Frank Sinatra - Alleged Organized Crime Links

Alleged Organized Crime Links

Sinatra garnered considerable attention due to his alleged personal and professional links with organized crime, including figures such as Carlo Gambino, Sam Giancana, Lucky Luciano, and Joseph Fischetti. The Federal Bureau of Investigation kept records amounting to 2,403 pages on Sinatra. With his alleged Mafia ties, his ardent New Deal politics and his friendship with John F. Kennedy, he was a natural target for J. Edgar Hoover's FBI. The FBI kept Sinatra under surveillance for almost five decades beginning in the 1940s. The documents include accounts of Sinatra as the target of death threats and extortion schemes. They also portray rampant paranoia and strange obsessions at the FBI and reveal nearly every celebrated Sinatra foible and peccadillo.

For a year Hoover investigated Sinatra's alleged Communist affiliations, but found no evidence. The files include his rendezvous with prostitutes, and his extramarital affair with Ava Gardner, which preceded their marriage. Celebrities mentioned in the files are Dean Martin, Marilyn Monroe, Peter Lawford, and Giancana's girlfriend, singer Phyllis McGuire.

The FBI's secret dossier on Sinatra was released in 1998 in response to Freedom of Information Act requests.

The released FBI files reveal some tantalizing insights into Sinatra’s lifetime consistency in pursuing and embracing seemingly conflicting affiliations. But Sinatra’s alliances had a practical aspect. They were adaptive mechanisms for behavior motivated by self-interest and inner anxieties. In September 1950 Sinatra felt particularly vulnerable. He was in a panic over his moribund career and haunted by the continual speculations and innuendos in circulation regarding his draft status in World War II. Sinatra “was scared, his career had sprung a leak.” In a letter dated September 17, 1950, to Clyde Tolson, Deputy FBI Director, Sinatra offered to be of service to the FBI as an informer. An excerpted passage from a memo in FBI files states that Sinatra “feels he can be of help as a result of going anywhere the Bureau desires and contacting any people from whom he might be able to obtain information. Sinatra feels as a result of his publicity he can operate without suspicion…he is willing to go the whole way.” The FBI declined his assistance.

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