Mobsters – History on some of the most infamous gangsters. (Part 2) ToT#008

Written by on October 9, 2017

This is part two of our two part series on Mobsters and the history of the most infamous gangsters. Last week we covered John Dillinger and Bonnie and Clyde. Today we will be discussing Al Capone and Bugsy Siegel. To listen to part 1, visit:

Bugsy Siegel


Ben Siegel was born on February 28,1906 in Brooklyn, New York to Jewish immigrants, and raised in the crime ridden Williamsburg. In 1918, Siegel became friends with Meyer Lansky and started the Bugs-Meyer Gang. This was a violent group of Jewish mobsters who ran a group of hitmen called Murder, Inc.


In 1920, a group of Italian mobsters across the country banded together to form the National Syndicate. Bugsy played a major role for the syndicate as a hitman.


In 1937, Siegel decided to take his rackets to the west coast. He found great success and wealth in California and became a prominent figure amongst the social elite.


He ended up marrying actress Virginia Hill and the two of them moved to Las Vegas with dreams of building a casino. They were able to do this via financial support from the eastern crime syndicate.


Bugsy had a budget of 1.5 million dollars to build his casino. The casino ended up costing over 6 million dollars. Once Meyer Lansky, now a major leader in the eastern crime syndicate, found out the overages were due to Siegel’s mismanagement he was furious.


On June 20, 1947, Bugsy Siegel was brutally murdered and three of Lansky’s men stormed into Siegel’s new hotel and claimed new ownership. Lansky denied any involvement but it widely assumed the eastern syndicate issued a hit on Bugsy Siegel.


Little-known facts about Bugsy Siegel


  1. Siegel became a gangster as a teenager
  2. He also hated his nickname. The name stemmed from kids saying he was “crazy as a bed bug”. He wanted to be called Ben.
  3. He was friends with many movie stars including Cary Grant, Frank Sinatra, and Jean Harlow
  4. He led a search for buried treasure in Costa Rica
  5. He was never convicted of a serious crime
  6. Tried to sell explosives to Benito Mussolini
    1. By far the strangest chapter in Siegel’s career unfolded in 1939, when he partnered with a Hollywood socialite named Countess Dorothy di Frasso in a scheme to peddle arms to the fascist Italian government. According to historian Larry Gragg, the deal centered on a newfangled explosive called atomite, which was supposedly more powerful than dynamite. Siegel and the Countess hoped to secure a contract to sell it to dictator Benito Mussolini, but their plan went up in smoke after the atomite failed to impress during a demonstration. Before they left Rome, the pair reportedly crossed paths with Adolf Hitler’s second-in-command, Hermann Göring, who was in town for an audience with Mussolini. Siegel, who was Jewish, would later quip that he wished he had assassinated the high-ranking Nazi when he had the chance.


His murder is still unsolved


Al Capone


Surprisingly, Al Capone came from a professional and respectable family.


Alphonzo Capone was born in New York City in 1899. His father and Mother were Italian immigrants who came over to America 1894.


He grew up in very poor housing new the Navy Yard. The neighborhoods proximity to these docks made it a breeding ground for illegal activity including drugs, alcohol, gambling, and violence. While this probably contributed to Capone’s future it was his school life that played the biggest role in shaping his future.


He attended a catholic school that made it common practice to mercilessly beat any children who stepped out of line. When he was 14 he fought back and hit a female teacher. He was expelled for this and never went back to school.


It was then that Capone met the man who would become his teacher and mentor in the world of crime, Johnny Torrio. Torrio always thought that racketeering should have a very respectable image as opposed to the then crude and violent culture. (Corporate Empire) Capone joined the James Street Boys gang which eventually became the Five Points Gang.


It was during this time in his youth that he earned his nickname, “Scarface”. He got into a bar fight with someone and had his left cheek slashed with a razor. The movie “Scarface” is loosely based off the life of Al Capone.


Torrio ended up moving to Chicago 1909 because the the brothel business was catching fire there. After he got his racket set up, he had Capone move to Chicago as well to help run it.


When prohibition began, a whole new business venture presented itself. With the bootlegging of alcohol, Torrio and Capone made a fortune off the people’s need for a drink during one of the most depressing era’s in American history.


In 1925, Torrio retired and Capone became Chicago’s new crime boss. He began gunning down rival crime bosses to expand his territory for gambling, prostitution and bootlegging.


When Chicago began to crack down hard on racketeering, Capone’s move was to move his base of operations into Cicero and infiltrate its local government. Cicero being a much smaller area made it easier to plant seeds of corruption. They were than able to continue their operations with less concern of law enforcement.


Capone prided himself in controlling his temper. That was until he learned about one his friends being attacked by low level gang member. His response to that? He shot him in the back of the head in the middle of public bar. There weren’t very many witnesses (either no one saw it or no one was brave enough to talk) so Capone got away with the murder. But the public violence he displayed gained him a lot more notoriety. For better or worse.


Capone’s next venture was to smuggle whiskey into Chicago from his connection in New York. This was man was named Frankie Yale and he was also the leader of a gang in New York called the Black Handers. Yale also owned a bar called the Adonis Social Club, and during the Christmas of 1925 Yale invited Capone to attend a party at the club. Word began to spread that Richard “Peg-Leg” Lonergan, the leader of a rival Irish gang known as the White Handers, would be crashing the party. A mass hit was planned by Capone to eliminate the White Handers’ leadership. This event is known as the Adonis Club Massacre. 5 people were killed. No one would talk to the police about it. (one guy survived)


The bootlegging of whiskey from New York was very successful and life was good for Capone. That is until a prosecutor by the name of Billy McSwiggin was killed the crossfire of a gang shootout. Capone was blamed for the incident but there wasn’t enough evidence to convict him. However, the public backlash from the violence was beginning to pick up steam and many people began calling for Capone’s head.


The police were trying to take Capone down but they never had enough evidence to charge him. So, they started to continually raid his brothels and gambling dens to try and cut into his profits.


The heat became hot enough for Capone to go into hiding for three months one summer. Realizing that he couldn’t hide forever, Capone made the gutsy decision to hand himself into the police in hope that they still hadn’t gathered enough evidence to charge him formally. He was accurate in those hopes and he was free to go.


Capone decided to meet with fellow gang leaders and mediate a peace treaty between them to stop the violence. Fewer acts of gang violence would make it easier for them to operate. Capone appeared untouchable.


In May of 1927, the Supreme Court ruled that bootleggers would be forced to pay income tax on their illegal bootlegging businesses. It wasn’t long until the Special Intelligence Unit under the lead of Elmer Irey of the IRS decided to go after Capone.


Capone was very careful with his purchases and almost exclusively dealt in cash. Except for one major purchase that he and his wife made in Miami when they bought the Palm Island Estate and began major renovations. This was proof of significant income for Capone and it peaked the interest of the IRS’ investigation.


Meanwhile, the gang violence started back up in Chicago, and Capone’s whiskey shipments were being hijacked. Capone quickly became suspicious of the Frankie Yale, his business partner, and had him gunned down with a tommy gun.


Capone was still having problems with another Chicago gang called the North Siders. Their leader, Bugs Moran, had been a rival of Capone’s for some time now and even tried to kill Capone’s friend Jack McGurn at one point.


On February 14th, 1929, seven members of the North Siders gang were shot down by four men in a parking garage. Two of the men were dressed as police officers and the other two were dressed in suits. Capone had worked with members of other local gangs to arrange a meetup to drop off stolen whisky for the North Siders gang and kill their leader, Bugs Moran. Moran was late leaving his hotel that morning and was spooked when they passed a cop car near the garage. It is most likely that the gunmen mistook one of the other victims for Moran and opened fire. This event is known as the St. Valentine’s Day Massacre.

(Frank Gusenberg questioned by police)


Emer Irey was still working on a case to bring Capone down. He managed to plant agents inside of the Capone’s organization to gather evidence against him. Eventually they had what they needed to try him in front of a jury. They managed to secure two former bookeepers from the Capone operation in police protection to testify on tax evasion.


At the same time, an agent named Eliot Ness, angered by the murder of a friend at the hand of Capone’s dealings, was able to uncover his illegal bootlegging operation. As a result of multiple prohibition violations, millions of dollars of brewing equipment was seized and thousands of gallons of alcohol was discarded.


The indictment for tax evasion would take precedent however. Capone and 68 gang members were indicted with over 5000 counts of tax evasion. Capone’s total alone was over $200,000.


Capone was close to making a plea deal, but public outrage was so high that the prosecutors took it off the table and went to trial.


The trial date was October 6th, 1931. Knowing that Capone had undoubtedly managed to bribe the jury, when the judge entered the chambers he immediately dismissed the jury and brought in a backup jury from another room that was sequestered under police protection for the entire trial. Capone and his lawyer were stunned.


Capone was found guilty of several counts of tax evasion and sentenced to 11 years in prison and $80,000 in fines and court costs.


In 1934 he was transferred from Atlanta to Alcatraz in San Francisco where he spent the rest of his time in isolation. His mind slowly began to deteriorate due to contracting tertiary syphilis. He was released after 6 ½ years for good behavior.


He died in his Palm Island Estate from cardiac arrest in 1947 at the age of 48.


Little know facts about Al Capone


  1. He hated his famous nickname. Only the press called him that.
  2. Capone’s gang earned $100 million annually
  3. He was never charged in connection with the St. Valentine’s Day Massacre
  4. Eliot Ness’ role in bringing down Capone is greatly exaggerated
  5. Capone was never convicted of murder
  6. He is among the first federal prisoners at Alcatraz
  7. He spent his final years in seclusion



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