To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City

The Plaid Zebra

The city of Chicago was home to some of America’s most notorious gangsters. The violence escalated with an all-out gang war between the North Side and the South Side. Names such as Dean O’Banion, Al Capone, Hymie Weiss, Johnny Torrio and many others became infamous around the city as they bootlegged and murdered their way to a fortune. However, the fates of a large majority of these gangsters served proof that ‘crime doesn’t pay.’ While Al Capone survived the bloody feuds of the 1920s and 1930s, he was one of the few major criminal figures that didn’t meet his maker at the point of a gun. In this piece, I look at 7 of the most notorious gangsters to live and die in Chicago.

1 – Dean O’Banion

Dean O’Banion was born in Illinois on July 8, 1892, and is considered as the first great gangster of Chicago’s North Side. Although the newspapers of the era spelled his first name as ‘Dion,’ he always used ‘Dean.’ His family moved to Chicago from the town of Maroa in 1901 after his mother died. The O’Banions settled in an Irish area called Kilgubbin, also known as ‘Little Hell’ due to the high level of crime. O’Banion was not only a violent gangster, but he was also an excellent singer and had a genuine love of floral arrangement.

Dean O Banion. Den of Geek

He joined the Little Hell gang as a youth and met Hymie Weiss, Vincent Drucci, and George Moran who would help him found the North Side Gang later in life. O’Banion was known for his mischievous sense of humor and regularly played jokes on his gang friends. He earned the name ‘gimpy’ after an accident where a car he was sitting on stalled and rolled backward. He fell, and the vehicle ran him over, and although he was lucky to survive, his left leg was one inch shorter than the right, so he walked with a limp until his death.

Like every other gangster, O’Banion began his criminal career with petty thieving. He served 3 months in a correctional facility in 1909 for stealing stamps, and in 1911, he received a short prison sentence for assault with a blackjack and possession of deadly weapons. Despite leading one of the city’s biggest gangs later in life, this was the last time he ever went to prison.

He started an extremely successful bootlegging operation in 1920 and earned up to $1 million a year selling liquor at his peak. His gang became known for committing major heists including the theft of $100,000 worth of Canadian whiskey and stealing 1,750 barrels of whiskey from Sibly Distillery. By now, O’Banion faced fierce competition from the South Side Gang led by Johnny Torrio.

O’Banion’s gang started to hijack the Genna Brothers’ liquor shipments, and in February 1924, he tried to frame Capone and Torrio for the murder of John Duffy, a North Side ‘hanger-on’. In fact, it was O’Banion’s crew who killed Duffy. The final straw for Torrio came when O’Banion sold his rights to the Sieben Brewery to the South Side Leader for $500,000. The police raided the brewery on the night of O’Banion’s last shipment and arrested him, Torrio and several others. O’Banion got off lightly as it was his first arrest for breaching Prohibition laws. Meanwhile, Torrio was indicted, and his one-time partner refused to give him the money back.

Torrio knew he had been double-crossed and ordered a hit on O’Banion. It transpired that the North Side Gang leader gained knowledge of the raid and used the information to steal from Torrio. On November 3, 1924, during a meeting with Al Capone and a few other important criminal figures, O’Banion refused to wipe out a debt owed by Angelo Genna as an act of good faith. Instead, he called Genna and demanded his money back. Mike Merlo and the Unione Siciliana refused to sanction the murder of O’Banion but when Merlo died on November 8, O’Banion’s days were numbered.

Torrio ordered the hit almost immediately after Merlo’s death, and on November 10, 1924, O’Banion was busy clipping chrysanthemums in his flower shop. His bodyguard was hung-over and was not available to protect his boss. Frankie Yale, Torrio and two of Capone’s gunmen entered the shop and shot O’Banion 6 times. He received a lavish funeral estimated to have cost over $100,000.