Sinatra garnered considerable attention due to his alleged personal and professional links with organized crime. Among these figures included Sam Giancana, Lucky Luciano, and Joseph Fischetti,The Federal Bureau of Investigation kept records amounting to 2,403 pages on Sinatra. With his 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 1940's with, for example, an erroneous report that the star paid $40,000 for his 4-F draft status, through the early 1980's when he was successful in efforts to get his Nevada Gaming license renewed. The documents include accounts of Sinatra as the target of death threats and extortion schemes. They also betray 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 came up empty-handed. Readers learn that the budding star, to get an exemption from military service, told draft-board doctors that he had an irrational fear of crowds. 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.