The President’s Best Friend


There were other differences. Lem was healthy; Jack’s health was precarious. During their years at Choate, Jack was chronically ill, susceptible to a variety of viral ailments, vulnerable to infection. A knee skinned on the tennis court, later infected, kept him in the infirmary for several weeks. A blood condition led to hospitalization during his fifth-form year. It was serious; Lem was among the students who prayed for him during evening chapel. Jack recovered and returned. Golf became his only official sport. Discontented with orders to avoid strenuous physical activity, he learned how to live vigorously with pain. His brother Robert would later write: “At least one half of the days that he spent on this earth were days of intense physical pain. He had scarlet fever when he was very young and serious back trouble when he was older. In between he had almost every other conceivable I ailment.”

Lem said that if he ever wrote Jack’s biography, he’d call B it John F. Kennedy: A Medical History . In fact, he rarely, if ever, heard Jack complain about his medical misfortunes. Lem usually knew nothing more about the diagnosis of an illness than that “a blood condition” was “serious.” Devoid of self-pity, Jack was either stoical about his afflictions or humorous. His letters to Lem from various hospitals were wry and sardonic. Often he repeated a joke started by his brother Robert, who had once expressed pity for any mosquito that took “the great risk of biting Jack Kennedy,” for surely Jack’s blood would poison the insect.

Kennedy was elected “Most Likely to Succeed”; Lem Billings was elected “Best Natured.”

Public Enemies Number One and Two both prayed a lot during that perilous week in February. After being expelled on Monday morning, Lem and Jack learned that one of the more compassionate assistant headmasters had persuaded George St. John to downgrade the sentence to strict probation. Despite the reprieve, there was still trouble ahead.

Mr. St. John sent cables to Mr. Kennedy and Mrs. Billings requesting that both come up to Choate for private conferences on Saturday. On Friday, Joseph P. Kennedy, chairman of the newly created Securities and Exchange Commission, sent a wire from Washington, stating that the earliest he could arrive in Wallingford was 12:15 on Sunday. Mrs. Romaine LeMoyne Billings, widowed, living in extremely modest circumstances since the death of her physician husband in 1933, would nevertheless make the journey from Pittsburgh.

Complications ensued. A telegram, addressed to Jack and Lem from Jack’s fifteen-year-old sister, Kathleen, and her roommate at the Convent of the Sacred Heart in Noroton, arrived on Saturday at the school office: DEAR PUBLIC ENEMIES ONE AND TWO. ALL OUR PRAYERS ARE UNITED WITH YOU AND THE ELEVEN OTHER MUCKS. WHEN THE OLD MEN ARRIVE SORRY WE WONT BE THERE FOR THE BURIAL .

Intercepted, opened, and read by the headmaster, the message further enraged George St. John. Lem and Jack were not given the telegram until after it had been shown to Mr. Kennedy. The private conferences, lasting most of Sunday afternoon, were held in the headmaster’s study. Jack and Lem were contrite. Promises for better behavior were made; parental displeasure was expressed. Mr. Kennedy slipped from stern disapproval into momentary blazes of steely Irish wit. “My mother’s reaction was ‘much ado about nothing,’” Lem would later recall. “So I was not terribly worried because, after all, we had done nothing overtly illegal. But, God, if my father had been alive, I wouldn’t have had a behind to sit on.”

They graduated in June. Kennedy was voted “Most Likely to Succeed,” outpolling the two runners-up with the largest plurality (thirty-seven votes) in the class elections. Billings was elected “Best Natured” with a plurality of twelve votes. They exchanged copies of their senior pictures; Kennedy signed his: “To Lemmer—the gayest soul I know. In memory of two tense years and in hopes of many more. Your old pal and supporter! Ken.” The picture that Lem gave to Jack was notable because, in fact, it was the second senior picture of Lem that had appeared in the Choate yearbook in two successive years.

“In 1934, at the end of Lem’s first senior year, he decided that he wanted to spend a second senior year at Choate because he and Jack were having such a fantastic time and he had found his first real friend,” said Peter W. Kaplan, who, a generation later, was one of Lem’s closest friends and the only person, outside Lem’s family, to whom Lem would acknowledge his actual age. “Lem asked permission to stay the extra year, and he got it. It was hard to believe; he was on scholarship, and this was the Depression, and it was an awful time for Lem. His father had died. His mother was having a tough time. But he wanted to stay at Choate, which he disliked intensely, to be with Jack, and he consciously adjusted the year of his birth to be the same age as his best friend.”