The mobster Frank Sinatra most admired was slaughtered - his head blown apart by a bullet: The singer's dangerous flirtation with the Mafia



The plausibility of author Mario Puzo was to blame.



In his book and film of The God­father, the flagging career of a singer named Johnny Fontane is rescued when he gets an important film part — thanks to a blood-­dripping racehorse’s head left by the Mafia as a warning in the studio boss’s bed.



To many people, ­Fontane just had to be a dead ringer for Frank Sinatra.

The photo that apparently links Frank Sinatra to the Mafia: Pictured with the singer are Tommy 'Fatso' Marson, Don Carlo Gambino 'The Godfather', and Jimmy 'The Weasel' Fratianno

Everyone knew Sinatra’s casting in the 1953 film From Here To Eternity led to a desperately needed revival of his fortunes. Everyone had heard the rumours of his Mafia connections. Puzo was of southern-Italian ancestry and steeped in his subject. His take in The Godfather, though fictional, seemed confirmation of a sort.

Numerous writers have put considerable effort into cobbling up a case that the Mob really was behind Frank getting the Oscar-winning part. In reality, though, he got it by a different sort of graft — his sheer persistence in pestering the studio, the producer, the director and the screen writer with a non-stop flood of telegrams over many months staking his claim.

His Italian origins helped only to the extent that he looked and sounded the part of the skinny, wise-cracking ­Private Angelo Maggio more than did his rival, the Jewish actor Eli Wallach. Oh, and Sinatra was so desperate for a break he also offered to waive his fee and work for an expenses-only deal of $1,000 a week.

As crazy as a bedbug: Sinatra would speak with awe about notorious Mafia hitman Bugsy Siegel

So, no Mafia involvement there. But if the suspicion continued to hang over Sinatra, it was no one’s fault but his own. He did have a real connection with the Mob and had done since childhood.

Growing up where and when he did, it would have been impossible not to come into contact with organised crime. In those days of Prohibition and the Depression, his hometown of Hoboken, New Jersey, was pretty mobbed-up.

Some say the little place his parents ran was a Mafia hotbed, frequented by big Mob names like Meyer Lansky, Bugsy Siegel, Dutch Schultz and Lucky Luciano, born in the same Sicilian ­village as Frank’s grandfather.

The link between these big cheeses of organised crime and the small-time Sinatras of Hoboken was liquor. Marty Sinatra bought bootleg booze from their lieutenants and at least once he rode shotgun on a shipment.

Then there were Frank’s uncles, Dominick and Lawrence, his mother Dolly’s brothers, who dabbled in crime. And in Dolly herself — ambitious, ­abusive, violent and vengeful — he had his own model for a Mafia chief.

Small wonder that when he met the real thing, he felt an instant pull. Small wonder too that when the real mafiosi met him, they smiled as they shook his hand.

It wasn’t just his celebrity; in their world celebrities were a dime a dozen. They also recognised the part of Dolly that he always carried with him — his own inner godfather. He wanted to be one of them and — in spirit and in part — he really was. As a result, the Mob would be a constant in his life.

We should not over-emphasise this connection — as many commentators have done — but nor should we underplay it. Some of it came with the territory of being a singer. As many entertainers of his era knew, it was impossible to play the clubs and not come into contact with organised crime.

Friend of the family: Mob boss Meyer Lansky was reported to be an acquaintance of Sinatra's parents

The ‘Boys’ backed the clubs, often secretly owning them and hiring front men for a legitimate face. They operated them as glamorous profit centres for their businesses — entertainment, liquor, gambling and prostitution.

During Sinatra’s early career, organised crime was a vast and dark under-culture — an alternative economy so huge one boss boasted: ‘We’re bigger than General Motors.’

It was a complex, vicious business, big fish eating smaller fish and operated by brute power. Frank found the aura of danger alluring as he mixed with the likes of Willie Moretti, the bald, wise-cracking Mafia boss of North Jersey, one of his neighbours.

When he moved from the east coast to Hollywood to live and work, he encountered one of the most dangerous and violent of them all — west coast boss Benny Siegel, known as Bugsy because he was ‘as 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.

He and his mate Phil Silvers (the comic actor, TV’s Sergeant Bilko) were enthralled. ‘They would brag about Bugsy,’ said Silvers’s 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.’

In February 1947 Frank relaxed at the Miami mansion of his friends, the ­Fischettis, first cousins of Al Capone and his bodyguards during Prohibition. He did small favours for them; they sent gifts. Then, accompanied by them, he flew to Havana, where he was photographed getting off the plane carrying a large, square case.

A vast amount of attention has been devoted to his four-day trip to Havana, his most blatant walk on the wild side with the Mob. At the Hotel Nacional a conference of top U.S. gangsters was under way, organised by the hotel’s co-owner, Jewish mobster Meyer Lansky (his silent partner was the corrupt Cuban president Fulgencio Batista), and presided over by infamous Mafia don Lucky Luciano.

Luciano had been deported from the U.S. but was using Cuba as an offshore base. Every important hood in the America had come to offer him fealty and thick envelopes of cash, his cut of their illegal activities.

Sinatra’s presence was no coincidence. Those on the invitation list had known for months that he would be there. He was welcome not just to sing and entertain them but because he was ‘respectful’ to the Boys.

But did respect translate into guilt by association? Did his sins run deeper?

Certainly Frank rubbed a lot of elbows in the four days. The conference was a veritable summit of crime. Some life-or-death decisions were made.

Sinatra was probably not privy to these discussions. He was there to provide a cover story and to admire and be admired. He was, Luciano later said, ‘a good kid and we was all proud of him’.

Frank performed, he glad-handed, and he was rewarded. Pre-Castro Havana was a 24-hour fiesta of pleasures. There was an orgy in his suite with 12 naked women — interrupted when a troop of Cuban girl guides, led by a nun, arrived to present the singer with a token of their esteem. He hustled the broads out of sight and addressed the guides in a silk dressing gown.

Frank’s hero worship of tough guys got him in way over his head. The court of public opinion would quickly take note of Sinatra’s new friends, and would react violently.

His presence was revealed by an American columnist who happened to be on the island at the same time and saw him disporting himself with Luciano and co.



‘Shame on you, Sinatra,’ he wrote, for setting such a terrible example to the ‘hordes of pimply, shrieking slaves’, the girls who were his fans.

Sinatra was stunned by the reaction and his immediate response was self-contradictory. ‘I was brought up to shake a man’s hand when I am introduced to him without first investigating his past,’ he declared. ‘Any report that I fraternised with goons or racketeers is a vicious lie.’

Pleasure palace: The National Hotel in Havana, Cuba, which had links to the Mafia - and where Sinatra stayed as a guest

After the trip, he told Hollywood gossip columnist Hedda Hopper that he had ‘dropped by a casino one night and was asked if I’d mind meeting a few people.



'I couldn’t refuse and I went through some routine introductions, scarcely paying attention to the names. One happened to be Lucky Luciano. Even if I’d caught his name, I probably wouldn’t have associated it with the notorious underworld character. I sat down at a table for about 15 minutes. Then I went back to my hotel. When such innocent acts are so distorted, you can’t win.’

But at the very least amiability was dangerously close to complicity, and all the more so when press attention focused on the suitcase he was carrying when he arrived. A story circulated that Frank had been acting as a courier for the Fischettis, carrying the $2 million in notes they owed to Luciano.

In December 1950, a Senate committee set up to investigate the Mafia called him to account. The committee’s lawyers proposed to question him publicly, which would have blown his career out of the water. His own lawyers secured an agreement that he would testify but in secrecy.

The hearing took place at 4am one morning in a lawyer’s office. Sinatra arrived on time — unusual for him — and without his characteristic swagger and bluster. The summons had thrown the fear of God into him.

‘He looked like a lost kitten, drawn, frightened to death,’ said Joseph ­Nellis, the committee’s lawyer.



‘He kept shooting his cuffs, straightening his tie, and he smoked constantly. His right hand shook so badly each time he tried to light a fresh cigarette that he had to hold it with his left.’

His nerves were even more shredded when Nellis revealed what he had up his sleeve — photos showing Frank with his arm around Luciano on the hotel balcony in Havana; Frank and Luciano at a nightclub surrounded by bottles and girls; Frank getting off the plane carrying that mystery suitcase.

Asked about the Fischettis, he said he barely knew them and that it was just coincidence that he was going to Havana for a few days of winter sunshine at the same time as them. He said that when he got off the plane he was carrying his usual ‘briefcase’ containing ‘sketching materials, crayons, shaving equipment, general toiletry’.

He then gave the committee a lengthy account of his time in Havana and the series of ‘accidental’ meetings he had with a group of gangsters who kept showing up wherever he went.



‘Did you ever learn what business they were in?’ he was asked. ‘No,’ he replied. ‘What’s your attraction to all these underworld characters?’ ‘I don’t have any attraction for them,’ he insisted.

Names of known mobsters were called out to him. Did he know them? ‘Just to say hello,’ he replied, but he was wringing his hands and his famous voice was wavering a little. ‘Surely you’re not going to put me on television and ruin me just because I know a lot of people?’ he pleaded.

That depended on the people. ‘Do you want me to believe,’ the lawyer demanded, ‘that you don’t know these people are hoodlums and gangsters who have committed many crimes and are probably members of a secret criminal club?’

‘No, of course not,’ Frank said. ‘I heard about the Mafia.’ But all he knew was that it was ‘some kind of shakedown operation’.

And that was the end of the interview. Frank was dismissed but with the threat hanging over him that he still might have to testify again and in public, in which case, as he told himself, as he downed one whisky after another back in his hotel room, he would be ‘well and truly f***ed’.

It didn’t come to that. Nellis didn’t doubt that Sinatra had been lying. On the other hand, he knew the singer was never going to admit he had been a bagman for Lucky Luciano and the Fischettis and there was a danger that a public hearing might backfire if Sinatra seemed victimised.

Frank was off the hook, and his dance with the Mob carried on for the rest of his life. His was a dangerous flirtation with men you were wise not to mess with.

The mobster he most admired, Bugsy Siegel, was slaughtered, his head blown apart by a bullet, for ­daring to skim off Mob money in Vegas. Chillingly, Frank discovered that Bugsy’s execution was one of those decisions made at the Havana summit he himself had attended. ­Willie Moretti went the same way.

So what can we make of Frank’s picaresque misadventures, his ­dabblings in the underworld of crime? What were they all about? At their heart, I believe, was his need to assert his manliness. In essence, great singer and artist though he was, Sinatra was a little guy. Though he made physical threats, not a ­single record exists of his ever having ­prevailed in a real fight.

How could such a person be a man among men? As his fame grew and hangers-on kowtowed and cowered, he came to believe in his own toughness. That’s why he liked to carry a gun. That’s why he hung around mobsters and was so desperate to be accepted by them.

● Adapted by Tony Rennell from Frank: The Making Of A Legend by James Kaplan, published by Sphere on November 4 at £25. © James Kaplan 2010. To order a copy at £20.99 (p&p free), call 0845 155 0720.



