Most historians believe this is just an urban legend. While that would be fun picture, it was most likely a malicious rumor.
In “Official and Confidential: The Secret Life of J. Edgar Hoover,” author Anthony Summers quotes Susan L. Rosenstiel as saying she once observed Hoover in a black dress and high heels at the Plaza Hotel. The story isn’t very credible. Rosenstiel’s husband was involved in organized crime, and Susan was once convicted of perjury in an unrelated case. Additionally, why would the head of the FBI put himself in a position to be easily blackmailed?
Far more likely (though never proven) was that Mr. Hoover was a closeted homosexual. Hoover was a lifelong bachelor, but he did have one constant companion — Clyde Tolson. The two were inseparable, even vacationing together. When Hoover died, he left his entire estate, valued at over $500,000, to Tolson. Additionally, it was Tolson who accepted the American flag used to drape Hoover’s casket.
Of course, just because two guys hang out together doesn’t mean they’re lovers. The fact is, nobody knows whether Hoover and Tolson were more than friends, but it’s interesting to note the two chose to be buried next to each other.