An Irish-American gangster, Dean O'Banion was a bootlegger and one of Al Capone's main rivals in Chicago.
Shortly after moving to Chicago from central Illinois, young O'Banion joined the Market Street Gang. The gang was hired by newspaper publishers to beat up any newsstand owner who didn't sell their papers. Later, O'Banion met the political bosses of the 42nd and 43rd wards, and was hired to help "influence" voters to steer the outcome of elections.
With the start of Prohibition in 1920, O'Banion launched a bootlegging operation. He made arrangements for beer deliveries from suppliers in Canada, and also cut deals with whiskey and gin distributors. O'Banion also stole alcohol from other bootleggers by hijacking their delivery trucks.
By eliminating his competition, O'Banion and his gang -- known at the North Side Gang -- ruled the North Side and the Gold Coast, the wealthiest areas of Chicago along Lake Michigan. At the height of his power, O'Banion was reportedly making about $1 million a year on the sale of booze.
In 1920, Johnny Torrio, the head of the predominantly Italian South Side mob (later known simply as "The Chicago Outfit"), and his lieutenant, Al Capone, met with all the Chicago bootleggers to divide the city into territories to avoid bloody turf battles. O'Banion accepted the agreement and was given control of the North Side and the Gold Coast. As part of the deal, O'Banion agreed to supply Torrio and Capone with some of his thugs to help them win the mayoral election of Cicero.
In 1921, O'Banion bought an interest in a flower shop on North State Street, across the street from the Holy Name Cathedral. Not only did he need a legitimate front for his criminal operations, but he was also quite fond of flowers, and his shop became the florist of choice for mob funerals, and the rooms above the shop were used as the headquarters for the North Side Gang. Whenever an organized crime figure was killed, etiquette demanded that his compatriots and his rivals -- even the killers -- spend thousands of dollars on floral tributes, usually at O'Banion's flower shop.
O'Banion lived with Torrio's deal for about three years before becoming dissatisfied. Following the Cicero election, the city had become a gold mine for the South Siders and O'Banion wanted a piece of the action. (Other bootleggers coveted O'Banion's turf, which included the wealthy, powerful and politically connected residents of the mansions along Lake Shore Drive.) To placate O'Banion, Torrio granted him some of Cicero's beer rights and a quarter-interest in a casino called The Ship. The enterprising O'Banion then convinced a number of speakeasies in other Chicago territories to move to his strip in Cicero, a move which had the potential to start a war among the bootleggers.
Meanwhile, the Genna brothers, who controlled Little Italy area west of Chicago's downtown, began marketing their whiskey in the North Side -- O'Banion's territory. O'Banion complained about the Gennas to Torrio, but Torrio did nothing. So O'Banion started hijacking Genna liquor shipments.
The tension among the gangs grew. The last straw for Torrio was O'Banion's treachery in the Sieben Brewery raid. Both O'Banion and Torrio held large stakes in the Sieben Brewery in Chicago. In May 1924, O'Banion learned that the police were planning to raid the brewery. Before the raid, O'Banion approached Torrio and told him he wanted to sell his share in the brewery, claiming that the Gennas scared him and he wanted to leave the rackets and retire to a ranch in Colorado. Torrio agreed to buy O'Banion's share and gave him half a million dollars. On the night of O'Banion's last shipment, the police swept into the brewery.
O'Banion, Torrio and numerous South Side gangsters were arrested. O'Banion got off easily because, unlike Torrio, he had no previous prohibition-related arrests. Torrio had to bail out himself and six associates, plus face later court charges with the possibility of jail time. O'Banion also refused to return the money Torrio had given him in the deal. Torrio soon realized he had been double-crossed. He had lost the brewery and $500,000 in cash, and had been humiliated. Torrio finally agreed to the Gennas' demand to kill O'Banion.
On the morning of Nov. 10, 1924, O'Banion was clipping chrysanthemums in the back room of his flower shop when three men entered. When O'Banion greeted them, one of the men grabbed his hand, and the other two pulled out guns and opened fire. O'Banion was shot six times and died instantly. O'Banion's murder was never solved, but the generally accepted theory is that the two shooters were members of the Chicago Outfit. O'Banion's death sparked a brutal five-year gang war between the North Side Gang and the Chicago Outfit that culminated in the killing of seven North Side Gang members in the St. Valentine's Day Massacre in 1929.
O'Banion was buried in Mount Carmel Cemetery in Hillside, in a $10,000 casket, and the funeral procession to Mount Carmel was a mile long, with 26 cars and trucks just to carry the flowers. An estimated 15,000 mourners came to the funeral service and burial, including the members of his North Side Gang, as well as Torrio; his top lieutenant, Al Capone; and the Genna brothers.
Even though O'Banion was a weekly visitor and a regular financial contributor to the Holy Name Cathedral, his grave was located in unconsecrated ground, as Cardinal Mundelein refused to allow such a notorious gangster to be buried among good Catholics. Five months later, his wife finally was able to move O'Banion's remains to the cemetery proper -- a few hundred feet from the Bishop's Mausoleum.
O'Banion's grave is marked with a tall obelisk, with a cross and the name "O'Banion" at the bottom.