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 Mussoli
ni. 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 made 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.