but others most probably true—of his self-indulgent sexual escapades. “We have only fifteen minutes,” he told a beautiful co-ed invited to his hotel room during a campaign stop in 1960. “I wish we had time for some foreplay,” he told another beauty he dated in the 1950s. One of Jack’s favorite sayings, one male friend said, was “slam, bam, thank you, ma’am.” A woman friend described him as “compulsive as Mussolini. Up against the wall, Signora, if you have five minutes, that sort of thing.” At a society party in New York he asked the artist William Walton how many women in the gathering of socialites he had slept with. When Walton gave him “a true count,” Jack said, “Wow, I envy you.” Walton replied: “Look, I was here earlier than you were.” And Jack responded, “I’m going to catch up.”

JACK’S DEVIL-MAY-CARE ATTITUDE found a fresh outlet in the summer of 1937 when his father sent him and Billings on a grand European tour. Because Billings could not afford the trip, Jack financed it. The journey was a kind of obligatory excursion for young gentlemen, an extension of the formal education they were getting at the best colleges in America. A firsthand acquaintance with the great sites of western Europe was a prerequisite for high social status. And Jack and Lem left few architectural wonders and major museums unvisited. Moreover, both of them took genuine satisfaction from schooling themselves in the great landmarks of the Old World. Their travels, as the old saw has it, were broadening. Ironically, Jack remained closed off from entire strata of society—blue-collar workers and African Americans—he would not glimpse until much later. Even then, he would find them difficult to viscerally understand.

Perhaps most important, the trip deepened Jack’s interest in foreign affairs. A diary he kept of the two months they spent abroad is largely a running commentary on public events and national character. They went first to France, where they spent the month of July touring in a convertible Jack brought across the Atlantic on the SS Washington. Taking in the sights of Beauvais, Rouen, Paris, Versailles, Chartres, Orléans, Amboise, Angoulême, St.-Jean-de-Luz, Lourdes, Toulouse, Carcassonne, Cannes, Biarritz, and Marseille, they also made a point of visiting World War I battlefields. Jack spoke as often as possible with Frenchmen about current events. He sounded them out on developments in America under Roosevelt’s New Deal and in Europe, where Nazi Germany and Fascist Italy raised concerns about another European war. Jack gained the impression “that while they all like 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.” Billings later remembered that they spent a lot of time visiting churches and museums and “interviewing French peasants in schoolboy French. We wanted to see what they thought of the Germans. They were so confident of the Maginot Line,” the fortresses on the Franco-German border.

“The distinguishing mark of the Frenchman,” Jack noted in his diary, “is his cabbage breath and the fact that there are no bath-tubs.” He was even more annoyed by their readiness to exploit American tourists for everything they could get. When they had dinner with a French officer they had picked up on their drive to Paris, Jack noted that he had “succeeded in making him pay for part of it.” He was particularly incensed by the efforts of hotels to squeeze higher rates out of them. “Have now acquired the habit,” he wrote on their fourth day in France, “of leaving the car around the block to keep the [hotel] price from going up. Had the lights [on the car] fixed and got another screwing. These French will try & rob at every turn.” “France,” he concluded, “is quite a primitive nation.”

He had no better opinion of the Spanish. The stories of atrocities in the Spanish civil war between Francisco Franco’s fascist rebels and the republican government in Madrid told to them by refugees in France seemed all too believable after they witnessed the barbarism of a bullfight in Biarritz on the Franco-Spanish border. “Very interesting but very cruel,” Jack recorded, “especially when the bull gored the horse. Believe all the atrocity stories now as these southerners, such as these French and Spanish, are happiest at scenes of cruelty. They thought funniest sight was when horse ran out of the ring with his guts trailing.” Billings later said, “Of course, we didn’t understand this temperament at all, and we were disgusted by it.”

The Italians made a better first impression on Jack. Their “streets are much more full and lively than those of France—and the whole race seems more attractive. Fascism seems to treat them well,” he wrote after two days in Italy. He was also “very impressed by some of the [twelve-year-old] children [his brother] Bobby’s age and by the fact that they all seem regimented.” Billings remembered that “Italy was cleaner and the people looked more prosperous than we had anticipated.” Within a few days, however, Jack was complaining that “the Italians are the noisiest race in existence—they have to be [in] on everything—even if it is only Billings blowing his nose.” By the time he left Italy, Jack saw the Italians as being as exploitive as the French. A battle with their hotel proprietor over the bill marked their departure from Rome. The man “turned out to be a terrific crook despite,” Jack wrote sarcastically, “[being] an Italian and a gentleman. Left Rome amidst the usual cursing porters.”

The Germans were even worse. Though they picked up some young German hitchhikers in Italy who seemed attractive enough, a conceit and near contempt for Americans in Germany offended them. “We had a terrible feeling about Germany,” Billings recalled, “and all the ‘Heil Hitler’ stuff…. They were extremely arrogant—the whole race was arrogant—the whole feeling of Germany was one of arrogance: the feeling that they were superior to us and wanting to show it.” The Germans were “insufferable,” Billings also said. “We just had awful experiences there. They were so haughty and so sure of themselves.” To mock them, Jack and Lem would answer Nazi salutes of “Heil Hitler” by throwing back their hands and saying, “Hi ya, Hitler.”

Of greater interest to Jack than the flaws he saw in each of these countries was the state of current relations among them and the likely course of future events. He also began to see how easy it was to fall into a distorted view of public affairs based more on personal bias than on informed understanding. In this he was starting to distance himself from his father, who saw the outside world primarily in personal terms.

Questions about international relations and Europe’s future intrigued Jack. He understood that the Spanish civil war was a focus for national rivalries between England, France, Italy, Germany, and Russia. England did not want the Mediterranean to become “a Fascist lake,” he noted. But how far it or any of the other countries would go to advance their respective interests seemed open to question. Because the competing nations seemed so intolerant of one another, Jack believed it likely that they would fight another war. He also pondered the comparative evils of fascism and communism. Whatever the advantages of one over the other, he concluded that “Fascism is the thing for Germany and Italy, Communism for Russia, and democracy for America and England.”

His curiosity about European power politics moved him to seek out Arnaldo Cortesi, the New York Times correspondent in Rome. Jack thought him “very interesting and [he] gave me some very good points.” Cortesi believed a war “unlikely as 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 also read John Gunther’s 1937 book Inside Europe, which he found illuminating, especially with regard to the Spanish civil war. But Jack did not take Cortesi’s or Gunther’s opinions as gospel. His trip showed him that Europe was in flux and that the continent’s political future was uncertain. At the end of his diary, he posed a series of questions to himself. Would Mussolini’s current popularity hold up after invading Ethiopia in 1935 and provoking widespread international criticism? Would Franco be able to win his civil war without Italo-German support? Could Germany and Italy, which had divergent interests, maintain an alliance? Did British military strength make a war less likely? And would fascism be possible in as wealthy and egalitarian a country as the United States?

Jack’s queries were as sophisticated as those of professional journalists and diplomats in Europe. They were also part of an understandable search by a bright, inquiring young man for a niche that separated him from his father and elder brother and satisfied an affinity for critical thinking about public affairs. Joe Sr. was the family’s moneymaking genius and Joe Jr. might be slated for a meteoric career in U.S. domestic politics, but Jack could imagine himself as the New York Times man in a major European capital, probing current realities and educating isolationist Americans about a world they wished to ignore.

Given how much the French, Germans, Italians, and Spanish offended him, it is puzzling that Jack did not embrace the prevailing isolationism of his father and most Americans. This may have been a way to separate himself from his brother. But more likely, the trip to Europe schooled him in the satisfaction of forming independent judgments rather than giving in to easier clichés about those “foreigners.” He understood that despite the physical and institutional distance between the United States and Europe, European affairs had a large impact on the Americas. An affinity for analyzing and explaining current conditions trumped feelings of antagonism and bias, which he believed informed the way his father and other isolationists saw the world.

The trip also strengthened Jack’s sense of privileged status. He and Billings ended their travels in Britain, where Joe arranged for them to stay at palatial English and Scottish homes. “Terrific big castle with beautiful furnished rooms,” Jack said of Sir Paul Latham’s residence in Sussex. (One bedroom was forty yards long.) Likewise, the estate of Scottish nobleman Sir James Calder impressed Jack and amazed Lem, who spent their visit fly-fishing and shooting rabbit and grouse.

For Jack, the lifestyle of these British aristocrats was not so removed from that of his father. From July 1934 to September 1935, when he served as chairman of the Securities and Exchange Commission, Joe had lived in a sumptuous 125-acre Maryland estate half an hour’s drive from Washington. The thirty-three-room rented mansion had been built by a multimillionaire Chicago businessman, Samuel Klump Martin III, and rivaled the great homes of English aristocrats. The living room was the size of a hotel lobby, and the dining room was modeled after one built for King James I of England. Twelve master bedrooms, a recreation room with several billiard tables and three Ping-Pong tables, a hundred-seat movie theater, and a large outdoor swimming pool surrounded by guest bath houses provided all the modern amenities.

In 1937–38, at the age of twenty, Jack saw himself and his family as a kind of American nobility. On returning home in September, Jack learned that Fortune magazine had published a cover article about his father, who since March had been serving as the chairman of a newly created U.S. Maritime Commission. Then, during the fall term, Jack had a personal victory when he received an invitation to the Spee, one of Harvard’s eight elite clubs that included only about a hundred out of the thousand students in the class of 1940. It was an honor neither his father nor Joe Jr. had managed to win. “It was a status symbol for him,” one of Jack’s classmates believed, “that at last the Kennedys were good enough.”

And then, in December 1937, President Roosevelt appointed Joseph Kennedy ambassador to Great Britain, America’s most prestigious diplomatic post. By choosing a self-made Irish American as his envoy, Roosevelt assumed that he would not become a captive of England’s conservative government and its appeasement policy toward Hitler’s Germany.

Whatever the president’s political purposes, the appointment gave Joe and his family an uncommon degree of social prominence. “The moment the appointment was proposed,” Rose said, “Joe accepted. It was the kind of appointment he had been waiting for all along.” Indeed, he had lobbied Roosevelt for it. When the president tried to get him to become secretary of commerce instead, Joe told Roosevelt’s son James: “London is where I want to go and it is the only place I intend to go.” Interior Secretary Harold Ickes asked White House insider Thomas Corcoran why Kennedy was so eager for the London post. “You don’t understand the Irish,” Corcoran answered. “London has always been a closed door to him. As Ambassador of the United States, Kennedy will have all doors open to him.” Joe, who was not sure how long the assignment would last, told an aide who accompanied him, “Don’t go buying a lot of luggage. We’re only going to get the family in the Social Register. When that’s done we come on back.”

Joe’s appointment also gave Jack an uncommon opportunity to be, however temporarily, a part of English high society. In July 1938, at the end of his sophomore year, he traveled to London to spend the summer working at the U.S. embassy. The work itself was less memorable than the social whirl Jack enjoyed. He found a warm welcome from England’s aristocracy and had ready access to the teas, balls, dances, regattas, and races that were part of their summer ritual. Although Jack looked “incredibly young for his age at 21,” he engaged his English friends with his bright, quick mind, highly developed sense of humor, and vitality about everything. In August, the family fled London for a villa in the south of France near Cannes, where they socialized with members of the English royal family. A final few days in London at the end of August gave Jack a close-up view of an evolving European crisis over Czechoslovakia, which Hitler had provoked by demanding that Prague give up its Sudetenland territory. In August, with the crisis unresolved, Jack returned to the States for his junior year at Harvard.

His summer in Europe had fired Jack’s imagination, and he was determined to return to the Continent. He asked and received permission from his advisers to take six courses in the fall term of 1938 and a semester’s leave in the spring of 1939, which he planned to spend in Europe working on an honor’s thesis about contemporary affairs. He promised his Harvard adviser that during his time abroad, he would read several assigned books on political philosophy, including Walter Lippmann’s The Good Society. He also pledged to gather material for a senior thesis on some aspect of international law and diplomacy or the history of international relations, which were listed as his special fields of interest. As impressive, he turned from a C into a B student and excelled in his government classes during the fall term.

A. Chester Hanford, the dean of Harvard College and Jack’s instructor in Government 9a, a course on American state government, remembered “a rather thin, somewhat reserved but pleasant young man with an open countenance which often wore an inquisitive look. He… took an active part in classroom discussion in which he made pertinent remarks.” But much to Hanford’s surprise, the grandson of Honey Fitz showed little interest in state politics. He “was more interested in the changing position of the American state, in federal-state relations and state constitutional development.” Jack’s examination papers gave evidence of independent thought and made Hanford “wonder if he [Jack] might not become a newspaper man.”

Jack made an even stronger impression on Professor Arthur Holcombe, whose Government 7 focused on national politics and the workings of Congress in particular. Holcombe “tried to teach… government as if it were a science.” Each student was required to study a congressman and assess his method of operation and his performance. Holcombe urged the class to substitute objective analysis for personal opinions, and this “scientific method” greatly appealed to Jack, who believed that politics should rest less on opinion than on facts.

Holcombe assigned Jack to study Bertram Snell, an upstate New York Republican whose principal distinction was his representation of the electric power interests in his region. Holcombe said that Jack “did a very superior job of investigating, and his final report was a masterpiece.” Of course, Jack had some advantages. As Holcombe noted, “When Christmas vacation came, he goes down to Washington, meets some of his father’s friends, gets a further line on his congressman and on Congress.”

When he finished the fall term, Jack made plans to sail for Europe at the end of February. First, however, he flew to New Orleans for Mardi Gras, where he was met at the airport by a girl he was dating and a Princeton friend, who was impressed that Jack had come by plane: “Not many people flew in those days,” the friend recalled. But Jack did, and then flew back to New York before boarding a luxury liner for Europe.

Although his father’s public image had taken a downturn in the fall of 1938, when he publicly expressed favor for Prime Minister Neville Chamberlain’s appeasement of Nazi Germany at Munich, Jack felt no discomfort with his father’s political pronouncements or his family identity. Although his father’s pro-Chamberlain speech “seemed to be unpopular with the Jews, etc.,” he wrote his parents, “[it] was considered to be very good by everyone who wasn’t bitterly anti-Fascist.” A new play, which he saw in New York and included several references to the Kennedys, greatly amused Jack. “It’s pretty funny,” he reported in the same letter, “and jokes about us get the biggest laughs whatever that signifies.”

As soon as he arrived in London, Jack resumed “having a great time,” he wrote Billings. He was working every day and “feeling very important as I go to work in my new cutaway.” He met the king “at a Court Levee. It takes place in the morning and you wear tails. The King stands & you go up and bow. Met Queen Mary and was at tea with the Princess Elizabeth with whom I made a great deal of time. Thursday night—am going to Court in my new silk breeches, which are cut to my crotch tightly and in which I look mighty attractive. Friday I leave for Rome as J.P. has been appointed to represent Roosevelt at the Pope’s coronation.”

When he returned from Rome in late March, Jack reported to Billings that they had had “a great time.” His youngest brother, Teddy, had received Communion from the new pope, Pius XII, “the first time that a Pope has ever done this in the last couple of hundred years.” The pope then gave the Sacrament to Joe, Jack, and his sister Eunice “at a private mass and all in all it was very impressive.” For all the sense of importance Jack gained from his father’s prominence and influence, he kept an irreverent sense of perspective that allowed him to see the comical side of his family’s social climbing. He wrote Billings: “They want to give Dad the title of Duke which will be hereditary and go to all of his family which will make me Duke John of Bronxville and perhaps if you suck around sufficiently I might knight you.” (In fact, Joe had a sense of limits about what an American public official could do and had no intention of asking the required permission of Congress to accept a title of nobility.)

Jack’s letters to Billings over the next several months describe a young man enjoying his privileged life. On the way back from Rome, he had stopped at the Paris embassy, where he had lunch with Carmel Offie, Ambassador William Bullitt’s principal aide, and was invited by them to stay at Bullitt’s residence. He “graciously declined,” as he wanted to get back to London for the Grand National steeplechase before returning to Paris for a month and then traveling to “Poland, Russia, etc.” As of this writing in March, he was not doing “much work but have been sporting around in my morning coat, my ‘Anthony Eden’ black Homburg and white gardenia.”

Two weeks later, he told Billings that he was “living like a king” at the Paris embassy, where Offie and he had become “the greatest of pals” and Bullitt had been very nice to him. He had lunch at the embassy with the famed aviator and isolationist Charles Lindbergh and his wife, Anne, “the most attractive couple I’ve ever seen.” He was “going skiing for a week in Switzerland which should be damn good fun.” Apparently, it was: “Plenty of action here, both on and off the skis,” he told Billings in a postcard. “Things have been humming since I got back from skiing,” he next wrote Lem. “Met a gal who used to live with the Duke of Kent and who is as she says ‘a member of the British Royal family by injections.’ She has terrific diamond bracelet that he gave her and a big ruby that the Marajah [sic] of Nepal gave her. I don’t know what she thinks she is going to get out of me but will see. Meanwhile very interesting as am seeing life.” And he was still living “like a king” at the embassy, where Bullitt “really fixes me up,” and Offie and he were served by “about 30 lackies.” Bullitt, Jack wrote, was always “trying, unsuccessfully, to pour champagne down my gullett [sic].”

But however welcoming Bullitt and Offie were, Jack did not like feeling dependent on their hospitality. He must have also sensed some hostility from Offie, who remembered “Jack sitting in my office and listening to telegrams being read or even reading various things which actually were none of his business but since he was who he was we didn’t throw him out.” Jack privately reciprocated the irritation: “Offie has just rung for me,” he wrote Lem, “so I guess I have to get the old paper ready and go in and wipe his arse.”

For all the fun, Jack had a keen sense of responsibility about using his uncommon opportunity to gather information for a senior thesis. Besides, the highly charged European political atmosphere, which many predicted would soon erupt in another war, fascinated him. However much he kept Lem Billings posted on his social triumphs, his letters to Lem and to his father in London were filled with details about German intentions toward Poland and the likely reactions of Britain, France, Russia, Romania, and Turkey. “The whole thing is damn interesting,” he told Billings. He found himself in the eye of the storm, traveling to Danzig and Warsaw in May, where he spoke to Nazi and Polish officials, and then on to Leningrad, Moscow, Kiev, Bucharest, Turkey, Jerusalem, Beirut, Damascus, and Athens. He received VIP treatment from the U.S. diplomatic missions everywhere he went, staying at a number of embassies along the way and talking with senior diplomats, including Ambassador Anthony Biddle in Warsaw and Charles E. Bohlen, the second secretary in Moscow.

Jack spent August traveling among England, France, Germany, and Italy in pursuit of more information for his senior thesis. He and Torbert MacDonald, his Harvard roommate who had come to England for a track meet, met fierce hostility in Munich from storm troopers who spotted the English license plates on their car. Against the advice of the U.S. embassy in Prague, Joe Kennedy arranged a visit by Jack to Czechoslovakia. The diplomat George F. Kennan, who was serving as a secretary of the legation, remembered how “furious” members of the embassy were at the demand. Joe Kennedy’s “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… had not already reported seemed… wholly absurd. That busy people should have their time taken up arranging his tour struck us as outrageous.” Jack saw matters differently, believing a firsthand look at Prague, now under Nazi control, would be invaluable, and his sense of entitlement left him indifferent to the complaints of the embassy.

In keeping with the peculiar way in which he moved between the serious and the frivolous at this time of his life, Jack spent part of August on the French Riviera, where his family had again rented a villa for the summer at Antibes. There he socialized with the famous movie actress Marlene Dietrich and her family, swimming with her daughter during the day and dancing with Marlene herself at night.

But the good times came to an abrupt end in September when Hitler invaded Poland and the British and the French declared war. Jack joined his parents and his brother Joe and sister Kathleen in the visitor’s gallery to watch Prime Minister Neville Chamberlain and members of Parliament, including Winston Churchill, explain Britain’s decision to fight. Churchill’s speech, giving evidence of the powerful oratory that would later inspire the nation in the darkest hours of the war, left an indelible impression on Jack. To Joe, the onset of war was an unprecedented disaster. He became tearful when Chamberlain declared that “everything that I have believed in during my public life has crashed in ruins.” In a telephone call to FDR, the inconsolable Joe Kennedy moaned, “It’s the end of the world… the end of everything.”

Jack now also got his first experience of hands-on diplomacy. His father sent him to Glasgow to attend to more than two hundred American citizens rescued by a British destroyer after their British liner carrying 1,400 passengers from Liverpool to New York had been sunk by a German submarine. More than a hundred people had lost their lives, including twenty-eight U.S. citizens. The surviving Americans were terrified at the suggestion that they board a U.S. ship without a military escort to ensure their safety, and Jack’s assurances that President Roosevelt and the embassy were confident that Germany would not attack a U.S. ship did not convince them. Although Jack recommended to his father that he try to meet the passengers’ demand, Joe believed it superfluous, and an unescorted U.S. freighter returned the citizens to the United States. Meanwhile, Jack flew on a Pan Am Clipper to Boston in time for his senior fall term.

More than anything, Jack’s travels encouraged an intellectual’s skepticism about the limits of human understanding and beliefs. When he returned to America in September, he asked a Catholic priest: “I saw the rock where our Lord ascended into Heaven in a cloud, and [in] the same area, I saw the place where Mohammed was carried up to Heaven on a white horse, and Mohammed has a big following and Christ has a big following, and why do you think we should believe Christ any more than Mohammed?” The priest urged Joe to get Jack some “instruction immediately, or else he would turn into a[n]… atheist if he didn’t get some of his problems straightened out.” When a friend at Harvard who thought Jack less than pious about his religion asked why he was going to church on a holy day, Jack “got this odd, hard look on his face” and replied, “This is one of the things I do for my father. The rest I do for myself.”

It was all part of Jack’s affinity for skepticism, which Payson S. Wild, one of his instructors in the fall of 1939, helped foster in a tutorial on political theory. Wild urged him to consider the question of why, given that there are a few people at the top and masses below, the masses obey. “He seemed really intrigued by that,” Wild recalled.

Jack gave expression to his independence—to his developing impulse to question prevailing wisdom—in an October 1939 editorial in the Harvard Crimson. Responding to the impression that “everyone here is ready to fight to the last Englishman,” Jack published a counterargument in the campus newspaper that essentially reflected the case his father was then making privately to President Roosevelt and the State Department. As much an expression of loyalty to Joe as of pleasure in running against majority opinion and presenting himself as someone with special understanding of international conditions, Jack urged a quick, negotiated end to the fighting through the good offices of President Roosevelt. Because it would require a third party to mediate a settlement, Jack thought that the “President is almost under an obligation to exert every office he possesses to bring about such a peace.”

Jack believed that both Germany and England were eager for an agreement. And though such a settlement would mean sacrificing Poland, it would likely save Britain and France from probable defeat. But it would have to be a “peace based on solid reality,” Jack asserted, which meant giving Germany a “free economic hand” in eastern Europe and a share of overseas colonies. Hitler would have to disarm in return for these conditions, but Jack did not think this was out of reach.

Jack’s misplaced hopes seem to have been more a case of taking issue with current assumptions than an expression of realism about European affairs developed in his recent travels. Nevertheless, his interest in exploring political questions—in honing his skills as a student of government—is striking. “He seemed to blossom once Joe was gone [to law school] and to feel more secure himself and to be more confident as his grades improved,” Wild said. As another token of Jack’s interest and vocational aspirations in 1939, he tried to become a member of the Crimson’s editorial board; but it already had a full complement of editors and he had to settle for a spot on the paper’s business board. He also occasionally wrote for the paper. An editorial in the Crimson and a speech before the YMCA and YWCA on how to restore peace made him feel like “quite a seer around here.” He also joked with his father that being an ambassador’s son who had spent time in Europe with prominent officials gave him added cachet with the girls. “I seem to be doing better with the girls so I guess you are doing your duty over there,” he wrote his father, “so before resigning give my social career a bit of consideration.”

In the fall of 1939, Jack’s interest in public affairs reflected itself in his course work. In four government classes, he focused on contemporary international politics. “The war clinched my thinking on international relations,” he said later. “The world had to get along together.” In addition to a course with Wild on elements of international law, he took Modern Imperialism, Principles of Politics, and Comparative Politics: Bureaucracy, Constitutional Government, and Dictatorship. Some papers Jack wrote for Wild’s course on neutral rights in wartime on the high seas made Wild think that Jack might become an attorney, but Jack displayed a greater interest in questions about power and the comparative workings and appeal of fascism, Nazism, capitalism, communism, and democracy. The challenge of distinguishing between rhetoric and realism in world affairs, between the ideals of international law and the hard actualities of why nations acted as they did, particularly engaged him.

THE PRINCIPAL OUTCOME of Jack’s travels and course work was a senior honor’s thesis on the origins of Britain’s appeasement policy. The history of how Jack wrote and published the thesis provides a microcosm of his privileged world. During Christmas vacation 1939 at Palm Beach, he spoke with British ambassador Lord Lothian, a guest at his father’s Florida home. In January, Jack stopped at the British embassy in Washington for a conversation with Lothian that, as Jack later wrote him, “started me out on the job.” Taking advantage of his father’s continued presence in London, Jack received invaluable help from James Seymour, the U.S. embassy press secretary, who sent him printed political pamphlets and other Conservative, Labour, and Liberal publications Jack could not obtain in the United States. His financial means also allowed him to use typists and stenographers to meet university deadlines.

Although the papers Jack wrote for his senior-year courses show an impressive capacity for academic study and analysis, it was the contemporary scene that above all interested him—in particular, the puzzle of how a power like Great Britain found itself in another potentially devastating war only twenty years after escaping from the most destructive conflict in history. Was it something peculiar to a democracy that accounted for this failure, or were forces at work here beyond any government’s control?

With only three months to complete the project, Jack committed himself with the same determination he had shown in fighting for a place on the Harvard football and swimming teams. Some of his Harvard friends remembered how he haunted the library of the Spee Club, where he worked on the thesis. They teased him about his “book,” poking fun at his seriousness and pretension at trying to write a groundbreaking work. “We used to tease him about it all the time,” one of them said, “because it was sort of his King Charles head that he was carrying around all the time: his famous thesis. We got so sick of hearing about it that I think he finally shut up.”

Seymour proved a fastidious research assistant who not only persuaded the English political parties to provide the publications Jack requested but also chased down books and articles on the subject at Chatham House, the Oxford University Press, and the British Museum Reading Room. Seymour’s efforts initially produced six large packages sent by diplomatic pouch to the State Department and then to Joe’s New York office. But Jack was not content with Seymour’s initial offering and pressed him for more: “Rush pacifist literature Oxford Cambridge Union report, etc.,” he cabled Seymour on February 9, “all parties business trade reports bearing on foreign policy[,] anything else.” “Dear Jack, your cables get tougher,” Seymour replied, but by the end of the month Jack had an additional twenty-two volumes of pamphlets and books.

The thesis of 148 pages, titled “Appeasement at Munich” and cumbersomely subtitled (“The Inevitable Result of the Slowness of Conversion of the British Democracy to Change from a Disarmament Policy to a Rearmament Policy”), was written in about two months with predictable writing and organizational problems and an inconsistent focus. The thesis was read by four faculty members. Although Professor Henry A. Yeomans saw it as “badly written,” he also described it as “a laborious, interesting and intelligent discussion of a difficult question” and rated it magna cum laude, the second-highest possible grade. Professor Carl J. Friedrich was more critical. He complained: “Fundamental premise never analyzed. Much too long, wordy, repetitious. Bibliography showy, but spotty. Title should be British armament policy up to Munich. Reasoning re: Munich inconclusive…. Many typographical errors. English diction defective.” On a more positive note, Friedrich said, “Yet, thesis shows real interest and reasonable amount of work, though labor of condensation would have helped.” He scored the work a cut below Yeomans as cum laude plus.

Bruce C. Hopper and Payson Wild, Jack’s thesis advisers, were more enthusiastic about the quality of his work. In retrospective assessments, Wild remembered Jack as “a deep thinker and a genuine intellectual” whose thesis had “normal problems” but not “great” ones; Hopper recalled Jack’s “imagination and diligence in preparedness as outstanding as of that time.” On rereading the thesis twenty-four years later, Hopper was “again elated by the maturity of judgment, beyond his years in 1939/1940, by his felicity of phrase, and graceful presentation.”

Yeomans and Friedrich were closer to the mark in their assessments. So was political scientist James MacGregor Burns, whose campaign biography of JFK in 1960 described the thesis as “a typical undergraduate effort—solemn and pedantic in tone, bristling with statistics and footnotes, a little weak in spelling and sentence structure.” Yet it was an impressive effort for so young a man who had never written anything more than a term paper.

Had John Kennedy never become a prominent world figure, his thesis would be little remembered. But because it gives clues to the development of his interest and understanding of foreign affairs, it has become a much discussed text. Two things seem most striking about the work: First, Jack’s unsuccessful effort at a scientific or objective history, and second, his attempt to draw a contemporary lesson for America from Britain’s failure to keep pace with German military might.

His objective, he states throughout the thesis, was to neither condemn nor excuse Prime Ministers Stanley Baldwin and Neville Chamberlain, but rather to get beyond assertions of blame and defense in order to understand what had happened. Yet Jack’s reach for objectivity is too facile. Though his thesis is indeed an interesting analysis of what caused Britain to act as it did at Munich, it is also quite clearly a defense of Baldwin, Chamberlain, and the appeasers. Jack argues that Britain’s failure to arm itself in the thirties forced it into the appeasement policy at Munich but that this failure was principally the consequence not of weak leadership on the part of the two prime ministers but of popular resistance led by the pacifists, advocates of collective security through the League of Nations, opponents of greater government spending, and shortsighted domestic politicians stressing narrow self-interest over larger national needs. No one who knew anything about Joe Kennedy’s pro-Chamberlain, pro-Munich views could miss the fact that the thesis could be read partly as a defense of Joe’s controversial position. Carl Friedrich privately said that the thesis should have been titled “While Daddy Slept.”

Yet dismissing the thesis as simply an answer to Joe’s critics is to miss Jack’s compelling central argument—one originally made by Alexis de Tocqueville over a hundred years before: Popular rule does not readily lend itself to the making of effective foreign policy. Democracies, Jack asserts, have a more difficult time than dictatorships in mobilizing resources for their defense. Only when a pervasive fear of losing national survival takes hold can a democracy like Britain or the United States persuade its citizens “to give up their personal interests, for the greater purpose. In other words, every group [in Britain] wanted rearmament but no group felt that there was any need for it to sacrifice its privileged position. This feeling in 1936 was to have a fatal influence in 1938” at Munich.

Jack saw his thesis as a cautionary message to Americans, who needed to learn from Britain’s mistakes. “In this calm acceptance of the theory that the democratic way is the best… lies the danger,” Jack wrote. “Why, exactly, is the democratic system better?… It is better because it allows for the full development of man as an individual. But… this only indicates that democracy is a ‘pleasanter’ form of government—not that it is the best form of government for meeting the present world problem. It may be a great system of government to live in internally but it’s [sic] weaknesses are great. We wish to preserve it here. If we are to do so, we must look at situations much more realistically than we do now.”

What seems most important now about Kennedy’s thesis is the extent to which he emphasizes the need for unsentimental realism about world affairs. Making judgments about international dangers by ignoring them or wishing them away is as dangerous as unthinking hostility to foreign rivals who may be useful temporary allies. Personal, self-serving convictions are as unconstructive as outdated ideologies in deciding what best serves a nation’s interests. Although he would not always be faithful to these propositions, they became mainstays of most of his later responses to foreign challenges.

The exploding world crisis encouraged Jack to turn his thesis into a book. It was not common for a Harvard undergraduate to instantly convert his honor’s paper into a major publication. As Harold Laski told Joe, “While it is the book of a lad with brains, it is very immature, it has no structure, and dwells almost wholly on the surface of things. In a good university, half a hundred seniors do books like this as part of their normal work in their final year. But they don’t publish them for the good reason that their importance lies solely in what they get out of doing them and not out of what they have to say. I don’t honestly think any publisher would have looked at that book of Jack’s if he had not been your son, and if you had not been ambassador. And those are not the right grounds for publication.”

However accurate Laski’s assessment of the thesis, he missed something others in America saw—namely, that international developments made Jack’s analysis a timely appeal to millions of Americans eager to consider a wise response to the European war. The collapse of France had made Americans feel more vulnerable to external attacks than at any time since the Franco-British abuse of neutral rights during the Napoleonic Wars.

New York Times columnist Arthur Krock, to whom Jack showed the thesis, thought “it was amateurish in many respects but not, certainly not, as much so as most writings in that category are.” “I told him,” Krock said, “I thought it would make a very welcome and very useful book.” And so Krock helped Jack with stylistic revisions and suggested a title, Why England Slept, mirroring Churchill’s While England Slept. Krock also gave Jack the name of an agent, who arranged a contract with Wilfred Funk, a small publishing house, after Harper & Brothers and Harcourt Brace both turned it down. Harpers thought the manuscript already eclipsed by current events, and Harcourt thought “sales possibilities too dim” and “things moving too fast” for a book on the British failure at Munich to command much interest in the United States.

They were wrong, but partly because Jack made revisions to the manuscript that gave it more balance and greater timeliness than the original. In deciding to try for publication, Jack understood that he needed to do it “as soon as possible, as I should get it out before… the issue becomes too dead.” He also accepted the recommendation of several English readers that he not place so much more blame on the public than on Baldwin and Chamberlain for Munich. Most important, he saw the need to say less about the shortcomings of democracy and more about its defense in present circumstances. Hitler’s victories in Europe and the feeling that Britain might succumb to Nazi aggression made it more appealing for Jack to emphasize not democracy’s weakness in meeting a foreign crisis but what America could do to ensure its national security in a dangerous world.

The book, which received almost uniformly glowing reviews and substantial sales in the United States and Britain, demonstrated that Jack had the wherewithal for a public career. No one, including Jack, was then thinking in terms of any run for office. But his success suggested that he was an astute observer of public mood and problems, especially as they related to international affairs. Neither Jack nor Joe foresaw the precise direction Jack’s life would now take, but Joe saw the book as a valuable first step for a young man reaching for public influence. “I read Jack’s book through and I think it is a swell job,” he wrote Rose. “There is no question that regardless of whether he makes any money out of it or not, he will have built himself a foundation for his reputation that will be of lasting value to him.” And to Jack he wrote: “The book will do you an amazing amount of good…. 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.”

For his part, Jack had few, if any, illusions about the book. He understood that circumstances more than his skill as a writer and analyst had given the book its resonance. But he also understood that seizing the main chance when it presented itself was not to be despised; he was more than happy, then, to devote his summer to publicizing and selling Why England Slept.

Kennedy friend Charles Spalding remembers visiting Jack at the Cape shortly after the book had appeared. “Jack was downstairs with a whole pile of these books…. It was just a wonderful disarray of papers, letters from Prime Ministers and congressmen and people you’ve heard about, some under wet bathing suits and some under the bed.” When Spalding asked how the book was selling, “[Jack’s] eyes lit up and he said, ‘Oh, very well. I’m seeing to that.’ He was seeing that the books were handed out and he was really moving the books…. It was just a sort of amusing pragmatism that he hadn’t just written the book and then he was going to just disappear. He was going to see that it got sold. He was just laughing at his own success…. He was doing everything he could to promote it. And he was good at that…. The interviews, radio programs, answering letters, autographing copies, sending them out, checking bookstores.”

IN THE SUMMER OF 1940, aside from promoting his book, Jack was at loss for what to do next. He had thoughts of attending Yale Law School, but health problems persuaded him to temporarily abandon such plans. In addition, he had doubts about a law career. It would mean not only competing with brother Joe, who was enrolled at Harvard, but also abandoning what Lem Billings called his intellectual interests. “I don’t think there was any question but that he was thinking he would go into journalism and teaching.” But like millions of other young Americans in 1940, the state of world affairs made private decisions hostage to public developments. “There was an awful vacuum there in 1940,” Lem remembered, “a very uncomfortable period for a guy who was graduating from school. I mean, what to do? We were so damn close to going to war…. You didn’t know what you were going to do[,] so what was the point of getting into any lifelong thing?” Everybody “was just sort of marking time.” The passage of a bill in September 1940 authorizing the first peacetime draft had put the country’s young men on notice that military service might take precedence over personal plans.

And so Jack went to Stanford in September to nurse himself back to health in the warm California sun. His graduate work, which lasted only one quarter, to December 1940, was supposed to focus on business studies, but his courses and interests remained in political science and international relations. A young woman he dated while in California remembered his attentiveness to contemporary events. “He was fascinated with the news. He always turned it on in the car, on the radio…. He was intrigued by what was going on in the world.” Another Stanford contemporary recalled Jack’s conversations with Stanford’s student body president about the nature of effective government leadership—he pointed to FDR as a model of how to make big changes without overturning traditional institutions. This student also remembered Jack’s telling him and other “remote westerners… that there was a war on, that it had been on for a year, and that we were going to get into it.” In December, he attended an Institute of World Affairs conference in Riverside, California, on current international problems, where he acted as a “rapporteur” for four of the sessions: “War and the Future World Economy,” “The Americas: Problems of Hemispheric Defense & Security,” “War and the Preservation of European Civilization,” and “Proposed Plans for Peace.”

His interest in overseas affairs was more than academic. When Joe resigned his ambassadorship in December 1940, Jack counseled him on what to say to insulate him from charges of appeasement and identification with Chamberlain’s failed policies. More important, he now convinced his father not to take issue with the Lend-Lease bill FDR proposed as a means to help Britain defeat Germany. If we failed to give this aid now and Britain were defeated, Jack argued, it would cost the United States much more later and might force us into a war with Hitler, which Joe, above all, wished to avoid. Under pressure from Roosevelt as well, Joe publicly accepted his son’s reasoning.

Jack’s term at Stanford was an interlude of no lasting consequence. His unresolved health difficulties drew him back to the East Coast at the start of 1941, where he busied himself for the first three months of the year with finding a ghostwriter for his father’s memoirs and thinking about renewing his application to Yale Law School. But when his mother and sister Eunice went to Latin America in the spring, Jack decided to join them and then travel on his own. He visited Argentina, Brazil, and Chile, with brief stops in Uruguay, Peru, Ecuador, Colombia, and Panama.

Although the trip was valuable, upon his return the direction of Jack’s life still remained unclear. There was, however, little question that it would sooner or later take a serious turn. However self-indulgent, Jack had no intention of becoming a career playboy trading on his father’s fame and influence. And Joe and Rose believed it inconceivable for any of their children to settle for a sybaritic life. The material benefits of their wealth were all too obvious, from the opulent houses to the cars, clothing, jewelry, foreign travel, lavish vacations, and parties at home and abroad with all the social lions of their time. But a life without ambition, without some larger purpose than one’s own needs and satisfaction, was never part of the Kennedy ethos. It is one of the great ironies of this family’s saga that however frivolous any of its members might be at one time or another, it was impermissible to make frivolity a way of life.

At the age of twenty-three, Jack understood that he needed a lifework; just as important, he had considerable confidence that he would succeed. His background and experience had created a belief in himself as someone special, as standing apart from the many other talented, promising young men he had met at home and abroad. His privileged life had opened the way for his success, but it was hardly the full measure of what would make for an uncommon life.