
Dean “Dion” O’Banion was a feared prohibition-era mobster, head of Chicago’s North Side Gang. Like many gangsters, his fatal flaw was greed. With Johnny Torrio of the Chicago Outfit, and the Genna Brothers of Little Italy, he had agreed to a lucrative deal that gave him control of Chicago’s Gold Coast. But he was always pushing for more profit. He bullied his way into shares of Torrio’s action but after a while these concessions did not satisfy him.
With dollar signs in his eyes, he resorted to double-crossing his partner. O’Banion and Torrio co-owned a profitable enterprise called the Sieben Brewery. When O’Banion caught wind of a planned police raid he approached Torrio, not to warn him, but to sell his stake. Torrio, suspecting nothing amiss, paid half a million dollars—more than 4 million in today’s money—to buy O’Banion out. The day after O’Banion took delivery of the cash, police raided the brewery and Torrio himself was arrested.
Torrio was smart, and it didn’t take long for him to figure out he had been played for a fool. Infuriated, he finally gave into longstanding demands from the Genna Brothers to have O’Banion eliminated. O’Banion owned a North Side flower shop where he liked to work building floral arrangements, and on the morning of November 10, 1924, Torrio henchmen Frankie Yale, John Scalise and Albert Anselmi entered the shop
O’Banion stepped forward to greet Frankie Yale, and Yale clamped his hand on O’Banion’s like a vice to immobilize him, while Scalise and Anselmi each shot him once in the chest, the throat, and the face. The six gunshots killed O’Banion instantly, and the gunmen made their escape. Dion O’Banion was gone, but over the next five years his North Side Gang would fight a bloody war with the Southsiders that would end with the St. Valentine’s Day Massacre of 1929. On that day the North Side Gang lost again, and Chicago officially belonged to the Chicago Outfit, which was now headed not by Johnny Torrio, who had retired, but by his former lieutenant—a man named Al Capone. Chicago would never be the same.