Chicago is well known for the notoriously infamous Al Capone and his bootlegging syndicate during the Prohibition Era of the United States. Formerly working under crime boss Johnny Torrio who steps down after a fight with the North Side Gang in 1925 to give power to Capone, he expands the bootlegging business, adding onto the many gang wars and battles with police. It was before Al Capone’s rise and fall that Charles Dean O’Banion, popularly known as Dion (in the media), met his fate in which Johnny Torrio may or may not have had some part in.
With the arrival of alcohol prohibition in the 1920’s, O’Banion saw opportunity and organized a bootlegging operation. He started with arranging shipments of Canadian beer and acquiring whiskey and gin distributors. He gained notoriety in the crime underworld after he schemed Chicago’s first liquor hijacking in 1921. Eliminating all his opposition, O’Banion took control of the North Side and Gold Coast, becoming known as the North Side Gang. In his height he would be raking in 1 million a year, famously stealing 100k worth of Canadian Whiskey and 1,750 barrels of whiskey from Sibly Distillery. He would open up a flower shop where as to manage his criminal operations thereafter.
Johnny Torrio, heading the much larger Chicago Outfit with Al Capone at his side, divided up Chicago bootlegging territories among the gangs, leaving O’Banion satisfied with his side of the city, but not for long. O’Banion wanted cut of South Side action and was given some of Cicero’s beer rights and a casino called the Ship, but it was not enough for Dean. He aggravates a potential bootlegging war when he convinces South Side speakeasies to work on his strip. Tensions grew as the Genna Brothers of Little Italy in Chicago cross North Side boundaries and O’Banion steals from them, as Torrio does nothing about the problem. The Genna’s attempted to gain approval to place a hit on O’Banion but their crime boss Mike Merlo denied the request.
More so, O’Banion does more to create hostility towards himself leading up to his assassination. In 1924 after learning of a police raid on Sieben Brewery, where he and Torrio held investments in, O’Banion convinced Torrio to buy his share in the brewery. On the night of the raid, the two were arrested and Dean refused to return Torrio’s money, who learned he had been double crossed. Later that year O’Banion took a visit to Colorado, where he purchased a shipment of weapons, including some Thompson submachine guns. He would come back to Chicago but not long enough live and use his new toys on his enemies. However the first recorded use of the Tommy Gun in Chicago is credited to O’Banion’s purchases.
In November of 1924, Dean got into a heated argument with one of the Genna’s over the phone. He threatened Angelo Genna over a debt at the Ship, demanding he pay it within the week. However it was Al Capone that raised to waive the debt in professional courtesy before the phone call even happened. Genna held no more restraint after the insult and with Mike Merlo, who denied the hit earlier, out of the picture due to illness, the Genna’s were free to move on O’Banion. On November 10, Frankie Yale caught Dean clipping chrysanthemums in the back room of Schofield (O’Banions flower shop). As Frankie shook his hand, he held his grip firm and gunmen John Scalise and Albert Anselmi fired two bullets into O’Bannion’s chest and throat. One of them firing a final shot in the back of his head as he lay on the floor. He Is buried in Mount Carmel Cementary in Hillside, Illinois.