The Rat Pack in Trouble

In his desire for respectability, Frank Sinatra threw himself into Senator John F. Kennedy’s 1960 Presidential campaign with a vengeance, campaigning for the candidate and gaining him exposure. Sinatra also helped the Kennedy campaign working as a go-between between JFK’s father, Joseph and the Chicago Mob, headed by Sam “Momo” Giancana, a mobster who by 1960 was suspected in having ordered the murders of over 600 people. During Sinatra’s lean years, when he couldn’t get a job anywhere, it was individuals like Giancana and others who hired him to sing in their nightclubs.

The Mafia had no desire to help the Kennedys. Robert “Bobby” Kennedy had been an active participant in Senate hearings to reveal mob corruption in labor unions. Sinatra made it a personal request on his part, and Giancana did see the benefits of having a President who owed him. JFK won the election.

Anticipating the heat would be off them, JFK surprised the Mob by making his 35-year-old brother, Bobby the Attorney General, the nation’s top law enforcement position. Despite his family’s use of the Mafia to get where they wanted to be, Bobby took on the Mob with a vengeance. He quadrupled the staff and funding of the organized crime section and set them to work.

In Sam (Sam Giancana’s nephew) and Chuck Giancana’s (his brother), Double Cross: The Story of the Man Who Controlled America, it was reported Giancana had this to say about the appointment: “It’s a brilliant move on Joe’s part. He’ll have Bobby wipe us out to cover their own dirty tracks and it’ll all be done in the name of the Kennedy ‘war on organized crime.’ Brilliant. Just fuckin’ brilliant.”

Bobby centered his investigation on Giancana, Johnny Roselli, Carlos Marcello, Mickey Cohen and Jimmy Hoffa. This was made especially clear when in 1961, Marcello, the boss of all bosses for Louisiana was targeted for deportation by Bobby. The U.S. government, after several failed attempts to deport him elsewhere, literally kidnapped Marcello and deposited him in the middle of the jungles of Guatemala. Marcello eventually made his way out of the jungle and snuck back into the U.S.

Numerous times, Giancana and his associates asked Sinatra to intervene on their behalf with the Kennedy’s. Unfortunately, now that the Kennedy’s had what they wanted, Sinatra’s influence was limited. The Mob realized this. Johnny Roselli made it clear to Giancana that they couldn’t count on Sinatra anymore. Seeing as Sinatra had made it personal and couldn’t deliver, the Kennedy’s put him, and by association his Rat Pack buddies, Dean Martin, Sammy Davis, Jr., and Peter Lawford, into danger.

FBI wiretaps recorded this conversation between Giancana and Johnny Formosa:

Formosa:  Let’s show ‘em. Let’s show those asshole Hollywood fruitcakes that they can’t get away with it as if nothing’s happened. Let’s hit Sinatra. Or I could whack out a couple of those other guys. Lawford and that Martin, and I could take that nigger [Sammy Davis, Jr.] and put his other eye out.

Giancana: No…I’ve got other plans for them.¹

Giancana’s plan involved using these performers and their influence with other performers to appear at the Villa Venice, a restaurant in a Chicago suburb he was renovating into a nightclub. Sinatra, Dean Martin and Sammy Davis, Jr. were rumored to have all performed there for free. The FBI was aware of this and questioned them. While Sammy said he was performing free because Sinatra requested it, when pushed further, he reportedly said, “Baby, let me say this. I got one eye, and that one eyes seeing a lot of things that my brain tells me I shouldn’t talk about. Because my brain says that if I do, my one eye might not be seeing anything after a while.”²

The Kennedy’s quickly severed their ties with Sinatra, which was made clear to the performer when the President cancelled his well-publicized West Coast stay at Sinatra’s Palm Springs home, which Sinatra was renovating into the Western White House, and stayed instead at Bing Crosby’s home—a Republican!

1 & 2. Kelly, Kitty. His Way: The Unauthorized Biography of Frank Sinatra. Bantam Books, 1986.