People say you’re fortunate if you have one or two people in your life outside of your family in whom you can completely confide and on whom you can completely count. Lem had such a friend in John. The pair met at a prestigious prep school, Choate, in the 1930s. Both boys were from wealthy families in the Northeast, and both came from families where the father was largely absent and distant. So, in many ways, it was quite natural that the two would become best chums.
They roomed together at the boarding school for several years. In fact, Lem, a year older than John, thought so much of the friendship that he agreed to re-do his senior year so he could graduate with his best friend. And John was forever grateful for Lem’s sacrifice. They formed a secret society, called the Muckers, whose aim was to play pranks on the staff and on the school at large. Each young man needed someone in his corner, someone who would have the other’s back unreservedly. And they were indeed that for each other. Then, in 1937, the pair spent that summer traveling around Europe. The bond between the two grew even tighter.
Now, at this point, we have to say what you might be thinking. Yes, there was a sexual attraction in play here, but it turned out that only Lem had romantic feelings. John didn’t, but that didn’t stop John from loving Lem as his best friend and closest confidant. John knew that Lem was gay. While Lem would have preferred something more that best friends, he was content that John was in his life in that role if nothing else.
And that’s the way the relationship remained. Lem was in John’s wedding. John’s wife would later joke that her marriage to John came with a built-in houseguest because Lem was always staying over. He often spent holidays at John’s family’s house, and, to keep people from gossiping, he even took John’s sisters to social events. But, society being what it was then, Lem had to remain in the closet.
Both young men served in World War 2 with distinction. They remained close after the war. In fact, they roomed together for a while as bachelors as John began his career and Lem put off attending Harvard Business School for a graduate degree. As John’s career took off, Lem became his closest advisor and confidant, a role he’d had since the two were at Choate together. He was at John’s side when John faced the toughest decisions of his life. John offered Lem positions that would let them work together, but Lem turned them down. He felt strongly that working together would somehow change the nature of the relationship, and he didn’t want to run that risk. John appreciated that sense of love and loyalty in his friend for the rest of his life.
So, yes; having a close companion and a loved and trusted best friend is a rare and precious thing. But the fact that he was gay is a major reason you don’t know the important role Lem Billings played in the life of John F. Kennedy.
The Rest of the Story 