The President’s Best Friend


Billings and Kennedy called each other Billy and Johnny, or any of a dozen nicknames that included, respectively, Lem, Lemmer, Leem, or Moynie; Jack, Ken, or Kenadosus. A 1935 yearbook photograph of the two of them roughhousing in a snowdrift was captioned “Leem and Rat-Face.” To their families, close friends, and a few genial masters, they were known as Lem and Jack. Now, in the school at large, they were identified with a dual nickname: Public Enemies Number One and Two. (Kennedy had somehow earned preeminent status.)

Both Public Enemies agreed that the headmaster’s punishment did not fit their crime; it was probably a personal matter, after all. Mr. St. John had been specifically irritated by the two of them ever since they had begun rooming together in the West Wing dormitory in the fall. He had even recommended to Jack’s father that the source of their childish behavior might be isolated if Jack and Lem were sent to a gland specialist.

The two friends had first met in the spring of 1933 when Jack was elected to the business board of The Brief , the school yearbook, which Lem had joined the previous year. From the outset they were inseparable. For Lem, Jack was the best thing about life at school. Jack knew how to create the kind of fun that lightened the mood of everyone around him. His high spirits were contagious. For Kennedy, Billings was more than just a partner in schoolboy crime. He was the first intimate friend Kennedy had found outside his own family.

The making of a best friend in preparatory school was no easy matter. Adolescence itself was ruled by codes that were as restrictive as those that Choate drilled into its students. In class an imaginative mind had to be forcibly restrained because it drew excessive attention to itself. Originality and sincerity were scorned. In athletics, rivalry was the highest form of affection. Emotional candor was suicidal. Yet, in their friendship, Billings and Kennedy discovered that they could enjoy each other without rivalry.

It was an important discovery. Both were second sons, both had older brothers who had gone to Choate, amassing an outstanding number of athletic and scholastic glories. F. Tremaine ("Josh") Billings, Jr., ’29, had been captain of the varsity football team, a letterman in three sports, president of his class, editor-in-chief of The Brief . Joseph P. Kennedy, Jr., ’33, had been vice-president of the St. Andrews Society (a charitable organization), a letterman on the undefeated football team of 1933, the winner of the Harvard Football Trophy (”awarded to that member of the Choate football squad who best combines scholarship and sportsmanship").

“Both of them had elder brothers who were very successful, who were prodigies in their own ways, and for whom there was great expectation,” said Robert F. Kennedy, Jr., who became Lem’s closest friend in the next generation. “Both Lem and Jack were almost runts of the litter. Lem’s father was always displeased with him. Lem was practically blind, he grew up scrawny, and he could never match his older brother. Jack’s older brother was really the hope of the family. So when Lem and Jack got together, it was almost as if they were thumbing their noses at the world, at all those expectations, particularly the way people underestimated the two of them. But together they really had everything. They loved each other and they got satisfaction out of the successes that each of them enjoyed.”


Instead of competing, Billings and Kennedy relied on one another. Both of them were exceptionally bright. Though not yet superior students, they shared a genuine respect for books and a passion for the fine points of history. Both were animated storytellers; invariably, one was the hero of the other’s favorite anecdotes. Both were outgoing, charming, curious. (“… P.S. Gertrude Stein lectured here,” Jack reported home to his parents. “LeMoyne + Moi rushed up and got her autograph and had a rare old conversation!”)

Their differences complemented each other. Physically, Lem was the stronger of the two. Jack was quicker, more graceful. Lean, lightweight, Kennedy possessed the kind of natural coordination and rhythm that enabled him to adapt readily to any sport. Billings played sports subjectively; his style was dogged, grinding, emotional. He was not a natural. Myopic since birth, he had difficulty catching Jack’s passes. “Can’t throw a ball, can’t catch a ball,” Lem would admit. “Any sport with strength—great! Anything with a ball— forget it .” Twenty pounds heavier than Jack, bigger than most of their classmates, Lem was captain of the varsity crew; he also earned letters in wrestling and football, as a lineman.