Frank Sinatra’s Friend Claimed He Barely Escaped Arrest for Smuggling Mafia Money

Though he always denied it, Frank Sinatra spent his life dogged by rumors that he was connected to the mafia. The stories were so persistent that the FBI tracked the celebrity for much of his life. Even his friends contributed to the rumors. Actor Jerry Lewis told a story about Sinatra smuggling cash through airport customs for the mafia. He claimed that the singer narrowly escaped arrest.

Frank Sinatra was on an FBI watchlist, partly for alleged mafia connections

People began whispering about Sinatra’s supposed connections to the mafia early in his career. He supposedly had ties to prominent figures in organized crime like Lucky Luciano and Sam Giancana. Some wondered if he used these connections to revitalize his career after it slowed down in the early 1950s. Because of this, the character of Johnny Fontane in The Godfather was reportedly inspired by the singer.

At least partly as a result, the FBI began compiling a file on Sinatra. They collected information about the singer from the 1940s to the 1980s, resulting in a file that reached over 2,000 pages per the BBC.

His friend alleged that he smuggled money through customs

Lewis, a longtime friend of Sinatra’s, added fuel to these rumors. Lewis, who befriended Sinatra in the late 1930s, claimed that the singer even smuggled money for the mafia on more than one occasion. 

“He volunteered to be a messenger for them,” Lewis said, per the book Sinatra: The Life by Anthony Summers and Robbyn Swan. “And he almost got caught once … in New York.”

According to Lewis, Sinatra carried “three and a half million in fifties” through the airport. Though Lewis may have been exaggerating the amount of money — that would be one heavy briefcase — he claimed that customs even opened the case. Sinatra reportedly only got away because of the swarming, impatient crowd behind him. Lewis alleged that customs couldn’t conduct a thorough enough search.

If they had, “we never would have heard of him again,” Lewis said.

Frank Sinatra denied having connections to the mafia

Though even his friends told stories about the singer’s mafia connections, Sinatra denied any involvement with organized crime. He was furious about his supposed depiction in The Godfather and tried to dodge these rumors throughout his life. His former manager Tony Oppedisano once said the rumors held little truth.

“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!’”

Sinatra believed that the rumors were primarily caused by his Italian heritage.

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

Sinatra even offered to work for the FBI as a way to neutralize the mafia stories. Unfortunately for him, the organization refused.