On another occasion, Jack and Lem and an alumnus of the school, Pete Caesar, left a Choate evening social with two girls, Olive Cawley and Pussy Brooks, and drove to a nearby farm. En route, the quintet noticed they were being followed by one of the school’s cars. On Jack’s suggestion, Pete and Pussy remained in the car while the other three dashed off unseen. When the campus cops arrived, they merely found an alumnus necking with his girl and drove on. Jack and Olive, meanwhile, had found a remote corner of a barn, and Lem planted himself in a haystack in another barn and waited quietly for everyone to finish.54
Having been rebuffed by Jack in no uncertain terms, Lem backed off and, it seems, never made the proposition again. He could only watch as Jack became increasingly infatuated with Cawley, a pretty and vibrant brunette who hailed from New York City and attended the private Kimberley School, in New Jersey.55 But it’s telling that Jack, contrary to what one would expect of a straight man in that era, did not break off the friendship. Even after it became incontrovertibly clear in later years that Lem was gay, the two remained close. “Jack was a hell of a forgiving guy,” their friend Rip Horton said. “He was terribly understanding.” Journalist Charles Bartlett, who befriended Jack and Lem after the Second World War, said much the same thing: “I liked Lem and saw that he was a good friend of Jack’s. Jack was not a judgmental type of guy. He accepted his friends without passing judgment on them.”56
The truth was that Jack enjoyed spending time with Lem, valued his friendship. The perspicacious Seymour St. John, in an interview half a century later, saw Lem as a tragic figure whose identity over time became entirely wrapped up in Jack Kennedy and his family, “who had nothing really to hold onto” until he found Jack. After that, “anything Jack did, he would follow right along with him and be the stooge.” But St. John also perceived the positive side of the friendship, not least for Jack, who could count on his friend to be the jester, to lift his spirits when he might otherwise have sunk into despair, with his chronic ailments and his ongoing rivalry with Joe Junior. “It was Billings’s loyalty that helped [Jack] to emerge from his adolescent trials with his confidence in himself strengthened rather than broken,” St. John said.57
Now, as they entered their final year (Lem could have finished in 1934, but, as if to demonstrate Seymour St. John’s point, he stayed on an extra year in order to be with Jack and their friends), they were determined to have a good time. Maher, sensing trouble, put them in a room right next to his own.58 The trouble came soon enough. Jack had brought with him from Hyannis Port a pristine old Victrola and a bunch of records, and in short order their room became the hangout spot for a dozen friends. Maher informed the headmaster of the noise and messiness, and before long George St. John stood before the student body in the long, formal English dining hall and spoke of a small group of selfish, pleasure-loving troublemakers who seemed intent on destroying the peace of the school. They were “muckers,” the headmaster said, nothing more than muckers, and he would not stand for it.59
Perfect, Jack and his buddies thought as they listened: muckers! The name fit them to a tee. The group promptly went into Wallingford and shelled out $12 each for a small gold charm in the shape of a shovel and engraved with the initials CMC, for Choate Muckers Club. (Another meaning of mucker was someone who, in the days before automobiles, shoveled horse manure off the streets.) Their subsequent antics were misdemeanors at worst—sneaking off school grounds for milkshakes and playing music after hours. Alcohol was never in the equation, and neither was smoking. For Spring Festival they planned to have each member arrive at the dance pulling his date on a shovel, then have photographs taken outside next to a manure pile, shovels in hand.60
St. John was furious when he learned of the scheme. At lunch in the dining hall, he read off the Muckers’ names, accused them of undermining Choate’s morals and integrity, and ordered them into his study. There he expelled them and ordered them to clear out of their rooms and prepare to depart the school. The astonished boys trudged back to their dorms and fretted about how to tell their parents, only to be called back into the headmaster’s study and informed that he had changed his mind: they would not be expelled after all. But there would be no more club, he told them, no more shenanigans, and they would be kept at school over the Easter break.61
At St. John’s request, Joe Kennedy and Lem’s mother, Romaine, traveled to the school to discuss the crisis. Their sons were the ringleaders, he told them, and he wanted them, as parents, to understand the seriousness of the situation. During the Kennedys’ session, father and son nodded politely at the headmaster’s stern words, and Jack expressed contrition. Mr. Kennedy professed to be appalled by the club’s actions, but inside he questioned what all the fuss was about. Himself an outsider in this elite Episcopalian milieu, he wondered if George St. John’s rumored anti-Catholicism played a role in his overheated approach to the affair. (For there was a third meaning of mucker: a lowly Irish Catholic immigrant who worked to clear the swamps of Boston’s Back Bay.) When St. John interrupted their conversation 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 Muckers Club had been mine, you can be sure it wouldn’t have started with an M!”62
Jack with three fellow “Muckers” on a street in Wallingford. From left: Ralph Horton, Lem Billings, Butch Schriber, and Jack.
One detects a sense of entitlement in how both Kennedys—father and son—reacted to the Muckers affair, a sense that the rules didn’t fully apply to Jack, and that St. John couldn’t really touch him. More than that, in Joe Kennedy’s handling of the episode there’s a strong whiff of fatherly pride. Well aware of his reputation for being a domineering, overbearing presence in his children’s lives, he worked to instill in them—and especially the boys—a certain irreverence and independence of mind. When Young Joe graduated from Choate in 1933, his father, upon the recommendation of Harvard Law School professor Felix Frankfurter, dispatched him to the London School of Economics to spend a year studying with Harold Laski, the distinguished socialist theorist and economist, before matriculating at Harvard. Laski’s political and economic philosophies were far from Kennedy’s own, but he reasoned that a sustained period under the Briton’s tutelage would broaden Joe Junior’s intellectual range and hone his ability to defend a more conservative position. Nor was this a newfound philosophy: visitors to the Kennedy home had long noted that during the mealtime seminars, Mr. Kennedy never pushed Joe or Jack or the other children to adopt his positions, but encouraged them to adopt and defend their own points of view.63
But being informed and opinionated was not enough—commitment and responsibility were essential, too. In this regard Jack remained for his father a source of worry, no less at the end of the Choate years than at the beginning. In letter after letter that final year (penned, mind you, while he headed a major new government agency in Washington), he nudged and cajoled his second son, urging him to finish, as he put it, in “a blaze of glory.” A missive from December 1934 gives the flavor:
After long experience in sizing up people, I definitely know you have the goods and you can go a long way. Now aren’t you foolish not to get all there is out of what God has given you and what you can do with it yourself? After all, I would be lacking even as a friend if I did not urge you to take advantage of the qualities you have. It is very difficult to make up fundamentals you have neglected when you were very young, and that is why I am urging you to do the best you can. I am not expecting too much, and I will not be disappointed if you don’t turn out to be a real genius, but I think you can be a really worthwhile citizen with good judgment and understanding.64
In the wake of the near expulsion in the spring, Choate gave three of the troublemakers an opportunity to meet with a Columbia University psychologist, Prescott Lecky. Jack, perhaps at his father’s urging, accepted the offer. Lecky reported that he found the young man to be very able, “but definitely in a trap, psychologically speaking. He has established a reputation in the family for thoughtlessness, sloppiness, and inefficiency, and he feels entirely at home in the role.” When Lecky asked him if he expected to succeed in the world with this attitude, Jack had no answer. “He thinks of himself as a self-reliant, intelligent, and courageous boy,” Lecky continued, “but he has never recognized the difficulty he will have in maintaining those definitions unless he sacrifices the defense devices that he has built up through the years. He does not worry about his sloppiness, he says, and has never been neat in his life; but it is obvious that he must worry sooner or later, or give up the definitions he values most.”
More than anything, Lecky determined, the source of Jack’s troubles could be found in the rivalry with Joe Junior. “My brother is the efficient one in the family,” Jack told him, “and I am the boy who doesn’t get things done. If my brother were not so efficient, it would be easier for me to be efficient. He does it so much better than I do.” Lecky concluded that “Jack is apparently avoiding comparison and withdraws from the race, so to speak, in order to convince himself that he is not trying.”65
It was an astute appraisal of a young man who had yet to find his way. Lecky was surely right that the sibling rivalry and the inferiority complex that resulted from his second-son status helped explain Jack’s anti-establishment flair and slacker ways. Then again, one could go too far with the notion. Perhaps a part of Jack was simply following in the footsteps of his father, a similarly indifferent student during his days at Boston Latin thirty years before.
Whatever the case, as Jack prepared to depart Choate that spring of 1935—aged eighteen, tall and wiry, with an angular, handsome face and a mop of hair that resisted all efforts at control—he could take a certain satisfaction from his four years at the school. His health travails had been at times all-consuming and, partly for that reason, his academic performance seldom went beyond middling. But he experienced a freedom he had never had before, especially after his brother’s departure at the midpoint. He met a lifelong friend in Lem Billings and enjoyed the conviviality of a large circle of other pals. What’s more, he learned during his Choate years how to get along on his own, independently, even in the face of adversity, and saw the degree to which he could use his charm and sense of humor to his advantage. “In any school he would have got away with some things, just on his smile,” George St. John conceded. “He was a very likeable person, very lovable.” One measure of that: despite ranking barely above the median in his class, Jack Kennedy was voted by his classmates “most likely to succeed.” No doubt the result owed a good deal to the Kennedys’ immense wealth, well known on campus, and to the energetic efforts of the ex-Muckers, led by Billings, to round up votes for their leader, but it also resulted from Jack’s popularity among his fellow students.66
The vote was Jack’s final poke in the eye to the Choate establishment, and it must have annoyed the school’s leaders to see their exasperating Mucker recognized in this way. But they could see the promise in the lad, more so than in his accomplished older brother, who lacked his creative intelligence. “Jack has a clever, individualist mind,” George St. John had told Mr. Kennedy some time before. “It is a harder mind to put in harness than Joe’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.”67
Assistant headmaster Wardell St. John had a similar inkling. “Jack has it in him to be a great leader of men,” he wrote at the end of spring term, “and somehow I have a feeling that he is going to be just that.”68
It was, time would reveal, a most penetrating pair of assessments.