Greg Lewis

Jack and Lem: A Friendship for Life 🇺🇸 In the autumn of 1933, two teenagers crossed paths at Choate School in Wallingford, Connecticut, and never really parted again. John Fitzgerald Kennedy, then fifteen, and Kirk LeMoyne “Lem” Billings, a year older, became roommates almost at once. They shared a sharp wit, a taste for mischief (they helped organize the school’s infamous “Muckers” prank crew), and an ease with each other that made the rest of the world feel secondary. Billings even repeated his senior year so they could graduate together. Four years later, after Kennedy’s time at Harvard had begun, the two young men boarded the S.S. Washington for a three-month journey across Europe. They drove a Ford convertible through France, Italy, Germany, and the Low Countries, sightseeing, talking to locals, and keeping diaries that still survive. In Germany they bought a dachshund puppy for eight dollars; Lem named him Dunker, Jack called him Offie. Kennedy’s allergies forced them to find the dog a new home in the Netherlands, but the episode became part of the trip’s lore. In Carcassonne, Kennedy climbed a castle wall; in Pisa and elsewhere they moved through a continent already shadowed by dictatorship, yet still open to two relatively carefree Americans. The journey deepened their bond and began shifting Kennedy away from the isolationism of his father’s circle. From that point forward, Lem was simply there. He was an usher at Kennedy’s wedding, a campaign presence, and later a near-permanent fixture in the White House—so familiar that younger Kennedys grew up assuming he was another older brother. Joseph Kennedy once called him “my second son.” When the presidency ended in Dallas on November 22, 1963, the loss hit Billings with singular force. Friends and biographers later described him as among the most shattered of those closest to Kennedy—“probably the saddest of the Kennedy ‘widows.’” He never fully recovered. Depression settled in; drinking intensified; after Robert Kennedy’s death in 1968 the spiral grew darker still. Billings lived until May 28, 1981, dying of a heart attack in his sleep in a Manhattan apartment at age sixty-five. He never married. The young men of the next Kennedy generation carried out his wish that they handle his casket, treating him to the end as one of their own. What remained was the record of a friendship that had begun in a Connecticut dormitory, been tested and sealed on the roads of pre-war Europe, and endured every season of Kennedy’s life until the day it stopped. 🇺🇸🫡