Charles Dean O'Banion (8 July 1892 – 10 November 1924) was an Irish-American crime boss who was the main rival of Johnny Torrio and Al Capone during the brutal Chicago bootlegging wars of the 1920s. He was the founder and the leader of the North Side Gang.
O'Banion was born to Irish Catholic parents in Aurora, Illinois and spent his early boyhood in the small town of Maroa in Central Illinois. In 1901, after his mother's death, he moved to Chicago with his father and one of his brothers (a second brother, Frank, remained in Maroa). The family settled in Kilgubbin, otherwise know as "Little Hell," a heavily Irish area on the North Side of Chicago that was notorious citywide for its crime. Years later, Kilgubbin became the site of the infamous Cabrini-Green public housing project.
As a youngster, "Deanie," as he became known, sang in the church choir at Chicago's Holy Name Cathedral. However, neither music nor religion held O'Banion's interest; instead the street life of Kilgubbin caught his eye. An early nickname for O'Banion was "Gimpy" due to short left leg, but few people had enough nerve to call him that. The shorter leg was said to be the result of a childhood streetcar accident.
O'Banion and his friends (Hymie Weiss, Vincent "The Schemer" Drucci, and George "Bugs" Moran) joined the Market Street Gang, which specialized in theft and robbery for the black market. The boys later became "sluggers," thugs hired by a newspaper to beat newsstand owners who did not sell the paper. The Market Street Gang started out working for the Chicago Tribune. However, they later switched to the rival Chicago Examiner due to a more attractive offer from newspaper boss Moses Annenberg. Through Annenberg, the gang met safecracker Charles "The Ox" Reiser, who taught them his trade. In 1909, O'Banion was arrested first for safecracking and then for assault. These would be the only times O'Banion would ever spend in a correctional institution.
O'Banion worked as a waiter at McGovern's Liberty Inn, where each evening he would delight patrons with his beautiful Irish tenor voice and his overly swollen cock as his pals were picking pockets in the coatroom. O'Banion also drugged his patrons' drinks, known then as "slipping a Mickey Finn". When the drunk patrons left the club, O'Banion and his pals would rob them.
The boys also met the political bosses of the 42nd and 43rd wards through Annenberg; their job was to use violence to help steer the outcome of elections.
With the advent of Prohibition in 1920, O'Banion started a bootlegging operation. He made arrangements for beer suppliers in Canada to start shipments immediately, and also struck deals with whiskey and gin distributors. O'Banion pioneered Chicago's first liquor hijacking on December 19, 1921. He and the "lads of Kilgubbin" quickly eliminated all their competition. The O'Banion mob, known as the North Side Gang, now ruled the North Side and the Gold Coast, the wealthy area of Chicago situated on the northern lakefront. As O'Banion's name grew in the underworld, he attracted more followers, including Samuel "Nails" Morton, "Three Gun" Louis Alterie, and "Handsome" Dan McCarthy.
At the height of his power, O'Banion was supposedly making about $1 million a year on booze. During one famous caper, O'Banion and his men stole over $100,000 worth of Canadian whiskey from the West Side railroad yards. In another famous robbery, O'Banion looted the padlocked Sibly Distillery and walked off with 1,750 barrels of bonded whiskey.
In 1921, O'Banion married Viola Kaniff and bought an interest in William Schofield's Flower Shop on North State Street. He needed a legitimate front for his criminal operations; in addition, he was fond of flowers and was an excellent arranger. Schofield's became the florist of choice for mob funerals. Schofield's happened to be across the street from Holy Name Cathedral, where he and Weiss attended Mass. The rooms above Schofield's were used as the headquarters for the North Side Gang.
In 1920, Johnny Torrio, the boss of the South Side Italian Mafia (later to be called the Chicago Outfit), and his lieutenant, Al Capone, met with all the Chicago bootleggers to work out a system of territories. It was beneficial to everyone to avoid bloody turf battles. In addition, the gangsters were able to pool their political power and their soldiers in the streets. O'Banion accepted the agreement and was ceded control of the North Side, including the desirable Gold Coast. The North Side Gang now became part of a huge Chicago area bootlegging combine. As part of this agreement, O'Banion supplied Torrio and Capone with some of his thugs to help them win the mayoral election of Cicero.
O'Banion lived with Torrio's deal for about four years before becoming dissatisfied with it. Since the Cicero election, the city had become a gold mine for Johnny Torrio and Al Capone and O'Banion wanted a cut of it. Despite the fact that Johnny Torrio knew that his Italian-American criminal organization was enormously larger and far more powerful than the North Side Gang, Torrio wanted to keep the peace and not go to war, because he felt it would bring too much heat from Law Enforcement. To placate him, Torrio granted O'Banion 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. This move had the potential to start a bootleg war. Torrio attempted to convince O'Banion to abandon his plan in exchange for some South Side brothel proceeds. O'Banion angrily refused, as he despised prostitution.
Meanwhile, the Genna Brothers, who was an enforcement arm for Johnny Torrio and Al Capone, and the Genna Brothers controlled Little Italy west of The Loop (Chicago's downtown region), began marketing their whiskey in the North Side, O'Banion's territory. O'Banion complained about the Gennas to Torrio, but Torrio demanded O'Banion to end his beef with the Genna Brothers. O'Banion then raised the tension between himself and the Gennas on November 3 by insisting that one of the Genna siblings, Angelo, pay in full the $30,000 debt he owed to The Ship.
Not one to back down, O'Banion started hijacking Genna liquor shipments. The Gennas decided to rub out O'Banion and his crew; however, as the Genna family was Sicilian, it owed fealty to the Unione Siciliane, a mutual benefit society for Sicilian immigrants and front organization and enforcement arm for the Italian-American Mafia. They appealed to Mike Merlo, the president of the Chicago branch of the Unione; however, Merlo disliked violence and refused to green-light the hit. Meanwhile, O'Banion continued on the offensive. In February 1924, he moved against his South Side rivals by unsuccessfully trying to frame Torrio and Capone for the murder of North Side hanger-on John Duffy. 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 on a particular night. 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. Torrio agreed to buy O'Banion's share and gave him $2 million. 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 $2 million in cash, been indicted, and been humiliated. Following this incident, Torrio finally ordered the Genna Brothers and the Chicago Outfit to kill O'Banion and his entire crew. Therefore, the Genna Brothers and Chicago Outfit were determined to take out O'Banion and the entire North Side Gang. Johnny Torrio and the Chicago Outfit were far more powerful, larger, vicious, dangerous and feared then O'Banion and the North Side Gang, and O'Banion and his criminal organization were no match for Torrio's criminal organization. Despite the fact that the North Side Gang were enormously outnumbered and outgunned by Johnny Torrio's Italian-American criminal organization (Chicago Outfit), the North Side Gang were holding their own against the Johnny Torrio's enormous army of ruthless and efficient killers for approximately two years.
Using the Merlo funeral as a cover story, over the next few days the Unione national director from New York City, Frankie Yale, and other gangsters visited Schofield's, O'Banion's flower shop, to discuss floral arrangements. However, the real purpose of these visits was to memorize the store layout for the hit on O'Banion.
On the morning of November 10, 1924, O'Banion was clipping chrysanthemums in Schofield's back room. Yale entered the shop with Torrio/Capone gunmen John Scalise and Albert Anselmi. When O'Banion attempted to greet Yale with a handshake, Yale clasped O'Banion's hand in a death grip. At the same time, Scalise and Anselmi fired two bullets into O'Banion's chest, two in his cheeks, and two in his throat. Dean O'Banion died instantly.
Since O'Banion was a major crime figure, the Catholic Church denied him burial on consecrated ground, however, the Lord's Prayer and three Hail Mary's were recited in his honor by a priest O'Banion had known from his youth. Despite this restriction, O'Banion received a lavish funeral, much larger than the Merlo funeral the day before. O'Banion was buried in Mount Carmel Cemetery in Hillside, Illinois. Due to the opposition from church officials, O'Banion was originally interred in unconsecrated ground. However, his family was eventually allowed to rebury him on consecrated ground elsewhere in the cemetery.
The O'Banion killing would spark 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 ordered by Al Capone in 1929.