Sinatra, the Mob and $3.5m - Books - Times Online
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May 10, 2005

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Sinatra, the Mob and $3.5m
Anthony Summers and Robbyn Swan
Frank Sinatra’s links to the Mafia were so close that he smuggled their illegal cash into the United States from Cuba, Anthony Summers and Robbyn Swan reveal in their new biography

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“DID I know those guys?” Frank Sinatra said late in life, when asked about his Mafia connections. “Sure, I knew some. I spent a lot of time working in saloons. And saloons are not run by the Christian Brothers. They came backstage. They thanked you. They offered you a drink. That was it. It doesn't matter any more, does it?”
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Far from merely having had incidental encounters with “some guys” in his youth, Sinatra had intimate relationships with vicious murderers, thieves and vice tsars. His business would be entwined with their rackets for 50 years.

The Mafia role in Sinatra’s career may have begun when a New Jersey mobster named Angelo “Gyp” de Carlo married into the Sinatra family. De Carlo was close to Lucky Luciano, the man credited with creating organised crime in America, and took a proprietary interest in entertainers, singers especially. At the time Frank was given his start, Luciano himself was in prison at Dannemora in upstate New York. He maintained a keen interest in his many “investments ”, which included saloons and gambling venues in New Jersey, and word filtered through to him about the progress of a young singer named Frank Sinatra.

“When I was in Dannemora,” he recalled years later, “the fellas who come to see me told me about him. They said he was a skinny kid from around Hoboken with a terrific voice — and 100 per cent Italian. He used to sing around the joints there, and all the guys liked him.” Two of Luciano’s visitors were the New Jersey mob boss Willie Moretti and, on a regular basis, New York’s Frank Costello.

A Bureau of Narcotics document on the Mafia was to state flatly that Frank was “ ‘discovered’ by Willie Moretti after pressure from Frank Costello and Lucky Luciano”. An FBI document quoted an informant as saying Sinatra “was originally ‘brought up’ by Frank Costello of New York”. And a 1944 report on crime in New Jersey noted that Moretti “had a financial interest in Frank Sinatra”. Later, engaged in conversations by agents on a pretext, the gangster “admitted his association” with Sinatra.

The Mob did Frank its first great favour early in the Second World War, when he was singing with the Tommy Dorsey band. Frank’s tantrums and moodiness became a nuisance to Dorsey, who himself had a short fuse. A real rift opened up between the two men, one that deepened in proportion to Frank’s success.

Frank worked through the summer of 1942 on a breakneck schedule that took the band to New York, Montreal, Detroit, Philadelphia, Baltimore, Washington, and on to the Midwest. In Washington, he told Dorsey that he was leaving. The bandleader had him sign a severance agreement, then reportedly shrugged: “Let him go. Might be the best thing for me.”

Frank sang with the band for the last time on September 10, 1942. Three months short of his 27th birthday, after nearly three years with the country’s top band, he was on his own — but with horrendous strings attached. Under the terms of the release, Frank had agreed to pay a third of all future earnings over $100 a week to Dorsey for the next ten years. Another 10 per cent “off the top” was to go to Dorsey’s manager. When he failed to honour the agreement, Dorsey and his manager sued. Then suddenly, two days after the suit had been filed in California, it was settled out of court.

“I hired a couple of lawyers to get me out of it,” Frank said a decade later. Dorsey’s version emerged in a 1951 magazine article. He had surrendered, Dorsey was quoted as saying, only after “he was visited by three businesslike men, who told him out of the sides of their mouths to ‘sign or else’.” The actor Brad Dexter, a friend of Sinatra, said Frank acknowledged to him that the story was true.

From the time the mob forced Dorsey to back down, according to the Federal Bureau of Narcotics department in the 1950s, Sinatra became “one of many in the entertainment world who knowingly collaborate with the Big Mob”. According to his friend Sonny King, Luciano and Frank Costello “assigned” two specific mafiosi to handle Sinatra. Joe Fischetti of Chicago, King said, was to “be around him all the time”. Sam Giancana, the future Chicago Mafia boss, was there to step in “if major things came up”.

On January 30, 1947, Frank took out a licence in California to carry a German Walther pistol. Questioned by a reporter at the sheriff’s office — someone tipped off the press that he was there — he said he needed the weapon for “a personal matter”. Carrying a handgun was to become routine for him. After obtaining the permit, Frank flew to New York to fulfil a radio commitment, then on to Miami. Before he went south, though, the columnist Earl Wilson got word of his journey, learnt who Frank’s host in Florida was to be — and was appalled. The host was the mobster Joe Fischetti, and the Miami Beach mansion at which Frank stayed belonged to Joe’s older brothers Charles and Rocco, often described as the heirs to Al Capone. The brothers were just back from attending Capone’s funeral in Chicago.

Frank joined the brothers in Miami at a pivotal moment for organised crime. Luciano was back in circulation. By then released from prison in New York and deported to Italy, he had travelled to Cuba — just 90 miles from the US — to resume direct control of his crime empire. Rocco and Joe Fischetti flew in on Pan Am from Miami on February 11, 1947. A still frame from newsreel footage shows them walking from the plane, Rocco to the rear, Joe in front with a hand up to his face. Between them, toting a sizeable piece of hand baggage, is Frank Sinatra.

Narcotics Bureau agents knew that Luciano was involved in huge casino and resort developments — and, they thought, in narcotics — in Cuba, and for that he needed access to vast sums of money. The bureau’s information, later corroborated by the Mafia boss himself, was that visiting associates carried huge cash sums to him in Havana.

There were suspicions that Frank and the former heavyweight boxing champion Jack Dempsey had acted as money couriers during the Cuba episode. Official records suggest that the Fischettis contributed as much as $2 million ($16 million today) and that Frank may have carried the cash into Havana in his hand luggage. After that allegation appeared in the press, Luciano denied it and Frank responded with derision. “If you can find me an attaché case that holds $2 million,” he said in evidence to the Nevada State Gaming Control Board, “I will give you the $2 million.” (The author Norman Mailer tried it, and discovered that in fact an even larger sum could be packed into an attaché case.)

Jerry Lewis said that Frank carried money for the Mafia on more than one occasion. Lewis had been born in New Jersey, and had been befriended by Sinatra’s mother Dolly when he was starting out. He had met Frank early on and became his friend, and knew some of the same mobsters.

In Frank’s case, Lewis said, the relationship with the Mob “had to do with the morality that a handshake goes before God. He volunteered to be a messenger for them. And he almost got caught once, in New York.”

Frank was going through Customs, Lewis explained, carrying a briefcase containing “three and a half million in fifties”. Customs opened the briefcase, then — because of the crowd pushing and shoving behind Frank — aborted the search and let him go on. “We would never have heard of him again,” Lewis reflected, had the cash been discovered.

At some point during Frank’s stay in Havana he performed for the assembled mobsters at a business banquet. Of the various matters on the agenda, one had to do with Bugsy Siegel, the veteran bootlegger, gambling racketeer, and killer operating on the American West Coast. Siegel’s latest and most grandiose project, the mob-funded Flamingo hotel and casino in Las Vegas, was going badly. Its opening a few weeks earlier had been a fiasco, and the hotel was temporarily closed. The mafiosi had learned that some of the millions of dollars entrusted to Siegel, including a huge sum contributed by the Fischetti brothers, had been siphoned into private accounts in Switzerland.

At the Mafia gathering in Cuba, Siegel was sentenced to death. He died in a hail of bullets a few months later, his execution approved by Luciano and directed, by one account, by Charles Fischetti. In Las Vegas the syndicate had taken over the Flamingo within hours, and went on to oversee the building of Las Vegas into America’s gambling and entertainment mecca, with Frank as star of stars.

Extracted from Sinatra: The Life by Anthony Summers and Robbyn Swan, to be published by Doubleday on May 17 and available from Books First at £16 (RRP £20) plus £2.25 p&p on 0870 1608080; www.timesonline.co.uk/booksfirstbuy