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Sinatra's Mob Ties. Legends, Lore, Fact and Fiction.


Frank Sinatra, has always been enigmatic character. Authors for 50 plus years, have written tell-alls which have often been fraught with tall tales and straight up lies. When you think of Sinatra, the word mafia is sure to come right afterwards. What gets distilled in the process of storytelling is the background and basis of those allegations.


What is accurate is this. Did Frank Sinatra have mob ties? Of course he did. Most of Hollywood back in the tinsel town days did. There wasn't a studio not controlled by the mafia. There wasn't a record company which didn't have a bargain with the mafia. Movies were often funded secretly by the mafia. Decca, which began as a British record company had deep mob ties and pockets. What you have to understand, because it often gets lost in translation is that the mafia didn't control the companies. Not directly. What the mafia controlled was the radio station playlists. They controlled what songs got played at the stations. Of 6,000 stations 4,000 of them were controlled by the mafia. If Frankie Lymon wanted his songs played, the mafia could control whether it did or not. Bribes, payoffs, or payola, was the structure the mob used.



In the early days of Sinatra's career, he had nothing. While he had a great voice, he was just another Italian crooner. Being talented wasn't enough. It was through two men whose help got Sinatra on the map. The first was Salvatore "Lucky" Luciano. It was through Luciano that Sinatra was able to get a decent photographer to take headshots of him. Luciano would pony up $50,000 to Sinatra as a gift to get those photographs done. Sinatra when he was born, had to be pulled from his mothers womb by forceps, which ripped the left side of his face from his ear to his jaw line. It's a scar you will see if you look close enough at photo's of Sinatra. While he would use makeup to attempt to hide those scars throughout his career, those were scars that left him insecure. Sinatra needed photographs to send as publicity and needed a professional who could shoot him from a side angle to avoid showing those scars. It was through Luciano that Sinatra was able to afford the photographer. Luciano, in turn then would send Frank to see Skinny D'Amato. Paul "Skinny" D'Amato was a mob gambling guru in New Jersey. D'Amato was close to Enoch "Nucky" Johnson. It's through Johnson that D;Amato would meet Marco Reginelli, who at the time was the underboss of the Philadelphia mafia. Reginelli was the guy who owned the 500 Club. D'Amato would start small, opening Luigi's on the Jersey shore, which was a restaurant/gambling hall. It would be through his associations of Johnson and Reginelli that he met Carlos Marcello and Sam Giancana.



What D'Amato was able to do was purchase the 500 Club in Atlantic City, and took what he learned from gambling and apply it to his club. The 500 Club became a front for illegal gambling and more. The 500 Club would become the go to place for gambling and entertainment. It was through Luciano, that Sinatra's name was floated to D'Amato. D'Amato didn't have to do Luciano any favors, but he did. He would book Frank Sinatra to sing at the 500 Club, and it skyrocketed Sinatra's career.


The 500 Club is also the place where Jerry Lewis notoriously lied to Skinny D'Amato, saying his comedy act was golden, and he told D'Amato that he and Dean Martin had a comedy act that was hilarious. Lewis lied, and quickly found Dean Martin in the hall and explained the situation. Lewis was terrified that if he was caught lying D'Amato would break his legs. Quickly Jerry scribbled some lines on a paper bag and explained the idea to Dean. Dean went along with the plan, only to save Jerry Lewis from getting killed, and the act worked. They would go on to become Martin and Lewis.


What D'Amato did for Sinatra, was give him his first big break. Frank went from being an obscure saloon singer into the world famous crooner almost overnight. Frank would then use Skinny to get other acts attention, like the Will Mastin Trio, and then Sammy Davis Jr. Even while Skinny helped Sinatra, Sinatra would never ever forget that help from both Luciano and D'Amato. It's the gift that would keep on giving to all the men associated. Booking Sinatra that first night, then followed by Martin and Lewis, it put the 500 Club on the map for entertainment on the east coast. Following those acts, Sinatra would help Jimmy Durante, Eartha Kitt, Nat King Cole, Milton Berle, and Liberace gigs there. It was the launchpad for so many stars.


That is a lot of the reason why Sinatra was beholden to mob guys. They gave him a job when nobody else would. They put food in his mouth, money in his pocket. They never asked anything of him in return. They liked Frank and they saw a skinny Italian kid from Hoboken, New Jersey trying to make it. They made Frank Sinatra a star in many ways, which is why when Sinatra would be badgered by the press, he would always defend his friend and deny their existence. Many over the years have written disparagingly about Sinatra wanting to be a mobster, and how he had asked them to kill several people who got in his way. While I cannot tell you for certain if he did, there are some instances where Sinatra blurred the lines between both worlds.



When Sinatra got started, he would eventually sign with Tommy Dorsey. This was before the 500 Club. Dorsey, who by all accounts, was a fantastic bandleader and conductor and arranger, didn't like been shown up by anyone. He would hire Sinatra to sing for Dorsey, and the more that Sinatra began to shine, the more Dorsey began to resent the "skinny wop." Dorsey was also smart enough to see the talent in Sinatra, and signed him to a long term contract which Sinatra at the time had no alternative but to sign. Sinatra needed money, he had a wife and a young child on the way. The contract, basically said, Sinatra would owe all royalties off his music and future music for the rest of his career. It meant if Sinatra left Dorsey, Dorsey owned his ass. As Sinatra's star began to rise, he began to get frustrated over the situation with Dorsey. Sinatra knew the contract wasn't exactly legally binding. He needed a way to get out, and he would find that in the form of the mafia. Sinatra went and visited some friends and they suggested Sinatra offer him money to get out of the contract. Sinatra who didn't have a ton of money didn't think that Dorsey would budge. He was told by Willie Moretti, who was a powerful member of the Genovese crime family, that if Dorsey was unwilling to accept the money, then he would handle it personally. Frank would go see Dorsey who refused a $75,000 dollar buyout. Sinatra would defer back to Moretti, who went to visit Dorsey. Moretti and three men would enter Dorsey's office, and stick the barrel of a gun into his mouth cracking out a few of his teeth in the process. He had a choice. "Either sign this contract with a pen, or your brains." Dorsey signed, and Sinatra was free.


Over the years, Sinatra would attend gala's and concerts and waive his fees especially if it was mafia connected. He never took a paycheck from the 500 Club, because of what Skinny had done for him. Luciano, was rewarded with an engraved cigarette case, inscribed "To My Dear Pal Charlie, from your friend Frank Sinatra." Sinatra was insanely grateful for everything Luciano and others had done for him. Even if at the time Sinatra had a steady and fruitful relationship with the mafia, there were also problems.



Even if Frank's friends were just friends, the FBI was watching and watching close. They had photos of him with Luciano, and other mobsters, and the FBI would begin their witch-hunts. In 1947, Sinatra would purchase a sprawling compound in Palms Springs, which would become a home of homes for the mob's elite when they were coming out to Vegas. The FBI was all over it. The mafia, was at the time a little bothered by Sinatra's gallivanting with Ava Gardner. Sinatra had left his wife for Gardner and the press was all over it. They knew with the press on his tail, the FBI wouldn't be far behind, and Luciano would send men to discuss the issue with Sinatra. They felt it looked bad for Sinatra to be cheating on his wife. It made the papers, it gave bad press and with bad press came too many eyes. By 1951, Senate Committee hearings(Kefauver) would begin on the mafia. At these hearings photo's were shown of Sinatra with Luciano in Havana, Cuba. Prior to the hearings, a lawyer representing the committee, Joe Nellis, wanted to speak with Sinatra. Sinatra had avoided him, but after being told he could talk voluntarily to the lawyer or be subpoenaed, Sinatra finally agreed to meet. The meeting would be held at 4 am, at an upper office of the Rockefeller Center. For two hours Nellis interrogated Sinatra with photos, wiretaps and allegations. Sinatra denied everything. He explained photos were photos, and that it didn't substantiate any criminal acts. He further poked Sinatra about his mother being an abortionist, which she was, to try and attempt to goad Sinatra into a fit of rage. Sinatra smirked, and just kept denying any associations hurled in Sinatra's direction by Nellis. Sinatra walked out of the meeting seething.


Sinatra had used the mob and they had used him. It was a beneficial relationship. It was Sinatra who flew to Cuba, on the guise of performing for a private party. The meaning of the trip was to hand over $3,000,000 in a duffle bag to Luciano, which was a cut from the rackets his still controlled in New York City. Sinatra just wasn't a courier for the mob, but he also had a bond with Luciano. That meeting, would become to be known as the Havana Conference. Over the years it was alleged that Sinatra in fact was the courier for drug profits for many of the five families of the New York mafia. It's an allegation never fully substantiated, so those rumors merit little truth.


When Sinatra's marriage hit the rocks with Gardner, and his voice began to suffer the wrath of overwork, Sinatra was done. His record label was fucking him, his voice was torn, his record sales had dropped and nobody wanted anything to do with Sinatra. It was a very dark time for him. All the adulation of young girls were replaced by a kid from Tupelo, Mississippi who had some swiveling hips. Sinatra was considered old news. For a year, he toiled in his own despair, desperate for something to change. That change came in the form of a screenplay he had read. From Here To Eternity was a script Sinatra adored. He saw something in Maggio that resonated with him. He saw himself in the character, and he knew that the film, was going to be big, and he wanted the role of Maggio.



The film was in control of Colombia Pictures, and studio head, Harry Cohn, wanted nothing to do with Sinatra. Cohn himself was a rapist, a thug, and a monster in Hollywood. He ran Colombia pictures like a serial killer. Cohn, who had a way with women, you know drugging them and essentially raping them, always did things his way. He liked to bed his stars, and if anyone else went near one of his stars and corrupted them sexually, his ire was something to behold. Sinatra, in the past had bedded a lot of stars. Cohn especially hated Sinatra, because Sinatra had bedded a few of his stars before he could get his way with them. When Sinatra sent word to Cohn that he'd like a role in the film, Cohn refused to even respond. He offered that Sinatra was talentless, old news, and that Sinatra's friends didn't scare him one bit. He knew of the rumors, and if you have ever seen The Godfather II film, you will know the scene where Woltz, screams "I ain't no band leader, I heard that story." It's picked from this event. Sinatra knew the role could change his career, it could give him life again. Cohn just refused, and Sinatra did what Sinatra always did when his back was up against the wall. He called in a favor.



That favor came in the form of Johnny Roselli. Roselli was the mobs representative in Hollywood. Roselli went to see Cohn at his office, and it wasn't the first time, as Roselli had at one other time threatened Cohn to leave the Three Stooges alone, or else. The Stooges had been systematically abused by Cohn over the years, and were often never financially compensated for their worth. After a dramatic event on the set of one of the Stooges shorts where he slapped and threatened Jerome "Curly" Howard, Moe Howard, would make a phone call to Meyer Lansky. Cohn was told if he ever abused any of them again, he would be killed. Johnny Roselli, would enter Cohn's officer with a gun in hand, and explained, Sinatra get's the role, or you will be killed. Bottom line. Sinatra gets the role, wins the best supporting actor award the next year, and his career blossoms again.



Nothing in life however is free. The mob needed a favor from Sinatra. The Kennedy's needed a favor from Sinatra. As Kennedy began to make headway into politics, specifically with the presidency in mind, Joe Kennedy knew he needed the help of friends. Joe Kennedy was a narcotics trafficker, bootlegger, and stock inside trader. The Kennedy's fortune came from criminality. Joe Kennedy's affiliations with the mafia went way back, and Joe Kennedy knew they needed help from Hollywood, as well as friends who could arrange help in southern states who would never ever back a Catholic. Through the grapevine, the mafia had been notified, that Joe Kennedy needed a favor. While they couldn't go see Kennedy, they needed someone who could without arousing suspicions. That man? Frank Sinatra. Sinatra would travel to see Joe Kennedy, where they discussed John F. Kennedy's and Joe Kennedy's expectations. Joe Kennedy wanted Hollywood to back Kennedy, and he knew Sinatra could get that done. Joe Kennedy also wanted Sinatra to speak with Sam Giancana about swing states and southern states and what could be done to help facilitate a win for his son. Sinatra left that day promising he would get Kennedy support in Los Angeles and anywhere else he could. We know the outcome. Kennedy wins, and becomes president. Sinatra who was a lifelong democrat, would switch to being a republican after Kennedy was killed. He never again donated another dime to the Republican Party. He knew he was used by the Kennedy's, and it left a bad taste in his mouth the rest of his life.



Many of Sinatra's affiliations were just that. He owed the men who gave him his career, and who resurrected it a million times over. They rarely asked for anything in return. That's where the lore really begins. Authors have taken stories and legends and inflated them into some off the biggest lies ever produced. Sinatra was a simple guy, with one simple philosophy. You never turn your back on those to helped you get to where you got. He knew who they were, he had one foot in and one foot out, but it never crossed the line in ways that journalists claim. He was never a made guy, was never ever proposed. Those are figments in informants imaginations. There were many times, that his associations came back to haunt him, and he never spilled his guts, even when it would have been better of if he had. One of his dreams got flushed down the toilet because of Sam Giancana. Sinatra wanted to own casino's. When Sinatra bought the Cal-Neva lodge, he intentionally had underground tunnels built so mob guys could come and not be seen publicly there. Giancana didn't care about Sinatra or the public's perception. Giancana refused to hide. The FBI would photo Giancana there, as well and John F. Kennedy, and that forced the Nevada Gaming Commission to revoke Sinatra's gambling license. Sinatra denied knowing Giancana, denied he had been there. Sinatra would lose his license and his dream. He never once uttered a word.


Sinatra, and everything he ever achieved will be tainted by goons, associations, and allegations. In an early days, everything Sinatra did, was normal. Studios were run by mobsters, everything was. Unions were controlled. Business was business. The sad fact is, many journalists love the salacious headlines, and they are unable to see the forrest through the trees. The things Sinatra did just for civil rights, and so many others, often gets forgotten in the longline of mafia innuendo. It's always going to be the negative highlights that are written about instead of the good things Sinatra did. I guess in the end, there is no money in telling good stories, just versions of them, which hold little bearing.

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