Bugsy Siegel Murdered on the Threshold of a New Beginning

42 Min Read

Benjamin Siegel. Not Ben, as his friends used to call him. Not Mr Siegel, as he was called by people who were not close to him. And certainly not Bugsy Siegel, as his youthful companions began to call him because of his extreme violence and unpredictability. At the age of forty, Benjamin Siegel no longer wanted to be a glamorous gangster with money and power, he wanted respect and respect. But he could not escape the past. It caught up with him at the age of 41. Or maybe not, because to this day, almost 70 years after his death and 110 years after his birth, no one knows who fired the 9 bullets that hit him on 20 June 1947 and prevented him from enjoying the heyday of the Flamingo, the outrageously expensive luxury hotel and casino he had built in the Las Vegas desert.

There was no one at the funeral except his ex-wife Esther, his daughters Barbara and Millcence, his brother Mario, a prominent doctor, and his sister Bessie and brother-in-law, neither his mafia friends nor his Hollywood friends.

Suddenly, no one wanted to know about the man who was born to Austro-Hungarian immigrants in New York on 28 February 1906, and who suffered such poverty that he moved from school to the streets at the age of ten and started his own business at the age of twelve with the slightly older Moe Sedway.

The duo charged foreign drivers for security. Clearly, they didn’t want it. They were out of steam. One of them tried to drive them away. Ben lost patience. He took kerosene, poured it over the ciza, set it on fire and demanded money from the poor man. He got it and the deal.

Bugsy Siegel was a violent bed wick

He was so explosive that even his friends were wary of him. “When he went crazy, he was like a gun,” one of them recalled. He was as crazy as a bedbug or a bedbug, they said, and then they derived the nickname Bugsy Siegel from the English word bug.

For them it was a compliment, for him such an insult that no one dared utter it in front of his eyes, especially not years later. The nickname reminded him at first of a poor childhood he wanted to know nothing more about, and then of gangster exploits he would have preferred to forget, although he still reacted with physical violence when he heard the word Bugsy.

But even though he was completely out of control when he was young, he was a perfect match for Meyer Lansky, a Polish Jewish immigrant four years his senior, a reserved and educated Meyer Lansky. One had the fists, the other the brains, and they joined forces in the Bug and Meyer Mob.

They gambled, extorted and “protected” in lower East Side Manhattan, and made such a good living dealing alcohol during Prohibition that by 1931, when Ben was 25, he owned a choice Manhattan apartment, even as America was drowning in the Great Depression.

Soon they were linked up with other Mafia bosses, and the Syndicate was formed, which framed the activities of the various Mafia families, and Siegel is also said to have been a founding member of Murder Inc., or the Murderers’ Association, which, if it existed, was supposedly an association of professional killers.

There is no evidence that Siegel was a hired killer and that Lansky lent him out to other bosses. Nor is it clear how many people he actually killed. Some say 12, others say 30, others say more, but these figures do not include the murders he committed in collaboration and those in which he was “only” a client.

His daughter Millcence still doesn’t believe her father killed anyone, but in 1930 he met Lucky Luciano, his right-hand man Joe Adonis and, a little later, the gangster Joe Massario, only to find the latter lying dead.

He is said to have been involved in his murder, thus consolidating his position in the mafia world, and he is also firmly entrenched in Virginia Hill, a blonde mafia courier ten years his junior. It was not a mad passion he could resist. He was only interested in Virginia because she had just been with Joe Adonis and he wanted to take her away from him to settle some old grudge.

After a night that would not be repeated for the next decade, Virginia, then barely of age, declared that she had never had better sex, and Ben was so convinced that he was the best lover and generally wonderful. His self-absorption became almost as legendary as his alleged murders, except that no one remembered him as a model husband, even though in 1929 he married his youthful love Esther Krakower and had two daughters with her, then cheated on her whenever he had time.

But he was discreet about it. “Style is the only thing that counts in life. Style. Without style and choice, a man is nothing, he might as well be dead,” he explained. He was full of money, buying the most expensive clothes he could find, wearing tailor-made jackets and silk shirts.

He was scared to death that he was going to lose his hair. He lost his life before he lost his hair, but as long as he had it, he put every hair thinning product he could find on his head. Although he was not yet thirty, he would diligently treat his face at night with creams to keep his skin moist, whatever they were at the time, so that he would wake up in the morning looking youthful.

It did, but it did not wake up increasingly popular. By 1937, rumours began to circulate that rivals were going to clean it up. When he was told that he was the target of a hired assassin, he laughed out loud, convinced of his inviolability.

But he had to take law enforcement seriously. He was arrested for everything from possession of drugs and weapons to murder and rape, but was convicted only twice, in 1930 for gambling and breaking up and in 1944 for illegal horse betting. Both times he paid only the fine.

The hardest one was when he was arrested for the murder of Harry Greenberg. He was jailed without bail, but was allowed to order food from the best restaurants and party in the evening in his clothes in nightclubs, which the public prosecutor only found out from the newspapers. In the end, the charges were dropped because the witness died in unexplained circumstances.

He did not take care of it himself. He was now in the years of hiring other people to kill him and trying to make his sinister reputation disappear as quickly as possible. There were many stories about his temper. One said that his partner in the theft had cheated, and Bagsy had shot him four times. He was not very accurate, so the man survived, but he visited him in hospital and tried to poison him again.

Another story explains how a gambler was caught cheating at poker. He shot him three times, put the body back in the chair and shot him again when he didn’t bet when it was his turn.

One says that the killer threw a bomb down his chimney. The wounded Siegel reportedly went to hospital. He was admitted, but he sneaked out of his room, murdered the ineffective killer and sneaked back into his hospital bed. His alibi for that night was perfect.

But now he didn’t want to know any more about all this. When the New York police were breathing down his neck and he was threatening mob business, Meyer Lansky, his youthful friend, wedding witness, colleague and now boss, sent him from New York to the West Coast, to Los Angeles.

Hollywood, I’m coming!

He made no complaints. He had had enough of his mafia life, at 27 he wanted a fresh start. A life in which he would hang out with celebrities and maybe become one himself. He was convinced that he was more beautiful, more attractive and better than those people admired on the movie screens. His obsession with Hollywood was boundless, and his involvement in criminal business was equally boundless.

On the west coast of America, the New York Mafia slowly began to take over, and the Chicago Mafia collided with it. In the end, they agreed that the Chicago one would keep the unions and the film studios, while the New York one would get the prostitution, drugs and gambling. Even if the latter was illegal in California, business went on smoothly with a few bribes. The back rooms of the exclusive Los Angeles nightclubs were full, and so was the S.S. Rex, on which Siegel had set up a casino open 24 hours a day.

350 guests were entertained by an orchestra and guarded by armed security guards. Although the ship was not formally owned by the Mafia, the Mafia controlled it, and Siegel tried to attract ordinary people to it. Anyone who was prepared to believe that he was going to get rich overnight was welcome.

He later wanted to bring this model of operation to Las Vegas, and now, in the mid-1930s, he was trying to expand the telephone horse-betting network, which had previously been mainly run by the Chicago Mafia. They were extremely profitable. The Trans America Wire, for example, made a profit of eight million dollars a year, and it is true that Al Capone and the other Syndicate mafiosi also invested heavily in the telephone network. During the Second World War, their telephone lines reportedly broke down less frequently than those of the US Department of Defence.

Although Bugsy Siegel was also involved in drug smuggling from Mexico, nothing interested him as much as Hollywood. Immediately after arriving in Los Angeles, which was still relatively undeveloped at the time, he made contact with a youthful friend from Brooklyn, the now relatively well-known actor George Raft.

He started to visit him on shoots and once bet that he would have been a better actor than him if he had gone in front of the cameras alone. There were even rumours that he had gone on a test shoot, although this was unlikely because the film studios were controlled by his rivals and would never have allowed him to take part in a shoot.

However, as this was the era when gangsters were romanticised in films, Siegel, with his blue eyes, seductive smile and unmistakable style, easily won over one actor after another.

Jean Harlow was godmother to his daughter Millicent and a frequent guest in his 35-room Beverly Hills house, which was close to the homes of singer Bing Crosby and actors Judy Garland and Humphrey Bogart, with whom he enjoyed socialising.

In front of the house, he had a swimming pool made, 50 metres long and 25 metres wide, and next to the pool he built a changing house big enough for a family of five to live in. He brought his wife and two daughters from New York to live in this home, but few people knew about them because he kept them strictly hidden from the public. Almost no one knew what kind of father he was.

His daughter Millicent later recalled how spoilt she was while Daddy was still alive, and how he kept up to date with everything she and her sister were doing, even though he was often away. But when he was with them, he was “fun and joked a lot”.

He raised his daughters from a distance. In 1946, he discovered that Millicent smoked. He wrote to his ex-wife: “I don’t like her smoking at all, and I would suggest to her that smoking is not ladylike at all … Honestly, I hope she will stop smoking, because I don’t like it in women, and when I see her I will tell her just that.”

I will blow up Goering and Goebbels

That he counted singer Frank Sinatra among his friends is not surprising, because Sinatra was always on good terms with the Mafia, but Cary Grant also came to Ben’s house, and he partied with Lauren Bacall, had a fling with Hollywood siren Jean Harlow, reportedly fell in love with British actress Wendy Barrie, and had a great time with Countess Dorothy di Frasso, even though she was neither young nor beautiful, as were all his other female companions.

But she knew everyone worth knowing. While her husband was in Italy, she threw crazy parties, like a boxing match in her own backyard, and invited everyone who mattered. One by one, Benjamin Siegel met them, but they did not become his friends.

“If you show up in public with Ben Siegel, you’re going to be miserable. Suddenly nobody will want you in a film anymore”, for example George Raft warning actress Wendy Barrie not to get involved with him because she works for film studios controlled by a rival mafia.

The Countess di Frasso did not depend on her, but Siegel made her fear for the life of her husband and his family in Italy. Who would have known why, but in 1939 Bugsy Siegel agreed with the Countess to sell an experimental explosive to Benito Mussolini. They set off for Italy by boat, demonstrating that the explosive was more powerful than dynamite, and were completely burnt up in the demonstration.

Before they could return home from Rome, they were forced to meet Hermann Göring and Joseph Goebbels. Benjamin Siegel was Jewish. He announced to the Countess that he was going to blow them up, and she quickly played the family card, asking him to think how he would endanger the life of her husband and his family. He retreated, but later regretted it, saying he should have taken them out when he had the chance.

His relationship with the Countess was loosening, but that no longer mattered because a new woman, albeit an old acquaintance, had entered his life. One night almost a decade ago was enough to rekindle the passion between Ben and Virginia Hill.

For normal people it would have been exhausting: they hated each other, they fought, Virginia hit him in public and humiliated him in public, he did not oblige her, and the next moment they were back in bed, making it the longest relationship Siegel has had with his wife. It lasted until his death and, some believe, even cost him his life.

He and Virginia were also lovers on 7 December 1941, when the Japanese attacked Pearl Harbor and America entered the war. The Los Angeles area was flooded with crowds. Soldiers were on their way to the battlefields, new labour was pouring into the arms factories, and many were passing through Los Angeles. At 35, Ben was too old to enlist and decided to mind his own business.

In Los Angeles, they were no longer as profitable as they once were. Bribes were sky-high, the cost of telephone horse-betting was high, and Siegel, representing the New York Mafia, still refused to join forces with Joe Dragna, who represented the Chicago mob, even though the latter had been pressuring him for some time.

I dream a dream

Ben was looking for new paths. In California, gambling was illegal, as was prostitution. In neighbouring Nevada, there was no problem with either. And there, just over the California border, lay Las Vegas. It wasn’t much, but it was a gambling town in the middle of the desert.

The story goes that in the spring of 1945, Siegel called his youthful friend Mo Sedway and invited him for a walk. They drove straight into the desert. They were walking among the cacti when Ben announced out loud how he was going to build a prestigious hotel where everything Monte Carlo had to offer would be legal – great food, great entertainment, luxurious rooms and the kind of elegant surroundings that Americans can now only admire in the movies.

Another version says he was sent to Las Vegas by an old friend, Meyer Lansky, to see if building there would pay off.

The third tells of Siegel and other mafia investors buying the El Cortez club in Las Vegas at the end of 1945, but encountering resistance from the local mafia because of their mafia background. When Ben heard that someone was building a hotel just outside the city, but had run into financial difficulties, he went looking for him. It turned out that Billy Wilkerson, the drunken founder of the Hollywood Reporter, had invested a fortune in his hotel and hadn’t even managed to start building it yet. Ben bought a two-thirds share of the investment from him.

Now, he is obsessed with the idea of a luxury hotel with a casino. For him, it was not a promising business opportunity, but a way out of the underworld and into a world where he would finally be respected and revered. A new life, he believed, would come from a hotel with a casino, frequented by the city’s wealthy, dressed in tuxedos and evening gowns, wearing fine jewellery. Gambling would no longer be a pastime for ordinary people, but for the chosen few.

And it doesn’t matter that everything around is desert. Sooner or later, air travel would expand there and Las Vegas would get its own airport, he assured the would-be investors, who knew that it was about a five-hour drive from Los Angeles to Las Vegas and that there was not a single tourist attraction in the vicinity, apart from Hoover Dam.

Benjamin Siegel had to work hard to convince Meyer Lansky, Lucky Luciano and other mobsters to give him the money, because he didn’t have the $1.2 million the project was supposed to cost, but he did it.

And when he did, he hired a builder, Dale Webb, and started to make his dream come true. The only problem was, he had no idea what he was doing. He was a good criminal, but a completely shit entrepreneur. Now he wanted one thing, in five minutes he wanted another. Web was constantly adjusting his plans, which made the work drag on and, above all, irritating. He also had contractors wrapped around his finger, charging him dearly for shitty materials, which he had no way of knowing, even though he was supervising the construction himself.

He was spending more and more time in the desert, and he was getting more and more nervous. His mafia inverstitors were pressuring him, and he was pressuring them, to open his money bag even more. The 1.2 million dollars he had invested quickly disappeared. He needed a new injection of cash. And then another. And another.

It was slowly turning into a nervous wreck. He and Virginia Hill were still a couple, but she only moved to the desert if it was really necessary. She hated it, and was allergic to cacti. She was disgusted by the idea of the hotel being built at all and was not sympathetic to her lover’s plight.

Flamingo in red numbers

But as if wanting a wife and a mistress were not enough, in December 1945 his wife rebelled against him. She wanted a divorce. Siegel said no. True, it was hard to imagine him without the long-legged blonde at his side, but he was a traditionalist: a mistress included home, family and children. They had to stay.

But soon he could take no more. The hotel and Virginia had taken so much of his energy that he wanted to close at least one battlefield. He agreed to a divorce. He now devoted himself entirely to the hotel, which he named the Flamingo after Virginia. He called her the Flamingo because of her long legs, although he had not come up with the idea himself, but the Mexicans had had the idea when she was across the border.

The two-legged flamingo he drove somehow, the brick one he had problems with. He wanted to open it by the end of 1946. He had to. Costs were rising, there was no income, and there was no end in sight to the building work. Lucky Luciano was nervous, Meyer Lansky was pressing him. What was happening to their money?

They were all pretty much on the edge. Once, Del Webb, a builder, overheard Ben threatening to “take someone out”. He became nervous. Siegel noticed this. “Don’t worry, Del. We’re just killing each other,” Ben told him jokingly.

Even though he was a criminal, he had a reputation for honesty. But the costs were simply too high. Was he stealing money from his investors? Before the hotel was finished, he had swallowed up almost USD 7 million, which was unimaginably large. Many were convinced that he knew the world of crime too well to cheat, but on the other hand, he was so self-absorbed that he could believe in his own integrity.

In any case, all his thoughts were with the brick flamingo. He was so focused on it that he didn’t even want to deal with Joe Dragne, who still wanted to join forces on the telephone betting. He had dismissed him, convinced that he was still trusted in New York, but Frank Costello, who was now in charge of the Syndicate, was increasingly doubtful.

Virginia Hill also deepened the uncertainty. Ben didn’t know that she worked for the Chicago mafia and that the reason she ended up in his bed in the first place was because she was told to. Whatever her attitude towards him, what she found out, she told on.

The closer the opening day, 26 December 1946, got, the more she had to say. Siegel was once again left penniless, so actor George Raft had to lend him $100,000. On the big day, of course, everything went wrong.

Many rooms were unfinished, so guests had to sleep elsewhere. There was no silverware and no real glasses. It was raining cats and dogs, so many celebrities didn’t turn up, but Clark Gable, Judy Garland and Joan Crawford did, even though it was the day after Christmas. Siegel would have delayed the opening, but he couldn’t, because the casino had to start making a profit.

But in the first week, it recorded only losses. There were rumours that local bigwigs and the Chicago mafia were conspiring against him. The Flamingo, the only truly luxurious hotel among the ordinary, was blackballed by the public as a meeting place for potentially violent gangsters and should be avoided. They sent corrupt card dealers there and did what they could to keep the casino from flourishing.

After a disastrous first month, Siegel really had to close it down and now he could no longer reassure investors that all he needed was a little more time and a little more money. Meyer Lansky reportedly tried to defend him against the mafia bosses linked to the Syndicate, but even he did not have endless faith in him.

Doubting whether his financial affairs were really clean, he lent him a month to put things in order and fresh money to finish the work. In March 1947, he reopened the hotel. He hired 34-year-old Hank Greenspun to write a column about him and went into business.

It was better than the first time, but still not good. People were overcome with curiosity and wanted to see a gambling palace, complete with expensive furniture and sewage pipes leading into every room, but that wasn’t enough. March ended in the red and so did April. Only May was positive, but it came too late.

A mistress beaten and raped

Virginia Hill, who came to the hotel opening, has since returned to her rented house in Beverly Hills. Ben Siegel stayed in Los Angeles so that he could hop over to Las Vegas at any time. He was on the verge of a nervous breakdown. He was now at loggerheads with two of his old friends, Moe Sedway, the hotel’s bookkeeper of sorts, and Gus Greenbaum, who managed the El Cortez. In a bad moment, he fired Sedway and even banned him from the Flamingo.

Things got so out of hand that New York mob boss Frank Castello sent Lansky to Los Angeles to find out what was going on. Is Siegel stealing? No, he insisted again, he just needs a little more time. It was May, and Lansky once again took his side. Or so it seemed.

Ben Siegel went to see Virginia. They were in the garden when she started shouting at him. They had another crazy fight. She humiliated him and made fun of his manhood. Everybody could hear her, she was so loud. For the explosive Siegel, who was already at his wit’s end, it was a drop over the edge. He dragged her into the house, beat her badly and raped her.

Then he went to Las Vegas and she went to Chicago on 10 June 1947. He was just a stop on her way to Paris, where she flew on 16 June.

In Los Angeles, Siegel was turned against by his own bookmakers for insisting on paying double. They stood up to him. He had to admit to himself that the reins of business were slipping out of his hands.

On 20 June 1947, he arrived in Los Angeles and drove straight to Virginia Hill’s house. Whenever he was in the vicinity, he stayed with her. He didn’t mind that her 19-year-old brother Chick lived there with his girlfriend. He trusted him, so much so that he didn’t even mind that one of his teenage daughters was head over heels in love with him.

One version of the events of that day is that he met up with an old friend, Allan Smiley. He did not know that he was connected to the Chicago Mafia. They went for dinner and then drinks at the house.

Allan was to make sure that the curtains were open so that Siegel was sitting in the right place and reading the newspaper at the right time. At about 10.45 Smiley was to leave the room to get them drinks, and that is when the first shot was fired. Eight more shots were then fired from a military rifle.

One bullet pierced Siegel’s right cheekbone and exited on the left side of his neck. The other hit the bridge of his nose with such force that his left eye popped out. It actually flew 4.5 metres across the room. The next two bullets hit the body and the remaining five missed.

Twenty minutes later, Moe Sedway and Gus Greenbaum announced they were taking over at the Flamingo. They did not mention Ben’s death, but no one objected.

The police arrived at the scene and immediately concluded that it was a mafia clear-up. They photographed the body and the photos were leaked to the public. Benjamin Siegel, whose handsome face meant everything to him, died with his life completely shattered. A man who had hoped to become respectable ended up in the headlines as a common gangster, which he was.

The final blow was dealt posthumously when a photo of his corpse from the morgue was published. On the slip indicating the identity of the corpse, the surname was spelled wrong: Seigel instead of Siegel. Benjamin was once again a nobody.

The police did not bother to solve the murder, and they never did. Countless perpetrators came forward, but the police wrote them all off because they were just looking for attention. And theories about who killed him proliferated.

Who signed the death warrant?

One said he died of passion. The blue envelope he received shortly after beating and raping Virginia supposedly contained a warning not to treat women like that. According to this theory, he was put down by Virginia’s brother Chick.

There is no evidence for this, just as there is none for the claim that sex with Benjamin Siegel was just business for Virginia Hill, as some people believe. In any case, she attempted suicide 5 times in the 12 months after his death. Not once before that.

She lived for another 18 years. It was her biographer who introduced another possible killer, Eddie Cannizzaro. He was supposedly a mercenary of Joe Dragne, who at the time wanted the betting business by all means, but did not murder his rival on his own. He had allegedly obtained the approval of the New York Syndicate beforehand, and thus of Meyer Lansky. After the murder, Dragne truly regained the power he once had.

A third version says he was murdered by his own investors, convinced that he had robbed them. Even today, some believe that Ben put a little something in his own pocket.

Siegler’s daughter doubts that Lansky not only agreed to the murder, but even ordered it, as some believe. After his father’s death, Lansky helped the family a lot, although it is true that he was not present at the funeral, but no mafioso showed up.

There are more theories, but one of the most interesting is again a romantic one, but it is not about the love life of Benjamin Siegel, but of his friend Mo Sedway. He was a bachelor until, in 1935, at the age of 41, he fell in love with a belligerent teenage girl, 17-year-old Bee. She turned him around so much that he married her, but then he had other women and she lived the life she wanted.

In 1947, their family life was special: Moe, Bee and her lover Moose lived in the house. Bee fell in love and immediately asked her husband for a divorce. Instead of agreeing, he got together with his lover and made a deal: when he was in town, Bee would be his, when he was out of town, he could have her, and the three of them would live in the same house.

They were doing great, but relations between Bugsy Siegel and Sedway were going downhill. Bugsy was reportedly fed up with Moe reporting his every move to New York, so at a meeting in March 1947 he reportedly suggested that Moe be removed. He would dispose of the corpse, he reportedly explained, by dismembering it and mixing it with the hotel’s kitchen scraps.

He must have scared his allies a little, because Moe was his childhood friend after all. Moe got wind of the idea and Bee ordered her lover, two years her junior, a descendant of Yugoslav immigrants, not to move from her husband. Apparently, he had become his shadow.

But three months after the first meeting, there was to be a second, only this time they agreed to remove Bugsy Siegel. Meyer Lansky was also supposedly in favour, but demanded that no one from the “family” should be involved. Moose did not belong there, but he reportedly volunteered himself as the murderer. He knew how to shoot because he had hunted with his father.

So he was supposed to have chased Bugsy Siegel that day and then waited for him to relax in the house. When evening fell, he walked to the window frame and shot nine times. After the murder, he drove away quickly, stopping only in Santa Monica to dispose of the gun.

In the following days, Bee helped Esther and Ben’s daughters buy dresses for the funeral. She didn’t go.

As her husband Moe Sedway took control of Flamingo, he became the prime suspect. He was questioned several times but had nothing to say. Each time, he was taken home by Moose and Bee.

They lived in harmony until 1952, when Moe died of a heart attack. That same year, Moose fulfilled the promise he had made to him before he moved into his house: he married his widow and became a father to his son, who many believe was in fact Moose’s biological son.

Bee drank herself unconscious for a year after her husband’s death, then suddenly sobered up and stopped touching alcohol. She only told Bee that Bugsy Siegel’s killer was her second husband and that he had done it for her, even though everyone described him as a gentle soul, after everyone who could corroborate her story had died.

And so the mystery lives on, as do the many myths that have been woven around the name Benjamin Bugsy Siegel. His hotel is no more. In 1993, it was demolished and replaced by a new one with the same name. Las Vegas became the gambling mecca he dreamed of, although today it is probably too small for his taste.

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