Frank Sinatra Was Nearly the Target of a Mafia Hit Because of a Failure With John F. Kennedy

For much of his life, Frank Sinatra dealt with allegations that he had ties to the mafia. The singer denied these rumors, but they have persisted even after his death. His associations allegedly grew irritated with him because Sinatra failed to get them a direct line to the Kennedy White House. In a conversation in a bugged restaurant, one reportedly offered to get rid of Sinatra and his friends.

A black and white picture of Frank Sinatra sitting in the back seat of a car.
Frank Sinatra | Bettmann/Contributor via Getty

Frank Sinatra allegedly had mafia ties 

Sinatra began dealing with whispers about his alleged mob ties early in his career. This, coupled with his left-leaning politics, meant that the FBI began tracking him. The rumors were so prevalent that the character of Johnny Fontane in The Godfather was based on Sinatra, a fact that the singer abhorred. 

Some of Sinatra’s associations were, undoubtedly, part of organized crime families. He was close with Lucky Luciano and Sam Giancana. Still, Sinatra denied being at all involved in organized crime. 

“Wiseguys wanted to be in Frank’s inner circle and he did his best to juggle that and not let it get too heavy, but you know some people would go overboard,” his manager Tony Oppedisano told Page Six. “Some of the guys became friends over the years and they would try to do things for him that he never asked them to do. He’d say, ‘If these guys really want to do me a favor, I wish they’d stop doing me favors!'”

The singer’s alleged mob associations grew frustrated with him

In the 1960s, Sinatra began campaigning for John F. Kennedy. The men became close friends. His alleged mafia associations hoped that Sinatra’s connection to the president would mean the government wouldn’t crack down on the mob. It didn’t work out this way. While the Kennedy family appreciated Sinatra’s help with the election, Attorney General Robert Kennedy was tough on the mafia.

“By 1962, it was obvious that the Justice Department wouldn’t go easy on the mob, and Sam Giancana was furious with the Kennedys and Frank Sinatra because he thought they owed him something,” explained NPR reporter Alex Chadwick.

Giancana and his associates met in a suburban Chicago restaurant in 1961 to discuss Sinatra. Per a 1981 article in the Wall Street Journal, the FBI had bugged the restaurant.

“They can’t get away with it as if nothing’s happened,” one man said. “Let’s hit Sinatra. Or I could whack out a couple of those other guys.”

Giancana responded by saying that he had other plans for Sinatra. Some wonder if he was referring to a 1962 Rat Pack performance at a mob-run Chicago club. During the performance, Dean Martin made a joke about not being paid for the performance and, given the audience’s laughter, they appeared to get the joke. 

Frank Sinatra’s relationship with John F. Kennedy fell apart because of the mafia

Sinatra and Kennedy’s friendship ultimately crumbled because of the singer’s alleged mob affiliation. The breaking point came when Sinatra had a private suite and helipad built at his home in anticipation of a visit by the president. Ultimately, though, Robert Kennedy believed it was best to steer clear of Sinatra. 

In a rage, the singer took a sledgehammer to the helipad. He never forgave Robert Kennedy for the slight.

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