Frank Sinatra’s Shady Dealings Could’ve Caused Problems for Ronald Reagan

Frank Sinatra had friendships with two separate presidents, John F. Kennedy and Ronald Reagan. While his level of fame was helpful to politicians when Sinatra endorsed them, some worried about the optics of a friendship with the crooner. Sinatra allegedly had mafia connections, which damaged his friendship with Kennedy. Some speculated that his friendship with Reagan could be bad for the president.

A black and white picture of Ronald Reagan and Frank Sinatra shaking hands.
Ronald Reagan and Frank Sinatra | Bettmann/Contributor via Getty

Frank Sinatra didn’t like Ronald Reagan at first

Sinatra did not like Reagan when he met him as an actor. 

“He told me that he thought Ronald Reagan was ‘a stupid bore who couldn’t get a job in pictures, which was why he went into politics,'” Shirley MacLaine wrote in her memoir My Lucky Stars: A Hollywood Memoir, per Vanity Fair. “He threatened to move out of California if Reagan ever got elected to public office.”

Sinatra did not like Nancy Reagan either. 

“He thought Nancy was ‘a dumb broad with fat ankles who couldn’t act,'” MacLaine wrote. “I heard him scream and curse at the television set when they appeared.”

Some wondered if Frank Sinatra’s alleged mafia connections would impact Ronald Reagan

As he got older, though, Sinatra softened his opinion on the Reagans. MacLaine believes that Sinatra’s friendship with him occurred because the Kennedy family snubbed him, not shifting political beliefs. Regardless, Sinatra befriended Reagan. Some thought this would harm Reagan’s political career.

Per a 1981 article in the Wall Street Journal, Sinatra, Dean Martin, and Sammy Davis Jr. performed unpaid concerts at a mafia-run club in suburban Illinois in 1976. The club owners and other Sinatra associates were later under scrutiny by federal attorneys for swindling. Several men were found guilty in the case, and others were under suspicion. One of these people was Sinatra.

At the same time, Sinatra played a prominent role in Reagan’s inauguration party, and Reagan attended Sinatra’s wedding. Some wondered if the two men’s close relationship would help Sinatra avoid federal scrutiny in the investigation. Reagan avoided commenting on the investigation but offered a vague statement about the allegations. 

“We’ve heard those things about Frank for years, and we just hope none of them are true.”

The singer also had a friendship with John F. Kennedy

Sinatra was also close friends with Kennedy. He met the former president through their mutual connection, Peter Lawford. They were close friends by the time Kennedy began campaigning for president. 

Sinatra openly endorsed Kennedy, so he hosted donor events and allowed the campaign to use his private jet. Sinatra also hosted the pre-inauguration gala after Kennedy was elected.

Related

Frank Sinatra Made a Phone Call Trying to Help Elvis: ‘He’s Too Young to Die’

Their relationship was irreparably damaged because of Sinatra’s alleged mafia connections. Sinatra built a presidential suite and helipad at his home in California. The president was supposed to stay with the singer, but Robert Kennedy felt it was best to stay distant from Sinatra. Instead, Kennedy stayed with Bing Crosby.

Sinatra was so furious that he took a sledgehammer to the helipad. He never forgave Robert Kennedy for the decision.