stylistic:tone
Alleged organized-crime links and Cal Neva Lodge

Sinatra became the stereotype of the "tough working-class Italian American," something which he embraced. He said that if it had not been for his interest in music, he would have likely ended up in a life of crime. Willie Moretti was Sinatra's godfather and the notorious underboss of the Genovese crime family, and he helped Sinatra in exchange for kickbacks and was reported to have intervened in releasing Sinatra from his contract with Tommy Dorsey. Sinatra was present at the Mafia Havana Conference in 1946, and the press learned of his being there with Lucky Luciano. One newspaper published the headline "Shame, Sinatra." He was reported to be a good friend of mobster Sam Giancana, Kelley quoted Jo-Carrol Silvers that Sinatra "adored" Bugsy Siegel and boasted to friends about him and how many people Siegel had killed. Kelley says that Sinatra and mobster Joseph Fischetti had been good friends from 1938 onward and acted like "Sicilian brothers". She also states that Sinatra and Hank Sanicola were financial partners with Mickey Cohen in the gossip magazine Hollywood Night Life.

The FBI kept records amounting to 2,403 pages on Sinatra, who was a natural target with his alleged Mafia ties, his ardent New Deal politics, and his friendship with John F. Kennedy. The FBI kept him 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. The FBI documented that Sinatra was losing esteem with the Mafia as he grew closer to President Kennedy, whose younger brother Attorney General Robert F. Kennedy was leading a crackdown on organized crime. Sinatra said he was not involved: "Any report that I fraternized with goons or racketeers is a vicious lie."

In 1960, Sinatra bought a share in the Cal Neva Lodge & Casino, a casino hotel on the shore of Lake Tahoe. Sinatra built the Celebrity Room theater, which attracted his show business friends Red Skelton, Marilyn Monroe, Victor Borge, Joe E. Lewis, Lucille Ball, Lena Horne, Juliet Prowse, the McGuire Sisters, and others. By 1962, he reportedly held a 50-percent share in the hotel. Sinatra's gambling license was temporarily suspended by the Nevada Gaming Control Board in 1963 after Giancana was spotted on the premises. Due to ongoing pressure from the FBI and Nevada Gaming Commission on mobster control of casinos, Sinatra agreed to give up his share in Cal Neva and the Sands. That year, his son Frank Jr. was kidnapped but was eventually released unharmed. Sinatra's gambling license was restored in February 1981, following support from Ronald Reagan.