Defying the Rules
Jack's lack of effort and his medical problems were just the beginning of his problems at school. The headmaster of Choate, George St. John, soon found that Jack was just the opposite of his brother Joe.
The Muckers Club
Jack was a troublemaker, and his greatest act of defiance came with the formation of the Muckers Club. St. John's repetitive lectures in chapel about the troublemakers, or muckers as he liked to call them, inspired Jack, Lem Billings, and other friends to organize the club. This was almost the last straw for St. John, who considered the club just another negative mark on Jack's record. When he became aware of the club, he met with Joe Kennedy and Jack in his office. St. John was ready to expel Jack from school, but Joe, although angry with his son, convinced the headmaster to let Jack stay as long as he agreed to dissolve the club.
Following in His Father's Footsteps
It was no secret, not even to Rose, that Joe Kennedy had a long history of extramarital affairs. It was not uncommon for him to invite his newest girlfriend to the Kennedy home, where they innocently dined with the family. The actress Gloria Swanson was among the women who went in and out of the Kennedy home in the 1920s. Rose, just like her own mother, played the polite hostess to her husband's mistress when the woman visited the Kennedy summer home.
It was Swanson, however, who nearly destroyed Rose and Joe's marriage. By the time of the affair, Joe had acquired three studios in Hollywood. He met Swanson at one of the studios during the filming of Queen Kelly. Unlike many of his other affairs, Joe became enthralled with Swanson and went to the Catholic Church in hope of attaining the approval to separate from Rose. Once separated, he planned to live with Swanson. When Cardinal O'Connell heard the plan, he made a visit to Swanson and asked her to end the relationship. Shortly thereafter, the affair ended.
Joe's less than secretive behavior had a lasting impact on his children, who knew of and even came to accept Joe's betrayal of their mother. Jack, in particular, came to admire his father's vigorous quest for fulfillment with numerous women. An impressed young Jack hoped that when he reached his father's age, he too would remain a playboy. According to his good friend Lem Billings, when Jack was seventeen he engaged in his first sexual encounter, with a Harlem prostitute.
“I was immediately captivated by Jack. He had the best sense of humor of anybody I had ever met…. He enjoyed things with such intensity that he made you feel that whatever you were doing was absolutely the most wonderful thing you possible could be doing.”
— Lem Billings, as quoted in The Fitzgeralds and the Kennedys: An American Saga
In spite of Jack's disobedience of school rules, sexual experimentation, and mediocre academic record, by the time that he graduated in 1935 he had acquired the coveted title of “most likely to succeed.” It was an unlikely title for Jack, considering that he graduated 65th out of 110, but there was something endearing about the Kennedy who was witty, fun, and laid back. Even headmaster St. John came to like him. One of the most attractive traits that St. John noticed about him was his ability to think independently. In fact, he found that the more time he spent with the student he had once called a “mucker,” the better he liked him. With such a likeable personality and a promising future, it came as no surprise to Jack's classmates, or to St. John, when Jack announced that he was headed for Princeton.