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The President’s Best Friend

July 2024
42min read

If he’d been the closest companion of the president of IBM, you might happen across his name in a privately printed memoir. But LeMoyne Billings was John Fitzgerald Kennedy’s best friend from Choate to the White House—and that makes him part of history.

CROATE, 1935

THIS TIME they were really in trouble. The twelve boys lined up in the headmaster’s office at the Choate School in Wallingford, Connecticut, awaited sentencing for their crime. It was Monday, February 11, a glowering, heavy-skied New England winter morning. The loudest sound in the headmaster’s chambers was the rattle and hiss of the radiator. The headmaster sat silent at his desk. Before announcing their punishment, he would wait until every one of the thirteen accused was in his presence. All of them were guilty. One of them was missing.

The tallest boy in the lineup, K. LeMoyne Billings, a bespectacled, six-foot-two-inch, 175-pound sixth former (senior), knew exactly where the missing boy was at that moment, but Billings was mostly concerned about the face he himself was presenting. Billings had difficulty with his face: the natural expression of his emotions was usually about half under control. His eyes, friendly, blue, and guileless, were nearly incapable of bluffing, and anyone who knew him well could detect the supreme effort of trying to keep his face from breaking into a vast and reckless smile.

So, for the moment, it was probably better that Billings’s best friend and roommate, John F. Kennedy, was missing. If there was a single offense that would surely and swiftly bring the end of all things to a Choate boy, it was laughter in the face of the angry headmaster.

To his students in general, and to LeMoyne Billings in particular, Headmaster George St. John was scary. Inscrutable monarch of Choate since 1908, his enforcement of rules, and his punishment of renegades, was harsh, inflexible, and final.

“Ten percent of the boys at Choate are muckers ,” St. John had thundered during his sermon in evening chapel the preceding month. He had gone on to portray the typical “mucker” as a “bad apple in the basket,” a boy who cut up in class, behaved impiously in chapel, and made a general nuisance of himself in the eyes of school and God. In the new term ahead, St. John warned, muckers would not be tolerated.

That evening after chapel, during the half hour before the bell rang for dinner, Billings and Kennedy reflected on the headmaster’s sermon. Life for sixth formers was deregulated to a small degree; they were allowed to play records on Victrolas in their rooms between chapel and dinner. Because the two boys roomed near the dining hall, the doorway often i got so jammed with students that Billinss and Kennedy had difficulty getting into their own room. That night they decided to form a club and offered membership to eleven of their closest friends, who would then share the exclusive privilege of listening to Kennedy’s Victrola. A resolution was unanimously carried, naming each member of the club president. Later on, each purchased a gold, charm-sized shovel upon which was engraved his initials, the abbreviated title “Pres.,” and the initials of the newly established institution, “CMC.”—Choate Muckers Club. The club broke none of Choate’s cardinal rules during its brief and risky existence. Its membership roster showed a majority of outstanding athletes (including four varsity captains), none of whom drank or smoked or sneaked into Wallingford after lights. But the Muckers did tend to be careless about Choate’s minor regulations. Occasionally, for instance, when they were supposed to be in class, a recurrence of “sore throats” permitted them to have their throats sprayed at the infirmary where they were issued a “tardy” slip, which they had to place on a clipboard in the headmaster’s office before returning immediately to class. But the tardy slips could be doctored with a pencil, crumpled, and presented as “absent” slips; so a few Muckers were not merely tardy but altogether absent from a class or two.

Now, on this grim Monday morning, John F. Kennedy was carrying such an absent slip to the clipboard in the headmaster’s office, unaware that the balance of the Muckers Club membership was assembled within. If he was startled when he entered the room, he did not show it.

Kennedy looked extremely inquisitive, LeMoyne Billings noticed, perhaps a little amused. Carrying himself with utter confidence, the five-foot-eleven-inch, 155-pound seventeenyear-old quietly joined his friends and the headmaster.

Mr. St. John briefly summarized his knowledge and opinion of the group’s immature behavior. Then he declared that the punishment for establishing an illegal club—indeed, deliberately giving it a mocking name, which he did not care to repeat—was expulsion. He told the boys to pack their trunks immediately and make arrangements to leave Choate by the end of the day. Their parents, he added, would be notified by the school. That was all.

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.

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.”


TAKING OFF HIS glasses, Lem opened the glass door of the shower stall in the bathroom adjoining Jack’s room. It was his first visit to Jack’s parents’ summer place, a roomy, white, green-shuttered house on a broad lawn facing Nantucket Sound. Everywhere there was the smell of salt and the newness of summer and the extraordinary mixture of sounds from nine children, their parents, governesses, maids, visiting cousins, and pets.

The daily schedule was more rigorous than at Choate. Lem had swum; run; played tennis; played softball; sailed (as Jack’s crew) and learned that a jib was necessary to win a race ("Lemmie never quite caught on to how a jib worked,” Eunice Kennedy Shriver recalled. “Jack would say, ‘Who’s going to pull up the jib, Billy? I’ve got the mainsail and the race starts in two minutes, so who’s going to pull up the jib , Billy?’”); learned that winning was necessary (to be invited back); played touch football; dropped passes (Jack’s); rushed in too fast on the enemy quarterback (Jack’s older brother, Joe); run some more (faster this time, away from Joe); been teased (by Jack’s sister Kathleen); joked about (by Jack’s nine-year-old brother, Robert); teased again (by Jack’s thirteen-year-old sister, Eunice); teased some more (by Jack’s ten-year-old sister, Patricia); pawed over (by a variety of more or less friendly dogs); and, finally, allowed to take a shower.

It was the first time he’d been alone all day. He was hot, exhausted, ready for a shower. He stepped into the stall, shut the door behind him (it opened inward), and turned on the cold-water faucet. …

In May, Joseph P. Kennedy had been thrown from a horse in Bronxville, New York, breaking his right leg and his left ankle. His doctor had prescribed scalding hot baths four times a day to heal the leg and the ankle. The Cape Cod house did not have sufficiently hot water, so Joseph Kennedy installed new boilers in the cellar. During installation of the pipes, the plumbers had apparently reversed the hot and cold taps.

Lem was very bright,” said Eunice Kennedy Shriver. “He absorbed the world in all its dimensions.”

A jet of scalding water shot out of the nozzle, hitting Lem on the chest. Struggling to open the door, he slipped and fell on his back. The boiling water poured forth. Lem yelled for help. He couldn’t get up. He writhed and kicked and caved in the shower wall. The metal soap dish cut a deep gash from his right ankle to his knee. Finally Mrs. Kennedy got him out. An ambulance took him to the hospital in Hyannis, where he remained for three weeks, with second- and third-degree burns.

It was not an unhappy time for the patient. He received sympathetic letters, telegrams, and visitors too. Besides his mother, Mrs. Kennedy and Jack’s sisters came regularly to Lem’s hospital room, bringing games and flowers and gentle joshing. Robert Kennedy, encouraged by his mother, made a daily visit. Bob was shy and good-humored; Lem liked him enormously. They got along well, but, years later, Bob would confess to Lem that although he had been genuinely concerned about Lem’s burns, one of the worst memories he had of his childhood was the stench of scalded flesh he had had to endure every day in Lem’s room.

It was also the first time that Lem and Jack had convalesced simultaneously. Both had come up to Cape Cod from Choate. Then, because of an intestinal disorder Jack had been sent to the Mayo Clinic in Rochester, Minnesota. They exchanged humorous letters from their respective hospital beds. “I feel very sorry for my family being burdened with you for 2 or 3 weeks,” Jack wrote, “but I am burdened with you for 9 mo .”

During that summer and the summers that followed before war broke out in Europe, Lem became a kind of ancillary brother in the Kennedy family. He was first and foremost Jack’s best friend, but he grew close to all the other children—“so close,” Patricia Kennedy Lawford later recalled, “that he was almost raised with us (Mother thinks he was!).” Lem participated enthusiastically in all the family events. He was not a timid visitor during the legendary current-affairs discussions led by Mr. Kennedy at family meals. “Of all the things you can say about Lem—that he was sweet and good and kind,” said Eunice Kennedy Shriver, “one quality that has to be remembered is that he was very bright. He had a great sense of history, he absorbed the world in all its dimensions, and he made everybody else look amusing. A lot of people would come in and be funny and make everyone laugh, and the manner in which they were funny had to do with their own ego. But Lem had the ability to make you feel funny and clever.”

Though Lem received his share of Mr. Kennedy’s famous icy looks of disapproval, he never met with the kind of coldness or uninterest that outsiders and a few of Jack’s other friends would later report about encounters with Mr. Kennedy. Probably Mr. Kennedy perceived that Lem’s dedication to Jack and the other children was as strong and enduring as that which any father could hope for his children to have from a friend. A few years later, Lem received a letter from Mr. Kennedy: “Dear Lem, this is as good a time to tell you that the Kennedy children from young Joe down should be very proud to be your friends, because year in and year out you have given them what few people really enjoy. True Friendship. I’m glad we all know you.


MADE IT BY GOD HOW ABOUT YOU , Jack wired to Lem from Hyannis Port on July 23. Lem was extremely anxious. He hadn’t heard anything from the Princeton admissions committee. Another telegram arrived. NO WORD FROM YOU YET VERY NERVOUS WIRE IMMEDIATELY—RIP Rip was Ralph D. Horton, Jr., a close friend of Lem’s and Jack’s who had been nicknamed Public Enemy Number Three during the Mucker Club episode at Choate. All three of them wanted to go to Princeton together. Two days later, Lem was at his mother’s new home in Baltimore when his acceptance to the Class of 1939 finally arrived; it had been sent first to the old address in Pittsburgh. Lem was mightily relieved.

In September, though, Jack announced that he was going to take a year off. His father had encouraged him to broaden his education by studying with the socialist professor Harold J. Laski at the London School of Economics. He cabled Lem: SEND GRAY HAT IMMEDIATELY. SAILING 1045 WEDNESDAY MORNING But in England, Kennedy became sick with jaundice and decided that Princeton’s Indian summer climate was a better place in which to recuperate than the dampness of London. Lem was in high spirits after receiving a wire from Jack on October 21 : ARRIVING PRINCETON THURSDAT AFTERNOON. HOPE YOU CAN ARRANGE ROOMING—KEN .

In the mid-thirties, Princeton undergraduates rented dormitory rooms on the basis of their individual financial capabilities. Wealthy students obtained the choicest suites. Lem, who was on scholarship, could only afford his share of one of the cheaper suites on campus. It was a twobedroom-plus-living-room arrangement on the fourth—and top—floor of South Reunion Hall. It had one closet, one radiator, and it cost $169 a year. Seventy-two steps separated the bedrooms from the bathroom in the cellar.

At first sight, Rip Horton agreed with Lem that the room was “terrible.” Horton, the son of a brewery owner, could have afforded a better suite, but he didn’t mind the place. And Kennedy, when he arrived, didn’t mind either. Living with Billings, they said, was more luxury than anyone could stand. Besides, the view of Nassau Hall across the treetops was magnificent. They made a joke of loudly counting off each step whenever they ascended from the bathroom.

It was a happy but brief autumn for the roommates of 9 South Reunion. By Christmas Jack’s jaundice had forced him to withdraw from the university. “I will always have a very tender spot in my heart for Old Nassau,” Jack later wrote to the class secretary.

The two friends began a feisty correspondence of telegrams. They sent so many wires back and forth that they became friendly with the postal telegraph manager in Princeton, an elderly woman named Mrs. Warren. HELLO MRS WARREN began Jack’s seventy-four-word message inviting Lem to Palm Beach for Christmas. ISN’T HE SWEET GIVE HIM MY LOVE was the message Mrs. Warren appended at the bottom of Jack’s telegram before delivering it to Lem. After a volley of wires discussing Lem’s financial uncertainty about the round-trip bus fare, a compromise was negotiated. Jack cabled: WILL PAY HALF OF BUS TICKET COMMA MY SHARE THUS AMOUNTING TO FIFTEEN SMACKEROOS … LET ME KNOW WHEN YOU ARRIVE HELLO MRS WARREN STOP—SWEET ESSENCE OF BUTTERMILK MERCY .

The Kennedys’ house in Palm Beach was a large, elegant white stucco villa facing the ocean. There was a well-tended lawn bordered by a seawall planted with tall royal palms; a series of front-shaded patios; a Grecian swimming pool. Beside the pool was a sun deck surrounded on all sides by tall adobe walls. This solarium, known as the Bullpen, contained cushioned benches, wicker furniture, and a telephone. It was here that Joseph P. Kennedy took the sun and conducted his business affairs by telephone, in privacy, and, sometimes, in the altogether.

Despite his continual bus-fare difficulties, Lem was a veteran of enough Palm Beach visits to know that under no circumstance was one allowed to enter or even look into the Bullpen when J. P. K. was there. During working hours, the door to the Bullpen was kept locked, and there was to be no noise in the pool area. So it was with not a little horror that Lem listened one sunny day to a proposition of Jack’s.

Lem had an excellent singing voice, and he knew a song that had become a favorite of Jack’s. It was not a Christmas carol. Jack especially liked the song when Lem sang it, which was often. Lem probably sang more renditions of “I’m No Angel” than Mae West, who had made the tune famous:

Aw, come on let me cling to you like a vine Make that low-down music trickle up your spine Baby, I can warm you with this love of mine I’m no an-gel! Aw, let me feel your fingers running through my hair I can give you kisses ‘till you walk on air Love me, honey, love me ‘till I just don’t care I’m no an-gel!

Although the lyrics embarrassed Lem, Jack was usually able to coerce him into singing them. Now Jack was making an astonishing offer. “In those days,” said Robert Kennedy, Jr., “a hundred dollars was a lot of money and Lem was very poor. Jack offered him a hundred dollars to go into the Bullpen and sing ’I’m No Angel’ to my grandfather. What Lem was supposed to do was knock at the Bullpen door, and when my grandfather opened it, naked, and probably already mad, Lem, who was wearing only a towel, was supposed to step in, drop the towel, and fling it to one side so that they would be facing each other absolutely naked. Then, Lem was supposed to say—‘Hi, Dad. I’ve always known you’ve wanted me to call you Dad. And these are words I’ve always wanted to tell you—’ and then he was supposed to burst forth with ‘Aw, come on let me cling to you like a vine…’”


This was one of the few occasions on which Lem did not yield. But he finally did sing “I’m No Angel” to Mr. Kennedy—both fully clothed—at the ambassador’s birthday party in 1961. Afterward he recounted the President’s earlier proposal, and the ambassador replied that Jack should have offered to pay him five hundred dollars to listen.


AFTER CHRISTMAS AND Easter at Palm Beach, Kennedy spent the remainder of that school year recuperating on a ranch in Arizona. His health improved. Encouraged by his father, Jack enrolled as a freshman at Harvard in the autumn of 1936. Lem, now a sophomore, continued on at Princeton. They regularly met in New York on weekends.

In its heyday, during the thirties, the Stork Club at 3 East Fifty-third Street was more than the most fashionable nightclub in Manhattan; it was a way of life. Kennedy would fly down from Boston; Billings would hitchhike into town from Princeton; they would meet (often at the Roosevelt Bar), pick up their dates (sometimes with one of Jack’s father’s cars), and go to the “Stoke” for a night of dancing. Lem was self-conscious about his lack of spending money. Kennedy matter-of-factly solved the problem by spending on an equal basis with Billings. They created their own ritual to avoid the embarrassment of a large bill: they would each order only one drink. (At the Stork Club, pretty girls in general, and Billings and Kennedy’s dates in particular, were usually given champagne on the house.) Then, during a lull in the dancing, the two would exit to a less expensive pub-style bar around the corner, where they would have a few glasses of beer before returning to their single, extravagant Stoke cocktail.

While Kennedy naturally accommodated himself to Billings’s spending limits, Billings, for his part, had to adjust his own cash flow to the slightly annoying paradox of Kennedy’s financial situation. It was, Lem believed, one of the great mysteries of life: Jack never had any cash in his pockets. Sometimes he didn’t even have pockets: his finely tailored evening clothes, suits, sports jackets, and trousers were in a perpetual state of being lost. It was the damnedest thing. Lem, who took possessions very seriously and couldn’t bear to lose a single one, was bewildered. Eventually he came to realize that although Jack provisionally had a room of his own in each of his parents’ houses, Jack had never grown up with just one room with one closet, or for that matter, one tuxedo, one dress suit, and so on. Money was not spent lavishly by Jack or his family, but where clothing was concerned, there were certainly multiple items, perhaps too many to keep track of.

So Lem, with some amusement, kept tabs on Jack’s wardrobe. “Dear LeMoyne, Many thanks for sending Jack’s tuxedo and the three blankets,” a Kennedy governess wrote from Bronxville after Jack had left Princeton. “Jack had wired me about the tuxedo, intimating I had given it away in the charity box but I wasn’t a bit scared as I thought it would arrive in the mail. … A package arrives for him almost daily containing various articles of wearing apparel he has dropped somewhere…”

Good-natured about Kennedy’s absentmindedness, Billings was humorously competitive about Kennedy’s popularity with girls. They each had a more or less steady girl friend throughout college: Billings dated Katharine Duncan Hartwell, a striking brunette from Stamford, Connecticut; Kennedy dated Olive Field Cawley. And both were successful with casual party dates, though Jack was the more sought after of the two. Lem constantly needled Jack about his success with girls, insisting it could only be attributed to his father’s wealth and fame. Kennedy disputed this theory, and ultimately decided to put it to the test. They agreed to switch names for one night. Ralph Horton arranged blind dates for them. Jack became LeMoyne Billings and turned over his father’s chauffeur-driven Rolls-Royce to Lem, who was introduced to his date as John F. Kennedy. The matter was settled to Jack’s satisfaction, Lem’s chagrin. “LeMoyne Billings” enjoyed a memorable date that night, “John Kennedy” had only a fair evening with his girl.


Increasingly their attention was drawn to the news from Europe. Nazi Berlin and Fascist Rome proclaimed a political Axis that year, Ethiopia fell to Mussolini, and the demilitarized zone of the Rhineland was suddenly occupied by the Nazi Führer. Germany and Italy both aided Franco’s forces in Spain’s Civil War. In May 1937 a short item appeared in a Pittsburgh newspaper: “Though all American passports legibly state, ‘Not good in Spain,’ ex-Pittsburgher K. LeMoyne Billings, son of Mrs. Frederic T. Billings who moved to Baltimore last year, and John Kennedy, son of Joseph P. Kennedy of Washington, will visit that war-torn country this summer for three weeks. They sail June 30 on the George Washington , will attempt to study war conditions.”

EUROPE, 1937

LEM AND JACK were on their own. The two-month grand tour began in Le Havre when Jack’s convertible Ford sedan was hauled off the boat. Kennedy had hopes of getting to Paris quickly, but before reaching the capital, Billings insisted on visiting every single cathedral town, from Rouen to Beauvais to the bomb-blasted ruins of Rheims. Billings had taken his first architecture course at Princeton and was now reaching a high pitch of excitement over the actual choir vaults and naves themselves. Usually a rapid motorist, Kennedy had to be content driving at cathedral pace while listening to Billings’s commentary on Gothic architecture.


Meanwhile, Jack’s traveling techniques got Lem involved in political discussions, nightlife, and events that were closed to the average tourist. Discovering a huge crowd swarming around Notre Dame in Paris, Jack led the way past police barricades and discovered that Cardinal Pacelli, the secretary of state of the Vatican (later Pope Pius XII), was celebrating Mass for the president of the Republic and numerous foreign dignitaries. Special passes were required, but Kennedy, with Billings in tow, marched straight up to the VIP portal and entered the cathedral without offering so much as a single word of his atrocious French. Billings was stopped, then pushed back into the crowd despite his protests in slightly less atrocious French.

At the Spanish border heavily armed guards turned them back. They stayed instead at nearby Saint-Jean-de-Luz with Kennedy’s Harvard classmate Alex de Portalis, whose family had a house on the Gulf of Gascogne.

Visiting Lourdes, Billings got sick. Next stop, Carcassonne, of which Kennedy remarked in his diary: “An old medieval town in perfect condition—which is more than can be said for Billings.” Despite Kennedy’s small winnings at the tables in Monte Carlo, they continued to stay in the cheapest hotels in deference to Billings’s budget. In Italy they attended a Mussolini rally, and Billings did impersonations of the Duce as they drove up to Germany.

The Germans would salute and say, “Heil Hitler.” Jack and Lem would wave and answer, “Hi ya, Hitler.”

Munich was their first exposure to the Nazis. Years later Lem would recount his impressions to Robert Kennedy, Jr.: “Lem said that he and Jack didn’t like the self-confidence of the Germans, the contempt. They saw contempt for Americans everywhere. The Germans would salute and say, ‘Heil Hitler!’ and Lem and Jack were expected to do the same. Instead, they got it down so that they just casually threw back their hands and waved, saying ‘Hi ya, Hitler.’” On the top floor of a beerhouse in Munich, they drank with a group of Blackshirt Nazi troopers, one of whom was Oxford-educated, chubby, and friendly. Confiding that Billings and Kennedy could take a couple of large beer mugs as souvenirs, he helpfully directed them to a door through which they were assured an undetected passage. No sooner had they followed his instructions than a waiter brusquely confiscated the mugs, detained them, and asked for their passports. Meanwhile, they saw the Blackshirt trooper gaping with laughter. They had no regrets about leaving Germany, with the one exception of having just missed seeing Hitler at a Nuremberg rally.

INTERLUDE: 1941-1945

CONTEMPLATING His future two months before graduation from Princeton in 1939, Lem wrote to Jack’s sister Kathleen: “None of us are worrying too much about jobs—this country is getting more and more war conscious—and we all expect to be over there at least by fall. … Last night at the movies they showed the newsreel pictures of our Air Force and Army maneuvers and everyone hysterically got up and cheered—even brother Jack’s flat feet and bad stomach won’t keep him out of this one.” As old classmates began to enlist after graduation, Lem grew increasingly anxious about his own medical defects. Poor eyesight would keep him out of any service if and when America entered the war in Europe. By September 1941 Jack had enlisted. After rejection by the Army and the Navy because of his bad back, Kennedy was granted a commission as an ensign in the Naval Reserve and went to work for the Office of Naval Intelligence in Washington. Lem, trying desperately to get into the Navy, made frequent exploratory trips to Washington. He stayed with Jack at his apartment in the Dorchester Hotel on Sixteenth Street. Both of them were frustrated that autumn: Jack by his inactive desk job, Lem by his inability to get any kind of military post: he had been rejected by the Army, the Navy, the Air Force—even the Coast Guard.


One Sunday, after Lem accompanied Jack to eleven o’clock Mass, they began the afternoon with their usual disagreement about touch football. It was the one issue that consistently disunited them throughout their friendship. Jack loved to go down to the sweeping greensward around the Washington Monument, where a serious game of touch could always be found on a Sunday afternoon. As usual, Lem reluctantly capitulated; as usual, Jack found the most challenging game on the Mall. Then he and Jack would be picked by separate teams, and before long Lem’s teammates would realize the terrible mistake they had made.

This particular Sunday was no different, except that after the game was over, and the two of them were driving back to Jack’s apartment, a broadcast crackled over the car radio: Japanese bombers had attacked Pearl Harbor. In the excitement of the moment Lem felt disappointed and extremely civilian. Unlike touch football, this was not a conflict he wanted to watch from the sidelines.

Kennedy was soon transferred to Naval Intelligence in Charleston, South Carolina; Billings returned to his job as a junior executive at the Coca-Cola Bottling Company in Bridgeport, Connecticut. Both men were restless. In February, Lem visited his friend in Charleston for a week and saw Jack give his first public speech.

The twenty-four-year-old John F. Kennedy lectured the workers of an armaments factory about two different kinds of incendiary bombs. At first Lem was nervous for Jack; the technical details of the assignment seemed hazarous, particularly for an inexperienced public speaker. In fact, Kennedy knew very little about any kind of incendiary bomb. Nevertheless, he carried off the presentation with flair. Lem was impressed. Jack was too. The speech went so well that Ensign Kennedy was emboldened to call for questions—a dreadful mistake, Lem thought. The first one came from a man who wanted to know precisely how to distinguish one kind of incendiary bomb from the other. Lem held his breath. “I’m glad you asked that question,” replied the unfazed Ensign Kennedy, pausing for a moment, “because in two weeks, a specialist will be coming down here and that is exactly what he wants to talk about.”

By the summer of 1942 both Billings and Kennedy were a few steps closer to the war. Curiously, Lem was the first to see action. While Jack was engaged in the officers’ training program at Northwestern University, Pvt. LeMoyne Billings was bound for Cairo aboard a ship sailing in a convoy out of New York Harbor. He had been accepted by the American Field Service, a paramilitary ambulance corps that soon went into the front lines of the desert fighting against Rommel’s forces in Egypt. Meanwhile, a few letters arrived from Jack. He had applied to the PT-boat training unit in Melville, Rhode Island, and was itching to get into the combat zone. While enduring the wait for sea duty, Jack told Lem, he often reminded himself of President Roosevelt’s famous words: “This war is bigger than you and me.” Finally, in February 1943, he received orders to the South Pacific as a replacement officer for Motor Torpedo Boat Squadron 2.

From North Africa, Lem wrote Jack long, graphic descriptions of the fighting and of his continuing struggle to get a naval commission. In May, Jack wrote back from his hut in the Solomon Islands, saying he was now skipper of his own boat, PT 109. He wished Lem were part of his crew.

During that summer Jack’s correspondence ceased for three worrisome months. Then, in September, Lem received a New York Times clipping from his mother: Jack’s bravery had saved the crew of PT 109 after a Japanese destroyer had cut the boat in two in the Blackett Strait. A few weeks later a long letter arrived from Jack, but the news was mostly about the large percentage of Jack’s old girl friends who had recently gotten married and about his desire to spend a month in Palm Beach with his family and Lem. He alluded to the PT 109 episode only briefly, laconically mentioning that he had lost his boat and some of his men.

By November, after receiving minor shrapnel wounds during Montgomery’s decisive victory at El Alamein, Lem was home. Jack, who was now executive officer of his squadron and commander of a new motor gunboat (PT 59), advised him to stay put and settle for 4-F.

Out of uniform, Lem was restless again. With the help of Ambassador Kennedy and Congressman John W. McCormack, he received a commission as an ensign in the U.S. Naval Reserve. Jack sent congratulations in his last letter from the South Pacific. Now a twice-decorated war hero, he returned home in January. Billings, the desert veteran and raw ensign, arrived in Palm Beach dressed in uniform. He had orders for sea duty aboard the attack transport U.S.S. Cecil , soon to depart for the South Pacific. Their reunion lasted until Easter. They both looked thinner, but they were whole. Their friendship, too, was intact; despite the war they were as youthful and exuberant as ever.

Two weeks after the Japanese surrendered in August 1945, Kennedy received word from Billings that he would remain aboard the Cecil in the South Pacific until February or March of 1946.

Kennedy had just returned from Europe, where he had spent a month in England, covering the British elections for the Hearst newspapers, and several weeks in Germany, accompanying Secretary of the Navy James V. Forrestal in Forrestal’s private plane. He said the trip had been “extremely interesting” but didn’t want to “bore [Lem] with the details,” which included, Lem later learned, a visit with Forrestal to the conference of Truman, Stalin, and Churchill in Potsdam, where John F. Kennedy first met Gen. Dwight D. Eisenhower.

“As to my present plans,” the young war hero continued, “I am making some speeches around—one is going to be at the Waldorf-Astoria in NY on Oct. 4th—the other speakers being Baruch, Dewey, and Byrnes—I suppose I’ll speak after Baruch and Dewey and just before Byrnes. ” He had also been made assistant to the chairman of the Boston Community Fund. “As you can see,” he told Lem, “I’m getting ready to throw my slightly frayed belt into the political arena any time now. I’m expecting you back to vote early and often. Would you suggest a question period after my speeches? It went so well the last time I tried it in the deep South…”

By December, Kathleen reported to Lem: “Jack never stops thinking and talking about his political career and is really interested in it. So you’d better prepare yourself to listen.”


DURING THE PRECEDING thirteen years, Lem had listened and watched and remained closely involved as Jack had grown almost annually into new roles: as the congressional candidate in the Eleventh District of Massachusetts; the freshman congressman; the junior senator; the husband of Jacqueline Bouvier; the patient undergoing a nearly fatal spinal operation; the Pulitzer Prize-winning author of Profiles in Courage ; the Vice-Presidential contender at the Democratic Convention in 1956; the father of a baby daughter, born in November 1957, whose sparkling eyes were revealed to the nation four months later in Life magazine, peeping at her father over the edge of her bassinet.

“The day will come,” Lem was warned, “when you won’t call him Jack. You’ll call him Mr. President.”

Meanwhile, Lem had been working with a different kind of effervescence. After graduating from the Harvard School of Business Administration in 1948, Billings had gone on to become a vice-president of the Emerson Drug Company in Baltimore and had developed a new product, Fizzies, which was an immediate, if brief, success.

In 1958 Billings was made vice-president of Lennen & Newell, a New York advertising firm; Kennedy was reelected to the Senate. One night that year, during a private dinner with Ambassador Kennedy at the Pavilion restaurant in New York, Lem made a light joke about Jack. Jack was not present. Joseph P. Kennedy was not amused. Lem listened with some incredulity as the ambassador sharply upbraided him, then explained that now was the time to learn that he should never again talk that way about Jack in public. “LeMoyne,” he said, “you are one of the people who must understand this. You can never know who might be listening. From here on, you must think of Jack less as a friend and more as a potential candidate for President of the United States.” Lem sat speechless, totally unprepared for the ambassador’s final remark: “I will tell you right now that the day is going to come when you will not call Jack ‘Jack’ You will call him ‘Mr. President.’”


ON NOVEMBER 8, election night, Lem sat listening to the nationwide returns in Robert Kennedy’s house, which had been turned into a communications command center, wired with webs of telex machines, televisions, and telephones connected directly to cities across the land and to Ambassador Kennedy’s house next door and to the candidate’s house across the lawn. Lem was confident that Jack was going to win. With the early returns showing a strong Kennedy lead over Nixon in the East and in parts of the South, he joined in the small, cheerful clusters of family and friends who were surrounded in the living room and on the sun porch by the upper-echelon campaign staff led by the candidate’s brother Robert. Ambassador Kennedy’s prediction to Lem seemed to be coming true.

As the long night wore on, Kennedy’s early lead shrank. Unexpected losses in Ohio and Wisconsin and early returns in the crucial states of California, Illinois, and Michigan were signaling danger. The traffic in the command post and on the lawns between the three houses swelled and ebbed, carrying bad news, then good news, then more bad news. Lem, who had been shuttling among all the houses throughout the evening, was one of those who did not go to bed until the outcome looked favorable, though still uncertain. Before turning in at the Joseph Kennedys', he decided to make one last visit to Jack’s house. Cutting through the gap in the shrubbery and then across the lawn, Lem was approaching the front porch when several men dressed in dark suits suddenly closed in on him and demanded identification. He had none. Naturally, he hadn’t figured on needing his wallet on election night in Hyannis Port. He explained who he was, but they would not allow him to enter the house. Lem was furious. He tried explaining again. He pointed out that he had just been in the house only an hour or so before, at 3:00 A.M., and wondered why they hadn’t taken notice of him then. They stood unmoved, and it occurred to Lem that he hadn’t been aware of the Secret Service’s presence up until this very moment. The day had finally come.

Jean Kennedy Smith happened to be passing by at that moment. The Secret Service men asked her to verify Lem’s identity. “Never seen him before in my life,” she replied and continued into the house. A few moments later, Jean returned, laughing, and Lem was permitted to enter the house of the next President of the United States.

MIAMI, 1960

AFTER HIS VICTORY , the President-elect took a few days’ rest in Palm Beach before building the new administration. He asked Lem to accompany him on the trip south on the Caroline . At Miami a motorcade was waiting on the tarmac. The President-elect smiled and waved to the crowd. Long gone from his face was the mischievous expression of schooldays; the rakish collegiate handsomeness; the wan, gaunt look of the congressional days. His weight of 172 pounds was now nearly equal to Lem’s. Now that both men were in their early forties, there was more physical similarity between them than there ever had been before. Yet Lem looked the older of the two, not just because he was, in fact, a year older, but because Kennedy appeared unimaginably young to be the most powerful man in the free world.

After greetings from the mayor of Miami and other local officials, there was a general move toward the limousines. Lem automatically followed Kennedy into the first car. He thought nothing of it. After all, he had been traveling beside Jack since they left the house in Hyannis Port and, for that matter, in similar situations all his life.

There was a pause. Lem sensed that something was not quite right. The President-elect looked sideways at him: “Well,” he said, grinning, “where do you want the mayor of Miami to sit?”

The President offered him three positions in his administration, but Lem respectfully declined.


CAN YOU IMAGINE -” Lem would later exclaim. “My best friend becomes President of the United States and I spend his presidency in Denmark ?” But Lem wasn’t going anywhere. Although the President-elect had offered Lem three positions in his administration—director of the Peace Corps, director of the proposed U.S. Travel Service, ambassador to Denmark—Lem had respectfully declined. He had come to the conclusion that working for the President in an official capacity would mean becoming an employee of his best friend. Besides, what role could be better than the one he had had for twenty-eight years? “Of the nine or ten men who were close to the President, I would say that Lem was Number One,” said Eunice Shriver. Maintaining the personal side of their friendship was more important to Lem than a job in the New frontier or … in Denmark! The truth was, said Peter Kaplan, “Lem could have done any number of jobs, but I think that he just wanted to be in that house with Jack.”

Two hours after John F. Kennedy took the presidential oath in the brilliant winter sun and frosty air on Capitol Plaza, Lem walked into the White House for the first time in his life. Lem considered it the perfect house for Jack; it contained privilege without ostentation, dignity and elegance without affectation, grandeur without pretension, unlimited opportunity. Entering the mansion with Eunice Shriver, Lem had a sudden flash of Gone With the Wind: the scene in which Mammy and Prissy accompany Scarlett into her new mansion in Atlanta—their struggles are over; Prissy looks around wide-eyed and declares: “Lawzy, we’s rich now!”

Before the inaugural balls that evening, they had a chance to look around upstairs. “We laughed a lot,” Eunice Shriver recalled, “and we scooted up to the Lincoln Room.” Lem was drawn to it: here was Abraham Lincoln’s dark, austere furniture arranged as it had been during his Presidency. The bed was massive and high. Lem and Eunice jumped up on it and had their picture taken. The window looked out across the South Lawn on the Washington Monument, surrounded by snow, blazing with light. All Washington seemed to be aglow that night.

Lem’s mother was also in town for the inauguration. Despite the formidable demands on his time, the President had ordered a memorandum sent to the inaugural garage concerning her arrangements for the Armory ball: This comes from the President-elect: Please have a special car take care of Mrs. F. T. Billings (78 years old) . Lem took enormous pleasure in Jack’s thoughtfulness.


As the new administration got under way, the White House became something of a home for Lem. Living in New York, working for Lennen & Newell, he often came to Washington and stayed in the mansion. Later, when the President appointed him a founding trustee of the National Cultural Center (which became the Kennedy Center for the Performing Arts), Lem visited even more frequently. The White House guards knew him well. The Secret Service gave him a code name. A guest room on the third floor more or less became Lem’s room; he was able to leave his things there.

Although the burdens of the Presidency dramatically changed Kennedy’s life, his enjoyment of companionship was as strong as ever. “The Presidency is not a very good place to make new friends,” he observed at a news conference. “I’m going to keep my old friends.” As Eunice Kennedy Shriver said: “He had a great capacity for this friendship. Well, it’s hard to describe it just as friendship; it was a complete liberation of the spirit. I think that’s what Lem did for President Kennedy. President Kennedy was a completely liberated man when he was with Lem.”

In the White House the President kidded Lem more than ever, especially at official ceremonies. The President never failed to introduce Lem formally to visiting heads of state, dignitaries, and celebrities, but the introduction was never simply a matter of “I would like you to meet my friend, LeMoyne Billings.” “He’d introduce me as Congressman Billings or Senator Billings, and even General Billings,” Lem would later recall. “The person, whoever it happened to be, would of course take him quite seriously, which was awfully funny until the President turned away to someone else, and I’d be left alone, standing there with this terrifically important individual. And then they would always turn to me and say, ‘Well, Senator, which state are you from?’ And I’d move away as fast as I could. What was I going to say?—‘Oh, the President was only kidding .’”

Once, when Kennedy convened a high-level meeting aboard the presidential yacht Honey Fitz , moored in Newport, the President stood at the head of the gangway, presenting all those coming aboard to the officer of the deck, a Navy captain in dress blues: “This is the secretary of state, Mr. Rusk; the secretary of defense, Mr. McNamara; General Taylor, the chairman of the Joint Chiefs of Staff…” and so on down the line until, at last, the President announced without any change of tone “This is Lieutenant Junior Grade Billings. ” The captain’s eyes swiveled dubiously from the lieutenant junior grade to the Commander-in-Chief (whose expression indicated that no error had been made) and back again to this bespectacled, forty-five-year-old junior officer in mufti.

The President also enjoyed practical jokes with longer fuses. One weekend in Newport in November 1961, he was the host at a luncheon at Hammersmith Farm for the visiting prime minister of India, Jawaharlal Nehru. The President and Nehru ate in the dining room, discussing matters of state, while Jacqueline Kennedy and Nehru’s daughter, Indira Gandhi, and Lem lunched in another room. Lem got along especially well with Madame Gandhi, a fact that Jacqueline mentioned to the President when they returned to Washington that evening for a state dinner at the White House.

The following weekend, Lem was back in Washington. Almost from the moment he arrived, a series of messages began coming from Blair House, where the prime minister’s daughter was staying. The messages were invitations from Madame Gandhi, requesting the pleasure of Lem’s company. Each one was more compelling than the last: Would Lem join her for luncheon? For tea? For dinner? For a drink after dinner? and so on, throughout the weekend. Lem was dumbfounded and a little pleased with himself. Repeatedly he returned the calls to Blair House, and each time was told that Madame Gandhi was out—she would, however, be back shortly and was expecting his call. It wasn’t until late Sunday evening that Lem discovered that Madame Gandhi’s passion for his company had been concocted by the President with the help of the White House switchboard.

On the other hand, Lem actually was friendly with Greta Garbo. He had met her on the Riviera and they hit it off immediately. Billings, of course, lost no time in telling the President about his famous new friend and Kennedy was suitably impressed. Eventually the President and the First Lady invited Garbo to dinner at the White House. Lem was to be the only other guest. He arrived glowing with anticipation. The President ushered him into the family dining room to say hello to his guest, remarking, in effect, how happy he was to have them both, as they were already well acquainted. With a spring in his step Lem came forward to say hello: “Greta!” Garbo turned, puzzled, to the President, “I have never seen this man before,” she said.


There followed an agonizing hour for Billings. He rattled off names, places, dates: nothing would penetrate Garbo’s inexplicable amnesia. The President was full of earnest curiosity about how such a mix-up could have occurred. Perhaps Lem had been friends with someone who looked like Garbo? Lem testily declared that that was impossible. He was mystified. It never struck him that the amazing memory lapse might have been contrived by the President of the United States. The game was kept up until the second course. It was, Lem later recalled, “one of the worst things I ever went through in my life. I was dying … dying.”

GLEN ORA, 1962

FOR LEM, THE BEST of times during the Kennedy Presidency were the weekends at the President’s Virginia retreat estate, Glen Ora. “Oftentimes when Jack wanted to relax,” Eunice Shriver recalled, “he would call Lem on the phone, or they would go out to the country—just the three of them: Jack, Jackie, and Lem. Jack liked to have Lem around. With Lem he didn’t have to talk politics all weekend long.”

The weekend would begin on Saturday morning. Lem would accompany the President on the trip by helicopter from the White House, arriving at Glen Ora in time for lunch. After the meal, Jacqueline would go riding, leaving Jack and Lem to stroll around the grounds. “They’d just be talking,” said Eunice Shriver, “just as if nothing had changed. They could talk about everything. Jack trusted Lem completely. Lem never used Jack for anything. His loyalty to Jack was always absolute. He never wrote about him. He was never disloyal, because he didn’t want to use what President Kennedy had said to him for any ego-building for himself.”

Jack told Lem that he would trade all his political success and money just to be out of pain.

On some weekends during their walks the President would discuss the political events of the week. During the weekend immediately before the Bay of Pigs invasion in 1961, and especially during the weekend after, the President talked extensively with Lem about his reactions to the situation in Cuba. But usually their conversations had nothing to do with the Presidency. Sometimes after lunch they would play an abbreviated golf game on the lawn. The President, having strained his back during a tree-planting ceremony in Canada in 1961, chipped his shots lightly but still with much greater accuracy than Lem, whose coordination was as bad as ever.

In the afternoon they rested. The President would take a long nap, sometimes easing the pain in his back with a heating pad. Lem could tell when the pain was intense only by looking at Kennedy’s face; he never heard the President discuss it, except for one occasion that Lem later described to Robert Kennedy, Jr., who recalled: “In 1962, when the President was in really bad pain, they were talking about this one day, and Jack told Lem, in all sincerity, that he would trade all of his political successes and all of his money for Lem’s health, just to be out of pain.”

Before dinner, they would play a spirited game of backgammon, betting at low stakes, accumulating debts they never paid to each other. Dinner was served early; these were quiet evenings of conversation and laughter. The President and his wife would retire early, and Lem would go upstairs with a book, and the day would be over.

It didn’t seem to matter that there were huge differences in their lives now. The President was a married man and a father. Lem was a bachelor. He was seeing various women—a well-known movie and television actress; an Italian baroness; a society lady in Nashville—yet to Lem, friendship had remained such a powerful, emotionally sustaining force that for himself marriage seemed superfluous. “Jack made a big difference in my life,” he would say years later. “Because of him, I was never lonely. He may have been the reason I never got married. I mean, I could have had a wife and a family, but what the hell. Do you think I would have had a better life having been Jack Kennedy’s best friend, having been with him during so many moments of his Presidency, having had my own room at the White House, having had the best friend anybody ever had—or having been married, and settled down, and living somewhere?” Lem enjoyed his independence and his bachelorhood. His appointment calendar for 1963 shows a busy social schedule—engagements with Mrs. Albert D. Lasker in January; skiing weekends with the attorney general and his family in February; lunch with Rip Horton in March; two visits to Camp David in April; trips to Hyannis Port in July and August, sandwiching in a visit to Mrs. Lasker’s Villa Florentina in Saint-Jean-Cap-Ferrat; an engagement in September listed simply “F Sinatra"; and a meeting with the President at the White House in October. The following appeared written in his datebook for November on the 22nd: “2:30—S. Smith 321 Park,” after which was later added a single word— canceled .

NOVEMBER 22, 1963

JUST BEFORE TWO in the afternoon, Lem had eaten lunch and was walking back to his office building on Madison Avenue. His stride, as usual, was brisk—all his weight bouncing forward off the balls of his feet. Passing through the lobby doors and into the building, he slowed down, then came to a halt. Something was happening. Office workers were exiting the elevators and the lobby. Some were stumbling. Some were staring. Some were standing stock-still, tears streaming down their faces. An acquaintance of Lem’s recognized him and, assuming that Lem already knew, came over to say: “I’m so sorry … about the President…”

Lem didn’t want to know any more.

Wheeling around, he dashed back out to the avenue, and began walking north, blindly. He saw nothing and heard nothing, yet everything around him was projecting the most cruel, dazzling, unnatural clarity he had ever known. He had no idea where he was going or if he was going to make it there. When he looked up, he found himself on Fifth Avenue at Fifty-first Street, in front of St. Patrick’s Cathedral.


He entered and sat in the cool darkness, sweating heavily and breathing deeply. He was unable to move. Some time passed. Then he was aware that the cathedral was quickly filling up around him, and he began to cry.

NEW YORK, 1981

INTO HIS SIXTY-FIFTH year Lem lived in a beaux-arts townhouse adjacent to the Guggenheim Museum. A visit to 5 East Eighty-eighth Street was itself like touring a museum. Every room was crammed full of carefully preserved treasures, overlapping collections of art and antiquities and early American furniture and personal mementos—all reminders that men in history had actually been alive. Lem lived alone, but he had become a friend and a kind of folk hero to a new generation. “To one generation of Kennedys he was a friend and gifted counselor, ” wrote Robert Kennedy, Jr.“To my generation he gave an even greater gift. The stories he told and the examples he set gave us all a link to our dead fathers and to the generation before us. The titans became men whom we should not fear to emulate.”

Lem continued to live as intensely in the present as he had in the past. His apartment was the focal point of ceaseless activity. It often had the spirit of a collegiate fraternity where anything might happen. Upon arrival you might suddenly be pulled into a chorus, singing of f-color limericks in the hallway or you might encounter one of Bobby Kennedy’s reptiles—a twelve-foot boa constrictor, for instance—somewhat under control in the hall closet. As in any fraternity, there were rituals that governed the evening. Lem would dispense dozens of stories and would illustrate them with primary source material. He would jump up, returning from his library with one of thirty large scrapbooks that he kept on a doubletiered, five-foot-long shelf, a multivolumed encyclopedia of life and friendships that spanned six decades. There was always a new scrapbook in progress.

Opening the book, Lem would point to a photograph and continue his story. Once background details were filled in, you would begin to feel the funny part of the story coming on; excitement would build; Lem would clench his fists and spread his arms in front of him. When he saw that you were laughing, that you truly understood how really awfully funny this situation had been , his fingers would explode from his fists, and he would laugh, a triumphant, colossal roar.

Lem would put down the scrapbook, and return to his objects: if a piece of scrimshaw was important to Lem, it was crucial for him to know how you felt about it. Sharing similar tastes was important; if you seemed indifferent, Lem would suddenly say, “Okay, if you could choose one thing in this whole house for your own, what would you pick?”

The decision seemed impossible, and it made you uneasy. Examining the room, you saw: a large Audubon folio print of a great-footed hawk; a collection of antique muskets; signed lithographs of Picasso and Miró and Dufy and Chagall; a large, stuffed gila monster; a framed series of twenty-four small, amusement-park-sized black-and-white photographs of Lem and Jack taken during summer vacation from Choate; a collection of antique weathervanes; a cow, two horses, a rooster; dozens of presidential medallions and coins set in Lucite; a framed series of three black-and-white photographs of Lem and Jack, each taken with the subjects sitting on the same outdoor chaise in Palm Beach, dated 1934, 1944, 1954; Lem’s small sixteen-year-old dog, Tolly, a pedigreed Basenji who was the great-grandson of a dog named Fulafire of the Congo; a collection of swan decoys; famed eighteenthcentury silhouettes of Lem’s maternal ancestors, the LeMoynes; dozens more photographs—Lem’s favorite niece, Sally Carpenter; his college roommate, Gus Stroud; Bobby Kennedy, Jr., handling a hawk; Sen. John Kennedy and his bride, Jacqueline, on their wedding day; Ambassador Joseph P. Kennedy posing formally with his family in the American Embassy in London; Kathleen Kennedy in a Red Cross uniform; President Kennedy on a lawn in Hyannis Port with the entire Kennedy family and Lem; Lem and Jack beside the pool in Palm Beach in 1934, holding aloft Jack’s wriggling younger brother Teddy; a collection of glass pigs; a bust of Charles Lindbergh; a Chippendale highboy upon which was displayed another host of photographs and two framed pencil sketches of John and Robert Kennedy, one of which was inscribed to Lem from Ethel Kennedy: “For Lem—Jack’s best friend…”

“Okay, man. You’ve seen my whole house—whatVe you going to pick?” You pointed to the framed series of twenty-four small photographs taken during Lem and Jack’s summer vacation from Choate. Lem gave you a look that said you were out of your mind. He was sincerely dumbfounded.

“You mean you wouldn’t want—.” Then he listed on his fingers the most expensive works of art in his collection.


Gaaaaad , man.” Lem was shaking his head. He looked confused, pained. You had let him down. There was no hope for you. “Why would you want those little pictures? I mean, I don’t understand you…”

Lem would illustrate his stories with primary source material. There was always a new scrapbook.

“I don’t know, Lem,” one finally mumbled, feeling massively inarticulate. “The two of you just look like you were having an awful lot of fun together.”

Lem regarded the photographs in a sudden wistful mood. For a moment his youthful demeanor vanished. He looked like a sixty-five-year-old man. His eyes revealed that perhaps he was in favor of one’s choice after all.


KIRK LEMOYNE BILLINGS’S coffin rested on a scaffold over the open grave in Allegheny Cemetery. Lem had had a heart attack on May 28, a day before the sixty-fourth anniversary of John F. Kennedy’s birthday.

The mourners, many of them in their twenties, gathered around Lem’s family plot, where he was going to rest beside his mother. Lem had wanted his casket carried to the grave by ten young friends. This ritual had been very important to him; it was the final act of friendship: to bear the weight of the dead friend’s body to its resting place. But now the coffin had already been set in place by professionals. There was a muted discussion about what to do. Finally the pallbearers, led by Robert Kennedy, Jr., lifted the coffin and carried it in a ceremonial march around the grave in the hot sunshine.

They held the coffin aloft throughout the service, sweat dripping from their faces. The minister recited the Protestant burial, adding a eulogy that celebrated Lem as “a prince of friendship.” A few women knelt to say the rosary and then kissed the casket before it was lowered.

Slowly the group disbanded, moving away from the grave and down the wooded hillside to a pond, where they opened bottles of champagne for a final toast. Eunice Kennedy Shriver was talking to a reporter from a Pittsburgh newspaper. She was nodding her head briskly. A question had been asked of her. “Yes,” she told the reporter, “Lem was President Kennedy’s best friend.” She paused, and then added: “And it is my impression that the feeling was mutual.”

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