Frank Sinatra and The Mob: The Real Story Behind His Mafia Connections

Frank Sinatra had the voice of an angel, but whispers of a devilish side followed him all his life. Though he laughed off rumors of Mafia ties and dodged congressional investigations, eyewitness accounts and a 2,400-page FBI file tell a different story.

Made In Sicily

Although Frank told audiences his family had come from Catania, Italy, a top genealogist who specializes in the study of Sicilian records took part in research that discovered the family actually came from Lercara Friddi, Sicily — the same small town that was home to the relatives of Lucky Luciano, the mastermind of the American Mafia.

Frank’s Parents

The singer grew up in Hoboken, N.J., where his parents, Marty and Dolly, ran a tavern during Prohibition. The Sinatras needed liquor for their bar and they needed protections, services only gangsters could supply. The Hoboken docks were a key transit point for booze shipments, and Marty Sinatra got involved.

“He aided in bootlegging,” Frank admitted years later. “His job was to follow the trucks with the booze so they weren’t hijacked … I remember in the middle of the night — I was only 3 or 4 years old — I heard sobs, terrible crying and wailing … I think my old man was a little slow and he got hit on the head. And he came home and he was bleeding all over the kitchen.”

Gunpoint Deal That Made Him A Star

Frank’s career took off after a suspiciously sudden release from a contract with bandleader Tommy Dorsey. When Frank told him he planned to quit, Dorsey was angry and said he had to stay until the end of his contract, two years away.

“You’re not gonna leave this band, not as easy as you think you are,” Dorsey told him.

But a few weeks later, Dorsey let Frank go free, no strings attached. Later, he told friends, “I was visited by Willie Moretti and a couple of his boys. Willie fingered a gun and told me he was glad to hear that I was letting Frank out of our deal. I took the hint … I got a piece of paper, a $1 check, and got out fast.” That move launched Frank’s solo career — and also deepened his debt to the underworld.

From that time on, Sinatra became “one of the many in the entertainment world who knowingly collaborates with the Big Mob,” said a government report.

The FBI’s Obsession With Frank

The FBI kept a 2,400-page file on Sinatra, tracking his movements for 40 years. They listed him as a “messenger” for the Mafia and documented ties to Sam Giancana (Chicago Outfit boss), Carlo Gambino, Willie Moretti and Joseph Fischetti (Capone associate).

Frank, who died at age 82 in 1998 after suffering a heart attack, was never charged because they never caught him in an actual crime, only “suspicious activities.” But he was watched like a hawk. They even took notes of the singer who met mob men in Cuba in 1947, when Lucky Luciano moved there to resume control of his empire after a stint in the slammer.

Several charges ran the spectrum but Frank denied it all. “Any report that I fraternize with gangsters and racketeers is a vicious lie,” he said, adding that he just happened to run “into” certain people.

In fact, he knew the FBI was eyeing him and he even sent an associate to J. Edgar Hoover’s office to offer his services as an informant. That way, he figured, he could protect himself from the rumors he was involved with the mob.

The Day JFK Cut Ties

Frank allegedly introduced Sam Giancana to John F. Kennedy’s campaign in 1960 to deliver votes for the future president. His plan backfired, but JFK was still elected. At one point, Frank was so proud and thrilled that the president was going to stay with him during a visit to California that he built a helipad at his Palm Springs estate where he could land.

But when JFK’s brother Robert again warned him of Sinatra’s mob ties, the brothers’ feelings for Frank changed — and the president decided he would stay at Bing Crosby’s mansion instead.

Ol’ Blue Eyes was so angry and humiliated he destroyed the helipad with a sledgehammer — and cut ties with the Kennedys for good.

Hollywood Strong-Armed

In 1953, Frank’s career was floundering and the end of his marriage to Ava Gardner had left him haggard and depressed. Then, suddenly, he landed the role of Maggio in From Here to Eternity. Sinatra even won an Oscar.

At first, producer Harry Cohn turned Frank down, yelling he would not have “that bum” in his studio. But high-ranking capo Jimmy “Blue Eyes” Alo made a call to Cohn, after saying, “Cohn. He owes us.”

Hours later, Cohn hired Sinatra. His widow, Joan, later described how “two gentlemen from the mob turned up at Columbia Pictures and told Harry he was going to cast Sinatra.”

Vegas Rat Pack

Frank’s Las Vegas reign at the Sands Hotel wasn’t just entertainment, it was business. The Sands was run by Chicago mobsters, and Frank performed and partied with them regularly. He even introduced wise guy Sam Giancana to Marilyn Monroe. Mob insiders said Sinatra was a trusted “bridge” between the underworld and the upper class.

A retired FBI agent says “a few times a year, they’d trail Vegas mobsters to the airport, where they’d pick up Sinatra. They’d spend the weekend socializing … and he didn’t make any apologies about it. Those were his friends. The fact that they were known hoodlums and murderers didn’t matter to him. He didn’t care. He was going to hang around with who he wanted to hang around with.”