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Frank Sinatra

(1915–1998)
Mafia’s favorite singer

Frank Sinatra

Sinatra and the mob—it’s an old and long, long story and perhaps less significant than one might think. Some feel there is much to be made of it. Sinatra himself felt too much was made of it. He was in showbiz, he said, and there is no way to avoid gangsters all of the time.

Charles “Lucky” Luciano

Still, it’s closer to the truth to say that Sinatra went out of his way to be with them than to avoid them. He flew to Havana in 1946 to attend a big underworld bash for Lucky Luciano (who had only months before been deported back to Italy after being paroled from his organized prostitution conviction). Later, when Luciano was away from his home in Naples, Italian police found a gold cigarette case with the inscription: “To my dear pal Lucky, from his friend, Frank Sinatra.”

Joe Adonis

During the Kefauver investigation, Sinatra was questioned in advance by committee counsel Joseph L. Nellis to determine if he should be called to testify. At a 4 A.M. meeting held in an office atop Rockefeller Center, Sinatra was asked about mobsters he knew, and he acknowledged “knowing” or “seeing” or saying “hello” and “goodbye” to an impressive—but possibly incomplete—list of them: Lucky Luciano; the brothers Fischetti, Joe, Rocco and Charles, cousins of Al Capone and powers in the Chicago Outfit; Meyer Lansky; Frank Costello; Joe Adonis; Longy Zwillman; Willie Moretti; Jerry Catena and Bugsy Siegel. Ultimately the Kefauver Committee did not call Sinatra. With Sinatra’s career then in decline, the committee felt no real purpose would be served by lambasting him in public and perhaps finishing off his career. Implicit in that decision was the fact that Sinatra, even if the senators didn’t know it at the time, was little more than a Mafia groupie. Joe E. Lewis and Jimmy Durante would qualify just as readily.

Meyer Lansky

Abner “Longie” Zwillman

After the hearings Sinatra’s career revitalized, and he continued to be linked with mafiosi, but it would be hard to tell whether Sinatra was more entranced with mobsters or they with him. Each at various times may have gained something from the other. Ralph Salerno, a specialist on organized crime formerly with the New York Police Department, quoted by Nicholas Gage in The Mafia Is Not an Equal Opportunity Employer, was upset that people, knowing Sinatra was an acquaintance of presidents and kings, would figure his other pals were okay. “That’s the service Sinatra renders his gangster friends,” says Salerno. “You’d think a guy like Sinatra would care about that. But he doesn’t. He doesn’t give a damn.”

Frank Costello

Benjamin “Bugsy” Siegel

Actually the mob was able to use Sinatra and his P.R. clout many times. When Doc Stacher, Meyer Lansky’s close associate, was building the Sands in Las Vegas, he told interviewers years later, “we . . . sold Frank Sinatra a nine percent stake in the hotel. Frank was flattered to be invited, but the object was to get him to perform there, because there’s no bigger draw in Las Vegas. When Frankie was performing, the hotel really filled up.”

Willie Moretti

Sinatra’s first gangster friend appears to have been Willie Moretti, the New Jersey extortionist, narcotics trafficker and murderer. Moretti, also known as Willie Moore, took a liking to the young fellow New Jerseyan and helped him get some band dates when he was struggling in local clubs and roadhouses for peanuts.

Then Sinatra recorded his first hit song with Harry James in 1939, “All or Nothing at All,” and eventually went to work for Tommy Dorsey for what seemed an astronomical salary of $125 a week. A myth built up after Sinatra and Dorsey had parted that they remained warm friends. “Hot enemies” would have been a better description. Sinatra’s popularity had soared. Bobbysoxers followed him everywhere. He desperately wanted to dump Dorsey, and the underworld story has long circulated that Willie Moretti came to the rescue. Moretti was said to have obtained Sinatra’s release from the band leader in convincing Mafia style, jamming a gun in Dorsey’s mouth. The hard bargaining that followed called for Dorsey to get $1 in compensation for selling him Sinatra’s contract.

Not that Moretti didn’t also chastise the singer at times. When Sinatra’s marriage to his first wife, Nancy, was busting up and he was planning to marry Ava Gardner, the mobster wired Sinatra: “I AM VERY MUCH SURPRISED WHAT I HAVE BEEN READING IN THE NEWSPAPERS BETWEEN YOU AND YOUR DARLING WIFE. REMEMBER YOU HAVE A DECENT WIFE AND CHILDREN. YOU SHOULD BE VERY HAPPY. REGARDS TO ALL. WILLIE MOORE.”

As it turned out, Sinatra had little more time in which to offend Moretti. The mafioso was executed by the mob. His advanced syphilis affected his brain, and it was feared he was revealing too much about Mafia operations.

Sam Giancana

John “Handsome Johnny” Roselli

In later years Sinatra was frequently linked with a number of other top mafiosi, especially Sam Giancana and Johnny Roselli, the Chicago mob honchos. Sinatra was embarrassed with a news photograph showing him with an arm around Luciano at the time of the infamous Havana gathering. In more recent years another widely published photograph, taken in Sinatra’s dressing room at the Westchester, New York, Premier Theater, shows the star grinning widely in the company of such mafiosi as the late Carlo Gambino, hit man-cum-informer Jimmy “the Weasel” Fratianno, and others later convicted and sentenced for fraud and skimming the theater’s box office.

Frank Sinatra with Tommy Marson, Carlo Gambino and Jimmy Fratianno

In 1985, cartoonist Garry Trudeau depicted a tribute to Sinatra by President Ronald Reagan and followed it in the next panel with the Westchester theater photo. Outraged, Sinatra issued a statement through his personal public relations firm: “Garry Trudeau makes his living by his attempts at humor without regard to fairness or decency. I don’t know if he has made any effort on behalf of others or done anything to help the less fortunate in this country or elsewhere. I am happy to have the President and the people of the United States judge us by our respective track records.”

Over the years Sinatra was as thick with presidents and presidential candidates as with mafiosi. He had close ties with John Kennedy (until barred from the White House by Robert Kennedy after he checked Sinatra’s background), Hubert Humphrey (who scheduled him for a series of fund-raising concerts but quietly dropped him from the campaign in 1968 after a Wall Street Journal piece listed some of his underworld relationships), Richard Nixon, Spiro Agnew, Gerald Ford and, of course, President Reagan.

Jimmy the Weasel, after he turned informer, was apparently quite upset when the Federal Strike Force didn’t go ahead with a case that had what he clearly regarded as Sinatra star quality. According to Fratianno, Sinatra “gofer” Jilly Rizzo approached him and complained about a former Sinatra security guard the singer had fired; he was supposedly supplying the weekly tabloids with material about Sinatra. The word was that the man, Andy “Banjo” Celentano, was about to write a book about Sinatra. The Weasel quoted Rizzo as saying: “We want this guy stopped once and for all,” meaning that Celantano should have his legs broken and be put in the hospital. “Let’s see if he gets the message.” Fratianno accepted the assignment to watch Celentano, but neither he nor other California mafiosi could locate their target. Celentano solved their problem altogether by suffering a fatal heart attack on October 8, 1977.

Clearly, the Weasel saw a delightful show trial in his revelations and was disappointed when the Federal Strike Force showed little interest in the matter. There was no evidence tying in Sinatra, and certainly federal lawyers weren’t wild about pursuing Jilly Rizzo. Not when, as one told Fratianno, “you’ve got a chance to put bosses in prison. Those are one-in-a-lifetime chances. With an informant-type witness, overexposure is a terminal disease.” Politely, the government was telling Fratianno that there was no legal case and they were not going to let him grab headlines for scandal purposes.

Unlike with cartoonist Trudeau, Sinatra expressed no outrage when deadly hit man Fratianno recounted the details of the alleged incident in his book The Last Mafioso.