1. Hoover was a gay cross-dresser.
Despite rampant speculation — that Hoover was gay, a cross-dresser or had no sex life — the truth about his sex life is nearly impossible to pin down. Hoover was married to his job and zealously protective of his public image. He lived in an era when being outed as gay would cost anyone his career and reputation, and he was not one to risk such consequences.
The story that Hoover, a lifelong bachelor, participated in cross-dressing, all-male sex parties in New York hotel rooms, as reported by British writer Anthony Summers in a 1993 biography, has been widely debunked by historians. The story’s source, the wife of a businessman and Hoover confidante, had a grudge from a contested divorce, and other investigations of the story came up empty.
If Hoover did have a gay relationship, most likely it was with his longtime FBI associate director, Clyde Tolson, another lifelong bachelor — but even this is disputed. Hoover and Tolson worked together more than 40 years. They traveled on vacation and official business, rode to work together, shared lunch nearly every day at Washington’s Mayflower hotel and sometimes even wore matching suits. Hoover, at his death, left Tolson most of his estate. Their relationship, by all appearances, was stable, discreet and long-lasting. But what they did physically behind closed doors, if anything, they kept between them.