EXCLUSIVE: More than a bromance - the intimate relationship between John F. Kennedy and his gay friend - from prep school to the White House - where pal had his own room, much to Jackie's chagrin

  • Born 100 years ago, John F. Kennedy was revered as the 35th president president but quietly chided for his womanizing
  • One of his closest relationships was with his gay best friend and prep school roommate Lem Billings
  • Billings told JFK about his romantic intentions toward him in a love note written on a piece of toilet paper at their elite Connecticut boarding school
  • The future president wrote back  'I'm not that kind of boy' 
  • But one point Billings confided  that his friendship with the future president 'included oral sex, with Jack always on the receiving end'
  • They remained close even after the election, despite warnings from JFK's advisers who thought Russian agents could use the relationship as blackmail
  • After JFK's assassination, Billings had romantic feelings for JFK's nephew, Bobby Kennedy Jr.

Jerry Oppenheimer is a New York Times bestselling author who has written two books about the Kennedys. His latest book, The Kardashians: An American Drama, will be published in September. 

John F. Kennedy, whose 100th birthday is being celebrated this year with a Kennedy Centennial postage stamp, TV memorials, a slew of books, and much media coverage, was revered as the 35th president of the United States. 

But the man married to Jackie Kennedy was quietly chided for his compulsive philandering. The one iconic photo of President John F. Kennedy up close and personal with a woman other than Jackie  shows him and his attorney general brother, Robert, coming on to curvaceous Marilyn Monroe at a party. 

While the photo of Kennedy cozying up to Monroe is the best known of him with one of his purported lovers, other far less public snapshots show the flip side of Kennedy's intimate relationships.

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A different side of JFK: John F. Kennedy and Lem Billings met at Choate Rosemary Hall and became lifelong friends. Billings would later spend nights in the White House where he had his own room 

A different side of JFK: John F. Kennedy and Lem Billings met at Choate Rosemary Hall and became lifelong friends. Billings would later spend nights in the White House where he had his own room 

Schoolboy crush? Lem Billings and John F Kennedy were practically inseparable in prep school. Billings reportedly wrote the future president a love note on a piece of toilet paper (pictured at the Kennedys' Palm Beach estate)

Schoolboy crush? Lem Billings and John F Kennedy were practically inseparable in prep school. Billings reportedly wrote the future president a love note on a piece of toilet paper (pictured at the Kennedys' Palm Beach estate)

JFK was famous for his womanizing habits, but one of his closest relationships was with Lem Billings. Billings reportedly told Kennedy of his romantic intentions in prep school (JFK pictured chatting with Marilyn Monroe and Robert F Kennedy) 

JFK was famous for his womanizing habits, but one of his closest relationships was with Lem Billings. Billings reportedly told Kennedy of his romantic intentions in prep school (JFK pictured chatting with Marilyn Monroe and Robert F Kennedy) 

Among the snapshots is one that shows a handsome pre-presidential Kennedy sunning himself, sprawled on a chaise at Patriarch Joe Kennedy's Palm Beach estate. And seated close to Kennedy is his shirtless, tanned and oiled best friend forever, his very gay chum, Kirk LeMoyne 'Lem' Billings.

While JFK is legendarily known as a master womanizer who frequently cheated on his first lady, his curious three-decades long intimate friendship with Billings suggests more than a simple bromance.

They met in 1933 in their sophomore year at Choate Rosemary Hall, the exclusive Connecticut prep school, when both were teenagers, working together on their class's yearbook, and Billings instantly became attracted sexually and otherwise to the handsome scion of America's self-styled royal family.

Their very intimate relationship would last from those school days to Billings even having a room in the Kennedy White House – distressing for the first lady – to the day of Kennedy's assassination.

Details of Lem Billings and JFK's three decade relationship are revealed in 'Robert F. Kennedy Jr. And The Dark Side Of The Dream'

Details of Lem Billings and JFK's three decade relationship are revealed in 'Robert F. Kennedy Jr. And The Dark Side Of The Dream'

One of the most credible accounts of the Kennedy-Billings relationship was told by David Pitts, who I interviewed extensively for my book, Robert F. Kennedy Jr. And The Dark Side Of The Dream, because the strapping, bespectacled Billings, with a high-pitched, effeminate voice, would later become the fawning surrogate father – and fellow drug user – of JFK's nephew, Bobby Kennedy Jr., with whom Billings also had intense romantic feelings.

As one source told me, 'Young Bobby replaced Jack in Lem's heart of hearts.'

Billings, who was a year older than Jack Kennedy, made his desire known while the two were still at Choate in a bizarre love note, penned on a piece of toilet paper that could be disposed of easily to avoid incrimination at a time when homosexuality was illicit. 

While Billings' missive is long gone, a startled Kennedy responded, 'Please don't write to me on toilet paper anymore. I'm not that kind of boy.'

But Kennedy's reaction to Billings gay come-on soon changed and he became more amenable to his friend's advances, according to the writer Lawrence J. Quirk, author of 'The Kennedys in Hollywood.' Quirk had met Billings in the mid-Forties when both were volunteers in Jack Kennedy's first congressional campaign. 

Lem Billings relaxed on the Kennedys' Palm Beach estate the summer of 1936.  The Kennedys tolerated his homosexuality, which was considered taboo at the time 

Lem Billings relaxed on the Kennedys' Palm Beach estate the summer of 1936.  The Kennedys tolerated his homosexuality, which was considered taboo at the time 

Lawrence J. Quirk, the author of 'The Kennedys in Hollywood' said Billings and JFK's relationship turned sexual at a point. Kennedy was allegedly on the receiving end of oral sex

Lawrence J. Quirk, the author of 'The Kennedys in Hollywood' said Billings and JFK's relationship turned sexual at a point. Kennedy was allegedly on the receiving end of oral sex

Quirk immediately pegged Billings as gay, noting his 'high, screechy laugh,' and 'high nasal whine of a voice.' As they became close, Billings confided that his relationship with Kennedy was, in fact, sexual, to a point.

According to Quirk, Billings revealed that his friendship with the future president of the United States 'included oral sex, with Jack always on the receiving end.'

Their arrangement, Quirk asserted, 'enabled Jack to sustain his self-delusion that straight men who received oral sex from other males were really only straights looking for sexual release,' and he further observed, 'Jack was in love with Lem being in love with him and considered him the ideal follower adorer.'

The Kennedy patriarch, Joe, a noted philanderer himself, was suspicious of Billings' sexual preference from the start of his son's close friendship with him. He noted that everywhere Jack went, Billings was sure to follow, like a puppy dog. On school breaks, Jack often brought Billings home with him, sparking Joe Kennedy to complain to his wife, Rose, 'Do we have to have that q***r around all summer?'

Still, the Kennedy clan accepted – even welcomed – Lem Billings into their exclusive inner-circle, practically adopting him, and he became a part of the family.

As Billings' biographer David Pitts told me, 'Once JFK decided that Billings was his best friend – like it or leave, everybody in the family sort of fell in line with that. The Kennedys were a liberal family and one that tolerated a lot of heterosexual promiscuity as well.'

Roommates: JFK and Billings (right) roomed at Choate and again at Princeton (pictured mid-1930s outside a drugstore with roommate Ralph Horton Jr) 

Roommates: JFK and Billings (right) roomed at Choate and again at Princeton (pictured mid-1930s outside a drugstore with roommate Ralph Horton Jr) 

JFK's sister Eunice Kennedy Shriver said his relationship with Billings was a 'complete liberation of the spirit' for Jack  (Pictured on their Christmas card with fellow Princeton roommate Ralph Horton Jr)

JFK's sister Eunice Kennedy Shriver said his relationship with Billings was a 'complete liberation of the spirit' for Jack  (Pictured on their Christmas card with fellow Princeton roommate Ralph Horton Jr)

While her husband had his qualms about Billings and couldn't stand to have him around, the matriarch Rose Fitzgerald Kennedy, had a different take. In her memoir, Times To Remember, published eleven years after Jack's assassination in Dallas in 1963, she wrote that Billings had 'remained Jack's lifelong close friend, confidant, sharer in old memories and new experiences…He has really been part of 'our family' since that first time he showed up at our house as one of 'Jack's surprises.'

One of Jack's five sisters, Eunice Kennedy Shriver, found it hard to describe her brother's relationship with Billings, once stating, 'It was a complete liberation of the spirit…' for Jack, and that her brother was a 'complete liberated man when he was with Lem.'

But Billings was embarrassed about his effeminate mannerisms – he'd remain publicly closeted for his lifetime. 'People think I'm a joke,' he once acknowledged. 'They make fun of my voice. But I'm stuck with the Kennedys emotionally, and I will be to the end of my life.'

Jacqueline Kennedy was reportedly unhappuabout her husband and Billings' three decade long relationship. The president was famously believed to have affairs during their marriage

Jacqueline Kennedy was reportedly unhappuabout her husband and Billings' three decade long relationship. The president was famously believed to have affairs during their marriage

When their brother Bobby married Ethel Skakel in a royal-like wedding in Greenwich, Connecticut, the staunchly conservative republican and seemingly homophobic Skakels let their feelings about Billings' gayness be known. 

Ethel's alcoholic, philandering brother, George Skakel Jr., actually booted Billings in the a** at the church, knocking him into the aisle. And George Terrian, the alcoholic husband of Ethel Kennedy's alcoholic, pill-popping sister, Georgeann, told me in interviews for my book 'The Other Mrs. Kennedy' that, 'Everyone in the family knew Lem was q***r – the Kennedys, the Skakels, everyone.'

After the assassination of Robert Kennedy, a distraught Ethel turned over her son, Bobby Jr., to Billings to act as his surrogate father, sparking her brother-in-law, Terrien – RFK's roommate at the University of Virginia law school – to wonder why she would allow 'Lem to have such an intimate relationship' with her troubled third born, who would go on to have a a bizarre relationship with Billings, including the taking of drugs.

JFK appeared to be in love with the idea of Billings being in love with him. Their lifelong relationship caused some of the presidents advisers to fear Russian agents may use the information as blackmail

JFK appeared to be in love with the idea of Billings being in love with him. Their lifelong relationship caused some of the presidents advisers to fear Russian agents may use the information as blackmail

After Jack Kennedy's election to the presidency, Billings was a constant presence and overnight guest at the White House. Knowing the kind of intimate relationship that he had with the president, advisers were concerned about political repercussions, and even blackmail. 

The Cold War was still raging, and there was fear Russian agents might use the friendship against Kennedy.

Gore Vidal, the writer who claimed he viewed homosexuality as normal as heterosexuality, disparaged the JFK-Billings relationship during the Kennedy administration.

 He once called Billings the 'chief f****t at Camelot.' As for Kennedy himself, Vidal asserted that the president 'felt quite comfortable in the company of homosexuals as long as they were smart enough to hold his interest.'

White House visitor: Billings often spent the night at the White House, which upset Jackie Kennedy. She reportedly had a love-hate relationship with her husband's best friend

White House visitor: Billings often spent the night at the White House, which upset Jackie Kennedy. She reportedly had a love-hate relationship with her husband's best friend

The first lady, Jackie, had something of a love-hate relationship with Billings. But was reportedly upset that her husband spent so much time with him, and that he often stayed overnight at the White House.

Like the rest of the free world, Billings was devastated when President Kennedy was assassinated. The biographer Sally Bedell Smith, referred to Billings in one of her books as 'probably the saddest of the Kennedy widows.'

After the assassination of RFK in 1968, the flamboyant Billings transferred his obsessive affection for Jack, to handsome teenager Bobby Jr.

David Pitts, the author of 'Jack and Lem: The Untold Story of an Extraordinary Friendship,' told me, 'Lem was a gay man and he had a 14-year-old, good-looking kid living in his house with him and there had been rumors because of that. I have no evidence one way or another, but I would discount [any sexual activity.]

Still, Billings was viewed by many I interviewed for my biography of RFK Jr. as his gay Svengali who guided and literally tried to control every aspect of Bobby Jr.'s life from the time he was in his mid-teens.

During the night of May 28, 1981—almost two decades after JFK's untimely death – 65-year-old Lem Billings died in his sleep of an apparent heart attack.

Billings had once told Bobby that when he died he wanted the pall-bearers to be members of Bobby's circle of young friends, whom he knew well and with whom he had done drugs.

Lem Billings and Bobby Kennedy Jr became close after JFK's death and allegedly took drugs together. When Billings died of a heart attack in 1981, Bobby Jr gave the eulogy (From left to right: Lem Billings, Bobby Kennedy Jr and Ethel Kennedy)

Lem Billings and Bobby Kennedy Jr became close after JFK's death and allegedly took drugs together. When Billings died of a heart attack in 1981, Bobby Jr gave the eulogy (From left to right: Lem Billings, Bobby Kennedy Jr and Ethel Kennedy)

Part of the family: From childhood to adulthood, Billings stayed close to Jack Kennedy and his family. When JFK was assassinated, he turned his attention to his nephew Bobby Kennedy Jr

Part of the family: From childhood to adulthood, Billings stayed close to Jack Kennedy and his family. When JFK was assassinated, he turned his attention to his nephew Bobby Kennedy Jr

 It was Bobby Kennedy Jr. who gave the eulogy.

'I'm sure he's already organizing everything in heaven so it will be completely ready for us – with just the right Early American furniture, the right curtains, the right rugs, the right paintings, and everything ready for a big, big party.

'Yesterday was Jack's birthday. Jack's best friend was Lem, and he would want to remind everyone of that today. I am sure the good Lord knows that heaven is Jesus and Lem and Jack and Bobby loving one another.' 

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