Over the course of his life, John F. Kennedy spent time with many famous faces, but perhaps his most curious friendship was his short-lived camaraderie with entertainer Frank Sinatra. The following excerpt from Handsome Johnny, Lee Server's biography of West Coast mobster Johnny Rosselli, details why Sinatra fell out of favor with the Kennedy family.
The story behind Sinatra’s dismissal from the Kennedy inner circle, the accepted narrative, had it that the FBI’s J. Edgar Hoover met with the attorney general not long before the president’s Palm Springs getaway and warned him to separate his brother from Sinatra, providing ample proof of the singer’s close relationship with Sam Giancana and assorted other gangsters. Shocked and alarmed, as the story goes, Bobby ran to Jack in the Oval Office and demanded he cease all contact with the man.
The sequence of events seems essentially right, except for the quaint idea that Bobby—or anybody else who read a newspaper or gossip column over the previous twenty years—was unaware of Sinatra’s fraternizing with the Mob. If Frank’s fondness for gangsters had survived this long without making much trouble for the administration, why would it cause such an eruption now?
There was a variant of the story, and a more plausible—and altogether more personal—basis for Bobby’s abrupt banishment of Sinatra from his brother Jack’s life. This version was revealed—under oath—by Joe Shimon, the DC police detective who maintained close connections with the FBI and with Sam Giancana and Johnny Rosselli.
Handsome Johnny: The Life and Death of Johnny Rosselli
As Shimon heard from his federal source, Hoover had come to Bobby Kennedy in March with some of the latest audio from Giancana’s bugged telephones. Hoover played the selected tape and they listened to Giancana and Sinatra in private conversation.
The gangster demanding the singer get them relief from the government. Sinatra telling Giancana he was working on it. The telling was blunt, ugly. Sinatra, the dialogue made clear, was having an affair with the president’s sister, Pat Kennedy Lawford (Peter’s wife).
He was fucking the sister, Sinatra told Giancana, to get her to use her influence on the brothers. Sinatra made it sound like quite a sacrifice. He vowed he would “sleep with this goddamn bitch until I get something going.”
“The tapes were played to Bobby,” said Shimon, “And Bobby went, ‘WHOA. . . .’ And overnight you saw Sinatra out. No more White House. No nothing. Shut him off.”
With Joe Kennedy in limbo, and Frank Sinatra eighty-sixed, the Mob now saw no hope of cashing in on election favors granted. The government’s crackdown on crime continued. Racketeers lost money, lost face, went to jail. Giancana seethed with paranoia and indignation. He couldn’t do as Accardo ordered. He wouldn’t keep his head down, his mouth shut. He said, If they wanted to fuck with him, he’d fuck them back. He’d use their own weapons.
In June ’63 Giancana went to court. He sued the FBI for harassment, invasion of privacy. The Feds refused to defend themselves, believing that the court did not have jurisdiction. Giancana won the case. The judge in Chicago granted an injunction limiting the amount and nature of FBI surveillance. They were allowed just one car to follow him, and the car could park no closer than one block from his family home.
The ruling even specified the distance agents had to keep from the mobster’s golf game. Giancana was jubilant. For as long as it lasted. The ruling came down from the U.S. Court of Appeals: The defendants were “not subject to direction by the courts as to how they shall perform the duties imposed by law upon them.” The injunction was stayed, and a year later the original ruling was vacated. The Feds went back to the business of driving Giancana mad.
Copyright © 2018 by Lee Server in Handsome Johnny: The Life and Death of Johnny Rosselli: Gentleman Gangster, Hollywood Producer, CIA Assassin and reprinted by permission of St. Martin’s Press.
