Charles Dean O'Banion (July 8, 1892 – November 10, 1924) was an American mobster who was the main rival of Johnny Torrio and Al Capone during the brutal Chicago bootlegging wars of the 1920s.

He led the North Side Gang until 1924, when he was shot and killed, reportedly by Frankie Yale, John Scalise and Albert Anselmi.

The family settled in Kilgubbin, otherwise known as, "Little Hell," a heavily Irish area on the North Side of Chicago that was notorious citywide for its crime.

However, they later switched to the rival Chicago Examiner due to a more attractive offer from newspaper boss Moses Annenberg.

O'Banion worked as a waiter at McGovern's Liberty Inn, where each evening he would delight patrons with his beautiful Irish tenor voice as his pals were picking pockets in the coatroom.

In December 1919, shortly before Prohibition came into effect, O'Banion was walking down Chicago Street when he came across a parked liquor truck.

He arranged for beer suppliers in Canada to start shipments immediately, and also struck deals with whiskey and gin distributors.

As O'Banion's name grew in the underworld, he attracted more followers, including Samuel "Nails" Morton, Louis "Two Gun" Alterie, and "Handsome" Dan McCarthy.

During one famous caper, O'Banion and his men stole over $100,000 worth of Canadian whiskey from the West Side railroad yards.

Since a recent election in neighboring Cicero, Illinois, the city had become a gold mine for the South Siders and O'Banion wanted a cut of it.

To placate him, Torrio granted O'Banion some of Cicero's beer rights and a quarter-interest in a casino called The Ship.

Torrio attempted to convince O'Banion to abandon his plan in exchange for some South Side brothel proceeds.

Meanwhile, the Genna Brothers, who controlled Little Italy west of The Loop (Chicago's downtown region), began marketing their whiskey in the North Side, O'Banion's territory.

The subsequent investigation brought unwanted attention from law enforcement on the club, as it was a source of illegal gambling, prostitution and bootlegging.

Nevertheless, Torrio was willing to overlook this insult in order to maintain peace in the Chicago underworld, until O'Banion himself made the situation irretrievable later that year.

During the summer of 1924, O'Banion and his wife Viola took a long vacation at the Colorado dude ranch of his henchman Louis Alterie.

On his way back to Chicago, O'Banion purchased a large supply of weapons in Denver, including three Thompson submachine guns, or "baby machine guns", as they were referred to in a local newspaper (At the time, the manufacturer, the Auto-Ordnance Company, was advertising the weapon to ranchers as a means of dealing with animal predators, which clearly brought it to the attention of O'Banion.).

McErlane used this Thompson in an unsuccessful attempt to kill Spike O'Donnell in September 1925 in what is believed to have been the first recorded use of a "Tommy gun" in Chicago's history.

Their disagreement concerned a debt Genna had incurred at The Ship, the casino that the North Side gang boss owned a piece of along with the Chicago Outfit.

Using the Merlo funeral as a cover story, over the next few days Brooklyn gangster Frankie Yale and others visited Schofield's, O'Banion's flower shop, to discuss floral arrangements.

Since O'Banion was a major organized crime figure, the Archdiocese of Chicago denied him burial in consecrated ground.

In the early years of the "Public Enemy" era, Dean O'Banion and other Irish mobsters of the previous decade served as the basis for many gangster films of the 1930s.

James Cagney, for example, based his character on O'Banion and his lieutenant Earl "Hymie" Weiss in the 1931 film The Public Enemy.

[5] Seasons 3 and 4 of the HBO series Boardwalk Empire featured a fictional version of O'Banion, portrayed by Arron Shiver.

O'Banion's twin careers as a florist and Chicago gangster is reflected in the character of Giuseppe Givola in Bertolt Brecht's play The Resistible Rise of Arturo Ui.