You will be redirected back to your article in seconds

Taking aim at the mob connection

Newspaper stories and rumors about Frank Sinatra’s connections to the mob dog his life like a dark shadow.

“Sure, I knew some of those guys,” he once told writer Pete Hamill. “I spent a lot of time in saloons. And saloons are not run by the Christian Brothers. There were a lot of guys around, and they came out of Prohibition, and they ran pretty good saloons.

“I was a kid. I worked in the places that were open. They paid you, and the checks didn’t bounce. I didn’t meet any Nobel Prize winners in saloons. But if Francis of Assisi was a singer and worked in saloons, he would’ve met the same guys.”

A 1947 trip to Havana made headlines when he was photographed with deported Mafioso Lucky Luciano. “I was brought up to shake a man’s hand when I am introduced to him, without first investigating his past,” Sinatra explained.

Later, he was photographed backstage at the Westchester Premier Theater with mob boss Carlo Gambino.

Sinatra’s handshaking grabbed the attention of the U.S. Dept. of Justice. Their surveillance had Sinatra in contact with 10 of the country’s heavy hoods, according to a 19-page memo dated 1962. Despite FBI probes, a 1980 federal grand jury investigation, and a subpoenaed appearance before a Senate crime committee that eventually ended up apologizing to him, Sinatra was never indicted or convicted of any crime.

But the script of CBS’ “Sinatra” biopic that he personally approved makes no bones about his associations. When his Havana trip with Joe Fischetti and meeting with Luciano hits the papers, he defends himself, “I grew up in Little Italy, Hoboken, New Jersey, with Joe Fischetti and half these other monkeys.”

Giancana was the mob boss in Chicago, Al Capone’s former driver.

According to the script, during the 1960 election campaign Joseph Kennedy tells Sinatra, “We need a boost from our friends in Chicago who control the unions.

“They could win this race for us. But Jack Kennedy can’t be involved.

“It all must be arranged as a favor to Sinatra.”

Golf buddies

Sinatra plays golf with Giancana. The Chicago mob boss agrees to help Kennedy in the West Virginia primary, adding, “And tell his old man I said hello.”

But after the election, attorney general Robert Kennedy began cracking down on organized crime. Again, according to the script, the Chicago gang feels betrayed, since their support in West Virginia and Illinois had been the 120,000 -vote margin that put Kennedy in the White House.

One, Johnny Formosa, wants to whack Sinatra as a signal to Kennedy, but Giancana says, “You let me take care of Sinatra.”

At Robert Kennedy’s insistence, the President, on a vacation in Palm Springs, snubbed Sinatra, who had prepared his palatial home especially for the visit. Instead, President Kennedy was the guest of Bing Crosby, a lifelong Republican. Sinatra was devastated and enraged.

In 1962, Sinatra, Dean Martin and Sammy Davis Jr. played a special unpaid engagement at the Villa Venice, a club Giancana owned northwest of Chicago, an appearance the FBI later investigated. A scene cut from the TV show clearly indicates “two shows a night, for as long as Giancana wants, at zero dollars a show,” to bail out Sinatra.

By then Sinatra owned the Cal-Neva Lodge in Lake Tahoe. In 1963, the Nevada Gaming Control Board charged that Giancana had been a weeklong guest. The known criminal’s presence was cause enough to revoke the casino’s gambling license. Rather than fight the revocation order, Sinatra sold his interest in the club.

A decade later in Chicago Giancana was murdered in his home.

“It doesn’t matter anymore, does it?” Sinatra once told a reporter who asked about his mob connections. “Most of the guys I knew, or met, are dead.”

More Music

More From Our Brands

Access exclusive content