The mobster Hollywood adored: He was America's biggest bootlegger, tried to sell bombs to Mussolini and carried out his own hits. Now a new book asks - why was 1930s gangster Bugsy Siegel Tinseltown's darling?

 Whether it was the old guard such as Cary Grant, Clark Gable and Ava Gardner, or young pretenders like Tony Curtis and Frank Sinatra, Hollywood turned out en masse to Bugsy Siegel's lavish parties. With his piercing blue eyes, handsome features, suave charm and impeccable wardrobe, Siegel was a match for almost any of them in looks, wealth and even narcissism.

However, there was another good reason not to pass up an invitation to his Beverly Hills mansion — let's just say you didn't really want to disappoint the host.

He had a violent, hair-trigger temper that could be set off just by calling him Bugsy, a nickname he loathed, or asking him too closely about what he did for a living.

For in a town of fake tough guys, fake guns and fake blood, Benjamin Siegel was the real thing — a brutal gangster boss so sadistic he usually carried out the killings he ordered himself.

He hankered secretly to be a film star like his boyhood friend George Raft just as the real stars hankered to rub shoulders — or more — with him.

Siegel would become the first mobster to invest heavily in Las Vegas and the only one who tried to sell explosives to Benito Mussolini. But his air of menace — unlike so much in Tinseltown — was not remotely inauthentic and, even after becoming famous, Bugsy would occasionally hop back to New York to shoot someone dead in a crowded restaurant.

Bugsy Siegel's extraordinary life was the basis for the 1991 feature film Bugsy in which Warren Beatty played him as a smooth and irresistible lady's man and Beatty's fiancee Annette Bening was his devoted actress lover, Virginia Hill

Bugsy Siegel's extraordinary life was the basis for the 1991 feature film Bugsy in which Warren Beatty played him as a smooth and irresistible lady's man and Beatty's fiancee Annette Bening was his devoted actress lover, Virginia Hill

As Cary Grant once advised James Stewart, virtually the only star who didn't see Siegel's sinister appeal: 'Look, Jim, the guy's best pal is George Raft, and George says if Benny wants you to be his friend, you be his friend.'

Siegel's extraordinary life was the basis for the 1991 feature film Bugsy in which Warren Beatty played him as a smooth and irresistible lady's man and Beatty's fiancee Annette Bening was his devoted actress lover, Virginia Hill.

However, as revealed in a new biography, Bugsy Siegel: The Dark Side Of The American Dream, by Michael Shnayerson, Hollywood had once again white-washed a psychopath.

Siegel privately admitted to 12 murders, but the FBI estimated it at 30. As for his paramour, Hill was a street-hardened gangster's moll who slept with most of Hollywood and the Mafia.

Born in New York in 1906 to impoverished Jewish immigrants from Austria-Hungary, Siegel was in a Lower East Side street gang by the age of 12, extorting money from street peddlers and carriage drivers.

He earned a reputation for being utterly fearless and so violent that he was nicknamed Bugsy, as in the American phrase 'crazy as a bedbug'. The beginning of Prohibition in 1920 quickly turned petty street thugs like Siegel and his pal Meyer Lansky into big-time criminals smuggling alcohol from Britain, and within a decade they were the biggest bootleggers in the U.S..

Siegel killed enemies without compunction. When a rival injured him by lowering a bomb down his chimney, Siegel sneaked out of his hospital room, shot dead the would-be assassin, and got back to bed before anyone noticed.

In 1931, the Jewish mobsters teamed up with Irish and Italian hoodlums, including Lucky Luciano, a Sicilian future 'godfather', to form 'The Syndicate' to 'minimise bloodshed and maximise profits'.

When, however, the violence continued, Siegel and Lansky set up a squad of contract killers called Murder Incorporated, which enforced The Syndicate's will by racking up a body count estimated at anything from 400 to 1,000.

He had a violent, hair-trigger temper that could be set off just by calling him Bugsy, a nickname he loathed, or asking him too closely about what he did for a living. For in a town of fake tough guys, fake guns and fake blood, Benjamin Siegel was the real thing ¿ a brutal gangster boss so sadistic he usually carried out the killings he ordered himself

He had a violent, hair-trigger temper that could be set off just by calling him Bugsy, a nickname he loathed, or asking him too closely about what he did for a living. For in a town of fake tough guys, fake guns and fake blood, Benjamin Siegel was the real thing — a brutal gangster boss so sadistic he usually carried out the killings he ordered himself

Bugsy moved to Los Angeles in 1932 as his gang started a gambling racket. They also smuggled in drugs, including heroin, from Mexico. He persuaded his wife Esther to stay at home to look after their two daughters while he headed off to enjoy himself with the stars — and starlets.

His old friend George Raft, a former 'wheel man' (driver) for the New York mob, had already become a star after playing Al Capone in the original Scarface.

Raft got his break because Hollywood screen writers had been ordered to churn out endless gangster films but needed a real one to tell them how to write convincing dialogue.

Studio bosses weren't the only ones in Los Angeles fascinated by gangsters. The film stars were 'bowled over' by the flashy Siegel, who with his good looks, trim figure and astonishing vanity — he exercised obsessively and wore a chinstrap in bed to keep his skin from wrinkling — seemed more like a Hollywood actor who simply played mobsters.

He had a string of actress girlfriends, starting with a blonde French-woman, Ketti Gallian, on whom he spent $50,000 for elocution lessons in a failed attempt to help her lose her incomprehensible accent.

He later had a long affair with a British actress, Wendy Barrie, to whom he even became engaged (while still married to long-suffering wife Esther). However, even as he charmed Hollywood, he continued to go back East occasionally to do the odd contract killing for his gangland friends.

By then, his wife had divorced him because he had a controlling new lover ¿ Virginia Hill, a ravishing nymphomaniac who made a living carrying money around for the Chicago mafia

By then, his wife had divorced him because he had a controlling new lover — Virginia Hill, a ravishing nymphomaniac who made a living carrying money around for the Chicago mafia

One of the first stars he met was platinum-blonde bombshell Jean Harlow. Siegel wanted to bed her and approached Jimmy Stewart, who had previously had a fling with her.

'Jean's a good friend of yours,' Siegel told the actor. 'How about you tell her to go out with me.' To which Stewart pluckily responded, 'You go to hell.'

Stewart told his future wife, Gloria, that he'd been terrified Siegel would pull out a gun and shoot him on the spot. Shnayerson believes Stewart's height — 6 ft 3 in — 'seemed to keep Siegel from doing anything rash'.

As for Harlow, any dalliance with Siegel was cut short when she died of a cerebral edema — a build-up of fluid in the brain resulting from kidney failure — aged 26.

Anxious to find a home fit to entertain Hollywood royalty, Siegel decided he had to build one, and spent $180,000 on a 10,000 sq ft, 23-room mansion — complete with hidden escape hatches and secret cabinets stocked with guns — at a time when the average U.S. home cost less than $3,000. 'This was the American dream, all right, and Siegel was proof that anyone with guts, good taste and a gun could grab it,' says his biographer.


Another of Siegel's mistresses was Dorothy di Frasso, an heiress who had married an Italian count. Between her and George Raft, Bugsy soon knew virtually everyone who mattered in Hollywood. Ironically, as they flocked to his glittering parties, Siegel was fleecing their industry, extorting cinemas and even film studios through protection rackets and his influence on corrupt film industry unions.

Yet even as he was strong-arming the studios, Siegel was asking them to make him a star.

He told studio bosses he even had footage to show them of his acting — astonishingly, Siegel had once gone to watch George Raft film a movie with Marlene Dietrich and, at one point, had ordered the director to film him instead of Raft in a scene. It turned out he had already learnt all Raft's lines and even his gestures.

It's unclear whether any studio chief saw Siegel's unorthodox showreel but Shnayerson observes that Bugsy was far too hot-tempered for an acting career: 'an audition might have ended in bloodshed'. There is certainly no record of him having had any acting roles.

By 1938, Siegel's mansion was completed and he and wife Esther, who had joined him in LA, began throwing parties. The guest list boasted everyone from Fred Astaire to Gary Cooper.

One of the first stars he met was platinum-blonde bombshell Jean Harlow. Siegel wanted to bed her and approached Jimmy Stewart, who had previously had a fling with her

One of the first stars he met was platinum-blonde bombshell Jean Harlow. Siegel wanted to bed her and approached Jimmy Stewart, who had previously had a fling with her

It wasn't as if the stars didn't know what he did. Repulsively, that was why many of them were there. Sgt. Bilko star Phil Silvers's wife Jo-Carroll Dennison said the actors were all enthralled by him.

'They would brag about Bugsy, what he'd done and how many people he'd killed,' she said.

'They'd argue about whether Bugsy preferred to shoot his victims or simply chop them up with axes.' She said she never forgot 'the awe that Frank [Sinatra] had in his voice when he talked about him. He wanted to emulate Bugsy'.

Hollywood columnist Florabel Muir agreed, observing how Siegel was 'one of the most fabulous characters' ever to pitch up on the LA social scene.

'He was the storybook gangster to the romantic, emotional, almost-childlike adults who populate the movie colony,' she said witheringly.

'For women, especially, he had a strange fascination . . . some of them who would never have dared date him enjoyed a delicious tingle along their spines at the thought of doing so.'

Every top-flight star accepted a Siegel invitation except the upstanding Jimmy Stewart who pleaded unsuccessfully with his fellow thespians to shun the monster.

The 'good guy' in so many films, Stewart even once denounced Siegel to his face. Bugsy's temper instantly flared and a worried Raft rushed in to calm him down.

'If Siegel wants to try his luck with me, let him take his best shot,' retorted Stewart, who was perhaps in danger of believing his own on-screen persona. 'If he takes his best shot, it'll be the last shot you hear,' Raft advised him.

However, as Stewart's wife Gloria observed, Jimmy's quest was pointless for, as far as most movie stars were concerned, 'the only people who could be remotely more glamorous were royalty and big-time gangsters'.

Attending the mobster's parties came with a price, however. Siegel often charmingly asked his celebrity guests for small loans, perhaps a thousand dollars each time, correctly judging that nobody would ask to be repaid.

A record book found in a secret compartment of his house later showed he had acquired hundreds of thousands of dollars this way.

Siegel's most jaw-dropping attempt to make money came when he tried to sell explosives to Mussolini. His lover, Countess di Frasso, had heard about a new type of explosive called Atomite that detonated soundlessly and smokelessly.

She used her Italian connections to pitch it to the fascist leader and he made a down payment of $40,000. In 1939, she and Siegel sailed to Rome but the deal fell through when the explosive failed to work in a demonstration.

On their way out of Mussolini's villa, they met Nazi Hermann Goering on his way in. Siegel, who naturally was armed and, as a Jew, hated the Nazis, considered killing Goering on the spot but di Frasso dissuaded him.

Although his career was steeped in bloodshed, including several high-profile murders, Siegel was never convicted of a serious crime.

In fact he was only found guilty of two minor offences, a 1930 charge of 'gambling and vagrancy' and, 14 years later, of 'placing bets illegally on a horse race'. He escaped both times with a fine.

Witnesses had a habit of disappearing as they did in 1941 when he was arrested for the murder of underworld kingpin Harry Greenberg. Despite six police guards, the mobster witness was thrown to his death from a hotel-room window wrapped in bedsheets.

In 1946, Siegel 'went legit' (up to a point) by moving into casinos, specifically a flashy Las Vegas hotel and casino called The Flamingo. Using Mob money, he spent a jaw-dropping $6 million turning The Flamingo into the most lavish joint in town.

By then, his wife had divorced him because he had a controlling new lover — Virginia Hill, a ravishing nymphomaniac who made a living carrying money around for the Chicago mafia.

Hill, an aspiring actress, shared his violent temper and was mind-boggingly extravagant, once spending $10,000 on a single dinner party.

Hill was to prove Bugsy's undoing, the new biography argues. Allegations that she was skimming serious sums from The Flamingo's takings and stashing it away in Switzerland reached Mafia chiefs who had funded the project and were already furious it wasn't turning a profit.

It hadn't helped that Bugsy, hopelessly out of his depth, had filled the moat surrounding the casino with a flock of pink flamingoes that had promptly all died in the heat.

Siegel was reading a newspaper in Hill's Vegas home one night in June 1947 when an unknown gunman armed with a rifle shot him five times through the window, killing him instantly.

One of the bullets propelled his right eye 15 feet across the room, embedding it in the opposite wall. The murder remains a mystery although Shnayerson believes The Syndicate did a deal with Virginia, who arranged for her soldier brother or one of his Army friends to do it. Mafiosi, he notes, never used rifles.

The rapacious mobster who'd captivated Hollywood met a fate worthy of one of its goriest gangster films.

The mobster Hollywood adored: He was America's biggest bootlegger, tried to sell bombs to Mussolini and carried out his own hits. Now a new book asks - why was 1930s gangster Bugsy Siegel Tinseltown's darling? The mobster Hollywood adored: He was America's biggest bootlegger, tried to sell bombs to Mussolini and carried out his own hits. Now a new book asks - why was 1930s gangster Bugsy Siegel Tinseltown's darling? Reviewed by Your Destination on April 09, 2021 Rating: 5

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