Was J. Edgar Hoover a cross-dresser?

Illustration by Slug Signorino

Cecil replies:

One more example of how the oligarchs plot to keep the truth from us, you’re thinking — not that this is something you necessarily want to see covered in sixth grade social studies. In point of fact, however, the alleged transvestitism of John Edgar Hoover, director of the FBI from 1924 until his death in 1972, has never been established, and reputable historians say it’s an urban legend.

The story probably got its start because of more plausible rumors that Hoover was gay. He and his right-hand man, Clyde Tolson, were constant companions for more than 40 years, even vacationing together, and both remained lifelong bachelors. (Hoover lived with his mom until she died in 1938.) They say Richard Nixon, on hearing of Hoover’s death, exclaimed with his customary delicacy, “Jesus Christ! That old cocksucker!”

The cross-dressing thing, however, is a definite no. The story appears in Official and Confidential: The Secret Life of J. Edgar Hoover (1993), a gossipy biography by British journalist Anthony Summers, who has also written a JFK assassination conspiracy book. Summers says he got his info from Susan Rosenstiel, fourth wife of Lewis Rosenstiel, chairman of Schenley Industries, a liquor distiller with reputed mob connections.

Ms. Rosenstiel claimed that in 1958 she and her husband went to a party at a New York hotel, where they met Hoover and McCarthy witch-hunt lawyer Roy Cohn. Hoover, whom Cohn introduced as “Mary,” was supposedly wearing a wig, a black dress, lace stockings, and high heels. Hoover went into a bedroom, took off his skirt to reveal a garter belt, and had a couple of blond boys — one wearing rubber gloves — “work on him with their hands.” Cohn and Hoover then watched while Lewis Rosenstiel had sex with the boys.

A year later Ms. Rosenstiel attended another party at the same hotel; this time Hoover wore a red dress and a black feather boa. He had one of the blond boys, who were now dressed in leather, read to him from a Bible while the other “played” with him. Hoover then grabbed the Bible, tossed it down, and told the first boy to join in.

Most researchers, including many hostile to Hoover, say this story is ludicrous. In a 1993 Esquire article, journalist Peter Maas wrote that Susan Rosenstiel, the sole source of the cross-dressing allegations, had “been trying to peddle this story for years,” apparently because she believed Hoover had put FBI agents on her tail to help her husband during their divorce. According to Ronald Kessler, author of The Bureau: The Secret History of the FBI (2002), Ms. Rosenstiel did jail time for perjury in connection with a 1971 case.

Even if we set aside the teller’s credibility, it’s difficult to take this tale seriously. Hoover was an old hand at blackmail — he used incriminating information his agency collected about prominent people to maintain his hold on office and otherwise get his way. Would a man with so many enemies put himself in a position to be blackmailed by waltzing around a hotel in drag?

Summers also claims that the FBI gave the Mafia a pass for many years because mob boss Meyer Lansky had a photo of Hoover and Tolson having sex. (Apparently a photo of two men humping on a beach did exist, but one source who claims he saw it says it was too blurry to permit the men to be identified.) Though Hoover did appear reluctant to go after organized crime, most observers think that was because he preferred easy targets to bulk up his arrest records. Once ordered to take on the mob by Robert Kennedy, Hoover pursued Lansky in particular with zeal — irrational behavior if Lansky could expose him. Maas also wrote that when he asked Lansky’s closest associate about the photo, the old mafioso replied, “Are you nuts?”

Which brings us back to Tolson, and to Hoover’s rumored homosexuality. There were hints about this throughout the FBI boss’s career, some of them a little silly. A 1930s magazine article, for example, describes Hoover’s mincing step. He was a bit dandyish, favoring white linen suits as a young man; he had classical statues of male nudes at his home, and one of his hobbies was antique collecting. On the more serious side, many people sensed that his long relationship with Tolson was more than a friendship — the pair never lived together, but they’re buried side by side. Today some gay activists include Hoover and Tolson in their pantheons of famous gay couples.

Appearances notwithstanding, no one has found concrete evidence that the two men were anything other than buddies. Given Hoover’s ability to cover his tracks — his associates, with Tolson’s help, destroyed many of his files upon his death — it’s unlikely anyone ever will.

Cecil Adams

Send questions to Cecil via cecil@straightdope.com.