Maureen Callahan’s article explores the decades-long intimate relationship between John F. Kennedy (JFK) and his lifelong friend Kirk LeMoyne “Lem” Billings. The story suggests that their relationship was not only an unusually close friendship but potentially a romantic and sexual one, spanning over 30 years.
A Bond Formed in Youth JFK and Lem Billings met as teenagers at the elite Choate boarding school in Connecticut during the 1930s. They quickly became inseparable, forming what many considered to be an unusually intense friendship. Callahan claims that they lost their virginity together, though details of this alleged encounter remain speculative.
Their relationship continued through college and into adulthood. While JFK became a war hero, a senator, and ultimately the 35th President of the United States, Lem was always by his side. Unlike many of JFK’s other friendships, which often revolved around political and strategic gain, his relationship with Lem was purely personal.
A Secret White House Bedroom One of the most intriguing claims in Callahan’s piece is that Lem Billings had his own room in the White House during JFK’s presidency. This was highly unusual, as even close political allies did not receive such privileges. The existence of a “secret bedroom” suggests that JFK and Lem shared a level of intimacy that went beyond conventional friendships.
While officially, Lem was never given an official role in JFK’s administration, he remained an ever-present figure in the president’s personal life. He was so trusted that he was even given access to the Kennedy children, particularly John Jr. and Caroline.
Erotic Letters & Jackie’s Anger Callahan’s article also highlights a collection of letters exchanged between JFK and Lem. These letters reportedly contained highly intimate and possibly erotic content. While the exact details remain unclear, it is said that Jacqueline Kennedy (Jackie) was aware of their correspondence and was deeply upset by the intensity of their relationship.
Jackie allegedly felt that Lem had a unique influence over her husband that no one else, including herself, could match. This frustration was compounded by the fact that JFK, who was notoriously unfaithful, seemed to have an emotional connection with Lem that went beyond physical affairs with women.
A Love That Endured Even after JFK’s assassination in 1963, Lem Billings remained close to the Kennedy family. He became something of a surrogate uncle to John F. Kennedy Jr., staying actively involved in his life. It is said that Lem never had a serious romantic relationship of his own, and some believe this was because he was deeply in love with JFK.
Lem Billings died in 1981, having spent much of his life devoted to the Kennedy family. His relationship with JFK remains a topic of speculation, with some believing it was a deeply emotional but platonic friendship, while others suggest it was an unspoken romance hidden due to the social norms of the time.
Historical Context & Speculation The idea that JFK may have had a secret gay relationship challenges the traditional image of the charismatic womanizer. While JFK’s affairs with women like Marilyn Monroe and Judith Exner are well-documented, his bond with Lem Billings adds another layer of complexity to his legacy.
Historians remain divided on whether their relationship was truly romantic. Some argue that their closeness was simply an example of an intensely deep male friendship, common in the early 20th century before modern attitudes about masculinity and sexuality emerged. Others, however, believe that the evidence—his letters, their shared experiences, and the secret White House bedroom—suggests that JFK and Lem shared a hidden love affair.
Final Thoughts Maureen Callahan’s revelations, as detailed in her book Ask Not: The Kennedys and the Women They Destroyed, add new intrigue to the Kennedy legacy. Whether JFK was bisexual or simply had a lifelong, deeply emotional friendship with Lem Billings, their relationship remains one of the most fascinating and mysterious aspects of his personal life.
Regardless of where the truth lies, it is undeniable that Lem Billings was one of the most important people in JFK’s life—perhaps more so than anyone else, including his wife.
