Dean O’Banion was born on July 8th, 1892 in Maroa Illinois. His father, Charles O’Banion was an Irish Immigrant. Charles was a house painter and took his family to Chicago and lived in a neighborhood known as Kilbubbin. Like Hell’s Kitchen in New York, it was called Little Hell because its poverty and crime. Dean attended the Holy Name Parochial School and served as an altar boy at the Catholic Holy Name Cathedral.

Dean O’Banion joined the Little Hell Gang. They sold newspapers and stole from stores and often mugged other residents. It was in this gang he met future fellow Chicago mob associates, Earl ‘Hymie’ Weiss, Vincent ‘the Schemer’ Drucci and George “Bugsy” Moran.

Dean O’Banion was always known as a wild child taking chances like riding on the back bumper of the street cars. Young Dean O’Banion was thrown to the ground by a sudden stop and the car ran over his leg. He survived but would walk with a limp because his left leg was an inch shorter than the other leg.

In his first encounter with the criminal justice system, a night watchman caught O’Banion stealing postage stamps from a drug store. The judge sentenced him to a 3-month term in a youth house of correction. This was the beginning of a life of crime, but he only served one more short term for assault and possession of deadly weapons. This was the last prison sentence he ever received.

When Prohibition began in 1920, O’Banion got in on the action and started his own bootlegging operation. He smuggled beer, whiskey and gin from Canada for distribution in Chicago.

As a cover for bootlegging and other criminal activities, he bought Schofields Flower Shop at 738 North State Street. Dean, found he liked flower arranging and actually worked in the shop. He had married a beautiful young girl, Viola Kaniff and brought home many bouquets.

O’Banion acted out his street gang roots when he conducted the first known hijacking of another bootlegger’s shipment of whiskey in 1921. He spotted the truckload of booze and jumped on the running board and took the driver hostage at gun point. He pushed the driver out and drove the truck to Morton’s garage. From there, he called other speakeasies and sold all the whiskey in 20 minutes.

As his reputation as an aggressive and feared gang leader grew, he became known as the leader of the O’Banion mob, also known as the North Side Gang. He attracted more gunmen as they realized he now ruled the North Side and the Gold Coast, the wealthy area of Chicago situated on the northern lake-front. Tough men like Louis ‘Three Gun’ Alterie, Samuel “Nails” Morton, and Dan “Handsome” McCarthy joined the North Side Gang.

He soon came into conflict with the Italian mob and their boss Johnny Torrio. The new Chicago Crime Syndicate wanted to control all other gangs in Chicago. Torrio and his lieutenant Al Capone met with O’Banion and Weiss to discuss recent hijackings of whiskey shipments. Torrio asked O’Banion to join the crime syndicate, which meant that O’Banion and the other syndicate members would have to respect each other’s territories and properties.

The usual method of operation for the Italian Syndicate was for all members to pay Torrio a portion of the profits for political protection and protection from other criminals. Johnny Torrio wanted to keep the Irish gangster inside their group and he even offered to make an exception in the case of the North Side gang and not require any tribute.  O’Banion agreed to join and to consolidate their new partnership, the two sides exchanged shares in each other’s businesses. Torrio got shares in some of O’Banion’s breweries and in return,