Dean O’Banion

Born: July 8, 1892, Maroa, Illinois
Died: November 10, 1924, Chicago
Nicknames: Deanie, Dion, Chicago’s Arch Killer, Boss of the 42nd and 43rd Wards, Gimpy
Associations: North Side Gang, Al Capone, Bugs Moran, St. Valentine’s Day Massacre

Charles Dean O’Banion graduated from the violent newspaper wars of early 20th century Chicago to become the chief bootlegging rival of mobsters Al Capone and Johnny Torrio – a job description that turned out to be fatal.

After the death of his mother around 1900, O’Banion moved with his family to a North Side neighborhood populated largely by other Irish-Americans. The neighborhood, then known as Kilgubbin after an Irish place name and now called Goose Island, was notorious for its high crime rate, and O’Banion by all accounts fit easily into that environment. In his teens, he formed a street gang with three others from the neighborhood with whom he would continue to associate throughout his life: Earl “Hymie” Weiss, Vincent “The Schemer” Drucci and George “Bugs” Moran.

Chicago of the period was, according to Mayor “Big Bill” Thompson, a “wide open city.” Wide open for rackets such as prostitution and gambling, and wide open for violent competition among gangsters. Bombings and murder would be met with token official resistance but often would be settled by uneasy truces among the rivals.

The violence extended to the press. O’Banion and his friends were “sluggers” for, first, the Chicago Tribune and later for the Tribune’s rival, the Chicago Examiner. Sluggers would intimidate sellers and readers of the wrong newspaper. Although played for laughs in stage and film in productions such as The Front Page, the Chicago newspaper wars were quite violent and included lethal gunfights in saloons and on the streets.

In 1909, O’Banion was arrested and convicted for robbery and assault.

The newspapers wars were a good warm-up for O’Banion’s work as a bootlegger when Prohibition came into effect in 1920. Chicago, with its large population of immigrants from Ireland, Germany, Italy and Eastern Europe, was a town that loved its beer, wine and liquor. Almost from the start, O’Banion’s North Side Gang was at odds with the South Side outfit led at the time by Torrio.

About 1921, O’Banion and Torrio – who actively wanted peace with his rival – worked out a deal that seemed to satisfy both the South Side gangsters and O’Banion’s group. O’Banion not only kept the North Side and the Gold Coast, a wealthy neighborhood on Lake Michigan, but he even got a slice of Cicero, a suburb controlled by Torrio and Capone on the South Side of Chicago, and they all shared profits from a lakefront casino called The Ship.

But eventually the peace broke down. O’Banion was enraged by efforts of a third gang, the Genna brothers’ West Side Gang, to expand its bootlegging and rackets operations into his territory. The Gennas were allied with Torrio’s South Side gang. O’Banion sealed his fate when he refused to forgive a gambling debt that one of the Gennas had racked up at The Ship.

O’Banion was in his North Side flower shop, a front for his Mob activities, when a Torrio associate from New York, Frankie Yale, visited, hand outstretched in friendship. With him were two known gunmen from the Genna organization. A few minutes later, O’Banion was dead of gunshot wounds in his flower shop.

His funeral was the biggest anyone could remember, and among those attending were Al Capone and members of the South Side Gang. But there soon would be other funerals. The Beer Wars, as they became known, were just beginning.

Torrio would escape an assassination attempt in 1925 and turn over his operation to Capone, the greatest gangster of all. O’Banion’s friend and conspirator Hymie Weiss, who was fingered as one of those who tried to kill Torrio, was gunned down in 1926. In 1929, in an effort to put the North Side Gang led then by Bugs Moran down for good, seven of the North Side mobsters were killed in the infamous St. Valentine’s Day Massacre, but Moran would survive through the end of Prohibition in 1933.