Lem Billings: JFK's gay boyfriend

JFK's love life was more complicated than the womanizing stories of Camelot.

Feb 26, 2025

JFK has been back in the headlines a lot lately, given the (hopefully) soon-to-be released files about his assassination. For many years, JFK has been portrayed as a womanizer who cheated on Jackie with many different women. But was that really true? Or was a lot of it a smokescreen to cover up JFK’s relationship with Lem Billings?

The Daily Mail had an interesting article about Billings and JFK today:

Of all the secrets nurtured by John F. Kennedy, his life-long love affair with another man was arguably the most risky.
Kirk LeMoyne Billings, who went by Lem, was 16 years old when he first met Jack Kennedy, then 15.
It was the fall of 1933. Both were enrolled at Choate, an elite all-boys boarding school in Connecticut.
For Lem, it was practically love at first sight. Jack Kennedy was everything he was not: roguish, charismatic, confident, effortlessly popular — not just with other students, but girls and women.
In the beginning, at least, Jack didn't realize that Lem harbored romantic feelings for him.
But at some point in their friendship, Lem confessed his desires to Jack in a message scrawled on toilet paper — a common trick at Choate, so that boys could easily swallow or destroy love notes to each other.
That note has been lost to history, but Jack's written response was not.
'Please don't write to me on toilet paper anymore,' Kennedy replied. 'I'm not that kind of boy.'

The relationship between JFK and Lem Billings

I remember reading about JFK’s friendship with Billings many years ago, when I was keenly interested in learning about the events that happened during Kennedy’s administration. Those were different times, and friendship was the context through which Billings was presented in the books I read about JFK. But it didn’t take a genius to read between the lines, since Billings never dated women, never married, and never had children. It was obvious there was more to his friendship with JFK than simply being boyhood friends.

I know that Kennedy being involved with Billings might come as a shock or surprise to some readers who aren’t familiar with JFK’s life. But it’s important to note that surface level appearances (which were what was presented to the public in the 50s and 60s) are not necessarily what’s actually happening behind closed doors. When I was young, I believed what I saw on the surface, but as you get older, you realize that there’s often much more to the situation, and that things are more complicated than you thought. That was the case with JFK, Jackie, and Lem Billings.

A photograph of Lem hoisting Jack up by his backside on campus from Jack's Choate scrapbook, along with the scribbled caption, 'Don't be so personal, LeMoyne'.

At this point in my life, very little surprises me about human beings and their sex lives. There’s nothing new under the sun in that regard, and you see the same shenanigans going on over and over again. I don’t doubt that the relationship between Billings and JFK has happened with other presidents going back to the beginning of the republic. Such things were better hidden in previous ages, where the presidency itself was more opaque and much that went on inside the White House and elsewhere was carefully hidden from public view.

Did JFK use Julius Caesar’s playbook?

As I noted above, JFK’s relationship with Billings makes me doubt at least some of the stories about his womanizing. JFK was supposedly involved with Marilyn Monroe and many other women. I don’t doubt that he dipped his wick in other women, but I cannot help but wonder if some of the stories were deliberately spread to cover up his relationship with Billings. After all, if you turn JFK into a super-stud who slept with a zillion women, then it makes it much easier to conceal his relationship with his friend.

Something similar happened during the Roman Republic with Julius Caesar. Rumors (possibly created by Caesar’s political enemies) suggested that he had had an affair with Nicomedes IV of Bithynia and that Caesar had been the passive partner in their sexual relationship. This gave rise to the unflattering label of Caesar by his enemies as “the queen of Bythnia.” Caesar’s response to this was to seduce and fuck many of the wives of Rome’s aristocratic class.

In other words, Caesar sort of slept his way to the top and, in the process, helped defray some of the political damage done by the rumors about him and Nicomedes. Caesar deflected the attack on his masculinity by his enemies by banging their wives whenever possible. In that sense, Caesar knew exactly what he was doing, and it worked. The old Bithynia rumors were still there, but everybody also knew that Caesar knew how to wield his dong as a political weapon whenever necessary.

JFK was a student of history and might have learned a thing or two from Caesar.

The media in the 1950s and 60s

In case you are wondering why none of this made it into the media at that time, you must understand that the media was very different back then. Certain things were open secrets known to reporters, but they would have never been put on television or into the newspapers. Even JFK’s affairs with women were not reported in the media, never mind a gay relationship with Billings.

It would have been unthinkable for a reporter to write a story about such things when Kennedy was president, though that obviously changed afterward. Now the media would gleefully report on every detail if something similar were to happen again with a different president. There would be no mercy from the media for any president who was caught with his pants down, regardless of whether he was with another man or with a woman.

Remember what happened with Bill Clinton and Monica Lewinsky? Bill Clinton was a great admirer of JFK’s and thought that he too could engage in sexual shenanigans in the White House. But Clinton did not realize how times had changed and that even the whiff of a sex scandal in the White House would get instance coverage around the world in the media. Clinton’s affair with Lewinsky blew up in his face and resulted in his impeachment. Bill Clinton was not JFK, and he found that out the hard way.

Jack and Lem sit aboard a boat off the coast of Hyannis Port, Massachusetts in July 1933, along with an unidentified girl.

Jack and Lem (right) outside a drugstore in the mid-1930s.

Jackie Kennedy and Lem Billings

Kennedy, of course, knew he had to marry a woman at some point. He could not have succeeded as a politician in those days had he remained a bachelor forever. But it wasn’t long before Jackie figured out what was what with Billings:

Early in their courtship, which began in 1952, Jackie knew two things: She wanted to marry Jack Kennedy, and that meant accepting Lem Billings and entering a love triangle.
Lem was, for Jack, non-negotiable.
Did Jackie know that her future husband had been intimate with Lem? That Jack and Lem joked about having a child together? That on a two-and-a-half month European trip they took together in 1937, they had jointly purchased a Dachshund that they named Dunker — a dog they quickly had to re-home due to Jack's allergies?
If so, she never said a thing.
Nor did she blanch when Jack's friend Langdon Marvin, the godson of President Franklin D. Roosevelt, told her one night that if Jack were to marry her, it was only 'because people are starting to call him a 'fairy'. In this country, if you're not married by 40, you're suspect.'
Jackie, however, had a gift for reading people. She quickly realized that Lem and Marvin were both in love with Jack and trying to scare her off.

You have to wonder about Jackie here. Was she really that in love with JFK, or did she see him as a vehicle to fame and fortune? She seemed to know what she was getting into, but did it anyway. I suppose she might have figured that the upsides of being JFK’s wife would outweigh the downsides, including his relationship with Lem Billings.

Still, it could not have been easy or pleasant for her to have to compete with Billings for JFK’s attention. Other women can be enough of a headache for a wife to deal with in a situation where her husband is rich, famous, and powerful. Having to deal with her husband being in a homoerotic, and sometimes outright sexual, relationship with another man had to have caused some stress on her part.

Jackie was a very sophisticated woman, however. Given her own background, I don’t think it was something that shocked her, and it obviously wasn’t enough to deter her from marrying JFK and becoming the mother of his children. Jackie was not some naive waif who had never been exposed to complicated relationship situations. She’d had plenty of that with her father, and it seemed to help her understand JFK and Lem Billings.

Eventually, it seems like she and Billings came to terms with each other, and life went on in the White House until JFK went to Dallas and only his body came back.

The sad life of Lem Billings

I want to close this post by stating that I think Lem Billings had a rather sad life. He was obviously in love with JFK, but after Kennedy’s murder, he never seemed to find his own life. He lived on, but still remained in JFK’s shadow, right up until the end of his own life at the age of 65 in 1981.

Perhaps it was just Lem Billing’s own internal emotional makeup that caused this? Or maybe it was the times that he had lived through? We’ll never really know, but it’s clear that when the bullet slammed into Kennedy’s head in Dallas, it also destroyed the one relationship that Lem Billings had clung to his entire adult life.

UPDATE: I forgot to explain the use of sexual labels in this article. For convenience, I have used the word “gay” to describe Lem Billings, but I have not done so for JFK. Why not? Sometimes human behavior transcends the labels created by the Alphabet Mafia.

In this case, we have two men that (according to the DM story) lost their virginity together by screwing the same female prostitute:

Such insults were part of Jack's love language, and Billings took them as such. When Jack came up with the idea that they should lose their virginity together — Jack, again, perhaps willfully oblivious to the intrinsic homoeroticism — Billings went along.
Off they travelled, from Choate, to a brothel in New York City. Jack insisted they should share the same prostitute.
Whether they shared this sexual encounter as a threesome remains unclear, but their friend Rip Horton later said that 'Billings and Jack came back in a terrible panic because of [venereal disease]. They went to a hospital and got all these medicines and creams.'

So technically, you could say that both men are “bisexual” since both have had sex with a woman.

But it’s obvious that, Lem Billings aside, JFK leaned toward women. Billings, on the other hand, obviously was in love with JFK and did not date or marry a woman. So, of the two men, I’d say that Billings was likely gay while JFK was bisexual.

One could also use the terms “hetero-flexible” for JFK (his dominant orientation was clearly toward women, with Billings likely being the sole exception since their relationship went all the way back to their adolescence) and “homo-flexible” for Billings (who seemed mostly gay but who apparently had sex with a woman on at least one occasion).

Those are probably more accurate than anything else, but, as I said above, I used “gay” for Billings in the title since it conveys his situation in a simpler way for readers.

I dislike getting caught in this annoying web of labels, but it was necessary to use some to try to describe the complicated relationship between these two men.