How Hollywood was dazzled by Bugsy Siegel: New biography tells how the bloodthirsty Las Vegas mobster dreamed of becoming a movie star and hobnobbed with celebrities like Cary Grant and Jean Harlow

• New biography of Bugsy Siegel tells how the infamous gangster hobnobbed with Hollywood stars and had dreams of becoming an actor
• He moved to Hollywood after prohibition to expand the mob’s criminal interests where he quickly befriended Gary Cooper, Cary Grant and Clark Gable
• Siegel arranged a screen test for himself, paid visits to studio heads Louis B. Mayer and Jack Warner and became a fixture at Hollywood hotspots like Ciro’s
• He had affairs with Jean Harlow, Ketti Gelman and Wendy Barrie but left his wife for Virginia Hill, a failed actress who moonlighted as a courier for the mob
• Siegel grew up in the Lower East Side tenements where he befriended fellow mobster, Meyer Lanksy and together they formed the hit squad, Murder Inc
• By the time Siegel was a teenager, he had already committed robbery, rape, murder and organized a ‘protection racket’ that forced pushcart peddlers to pay 
• Born to poor Jewish immigrants, Siegel is estimated to have made $100 million fortune through bootlegging, gambling, racketeering and murder-for-hire plots
• In 1946 he convinced the mob to finance building of The Flamingo hotel in Las Vegas – the ambitious project would eventually be his undoing
• Siegel was assassinated  while sitting in the Beverly Hills living room of Virginia Hill in 1947; the crime remains unsolved

A new biography of Bugsy Siegel reveals the hidden ambition of the notorious Las Vegas mobster who wanted to become a Hollywood star

It is considered the ‘Mona Lisa’ of all crime scene photos: Benjamin ‘Bugsy’ Siegel – the most dapper of Dons – was dead. Slumped over the chintz sofa of his girlfriend’s Beverly Hills home, the dashing gangster’s hands still clutched the newspaper he sat down to read. One of his intoxicating pale blue eyes was missing; shot out of its socket from a fusillade of bullets that shattered the window of the Moorish-style mansion. Seventy three years later, the crime remains unsolved.

It was in some ways the perfect Hollywood ending for the matinee-idol mobster who dreamt of making it ‘big’ in Tinseltown after he cut his teeth on the mean streets of the Lower East Side as a local street punk and went on to amass an estimated $100 million fortune through bootlegging, racketeering, gambling and murder.

Very few gangsters have since captured the public’s enduring fascination like Bugsy Siegel, a playboy gangster in custom pinstripe suits with a lot of audacity and charm. But belying the expensive haberdashery and intoxicating charisma was a ruthless killer, one who was prone to violent fits of rage.

His infamous hair-trigger temper earned him the nickname ‘Bugsy’ – he really was crazy as a bedbug, quick to anger, impulsive and always willing to kill. Together with his childhood friend, Meyer Lanksy; they co-founded Murder Inc., the Syndicate’s infamous hit squad responsible for over 1,000 contract killings. Ben Siegel was, as the FBI put it, ‘insane along certain lines.’

After prohibition ended, Siegel left New York City to expand his empire of vices on the West Coast where he nurtured his secret desire to become a movie star. Insofar that he arranged a screen test for himself, paid social visits to studio heads, Louis B. Mayer and Jack Warner and became a fixture at Hollywood hotspots like Ciro’s, The Trocadero and Clover Club.

Bowled over by his honeyed mannerisms and $200 suits, Siegel hobnobbed with the crème of Hollywood: Clark Gable, Cary Grant, Fred Astaire, Gary Cooper, Tony Curtis, Marlene Dietrich and Frank Sinatra. He had affairs with multiple actresses: Jean Harlow, Ketti Gelman and Wendy Barrie – all of which were mesmerized by the handsome menace.

‘He was the storybook gangster to the romantic, emotional, almost childlike adults who populate the movie colony,’ wrote Hollywood gossip columnist, Florabel Muir.

Michael Shnayerson’s new biography, Bugsy Siegel: The Dark Side of the American Dream tells the compelling story of how Bugsy Siegel almost succeeded in his silver screen endeavor. He was ‘both beautiful and violent’ writes Shnayerson, ‘a scintillating mix that goes through us in jolts of excitement, sensuality and fear.’ 

Born in abject poverty to an Orthodox Jewish immigrants in the Lower East Side, Benjamin ‘Bugsy’ Siegel saw an easy way out of the tenements through a life of crime. After making a fortune as a bootlegger during Prohibition, Siegel left New York City in 1933 to expand organized crime operations on the West Coast where he nurtured his secret desire to become a movie star. He arranged a screen test for himself, paid social visits to studio heads, Louis B. Mayer and Jack Warner and became a fixture at Hollywood hotspots like Ciro’s, The Trocadero and Clover Club while hobnobbing with Clark Gable, Cary Grant, and Marlene Dietrich

Bugsy Siegel was known for his elegant mannerisms and immaculate way of dressing, but beneath his honeyed mannerisms and expensive haberdashery was a bloodthirsty killer that the FBI described as ‘insane along certain lines.’ His volatile temper earned him the nickname ‘Bugsy’ – he ‘really was crazy as a bedbug, so quick to flare, so willing to kill,’ said Shnayerson

Siegel was ambushed while sitting in his girlfriend’s Beverly Hills home on June 20, 1947; he was just 41-years-old. The crime remains unsolved, but one theory posits that Siegel was skimming off the top amid exorbitant construction costs that were backed by mob bosses in the building of The Flamingo Hotel in Las Vegas. The budget soared from $1 million to $6 million 

Born into an impoverished family of eastern European immigrants, Siegel cut his teeth on the mean streets of the Lower East Side as a scrappy street punk who committed petty robberies and extorted local pushcart peddlers in a protection racket. If they didn’t pay up, he would threaten to incinerate their merchandise.

The young gangster-in-training was determined not to end up like his father who worked grueling hours as a pants presser at a sweatshop for meager wages. The Siegels lived in abject poverty and Bugsy saw that the streets offered an easier and more lucrative way out the tenements.

How Bugsy Siegel and Meyer Lansky started Murder Inc. 

Fortunes were made overnight during Prohibition, but the costs were also high as rivals ambushed one another’s booze-filled trucks on late-night country roads. In New York City, thousands of underlings died in the turf wars that followed. Most of the shoot-outs occurred along ethnic lines, it was the Jews versus the Italians versus the Irish.

The turning point came in 1931, when Lansky and Siegel, along with Lucky Luciano established ‘the Syndicate’ which brought enemies together to establish order in the underworld. The three gangsters had known each other since their childhood as neighborhood toughs.

It was divided into five families who worked together to minimize bloodshed and to maximize profits. Lucky Luciano was the ‘capo di tutti i capi’ also known as, the Godfather. ‘Money, not murder and revenge would be the modus operandi,’ wrote Shnayerson. They were ‘gangster capitalists now.’

The Bugs and Meyer mob turned into Murder Inc. which served as the Syndicate’s enforcement arm to protect their shared business interests. Siegel killed without remorse and took perverse pleasure in planning elaborate hits down to the last detail. More than just a killing machine, Murder Inc. evolved into a lucrative national business that would rub-out anyone as long as the pay was good enough.  

By the late 1930s, Murder Inc. is said to have killed close to one thousand men. 

When Siegel wasn’t busy putting the squeeze on Rivington Street merchants, he spent his time in the nickelodeon, captivated by the silent film stars of the day, such as Wallace Reid and his racing car dramas and Rudolph Valentino darkly brooding as ‘The Sheikh.’

It was on the streets that Bugsy met fellow ruffian Meyer Lansky – a neighborhood tough who had already earned his keep when he told Lucky Luciano to ‘go f*** yourself.’ Lansky was 16 when he stumbled upon 12-year-old Siegel reaching for a gun that slipped from his hands in a street fight. Just as cops were rounding the corner Lansky interjected and ordered Siegel to ‘drop the gun’ – narrowly saving the rogue adolescent from handcuffs.

Sensing a kindred spirit, the boys became lifelong friends and partners in crime. Both grew up in Orthodox Jewish families that immigrated to New York City to escape religious persecution and chase the opportunity of a better life, only to find more poverty and prejudice.

They established their own protection gang whose activities expanded into gambling and car theft. Later, the ‘Bugs and Meyer Mob’ morphed into ‘Murder Inc.’ – the cold-blooded enforcement arm of the National Crime Syndicate.

While Lansky was ‘short, homely, and cautious,’ wrote Shnayerson, Siegel was ‘dashingly handsome, with deep blue eyes, and a garrulous grin.’ Standing nearly 5’10, he was big enough to provide the muscle and his lust for violence earned him a fearsome reputation in the underworld.

To those who witnessed his volatility, Siegel seemed crazy, and so earned the nickname he loathed: ‘Bugsy.’

‘He was young but very brave,’ Lansky said to his biographers. ‘He liked guns. His big problem was that he was always ready to rush in first and shoot. No one reacted faster than Benny.’

The passing of Prohibition in 1920 provided a lucrative opportunity in the bootlegging business for Siegel and Lanksy. ‘With it came their graduation from urchins to farbrekhers— Yiddish for criminals—and almost unimaginable wealth,’ writes Shnayerson.

Arnold ‘The Brain’ Rothstein, a mob boss who reputedly fixed the 1919 World Series, was the first to jump into bootlegging on an international scale. He took Siegel and Lanksy under his wing after he was impressed by the two teenagers he met at a bar mitzvah in Brooklyn.

Soon the childhood pals were profiting royally by running all aspects of the illicit business from bootlegging to rum-running and distribution. They operated two speakeasies, one on Broome Street and another on Lewis. Siegel often showed a charming side while cutting a swath through New York City in monogrammed shirts, high-waisted pants with pegged cuffs, and custom-made alligator shoes.

He made his evening rounds at popular nightspots that no Jewish gangster would have been welcomed at before Prohibition: Club Durant, the 21 Club and Chumley’s in the West Village.

‘Class, that’s the only thing that counts in life,’ he Siegel. ‘Without class and style a man’s a bum, he might as well be dead.’ He spent lavishly as if money was no object. Getting it was a game, and spending it was an excuse to play it.

By the late 1920s, Siegel and Lansky were bringing more booze into the United States than any other bootleggers in the country. They claimed a dollar for every case of liquor that came through New York docks, which gave them clout, power, and a lot of cash. But he was about to reach for more, and little did everyone know that he set his sights on Hollywood.

The end of Prohibition in 1933 meant that organized crime had to look elsewhere for income. Flush with ill-gotton millions, the Syndicate focused on growing their gambling and racketeering interests outside of New York City. While most of America remained flat broke in the crucible of the Great Depression, mafia bosses hoped they could tap into Hollywood money where stars and producers still had loads of cash to burn. Thus, Siegel was installed as the mob’s ‘man on the coast’ in California.

‘It was, in retrospect, a perfect marriage of the man and the moment,’ said Shnayerson. ‘A move Ben Siegel was born to make.’

Without batting an eye, Siegel parked Esther, his long suffering wife, and their two daughters in Scarsdale mansion with a live-in maid, pool and butler before he headed do his fair share of womanizing in the halcyon days of old Hollywood. 

Tinseltown was fascinated by the soigne host who threw extravagant parties from his 23-room Beverly Hills mansion. ‘He was the storybook gangster to the romantic, emotional, almost childlike adults who populate the movie colony,’ wrote Hollywood gossip columnist, Florabel Muir

Siegel met his lifelong partner-in-crime, Meyer Lanksy (above) on the streets of lower Manhattan as a teenager and the two boys formed the ‘Bugs and Meyer Mob,’ which later morphed into ‘Murder Inc.’ – the cold-blooded enforcement arm of the National Crime Syndicate

Fellow mobster, George Raft (right) was Bugsy Siegel’s entree into Hollywood. Raft had grown up in a cold-water apartment in Hell’s Kitchen and, like Siegel, had become a scrappy fighter with a volatile temper, adroit enough with a knife to be called ‘The Snake.’ His gang boss, Owney Madden (who started the wold-famous Cotton Club) noticed Raft’s talent for dancing and took him to Hollywood where he made his debut in the 1932 film about Al Capone, Scarface. Jimmy Stewart’s wife said: ‘Stars liked even bigger stars; for them, the only people who could be remotely more glamorous were royalty and big-time gangsters’

When he first arrived in Los Angeles, Siegel was a friendless gangster in the city of broken dreams, except for one George Raft.

Raft, who had been a third tier mobster himself, had come to Hollywood and slipped the noose of his past, by making his mark in the 1932 crime melodrama ‘Scarface.’ He quickly became the poster boy for the quintessential movie gangster. For both Siegel and Raft, it was like looking in the mirror.

Bugsy yearned to meet the stars and studio heads whom Raft was gadding around with but knew he had to prove himself first. ‘Damned few people knew what made him tick,’ said Raft years later. ‘But I did. He came out here because he wanted to be somebody.’

Siegel swam everyday to keep his body in immaculate shape. Obsessed with calisthenics, he also built a state of the art gym at his Beverly Hills mansion that included a steam room and sauna. Shnayerson recounts a time Siegel sat ‘jaybird naked’ in the barber chair at Drucker’s, after which he stood to admire his toned physique in the full length mirror before putting his clothes on. If the camera wouldn’t admire Bugsy Siegel, Bugsy would

With a preternatural understanding of the importance of appearance, Siegel’s rented himself a massive home in Beverly Hills from the Metropolitan Opera singer, Lawrence Tibbett.

To anyone who asked, he called himself a ‘sportsman.’ It was a title he thought suggested wealth and sophistication. But really, it was a euphemism for gambling, extortion and contract killing. ‘He was reinventing himself in the town of reinvention, a most American enterprise,’ wrote Shnayerson.

Siegel got to work expanding the Syndicate’s control of the horse race wire at Santa Anita and Agua Caliente as well as the dog racing tracks in Culver City and Tijuana. He took over an illicit gambling operation in Redondo Beach and invested in the SS Rex – a floating casino anchored three miles off Santa Monica, just beyond the reach of the law. He was reputed to own part of the Beverly Wilshire Hotel, a nightclub called the Chi Chi and bought a stake in the Clover Club’s celebrity hotspot.

Siegel also devised a racket that squeezed studio heads for pay-off money to prevent union strikes among the Screen Extras Guild and the Los Angeles Teamsters. Sidney Kent, the president of Twentieth Century-Fox at the time told the FBI that the amounts were always modest. Shnayerson explained that this was intentional. ‘Siegel wanted something else from these studio heads. He wanted to be an actor. He even had footage of himself acting, if the studio heads cared to look.’

When he wasn’t busy muscling in on the local lords of vice, Siegel swanned around Tinseltown’s most exclusive circles and soon became a fixture in Hollywood nightlife. Especially at Ciro’s, the buzzing hive for kings and queens of the silver screen and the Trocadero, which he co-owned with LA gangster, Mickey Cohen.

‘He was one of the most fabulous characters ever to take part in the social activities of the city where fabulous characters gather like bees on clusters of sweet grapes,’ wrote gossip columnist Florabel Muir.

In a certain way, Bugsy Siegel was playing a part – one based on himself. And Hollywood did come calling, Cary Grant, Gary Cooper, Frank Sinatra, Fred Astaire, Clark Gable and their studio bosses; Jack Warner, and Louis B. Mayer, even young up and coming film stars like Tony Curtis would come to Bugsy’s Holmby Hills mansion to drink and gamble, and let their toupees down.

Increasingly his moves started to be covered in gossip columns, and while he craved the spotlight, he knew it was something he had to cautiously enjoy.

Shnayerson retells the story of how Siegel arranged an impromptu screen test for himself when he suddenly appeared on the set of a film Raft was making with Marlene Dietrich. Siegel sat captivated in the shadows, absorbing every detail. During a break in filming, the Hollywood-hopeful, flabbergasted the crew, and no doubt astonished his friend, Raft, by opening up a briefcase and pulling out a 16-mm camera. He asked the actor Mack Grey to film him as he proceeded to re-enact Raft’s part in the just completed scene, having memorized the actor’s lines, and mimicking his gestures to a tee.

It was a hopeless and embarrassing blunder. Siegel’s vicious Murder Inc. reputation preceded him and had a chilling effect on any Hollywood ambition he might have had. Turning Bugsy Siegel down could possibly cost a casting agent their life, or so they thought.

If he succeed as a movie star, then Bugsy Siegel could at least pretend to live and look like one.

He kept himself in immaculate condition by working out and swimming every morning at the local YMCA. After a shower and steam, Bugsy would return home and paw through the illuminated glass wardrobe where his clothes hung like museum pieces. 

$25 silk monogrammed shirts to accompany $200 bespoke Louis Roth suits and hand-made alligator shoes were the uniform that would carry him through the day. Part of this daily ritual also included a visit to Drucker’s, one of the more exclusive barbershops in Hollywood. There Siegel would be groomed for the Oscar that would never come; shaved, manicured, his hair cut, his shoulders massaged, his shoes shined.

Shnayerson recounts one barber’s memory of Siegel sitting ‘jaybird naked’ in the barber chair, after which he stood admiringly before Drucker’s full length mirror before putting his clothes on. If the camera wouldn’t admire Bugsy Siegel, Bugsy would.

His night-time routine would bring its own endless rituals. The face creams, the chinstrap to avoid a sagging jawline. And somewhat touchingly, the self-improvement regimen. He was particularly fond of a feature in The Reader’s Digest called ‘It Pays To Increase Your Word Power.’ Bugsy who never completed the seventh grade could be Henry Higgins to his own Liza Doolittle, practicing, and pronouncing these new words, like an actor memorizing his lines the night before a shoot.

With Esther and the children on the East Coast, Siegel enjoyed a string of high profile affairs. The first was to a French actress named Ketti Gallian who had a movie contract with Twentieth Century Fox. The flashy mobster lavished her with gifts and spent $50,000 trying to help lose her accent in vain. She returned to France after two movie flops.

Then there was Jean Harlow, MGM’s platinum blonde bombshell that he met through a New Jersey gangster named Longy Zwillman. Zwillman knew Harlow through her mobbed-up stepfather, Mario Bello and was instantly enamored with the young ingénue – so much so, that he procured her a two-picture deal at Columbia Pictures by giving studio head Harry Cohn a sweetheart loan for $500,000.

At the time, Harlow was still involved with Jimmy Stewart when Siegel made his move. ‘Jean’s a good friend of yours,’ he told Stewart. ‘How about you tell her to go out with me.’ To which Stewart apparently responded: ‘You go to hell.’

Inevitably, like many women before her, Harlow succumbed to Siegel’s endless charm and tantalizing aroma of danger. She eventually became a friend of the family before her untimely death at the age of 26, and agreed to be the unofficial godmother of Siegel’s five-year-old daughter, Millicent. 

If he couldn’t succeed as a movie star, Bugsy Siegel was determined to live and look like one. He kept himself in immaculate condition by swimming every morning at the local YMCA; after which he would return home to paw through the illuminated glass case that kept his $200 bespoke Louis Roth suits. Part of this daily routine also included a visit to Drucker’s (one of the more exclusive barbershops in Hollywood) where Siegel would be shaved, have his hair cut, shoulders massaged, nails manicured and shoes shined. At night he wore an elastic chinstrap that he thought would prevent his jawline from sagging 

While his wife Esther and two children behind on the East Coast, Siegel enjoyed a string of high profile affairs with famous women like Jean Harlow (above). She eventually became the unofficial godmother to Siegel’s eldest daughter. Harlow ran in mob circles through her step-father, Mario Bello. In fact her entree into Hollywood was paved by Longy Zwillman a capo so in love with the blonde bombshell that he procured her a two-picture deal at Columbia Pictures by giving studio head Harry Cohn a sweetheart loan for $500,000

Siegel’s first Hollywood paramour was a French actress named Ketti Gallian (left), who had a movie contract with Twentieth Century Fox. The flashy mobster lavished her with gifts and spent $50,000 trying to help lose her accent in vain. Later in 1941, Siegel fell in love with Wendy Barrie (an actress made famous for her role opposite Spencer Tracy in It’s a Small World). The couple carried out their affair while Siegel was still locked up in LA County Jail on murder charges and it is alleged that he secretly fathered her daughter, Caroline

Benjamin Siegel married Esther Krakower in 1927 when she was just 17. Despite the humiliation, she long tolerated his flings with Hollywood beauties, cross-country absences, and the painful public relationship with Countess Dorothy di Frasso.  By 1944, their marriage was all but over when Siegel met Virginia Hill, the woman who would ultimately force his hand at divorce. Long after his death in 1947, Esther insisted that Siegel was the only man she ever loved

At the Santa Anita racetrack, Siegel met socialite Dorothy di Frasso, a twice married countess who had just ended her affair with Gary Cooper. Di Frasso was known for throwing extravagant parties that entertained the titans of Tinseltown. One memorable fete saw her set up a prized boxing ring under floodlights in the garden of her Beverly Hills home. Professional boxers staged a bout, with Clark Gable and Frederic March serving as seconds. 

Almost twenty years Siegel’s senior, the madcap countess charmed 30-year-old Siegel into bed. Eventually the lovers settled into a friendship. In exchange for it, Siegel was granted entrée into haute Hollywood.

It didn’t take much for Siegel to make an impression. ‘Bugsy was so smooth, so charming, he was accepted in Beverly Hills society,’ said screenwriter Charles Bennett. Film stars were enthralled by the dangerous and debonair mobster with ice cold blue eyes. ‘He was the storybook gangster to the romantic, emotional, almost childlike adults who populate the movie colony,’ wrote Florabel Muir.

In order to entertain his new circle of friends, Siegel built a sprawling 23-room mansion in the tony Beverly Hills neighborhood of Holmby Hills. The sweeping staircase and sixty-foot living room was made to draw in Hollywood royalty – and indeed they showed up in droves.

Jimmy Stewart’s wife, Gloria said: ‘Stars liked even bigger stars; for them, the only people who could be remotely more glamorous were royalty and big-time gangsters.’

Guests of his infamous craps game parties studied their soigne host’s mannerisms with intense scrutiny. They were utterly fascinated by the bona-fide mobster with Hollywood-handsome looks. ‘He was a gangster capitalist and a gangster celebrity: Gatsby with a penchant to kill,’ said Shnayerson.

The 10,000 square foot palace cost $180,000 to complete ($3.2 million in today’s money) during a time when the average cost of a home in America was just under $3,000.

It was designed with all the trappings a veteran thug might need to obfuscate the law. A hidden hatch in the wardrobe led to the attic. A safe where Siegel kept his jewellery, important papers and two guns was concealed behind a set of fake book cases in the library. While the master bedroom featured a secret trap door that was controlled by a button. ‘I got two others in the house,’ he explained to Raft. ‘Maybe someday I gotta get out of here in a hurry.’

Eventually Siegel moved his family from New York into the Beverly Hills home. While he and Esther played host and hostess to Los Angeles, it didn’t however, squelch his penchant for extramarital affairs. Soon Siegel found himself juggling two new mistresses: the actress Marie ‘the body’ McDonald and Wendy Barrie (with whom he proposed to and allegedly fathered a secret daughter).

But individually, the stars began to notice something perplexing about their elegant host. Bugsy made a habit of asking them for loans that he never repaid. 

One time, Siegel asked George Raft for $20,000 to invest in the offshore casino, the SS Rex. Raft was in between films and didn’t have the money – but he knew better than to say ‘no’ to Bugsy. The next day, he drove 140 miles to visit the producer, Myron Selznick at his summer home so he could ask for an advance on his next film. It wasn’t the first time Raft lent money to Siegel, and it wouldn’t be his last.  

In 1938, Siegel turned to his former bedfellow, the Countess Dorothy di Frasso to bankroll another one of his many get-rich-quick schemes. Di Frasso heard there was $90 million of buried treasure on Cocos Island, off the coast of Costa Rica, and the two lovebirds quickly assembled a motley crew of crooks and socialites (including Jean Harlow’s mobbed up stepfather) to board a schooner for an ill-fated treasured hunting trip to Central America. The passengers spent days cutting through the thick jungle and dynamiting hillsides in a fruitless search for it.

In another hare-brained scheme, di Frasso and Siegel tried to peddle a new explosive called ‘Atomite’ that they claimed had the same power as an atom bomb but detonated without sound or flash. Using her Italian connections, di Frasso pitched it to Mussolini, who immediately ordered $40,000 worth of explosive. They traveled to Italy in the spring of 1939 but when the bomb failed to detonate, Mussolini was furious. The dictator evicted di Frasso from her husband’s sumptuous villa (that had ceilings painted by Raphael) and announced that he had two important guests to install there: Hermann Göring, head of the German Luftwaffe anf Paul Joseph Goebbels, Hitler’s minister of propaganda. 

Countess Dorothy di Frasso (left) and George Raft were responsible for introducing Siegel to haute Hollywood. Raft later said of his friend: ‘Damned few people knew what made him tick. But I did. He came out here because he wanted to be somebody.’ In fact, Raft was surprised when Siegel suddenly appeared on the set of a film he was making with Marlene Dietrich. As soon as the director yelled ‘Cut!’ – Siegel, pulled out a 16-mm camera from his  briefcase to stage an impromptu screen test where he re-enacted Raft’s scene, having already memorized his lines and gestures to a tee

Marlene Dietrich (left) and Charles Boyer pose for a picture at one of Countess Dorothy di Frasso’s (right) legendary parties. Siegel met the madcap countess (who was ten years his senior) at the Santa Anita racetrack. Di Frasso had just ended her affair with Gary Cooper and saw Siegel as her next piece of arm candy. In exchange for his romantic affection, he was introduced to the most exclusive circles in Beverly Hills society

 Tainted by a round of bad press, Siegel was eager to leave Los Angeles and soon set his sights on Las Vegas. He saw potential for a grandiose ‘carpet casino’ more suited to Monte Carlo than the desert sands of Nevada. Everything was converging to make the opportunity possible: cars with air conditioning made the drive from Los Angeles bearable and planes began making direct flights from thousands of miles away and a way-weary generation was eager to have fun

Virginia Hall, was the mob moll turned failed actress who would end up being Bugsy Siegel’s final girlfriend before he was ambushed in her Beverly Hills home in 1947. Their volatile relationship was defined by fierce arguments followed by bouts of lovemaking. Her former boyfriend and patron, gangster Joe Epstein told Lanksy: ‘Once that girl is under your skin, it’s like a cancer. It’s incurable.’ Inevitably, she would have a role in Siegel’s undoing. ‘She would bring chaos into Ben Siegel’s life, and chaos, in the end, was what would kill him,’ said fellow mob boss, Joe Adonis

Remarkably, up until 1941, Siegel still had a clean police record, which was something he prided himself on. It wasn’t until that Fall when he was put on trial for the murder of Harry ‘Big Greenie’ Greenberg. 

The dapper mobster was given preferential treatment at the LA County Jail, where he had special hand-tailored uniforms with notched lapels that were made of a soft, high-quality denim. He was allowed to sleep on the prison doctor’s comfortable bed and use his private shower. According to Shnayerson, he got to order takeout food from local restaurants, including caviar and roast pheasant from Ciro’s. During his 49 day stint, Siegel was allowed to leave 19 times and entertain his latest paramour, the redhead bombshell from It’s a Small World, Wendy Barrie. Siegel was eventually acquitted after two state witnesses mysteriously, ‘disappeared.’

In 1944, he was arrested again for bookmaking alongside George Raft and Allen Smiley when the LA sheriff’s Vice Squad busted their gambling room at the Sunset Towers hotel. The details were enough to prompt Siegel’s expulsion from the Hillcrest Country Club. At school, his daughter was teased for having a gangster father by her classmate, the son of Edward G. Robinson. ‘Millicent was too hurt to be struck by the irony that her classmate’s father had become a star by emulating thugs,’ wrote Shnayerson.

Tainted by a rash of bad press, Siegel was eager to leave Los Angeles and start over somewhere new. He suddenly found himself persona non grata in Tinseltown. Las Vegas had a humble scattering of small sawdust and wagon-wheel style casinos that catered to the locals. And as WWII came to an end, Siegel saw the potential for a grandiose ‘carpet casino’ more suited to Monte Carlo than the desert sands of Nevada. 

‘Everything was converging: cars making the drive from Los Angeles in shorter time, and with air-conditioning; planes making direct flights from thousands of miles away; a war-weary generation eager for fun, the naughtier the better.’

There was one other reason. Her name? Virginia Hall, the mob moll turned failed actress and Bugsy Siegel’s final girlfriend that would be end up being instrumental in his undoing. ‘She would bring chaos into Ben Siegel’s life, and chaos, in the end, was what would kill him,’ said fellow wise guy, Joe Adonis.

Siegel’s marriage to Esther was all but over after she moved back to New York City having long tolerated his Hollywood flings, protracted absences, and humiliating public affair with Countess Dorothy di Frasso. Now, her husband made no attempt at hiding the relationship with his new girlfriend.

Virginia Hill was one of ten children who grew up in abject poverty in Alabama to a violent, alcoholic father and a mother who ran a boardinghouse. She eloped at 15 with the scion of a wealthy southern family before divorcing with a sizable settlement. At age 17, she left home for Chicago where she found work as a waitress (by some accounts) and a prostitute, by other accounts. It was there that she met Joe Epstein, a trusted associate of Al Capone who was rumored to be gay.

Epstein kept Hill around as his beard, lavishing her with absurd sums of money while she openly dated his fellow gangsters. Shnayerson quotes her brother Chick who recalled her returning to their small hometown ‘in a factory-fresh LaSalle convertible, with her beautiful legs in shimmering silk, a fur neck piece touching the new sheen of her hair, and more gems than a Reno pawnshop.’

After two more failed marriages, one to a football player and another to a Mexican rhumba dancer; Virginia headed to Hollywood where she finagled a screen test at Universal, then a seven-year contract thanks to her beguiling charm and glamorous good looks.  

She was a fixture of the Trocadero, the Mocambo, and the Brown Derby. She was spotted around town with the actor Errol Flynn before their fling ended in a drunken brawl with Hill reportedly screaming at Flynn and throwing a drink in his face.

With Epstein’s money to burn, Hill threw expensive dinners at Ciro’s, which earned her a spot in the local newspaper as ‘the film city’s most generous party giver.’ Another columnist, Hedda Hopper wrote that ‘she had the swingingest parties in town.’

Siegel was absolutely infatuated with Virginia Hill. He bought her fur coats, diamond necklaces and a house in Miami. They carried out their torrid affair at various trysting spots around the city; their favorite being a penthouse at the Chateau Marmont where she bathed in Chanel No. 5 anticipating his visit.

Their relationship was chaotic and passionate. Shnayerson says the screenwriter Edward Anhalt lived in in a room across from ‘Mr. and Mrs. James Hill’ at the Chateau Marmont and ‘heard not just lovemaking but fierce arguments that sometimes came to blows.’ 

Bea Sedway, wife of Bugsy’s longtime gambling manager Moe Sedway, confirmed the two often fought, and that Hill would hurl objects at her lover. But Hill assured Bea Sedway these rows always led to marvelous bouts of makeup sex.

After a quick profit-making turnover for the El Cortez, Siegel set his sights on a bigger Las Vegas project. He joined up with William Wilkerson, owner of The Hollywood Reporter and a successful string of Los Angeles nightclubs (such as Ciro’s and the Trocadero). 

Wilkerson originally purchased the 33 acres of desert that would eventually become ‘The Flamingo Hotel.’ But within a few months, Siegel coerced his business partner into selling all his stakes in the Flamingo under threat of death. He and his Syndicate backers officially became the casino’s sole owners.

The name was rumored to be inspired by Virginia Hill’s long flamingo-like legs, and Siegel imported live pink flamingos to dress up the place for its grand opening, only for the exotic birds to die in the desert heat. 

For Siegel, the Flamingo offered a chance at legitimacy, a way out of organized crime. The Syndicate backed his ambitious plan with a $1 million dollar loan, but quickly became unhappy with his superfluous spending and mismanagement of money in supervising the construction of the Flamingo Hotel. 

Increasingly, his relationship with Hill was becoming more turbulent. A jealous row which ended in her attempting suicide proved to be a turning point in their relationship. She went back to her home in Beverly Hills before fleeing to Paris for a raunchy getaway with Nicolas Feuillatte, a young heir to the Mumm’s Champagne fortune. 

Siegel was hemorrhaging money and spared no expense in building materials that were still rationed from WWII, he even arranged Lucky Luciano to ship marble from Italy (where he had been deported for running a prostitution ring). He envisioned a lavish temple of gambling on the grand scale of movie sets and mansions that he had seen in Hollywood. He racked up $3 million in costs before the hotel was even half finished.

He compounded a series of mistakes when he decided to open the unfinished casino early to compensate for some of the construction expenses. He chartered a train from Union Pacific and private plane to transport some of his celebrity friends from Hollywood to celebrate its grand opening over Christmas, 1947. 

But while his desert dream was supposed to build an invisible red carpeted bridge across the desert from Los Angeles to Las Vegas – instead nobody showed up.

Increasingly, his relationship with Hill was becoming more turbulent. She was in part to blame for the misguided decision to open the hotel early. Shnayerson explains that Hill had been sent a flaming orange-red $3,500 gown designed by couturier Howard Greer that was created especially for the occasion, and insisted on wearing it.

But when Bugsy kept returning with his begging bowl, for more money from his gangster pals, either to further his dreams, or, as they suspected fill his pockets, that’s when the Syndicate decided that Bugsy Siegel could no longer be trusted. The Flamingo’s expensive failure eventually cost him his life. 

His death warrant was ordered and signed by Lucky Luciano at a secret Syndicate meeting in Havana. There was nothing his loyal friend, Meyer Lanksy could do to stop it. 

Siegel’s time ran out on June 20, 1947. 

Back in LA, on the last day of his life, he indulged himself with a stop at Drucker’s hair salon for the usual works. He went to dinner with Virginia’s brother, Chick Hill, his girlfriend Jerri Mason and friend, Allen Smiley.

Bugsy, Chick and Jerri were staying at Virginia’s Beverly Hills mansion while she was away in Europe. When Siegel flipped on the living room lights, an overwhelming floral smell had stopped him in his tracks. Chick recalled his mother’s superstition: ‘When someone smells flowers and there aren’t any in the house, it means they’re going to die.’  

Chick and Jerri retired to their bedroom upstairs. Siegel sat down on the chintz couch to read the newspaper. Meanwhile, outside the house, an unseen figure set his .30-.30 carbine on the rose trellis and prepared to unleash a hail of bullets into the window at close range. Siegel was killed instantly.

He was buried in the Jewish section of the Hollywood Forever Cemetery, not far from his childhood idols, Rudolph Valentino and Douglas Fairbanks. They would be eventually be joined by Judy Garland, Marion Davies, and John Huston. 

44-years-later, Benjamin ‘Bugsy’ Siegel’s long delayed Hollywood dream would finally be fulfilled, but only in death when movie-heartthrob Warren Beatty portrayed the dashing gangster in his the 1991 biopic. At last, Bugsy had finally made it.  

Siegel had hoped the Flamingo would let him go legit. He originally quoted his mafia backers $1 million in construction costs that soared to $6 million. The project was hemorrhaging money and the gangster was unraveling at the seams. Mob bosses felt that he could no longer be trusted and signed his death warrant

Chick Hill (Virginia Hill’s younger brother) and his girlfriend Jerri Mason were with Bugsy Siegel in the house when he was assassinated. Above pictures them waiting at the police station to be questioned 

Benjamin ‘Bugsy’ Siegel was shot in the living room of his girlfriend’s house at 810 Linden Drive in Beverly Hills. Though it’s suspected to be a mob hit, the case remains unsolved

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