In October 1931, Al Capone went to prison for tax evasion. Capone’s name is synonymous with Prohibition and mob rule in Chicago. But Capone was no ordinary thug.

1) Al Capone was born in Brooklyn

Even though he later ruled Chicago, Capone was involved with New York gangs starting at an early age and only moved to Chicago in his early twenties. He became head of the Chicago Outfit in 1923, a full four years after Prohibition began.

2) Capone’s older brother was a Prohibition agent in Nebraska

When people realized the brother’s connection to the most notorious criminal in Chicago, he was forced to resign his post.

3) Capone’s nickname was “Scarface” and he hated it

The scar on his face was the result of a bar fight with Frank Gallucio, after Capone insulted Gallucio’s sister. Capone later hired Gallucio as a bodyguard. In order to hide the scar, Capone almost always posed in profile for pictures.

4) At one point, Capone had as many as 10,000 people on his payroll

This included Chicago Mayor Bill Thompson (1927-1931). Capone paid off Mayor Thompson to assure that Capone and the Outfit could operate without legal intrusion. The Outfit not only smuggled liquor, but also ran illegal casinos, gambling games, and prostitution rings.

5) Capone’s favorite club was the Green Mill

This jazz club, still in operation today on Chicago’s north side, was supposedly Capone’s favorite hangout. Catch the right bartender on the right night and they may even show you the trap door behind the bar that Capone supposedly used to get out safely when he got the tip that the cops were on the way.

6) Capone thought of himself as a modern day “Robin Hood”

When the Outfit’s rival gang, the North Side Gang, led by Bugs Moran, attempted to assassinate Capone while he lunched at the Hawthorne Hotel in what might have been history’s first “drive-by shooting,” they sprayed the front of the building and its large picture window with bullets from their Tommy Guns. Capone escaped unscathed but a number of innocent bystanders were injured. Capone paid for all of their medical care.

7) Bugs Moran thought Capone was a “lowlife”

Moran, an Irish Catholic, claimed he was a better Catholic than the Italian Capone because Moran refused to run brothels, while Capone operated and visited them regularly.

8) Capone was far wealthier than any true Robin Hood would have been

Capone himself profited over $60 million on alcohol sales alone in 1927.

9) Capone was never busted for bootlegging or smuggling liquor

The federal government finally nabbed Capone on federal tax evasion in 1931. Federal income tax was made constitutional in 1913 by the Sixteenth Amendment and Congress promptly passed such a tax. In fact, Prohibition never would have been ratified if the Sixteenth Amendment had not become law: the vast majority of the operating budget of the U.S. government prior to the Sixteenth Amendment was from alcohol taxes. In order to pass Prohibition, the supporters of the movement first had to ensure that the government had another way to make money.

Capone’s defense team essentially argued that since Capone had made his money illegally, he shouldn’t have to pay federal income tax on it. The court didn’t buy that excuse. Capone was sent to Alcatraz in October 1931 and wasn’t paroled until 1939, six years after the end of Prohibition.

10) Capone died from complications of syphilis

Capone probably contracted syphilis as a teenager and was never treated. Soon after he was let out of jail, his health began deteriorating quickly. In 1946 his doctor announced that Capone had the brain function of a 12 year old. He went on crazy rants about Communists and foreigners and he was convinced that Bugs Moran was still trying to kill him. Meanwhile, Moran was in an Ohio penitentiary for robbing a bank messenger of $10,000.

11) Capone is buried in Mount Carmel Cemetery

That’s just outside of Chicago in the town of Hillside. Moran was released from prison in 1956 but a few months later he was arrested for bank robbery and sent to Leavenworth. He died less than two months later of lung cancer and was buried in the pauper’s grave at the prison.