Frank Sinatra and The Mob cover

Frank Sinatra and The Mob

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It is the most shocking scene in The Godfather – a horse’s head still dripping with blood is discovered in the bed of a Hollywood studio boss who dared to say no to the Mob. In the movie based on Mario Puzo’s best-selling novel, the macabre threat is enough to win fading lounge singer Johnny Fontaine the big screen part that will put him back on top.


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Frank Sinatra and The Mob

Passionate Role

It is the most shocking scene in The Godfather – a horse’s head still dripping with blood is discovered in the bed of a Hollywood studio boss who dared to say no to the Mob.

In the movie based on Mario Puzo’s best-selling novel, the macabre threat is enough to win fading lounge singer Johnny Fontaine the big screen part that will put him back on top.

It didn’t take much to connect the character of Fontaine to Frank Sinatra, who lobbied passionately to get the coveted role of wisecracking soldier Angelo Maggio in the 1953 classic ‘From Here to Eternity.’

Frank Sinatra, 1962

Frank Sinatra, 1962

Help From The Mafia

His then wife Ava Gardner pleaded her husband’s case with the producers and Sinatra agreed to a massive pay cut from the $130,000 he made from his previous film ‘Anchors Aweigh’ to just $8,000.

But the suspicion remains to this day that Sinatra had some help from the Mafia to get the job that would win him a Supporting Actor Oscar and rescue his career from the doldrums.

Although Sinatra would go to his grave publicly denying any personal links with the Mob, he wasn’t really fooling anybody, least of all the authorities who took a keen interest in his colorful friends down the years.

Not A One-Time Favor

If indeed it were true that “the boys” as he called mobsters did have a hand in ‘persuading’ the studio to hire Sinatra for ‘From Here To Eternity’, it certainly wouldn’t have been the only time he sought a favor from organized crime.

Growing up in Hoboken, New Jersey in a strong Italian-American neighborhood, it wasn’t as if the Mob was a mystery to him. The Cosa Nostra was a part of the fabric of his upbringing, with roots stretching way back to the northwest Sicilian town of Lercara Friddi where his grandfather – and notorious Chicago gangster Lucky Luciano – hailed from.

Lucky Luciano

Lucky Luciano

Dealing With Accusations

Marty O’Brien’s, the saloon Sinatra’s parents opened in Jersey City, was also said to have been frequented by Mafia “faces” like Meyer Lansky, Bugsy Siegel and Dutch Schultz.

So when Sinatra’s up-and-coming career as an arrogant young singer with the famed Tommy Dorsey Band hit its first roadblock, he knew where to turn. Sensing he was about to break through into the really big time in 1943, Sinatra wanted Dorsey to release him from the show band that had given him his first breakthrough.

But the bandleader wouldn’t free him from his contract and accused him of being disloyal.

Achieving His Freedom

It seemed like an impossible impasse. Then all of a sudden in August 1943 a deal was struck, with Dorsey paid $60,000 to give Sinatra his freedom to go out on his own.

It was only later that a more ominous story began to leak out involving Willie Moretti, the bald, fast-talking New Jersey crime boss who was a big admirer and friend of Sinatra.

According to Kitty Kelley in ‘His Way: The Unauthorized Biography of Frank Sinatra’ the story going around was that Moretti “had gone to Dorsey’s dressing room and demanded that he release the singer – using as persuasive argument a revolver he rammed down Dorsey’s throat.

“Supposedly, Dorsey thereupon sold Sinatra for one dollar,” she added.

Dealing With The Mob

Kelley wrote that Dorsey’s attorney denied his client was intimidated by the Mob, but the bandleader gave an interview in 1951 saying that after a breakdown in negotiations over Sinatra’s contract he was visited by three “businesslike men who told him out of the sides of their mouths to ‘sign or else.’”

Being an entertainer in those days it was virtually impossible not to come into contact with organized crime. Gangsters had bought up many of the big clubs – and would soon move into Las Vegas – and used them as legitimate fronts for their more shady dealings in gambling, prostitution and, later, drugs.

But friends said it was deeper than that with Sinatra. He was “fascinated” with the Mob and molded his behavior over the crime bosses he looked up to.

Mugshot of Bugsy Siegel, 1928

Mugshot of Bugsy Siegel, 1928

Fascinated By His Friend

Once Sinatra moved to the West Coast, he became friends with Benny Siegel, known as Bugsy because he was ‘crazy as a bedbug.’

“Stars like Humphrey Bogart, Jimmy Cagney and Edward G. Robinson might look tough on the screen, but Bugsy was the real thing. He killed people. Sinatra couldn’t get enough of him,” wrote biographer James Kaplan.

“He and his mate Phil Silvers (the comic actor, TV’s Sergeant Bilko) were enthralled.

‘They would brag about Bugsy,’ said Silvers’ wife, ‘what he’d done and how many people he’d killed. Sometimes they’d argue about whether Bugsy preferred to shoot his victims or simply chop them up with axes.’ She never forgot the awe Frank had in his voice when he talked about him. He wanted to emulate Bugsy.”

Becoming More Careless

By February 1947, Sinatra was becoming more careless about who he was seen out in public with and met up with the Fischetti brothers, three mobster brothers who were first cousins of Al Capone, at their mansion in Miami before flying with them to Havana, Cuba.

At the Hotel Nacional, a summit meeting of America’s top Mafia figures was under way presided over by the ‘Don of Dons’ Lucky Luciano. The bosses were there to pay court to Luciano, who had been deported from the United States and was using Cuba as his criminal headquarters – and Sinatra had been invited as their cover. They were all there, they claimed, to ‘honor that skinny little boy from Hoboken.”

Sinatra’s Trip Backfires

Kaplan wrote that Sinatra was rewarded for his presence with an orgy in his suite with a dozen naked women.

But the four-day trip was about to backfire on Sinatra. An American columnist just happened to be on the island and saw the singer cavorting with a who’s who of organized crime.

Robert Ruark wrote that by carousing with Luciano and his gangster pals, Sinatra was “setting a most peculiar example for his hordes of pimply, shrieking slaves.”

Shocked by the public response to the revelation Sinatra tried to deny any knowledge, saying he was simply asked to meet “a few people” one night when he dropped into a Havana casino.

A Serious Turn

“I was brought up to shake a man’s hand when I am introduced to him without first investigating his past,” he insisted.

"Any report that I fraternized with goons or racketeers is a vicious lie.”

The episode took an even more serious turn in December 1950 when Sinatra was called to give testimony about the visit to a Senate Committee set up to investigate the Mafia.

Looking unusually nervous, he was quizzed at the behind-closed-doors meeting about speculation that he’d acted as a courier for the Fischettis, carrying a bag containing $2 million in cash through customs into Cuba.

Making New Friends

He denied having anything but a passing knowledge of the Mob or of its members.

Luckily for Sinatra, the lawmakers, fearing they might be seen as victimizing the star, allowed him off the hook.

That didn’t mean he stayed away from the Mafia and he became close friends with another feared “Boss” Sam Giancana – the Chicago kingpin and a key player in the Mafia takeover of Las Vegas - who was an occasional guest at the entertainer’s Palm Springs compound.

In his memoir, ‘My Way’ – named after the signature song he wrote for Sinatra – Paul Anka said the Chairman of the Board was still closely linked to the Mob in his Rat Pack years.

Old Blue Eyes, 1957

Old Blue Eyes, 1957

Getting Caught

“Frank was tied up with the Mob to the degree where he did favors for them,” Anka wrote.

“He liked the thrill of being involved with gangsters. Jules Podell, the owner of the Copa, told me that he acted as a bagman for the Mafia a number of times, but they eventually stopped using him because he always got caught.”

On one occasion, he said Sinatra got stopped at customs in New York with $3 million in a briefcase.

Sinatra tried to bluff the agent who had opened the case, but what saved him was the growing line behind him, added Anka.

Getting Away With It

When the other passengers realized it was Sinatra ahead of them, they turned into a mob of fans pressing to get close.

Things were nearly out of control when the decision was made to wave the singer through. Sinatra may have worried about the consequences of his links to “the boys” and certainly sought to play it down in his advancing years, but he was never ashamed of it.

One of Sinatra’s last regrets, wrote Anka, was that he was passed over for Marlon Brando’s role in ‘The Godfather.’