John F. Kennedy and Lem Billings: Friendship, Power, and the Long Shadow of Speculation
- Daniel Holland
- Mar 5, 2023
- 7 min read
History often turns on public moments. Yet it is the private relationships that most reliably reveal how power was lived rather than performed. Few friendships of the twentieth century sit so awkwardly at this intersection as that between John F. Kennedy and Lem Billings. It was a bond formed in adolescence, carried through war and ambition, and finally tested by grief. For decades it has also been a relationship onto which others have projected assumptions about sexuality, loyalty, and influence at the heart of American politics.
What follows is not a bid to prove what cannot be proven. It is an attempt to set out, carefully and in full, what is known, what has been alleged, and why this friendship continues to attract attention long after both men are gone.
Choate, 1933: The Making of a First Friend
Billings, a 16 year old third year student, and Kennedy, then 15 and in his second year, met in the autumn term of 1933 at Choate Rosemary Hall in Wallingford, Connecticut. Choate was an elite preparatory school, formal in structure and ruthless in its social hierarchies. Kennedy arrived with money, name recognition, and a fragile constitution. Billings arrived on scholarship, tall at 6 foot 2 inches, weighing around 175 pounds, and known for his physical strength as a leading member of the Choate crew team.
They became close quickly. Together they formed a small prank club called “The Muckers,” a name that captured both adolescent rebellion and a taste for mischief. Their pranks were mostly minor, though one planned act involving horse manure in the school gym was abandoned after intervention from the headmaster. These stories mattered later not because they were remarkable, but because they established Billings as someone who made Kennedy laugh and feel included.
Billings’ financial situation was precarious during the Depression. His scholarship kept him at Choate, and he repeated his senior year so that he and Kennedy could graduate together in 1935. From Christmas 1933 onwards, Billings was welcomed into the Kennedy household in Palm Beach and increasingly treated as one of the family. Holidays, family events, and travel soon became routine.
One early document has been cited repeatedly in later biographies. Jerry Oppenheimer reports that Billings once wrote Kennedy a love note on a piece of toilet paper. Kennedy’s reply was curt but not cruel. “Please don’t write to me on toilet paper anymore. I’m not that kind of boy.” Whether this was a firm rejection, adolescent embarrassment, or simply humour is impossible to say. What is clear is that the friendship did not end. It deepened.
Europe, Princeton, and War
In the summer of 1937, Kennedy and Billings travelled through Europe together. These journeys mattered. Kennedy’s later political worldview was shaped by his observations of fascism and instability on the continent. Billings was present for those formative impressions, acting as companion and sounding board.
Billings graduated from Princeton University in 1939, majoring in art and architecture, and wrote his senior thesis on the painter Tintoretto. This detail is often overlooked, yet it hints at the role Billings would later play as Kennedy’s artistic adviser and cultural sounding board.
The Second World War separated the two men physically but not emotionally. Billings failed the medical tests required for military service in 1941, largely due to poor eyesight. With the support of Joseph P. Kennedy Sr., he joined the American Field Service ambulance unit and served in North Africa between 1942 and 1943. In 1944, he received a commission in the US Naval Reserve and served in the South Pacific until his discharge in 1946.
Kennedy, meanwhile, returned from war as a decorated naval officer. Their paths reconverged as Kennedy entered politics.
Politics, Loyalty, and the Campaign Years
Billings worked on Kennedy’s successful 1946 campaign for Congress. Soon after, he toured seven Latin American countries with Robert F. Kennedy. From 1946 to 1948 he attended Harvard Business School, earning an MBA, and then drifted through a series of jobs that never quite fit his temperament.
He sold Coca Cola dispensers, worked at a General Shoe store, and later became vice president of Emerson Drug Company in Baltimore. There he invented Fizzies, a powdered soft drink flavoured to mask the taste of sodium citrate. It became a minor 1950s craze.
By 1958 Billings had moved to Manhattan to work as an advertising executive at Lennen and Newell. He remained close to the Kennedy family. He was an usher at John F. Kennedy’s wedding to Jacqueline Kennedy Onassis in 1953 and again at the wedding of Kennedy’s sister Jean in 1956.
During the 1960 presidential campaign, Billings took leave from his job to work full time. He managed the Third Congressional District during the Wisconsin primary and became a general troubleshooter during the critical West Virginia primary. His role was never official, but it was constant.
The White House: Presence Without Portfolio
Once Kennedy entered the White House in 1961, Billings’ position became more visible and more controversial. Kennedy offered him senior roles including head of the Peace Corps, director of the US Travel Service, and ambassador to Denmark. Billings declined them all. “I realised that I did not want to work for the president because I felt it would change our relationship.”
Instead, he occupied an ambiguous space. He was appointed to boards and trusteeships, including the National Cultural Center which later became the Kennedy Center, and the planning board for the 1964 to 1965 New York World’s Fair. Yet his true influence lay in proximity.
Billings visited the White House most weekends. He had his own room on the third floor. A butler once commented on his belongings being left there, prompting the First Lady to reply, “He’s been my house guest since I was married.”
He organised dinner parties when Kennedy was alone, kept Jacqueline company when the President travelled, accompanied the family to church, delivered pets to the children, and joined foreign tours in 1961 and 1963. Some staff joked that they saw him so often they mistook him for Secret Service.
Historian Sally Bedell Smith later likened him to Leonard Zelig, always present in the background of important moments. He sat with the Kennedy family at the inauguration and walked just behind the widow at the funeral procession.
Rumours, Allegations, and the Problem of Proof
It is here that speculation intensifies. Lawrence J. Quirk claimed that Billings told him his relationship with Kennedy had been sexual. Quirk alleged that this involved oral sex with Kennedy always on the receiving end, framing it as part of Kennedy’s ability to maintain a self image as heterosexual.
Quirk wrote that Kennedy “was in love with Lem being in love with him and considered him the ideal follower adorer.” These claims remain uncorroborated. They are based on Quirk’s recollections and conversations rather than documentary evidence.
Other observers were sceptical. Journalist Ben Bradlee later said, “I suppose it’s known that Lem was gay. It impressed me that Jack had gay friends.” At the same time, he noted that no one spoke openly about sexuality during the White House years.
Writer Gore Vidal was far less kind, once calling Billings the “chief faggot at Camelot” and claiming Kennedy felt comfortable around homosexual men as long as they were intelligent enough to hold his interest. Vidal also believed Kennedy needed Billings practically. “He needed Lem Billings to get around better than a trained nurse,” he said, suggesting illness and chronic pain made Billings’ presence politically useful.
Ted Sorensen described Billings as “an admirer, almost a fawning admirer.” Arthur Schlesinger thought Billings glared suspiciously at anyone whose friendship with Kennedy post dated his own.
None of this proves a sexual relationship. It does, however, demonstrate how unusual the intimacy appeared to those around them.
It's also worth highlighting an image that's often miscaptioned, appearing over the years the below photo is indeed of a young JFK, however, archivists at the John F. Kennedy Presidential Library and Museum told Snopes that while the photo is genuine — that is, not digitally modified or created using artificial intelligence — and shows Kennedy, the man with him is likely not Billings.
The photo can be found in a scrapbook covering Kennedy's time at Choate Rosemary Hall, a private boarding school, where he graduated in the Class of 1935. An archivist at the presidential library also said the photo appeared in "Rose Kennedy's Family Album," a 2013 book consisting of 300 photos from the library's collection.
Grief, Control, and the Kennedy Children
Billings was devastated by Kennedy’s assassination in 1963. One historian later described him as “probably the saddest of the Kennedy widows.” He saw Kennedy for the last time just 9 days before his death, at a White House dinner with Greta Garbo.
After the assassination of Robert F. Kennedy in 1968, Billings’ grief deepened into depression and alcoholism. He became increasingly close to Robert Kennedy’s children, particularly Robert F. Kennedy Jr.. Oppenheimer described Billings as a “gay Svengali” figure who attempted to guide and control Bobby Jr.’s life during his teenage years. One source told him, “Young Bobby replaced Jack in Lem’s heart of hearts.”
These claims are contested. David Pitts, author of Jack and Lem, acknowledged rumours but stated he had no evidence of sexual activity and would discount it. What is not disputed is that Billings acted as a surrogate father figure at a time when the Kennedy family was fractured by violence and loss.
Ironically, members of the Skakel family had earlier been openly hostile to Billings. During Ethel Skakel’s wedding, her brother knocked Billings down the church aisle, a moment remembered by witnesses as both humiliating and telling.
Later Years and Death
In the 1970s Billings’ behaviour changed markedly. He struggled with substance abuse and was gradually discouraged from spending time with younger Kennedy men. Yet he remained tied to the family through trustee roles and social obligations.
Jacqueline Kennedy Onassis invited him to accompany her and the children to England in 1965 for the unveiling of the Kennedy memorial at Runnymede. He continued to attend major events and maintained friendships with Christopher Lawford and others.
In 1981, Billings died in his sleep following a heart attack in his Manhattan apartment. He was 65. His dying wish was that the young Kennedy men carry his coffin. When they arrived at the cemetery to find it already positioned, they lifted it and carried it around the gravesite before returning it to the plot. He is buried in Allegheny Cemetery in Pittsburgh.
At his funeral, Robert F. Kennedy Jr. delivered the eulogy. “I’m sure he’s already organising everything in heaven,” he said, “with just the right Early American furniture, the right curtains, the right rugs, the right paintings, and everything ready for a big, big party.”
What the Friendship Tells Us
Whether or not John F. Kennedy and Lem Billings were ever lovers may never be resolved. What can be said with confidence is that their relationship was unusually intense, emotionally asymmetrical, and enduring. It survived adolescence, war, ambition, marriage, and the pressures of the presidency.
In a political culture that prized masculine image and conformity, Billings occupied a precarious role. He was indispensable yet unofficial, visible yet undefined. That ambiguity is precisely why the friendship continues to fascinate. It forces historians to confront how much of power operates beyond formal titles and how deeply personal loyalty can shape public life.
