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Frank Sinatra’s alleged affiliation with the mob is the stuff of music legend. It was also enough to make the FBI keep a close eye on him. Despite this, Sinatra offered his assistance to the agency. Here’s how Sinatra suggested he could help the FBI and what they said in response.

Frank Sinatra wears a tan suit and bowtie.
Frank Sinatra | Silver Screen Collection/Getty Images

Frank Sinatra allegedly had mob ties

For years, rumors swirled that Sinatra was closely associated with several different mobsters. In 1947, Sinatra warmly greeted Lucky Luciano at a hotel in Havana, and many believed he had met with members of Al Capone’s gang. According to his former manager Tony Oppedisano, there was little truth to the rumors.

“Wiseguys wanted to be in Frank’s inner circle and he did his best to juggle that and not let it get too heavy, but you know some people would go overboard,” he told Page Six. “Some of the guys became friends over the years and they would try to do things for him that he never asked them to do. He’d say, ‘If these guys really want to do me a favor, I wish they’d stop doing me favors!’”

According to Oppedisano, Sinatra grew frustrated with the affiliation and believed it was primarily because of his Italian heritage.

“He said, ‘It’s only because my name ends in a vowel.’” 

He offered to work for the FBI

Starting in the 1940s, the FBI began compiling a file on Sinatra. This was partly because of the believed mob affiliation but also because of Sinatra’s general belief system. Sinatra held anti-racist, liberal views. In Red Scare-era America, the FBI took Sinatra’s left-leaning politics as a sign of communism. The agency compiled information on Sinatra from the 1940s to the 1980s, resulting in a file that stretched over 2,000 pages per the BBC.

Despite the surveillance, which included attempts to bug Sinatra’s home, the singer offered to become an informant for the FBI in the 1950s. Some speculate that Sinatra was hoping to neutralize rumors of his mob association. Unsurprisingly, though, the FBI turned him down. “We want nothing to do with him,” an aide to Herbert Hoover wrote in a report, per

Ultimately, though, little came of the surveillance and extensive report. According to the Washington Post, the file simply shows a man who had a “lifelong flirtation” with the mafia and a short fuse temper. Both of these traits were public knowledge before the investigation.

The FBI helped rescue Frank Sinatra’s son from kidnappers

Though Sinatra’s relationship with the FBI was often antagonistic, they once helped Sinatra get his son back from kidnappers. Frank Sinatra Jr., also a musician, was kidnapped for ransom in December 1963. Once the kidnappers received their money, they let Sinatra Jr. go. Shortly after this, the FBI arrested both kidnappers and recovered most of the ransom money.

Frank Sinatra stands with his arm around the shoulders of Frank Sinatra Jr. They both wear suits.
Frank Sinatra and Frank Sinatra Jr. | Keystone/Getty Images

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“I would like to express my deep appreciation and thanks for the excellent work of the FBI in securing the safe return of my son, in solving the crime, and for the tremendous amount of work I know they did in assisting the Department of Justice in prosecuting the crime,” Sinatra wrote in a letter to Hoover. 

At the very least, one part of Sinatra’s long history with the FBI was positive.