Bugsy Siegel - Mobster, Timeline and Personal Life

Benjamin Siegel was born on January 28, 1906, in Brooklyn, New York, into a poor Jewish family. They had immigrated from the present day Ukraine, then a part of Soviet Russia. Many other reports, however, trace his real origin to Austria.

His father, Max, and mother, Jennie, did some odd jobs to make enough money to survive and Siegel hated the life he was leading. He was the second of his parents’ five children, and the most fearless. He wanted to make big in life at any cost. His neighbourhood, infested with anti-social elements and constantly warring Italian and Irish gang, further pushed him into the world of crime.

Influenced by the neighbourhood criminals’ aura and authority, Benjamin decided to follow the same route. He started small with extorting money from the peddlers. In 1918, he came in touch with a hooligan Meyer Lansky. Bugsy and Meyer started their own gang and indulged in robbery, loots, and murders, and slowly grew their influence on local populace.

He famously hated his nickname ‘Bugsy,’ which was bestowed on him owing to the fact that he was short tempered and highly intuitive, ‘like a bedbug.’ He reportedly threatened everybody who called him by his nickname.

In the early 20’s, Italian mobster Charles ‘Lucky’ Luciano gathered the small scattered Italian gangs and started his own syndicate. By then, Bugsy had become a feared man in the streets of Brooklyn and hence, he secured for himself a place in the syndicate. Thus started his small but powerful era as one of the most dominant and feared gangsters in American organized crime history.

Bugsy joined hands with Frank Costello and Luciano, and took the charge of killing the mobster Joe ‘the boss’ Masseria. He is believed to be one of the four hitmen, who showered Joe with bullets in 1931. Salvatore Maranzano was another one of their targets and slowly, Luciano managed to kill all his rival gang members, which marked the beginning of the modern day American organized crime scene.

Subsequently, the National Crime Syndicate was formed, followed by ‘The Commission,’ which was set up to bring an end to the warring gangs. All the territories were divided so that no gang interferes into the operation of others. Siegel laid the foundation of Murder Inc. and continued working as a hitman. He kept evading the law, and the only time he was convicted was in Miami.

In 1932, Bugsy had a tussle with the notorious Fabrizzo Brothers, who attempted to get him murdered. Lansky and Bugsy hunted down the Fabrizzo brothers. As a result of this killing, the third Fabrizzo brother, Tony, went to the authorities and exposed the Murder Inc., which Siegel was running across the country. Siegel made an intricate plan and killed Tony, and had an alibi ready for him beforehand. In the mid-30s, he got the loan shark, Louis and Joseph Amberg, murdered.

By now, Siegel had come to realise that his life wasn’t safe anymore and he had to find a safe hideout. He chose California for his safe hideout. He collaborated with the local boss Jack Dragna and together they started gambling rackets. He brought his family along with him and started working towards establishing a wide gambling network. Boss Dragna had received special ‘messages’ to cooperate with Siegel and he did as he was told.

Siegel’s wealth, power and influence had grown immensely, and he started to hang out with Hollywood film elites. He was known to be friends with actors Gary Cooper, Clark Gable, and Cary Grant, and the studio executive Louis B. Mayer. His influence grew so much that he got the famous actress Jean Harlow to be his daughter’s godmother.

He also had romantic relationships with several actors. One of his affairs even took him to Italy where he befriended Mussolini and offered to sell him weapons. In late 30s, he went to Germany and met up with Nazi Germany’s Joseph Goebbels and Herman Goring, but he did not like them and even offered to kill them on contract.

He also extorted money from Hollywood stars and studios. It is said that he loaned more than $400,000 from actors and never paid them back, and nobody ever asked. He also forced the studios to pay him, as he would get the unions to go on strikes so that the work was stopped until Siegel’s demands were met. He was a feared man and nobody wanted a tussle with him.

In November 1939, Bugsy planned the murder of Harry Greenberg and shot him dead outside his house. Harry was a danger to the syndicate as he had threatened to call their racket off in front of the authorities. Albert Tannenbaum was one of the accused and he decided to testify against Siegel.

Siegel was taken in police custody and his detention made headlines as he was given a better treatment than other inmates. He refused to eat the prison food and was even allowed female visitors. In 1942, Siegel was finally acquitted due to the lack of sufficient evidence. For the next few years, Siegel was arrested many times, but he was acquitted every time.

In 1945, he finally decided to have a more conservative route and invested in Flamingo Hotel but he couldn’t keep it that way for long. The syndicate interference took place and in no time, Flamingo Hotel became a syndicate owned gambling centre.

In the mid-40s, Siegel lost almost all his money to gambling and luxury living. His chest puffing was slowly draining his bank accounts and even his previous reputation as a feared contract killer could not rescue him. Within no time, he was knee deep into debts.

The syndicate started asking for the returns on their investments, but Siegel wasn’t able to return it right away. He promised to pay them back in sometime and the bosses didn’t push him as he used to be a valuable man. Amidst all this, one thing became clear - Bugsy’s reign was over!

On June 20, 1947, Bugsy was sitting with his business associate Allen Smiley in his Beverly Hills’ home when he was attacked with a revolver. He took many bullets, including two in the head and died on the spot. The murder mystery of Bugsy Siegel remained officially unsolved.

Bugsy Siegel got married to his childhood girlfriend, Esta Krawoker, on January 28, 1929. Siegel was a notorious womanizer so the couple had problems from their initial days. Esta finally got the divorce in 1946 and left California with her daughters and got settled in New York.

Despite his notoriety as a dreaded gangster, there was a softer side to Bugsy. He gave quite a lot of money to charity and several witnesses claim that he came across as a kind hearted man to average people and said that ‘they only kill each other,’ meaning seldom do the gangsters like him harm the commoners.