Crime Library: Criminal Minds and Methods

Frank Sinatra and The Mob

"Now We Go See Frank"

The McGuire Sisters (AP)
The McGuire Sisters (AP)

One morning in June 1985, Frank Sinatra's breakfast must have been ruined by what he saw in the comics section of the morning newspaper. Doonesbury cartoonist Garry Trudeau had set his satirical sights on Sinatra after President Ronald Reagan awarded the singer the Medal of Freedom, the most prestigious civilian award in the country. At a gala ceremony on May 23 where actor Jimmy Stewart, marine explorer Jacques Cousteau and Mother Theresa were among the recipients, the president had praised Sinatra as "one of our most remarkable and distinguished Americans." In a departure from Trudeau's usual format of four drawn panels, the last panel in the strip showed a photograph of a smiling Sinatra surrounded by a gang of mobsters and mob associates, his arms draped around two of them. It was a frequently reprinted photograph from 1976 that Sinatra must have wished had never taken because it was used for the rest of his life as proof positive that he was all mobbed up.

Among the goodfellas and friends in the picture with Sinatra were capo di tutti capi Carlo Gambino, head of the crime family that bore his name; Gambino's brother-in-law Paul Castellano, who would later succeed Gambino as head of the family only to be gunned down in a palace coup orchestrated by his successor, John Gotti; and West Coast boss Jimmy "the Weasel" Fratianno who would later turns state's witness against his Mafia pals. The photo was taken backstage at the Westchester Premier Theater in Tarrytown, New York, on April 11, 1976. According to Fratianno in his authorized biography The Last Mafioso, it was Gambino's idea to go backstage and pay a visit on the singer.

The wiseguys had been seated together at the same table at the dinner theater, "lingering over coffee" after the show when someone came up to Gambino and whispered in his ear. The old don raised his hand, and everyone was suddenly silent. "'All right," he said, "Now we go see Frank."

Backstage, Sinatra "welcomed Gambino with a kiss and a hug." A photographer was present, and the men of honor gladly posed for a picture with the Chairman of the Board. Sinatra's star power dazzled even Gambino, one of the most cautious Mafia chieftains who had ever lived.

Maltese Cross
Maltese Cross

The mob had built the 3,500-seat theater with money from legitimate investors, and in its first year they had brought in $5.3 million by booking top-shelf acts like Sinatra, Dean Martin, and Steve Lawrence and Edie Gorme. But it was a typical mob bust-out scam in which the mobsters defrauded their investors and sucked every penny they could out of the business until it was teetering on the brink of bankruptcy. But unlike other bust-out scams, the mob was unwilling to let the Westchester Premier Theater wither away. It had proved to be a good money maker. All it needed was a little infusion of working capital to keep it going, and for that the mob turned to Sinatra, booking him for two dates in 1976 and another in 1977 for which he was paid his going rate. Sinatra's enormous popularity guaranteed sold-out shows, which gave the wiseguys enough money to keep their cash cow alive a little while longer.

The greed and chutzpah of a career criminal can never be underestimated. Sinatra had been good for the theater, but the way the wiseguys figured, he could be even better for them if he performed for free. It was Jimmy the Weasel who knew how to do it. Fratianno enticed Sinatra with the possibility of getting the singer inducted into the ultra-exclusive social order, the Knights of Malta. Fratianno even held out the carrot that he might be able to get Sinatra the Maltese Cross, an award for outstanding accomplishment, which had been awarded to only 700 people in the society's 1,000-year existence. Sinatra took the bait—hook, line and sinker. In a dubious private ceremony, a Hungarian named Ivan Markovics, who claimed to be a high-raking Knight, donned red silk robes and presented Sinatra with a scroll, several medals, a ceremonial passport, and a red flag with the white Maltese Cross. Afterward Fratianno confided in Sinatra that the Knights were hurting financially, and it would be a wonderful gesture if a new Knight could find some open dates on his calendar to do a few benefit concerts for them. Sinatra agreed to donate his services without hesitation. Fratianno suggested that they use the Westchester Premier Theater because things had always gone so well for Sinatra there in the past.

When Sinatra agreed to perform for the Knights, Fratianno thanked him profusely and told him that if he ever needed anything, just say the word. According to The Last Mafioso, Sinatra did have something he wanted done. A former bodyguard named Andy "Banjo" Celentano was planning to write a tell-all about his experiences working for the singer. Sinatra wanted the man sufficiently roughed up so that he would change his mind about becoming an author. Fratianno promised to take care of the situation, but he later revealed in court testimony that his legbreakers were never able to locate Mr. Celentano to deliver the message.

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