Crime Library: Criminal Minds and Methods

Frank Sinatra and The Mob

"Just Hello and Goodbye"

Charles "Lucky" Luciano mugshot
Charles "Lucky"
Luciano mugshot

"I almost fell off my chair," Joseph L. Nellis, a lawyer for the Kefauver crime committee, said about a package of surveillance photographs the senator gave him one day. "I opened the envelope and saw a picture of Sinatra with his arm around Lucky Luciano on the balcony of the Hotel Nacional in Havana." As told by Kitty Kelly in her book My Way, Nellis went on to describe other photos of Sinatra and Luciano at a nightclub surrounded with beautiful women, Sinatra getting off a plane at the airport in Havana carrying a suitcase, Sinatra with Chicago mobsters the Fischetti brothers—Charles, Rocco and Joe. The pictures had been taken in February 1947, and when Nellis saw them in 1950, they couldn't have been more shocking. Here was America's heartthrob, the crooner adored by legions of screaming bobbysoxers, keeping company with Lucky Luciano, the head of the world's largest drug cartel.

FBI intelligence had revealed that Sinatra had been vacationing with his wife Nancy in Miami in early February when he took a four-day side trip to Havana with the Fischetti brothers, leaving Nancy behind. The men arrived in Cuba on February 11, and by most accounts Sinatra had no idea exactly what he was getting into. He was good friends with Joe Fischetti who booked talent for mob-owned clubs around the country. Joe was the most affable of the three brothers, and he generally acted as front man for Charlie and Rocco, who carried more of the street in their demeanors. It was Joe who had convinced Sinatra to go to Havana with them to meet some of the "guys."

Sinatra probably didn't realize how many "guys" he was going to meet. The Mafia was holding a conference in Havana attended by some of the most notorious mob leaders in the world. The big shots were all there: Luciano, Frank Costello, Willie Moretti, Meyer Lansky, Albert "the Executioner" Anastasia, Joe Bonanno, Tommy "Three Fingers Brown" Lucchese, Joe Adonis, Chicago boss Tony Accardo, Carlos Marcello of New Orleans, and Florida boss Santo Trafficante, among many others. Sinatra's presence in Havana during that conference put him on the fed's radar screen, and he would never get off it.

Years later when questioned about the trip to Havana, Sinatra said that he had no idea that he was being taken to a major mob convention. But once he was there, he figured he couldn't just walk out. Even though he had realized that it would become a public relations disaster for him if it ever got to the press, he had decided to go with the flow and make the best of it.

The mobsters, for their part, liked his style and they liked his singing. They also liked the fact that he was an Italian-American kid from a tough, working-class town. They identified with him. Many of these gangsters also took credit for fostering his career, either financially or by hiring him in their clubs. Everyone, it seemed, wanted to claim a little stake in the skinny kid's success.

Lucky Luciano was a big fan of Sinatra's singing and said that was why he had been invited to Havana. Luciano claimed that Sinatra was not involved in anything illegal during that trip. The mobsters just wanted him there to add a little stardust to the gathering. Yes, Sinatra did give him an inscribed gold cigarette case, but many gifts were exchanged there. It was the norm for a Mafia conference like that. No big deal, according to Luciano.

Rockefeller Center (AP)
Rockefeller Center (AP)

But the Kefauver committee wanted to know what had been in the suitcase that Sinatra carried off the plane? Joseph Nellis asked to interview the singer to see if his testimony would be worth a subpoena to appear before the committee. Sinatra's lawyer, Sol Gelb, tried to dissuade Nellis, arguing that his client was innocent and that if he were forced to testify publicly in the company of men like Frank Costello, Meyer Lansky and Albert Anastasia, his career would be ruined. But Nellis would not be put off. After much back and forth, the lawyers agreed that Sinatra would sit for an interview with Nellis at a time when the press could be avoided. They agreed to meet at 4 a.m. in a law office on one of the upper floors of Rockefeller Center in Manhattan on March 1, 1951.

According to Nellis, Sinatra was nervous when he arrived and chain-smoked throughout the hour-long meeting. Nellis informed the singer that the U.S. Bureau of Narcotics believed he had delivered more than $100,000 in cash to Lucky Luciano at the Havana get-together. Sinatra denied it. Nellis asked about the suitcase he carried off the plane, and Sinatra said that it contained art supplies, his "razor and crayons." One of Sinatra's hobbies was sketching.

Nellis read off a long list of gangsters, including Joe Adonis, Bugsy Siegel, Longy Zwillman, Frank Costello and Meyer Lansky, and asked Sinatra how he had come to know the men. Sinatra said he had just happened to meet them at his singing engagements. Nellis asked if he'd ever had any business dealings with any of these men.

"No business," Sinatra said. "Just hello and goodbye."

Nellis asked Sinatra about his relationship with Willie Moretti.

Willie Moretti
Willie Moretti

Referring to Moretti at first by his alias, "Moore," Sinatra admitted that Moretti had secured a few club dates for him in his early years, but made it clear that he had never been involved with Moretti's illegal operations.

By the end of the meeting, Nellis decided that calling Sinatra before the committee in Washington would be less than enlightening. An entertainer with mere "hello and goodbye" relationships with gangsters was hardly worth the time and effort when compared with the real specimens being hauled before the committee. Sinatra escaped the hot glare of government scrutiny this time, but rumors and allegations in the press were becoming persistent. And over the years Sinatra did little to dispel them.

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