The Transvestism of John Edgar Hoover

by Timothy Chilman



Was J. Edgar Hoover a tranny?

The National Observer said that the name J. Edgar Hoover is associated with transvestism as closely as “Rolls” is with “Royce” and “Laurel” with “Hardy.” So what is the truth of it? Did he honestly feel more comfortable wearing a fluffy gown, a suspender belt, and false eyelashes?

Ralph de Toledano, a mainstay of the conservative movement in the United States throughout the latter half of the 20th century, said, “You know, there’d been a lot of talk about Hoover and this and that and the transvestite stuff and so on. Nonsense. Hoover had one wife, and that was his Federal Bureau of Investigation, that was his whole life.”

Hoover with Clyde Tolson, who was quite possibly his lover

Homosexuality on Hoover’s part was highly plausible. Hoover resided with his mother until her death in 1938. For over 40 years, he was inseparable from his right-hand man, Deputy Director of the FBI, Clyde Tolson. Both were bachelors and they vacationed together. Hoover and Tolson are buried side-by-side. Gay activists now have been known to include Hoover and Tolson in their lists of famous gay couples. The pair were treated as a couple by high society: Hoover would never be invited to dinner sans Tolson. They double-dated with Broadway star, Ethel Merman and Sherman Billingsley, the owner of the Stork Club, when the latter two were in the throes of an affair. They did the same with Richard and Pat Nixon. In the 1960s, FBI agents referred to them as “J. Edna” and “Mother Tolson.”

The film, J. Edgar, which was directed by Clint Eastwood, portrayed Hoover and Tolson as unrequited lovers. They kissed, held hands and quarreled like lovers, but may not have gone further than that. Hoover is seen donning his recently-deceased mother’s dress, but the film does not make him out to be a fully-fledged tranny. But then, it never mentioned COINTELPRO, either.

Hoover shortly before his appointment as head of the FBI

Rumors of Hoover’s homosexuality appeared as soon as he became head of the FBI in 1926. A magazine article in the 1930s described his “mincing” manner of walking. He was somewhat dandyish, and favored white linen suits as a young man. His voice was highly affected, and Leonardo DeCaprio had a hard time mimicking it in J. Edgar. Hoover kept classical statues of male nudes in his home. Many people sensed that his relationship with Tolson went beyond friendship. An article published by Fordham University, one of the best 60 universities in the United States, described Tolson as Hoover’s “true love.” When Hoover died in 1972, President Nixon exclaimed: “Jesus Christ! That old cocksucker!” He was perhaps not speaking figuratively.

The transvestism thing was described most comprehensively in Anthony Summers’ gossipy 1993 biography of Hoover, Official and Confidential: The Secret Life of J Edgar Hoover. Summers had previously written of the JFK assassination. He repeated explosive allegations by Susan, the one-time fourth wife of liquor magnate, Lewis Rosentiel, a bootlegger who made his fortune after the repeal of Prohibition by starting the United States’ largest distillery, Schenley Industries.

Susan says that she and her husband were met at the door of Manhattan’s Plaza Hotel by Roy Cohn, formerly an aide to Senator Jospeph McCarthy and a Republican power broker. Taken to the bedroom of a suite, Mrs. Rosentiel says she saw Hoover, whom she had met previously in her townhouse in the Upper East Side of New York. Mrs. Rosentiel’s husband had told her that Hoover granted him access to influential politicians, and he returned the favor by paying off his gambling debts.

Hoover was reportedly seen wearing stockings and a short skirt, Photo: Tvinhose1

According to Susan, Hoover was in drag: he wore a black dress that was “very fluffy, with flounces” in addition to “lace stockings, high heels, and a curly black wig.” He wore make-up, false eyelashes, and a very short skirt, the dirty slut. He sat with his legs crossed. Mrs. Rosentiel said Hoover looked like a flapper. Cohn had warned her not to comment, and gave the FBI Director’s name as “Mary” when he introduced her to him. Hoover said, “Good evening,” as if it were the first time they had met.

Two blond boys entered the “tremendous bedroom, with a bed like in Caesar’s time,” and on orgy commenced. Hoover removed his dress and underclothing, to reveal a garter belt. The boys “work[ed] on him with their hands,” with one wearing rubber gloves. Then, her husband “got into the act,” after which Cohn had “full sex” with both boys.

One year after, the same occurred again. Now, the boys wore leather, with Hoover in a red dress and black feather boa. One boy read from the Babble, while the other fondled Hoover wearing gloves. Hoover “grabbed the Bible, threw it down, and told the second boy to join the sex.” Mrs. Rosentiel’s husband invited her to participate, but she declined.

Do we trust the originator of this uncorroborated story? Hoover provided Lewis Rosenthiel with damaging information concerning his wife when they divorced in the late 1960s. Mrs. Rosentiel testified against her husband and his partners in organized crime. She spent a while at Riker’s Island for attempted perjury in 1971, having pleaded guilty. Journalist Ronald Kessler met her at her place, in a single-room occupancy hotel in New York which cost her $98.95 a night. She was paid by Summers, and again by Frontline and the BBC. Kessler said, “I believe that paying for information calls into question its credibility.”

Robert M. Morgenthau, later in life

Mrs. Rosentiel attempted to spread her story for years, once to an opponent of Hoover, attorney Robert M. Morgenthau of New York. She annoyed him with repeated phone calls after 5:30p.m. when his secretary had departed. He passed the information to William Hundley, the head of the Justice Department’s Organized Crime and Racketeering Section. Hundley asked a Justice Department attorney to investigate. Hundley said Mrs. Rosentiel “had a total ax to grind” and that her story was constructed “of whole cloth.” He told this to Summers, who was not deterred.

Outing” is the alleging that a prominent figure is gay, and in political cases uses gossip over sexual identity as a political weapon: the target is made out to be not only a pervert, but a hypocrite. During the presidency of Bill Clinton in the 1990s, sexual gossip was increasingly employed to articulate political resentment, a practice which had begun in the early nineteenth century.

Adlai Stevenson was persecuted by Hoover

Allegations of Hoover’s homosexuality were richly deserved. Hoover oversaw the spreading of accusations of homosexuality of political enemies such as then Illinois Governor and later two-time presidential candidate and U.N. ambassador, Adlai Stevenson. Articles by gay journalists in the early 1980s following a discrimination lawsuit by a gay FBI agent revealed that FBI agents collected the underwear of politicians for blackmail purposes. Hoover closely followed the sexual shenanigans of President Kennedy.

Mr. Rosentiel was linked to the Mafia figures, Frank Costello (formerly Francesco Castiglia) and Meyer Lansky at New York legislative committee hearings in 1970. Blackmail of politicians was central to Mafia operations. According to Summers, “several Mafia sources” claimed that Hoover was blackmailed over his sexuality using photographs of him and Tolson. A source who saw one photograph said it clearly depicted two men in sexual congress, but was too blurry to allow for identification.

A photographic record of his homosexuality could perhaps explain Hoover’s reluctance to even acknowledge the existence of organized crime, although some say this was because he preferred easy targets to more easily inflate his arrest statistics. The blurb of Summers’ book states, “Without this, the Mafia as we know it might never have gained its hold on America.” When world-class journalist Robert Mass asked one of Lansky’s closest associates about the photograph, the ancient mafioso replied: “Are you nuts?”

The Miami field office of the FBI complained that its investigation of Lansky, initiated by Hoover, was not generating enough meat to countenance the manpower devoted to it, prompting Hoover to reply that “Lansky has been designated for ‘crash’ investigation.” He said the significance of the endeavor could not be overemphasized, and that he desired a vigorous and detailed investigation. Lansky’s apartment was bugged. Hoover’s attitude to the Mob had changed after publicity surrounding the historic 1957 Appalachin Meeting of about 100 mobsters. Had the Mob had anything on Hoover, it would have turned up in the many wiretaps mounted after Appalachin. Let’s ignore that bit.

It is claimed that Wild Bill Donovan arranged for incriminating photographs of Hoover to be obtained when he conducted a feud with him.

Summers claimed that the photographs originated from the Office of Strategic Services, forerunner to the CIA. While feuding with OSS boss William “Wild Bill” Donovan, Hoover had attempted to obtain compromising information, as was his wont, and Donovan retaliated.

Is it plausible that the events Mrs. Rosentiel describes took place at a one of New York’s most fashionable hotels, rather than a safe house? It is as believable as the claim by Joe McCarthy that the State Department contained 205 known communists – which was widely circulated by the press with no further investigation. Let’s have some more of that.

The transvestism of John Edgar Hoover has not been proven and is highly unlikely. It has only one source, an embittered, impoverished perjurer. Even hardcore Pinkoes who resent all that Hoover stood for dismiss the story.

Was Hoover, the most powerful ever lawman of the United States, a tranny? Hell, yes! Come on, the guy was fucked-up. Were he not a tranny, he must have been a serial killer, rapist, or pedophile. This is actually the least worst option. After Hoover’s death, his associates, led by Tolson, destroyed many of his files. Hoover knew all about blackmail, having done so much of it, and it is no surprise that his tracks have been erased. Summers also says that Hoover ignored a warning of the Japanese attack on Pearl Harbor.


“Interview with Ralph de Toledano.” George Washington University. n.d. 7 August 2011. <>
Halsall, Paul. “Homosexuality and Catholicism Bibliography: Section XIV: Lesbian and Gay Christian Movies and TV.” Fordham University. n.d. 7 August 2011. <>
Hockenberry, John. “The Secrets of J. Edgar Hoover.” MSNBC. 12 April 2004. 7 August 2011. <>
Kessler, Ronald. “Did J. Edgar Hoover Really Wear Dresses?” History News Network. 22 July 2002. 7 August 2011. <>
Mashek, John. “Hoover Used Blackmail against JFK, Author Says.” Highbeam Research. n.d. 7 August 2011. <>
Potter, Claire. “Queer Hoover: Sex, Lies, and Political History.” Highbeam Research. 1 September 2006. 7 August 2011. <>
Pringle, Peter. “FBI chief exposed as a secret transvestite: Peter Pringle reports from New York on new allegations that J Edgar Hoover attended orgies, wearing a fluffy black dress to one, and was blackmailed into protecting the Mafia.” Independent. 6 February 1993. 7 August 2011. <>
Stove, R.J. “J. Edgar Hoover and the Ku Klux Klan.” National Observer. 1 June 2001. 7 August 2011.<>
Summers, Anthony. “Official and Confidential: The Secret Life of J. Edgar Hoover.” London: Weidenfeld & Nicolson. 1993