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. One time the street car stopped suddenly and Dean was thrown to the ground 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. A couple of years later when he was 19. O’Banion was arrested for assault with a blackjack. He was sentenced to a 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 into 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, O’Banion was bought in to some of Torrio’s distilleries and gambling dens.
Meanwhile, the Genna Brothers, who controlled Little Italy west of Chicago’s down town region, began marketing their whiskey in the O’Banion’s territory on the North Side. O’Banion complained about the Gennas to Torrio, but Torrio did nothing. It was not long before Torrio caught O’Banion cheating him out of a large sum of money, as much as ½ million dollars. O’Banion learned that the police were planning to raid The Sieben Brewery, a place O’Banion and Torrio owned jointly. Before the raid, O’Banion approached Torrio and told him he wanted to sell his share in the brewery. He claimed he wanted to leave the bootlegging racket. Torrio agreed to buy O’Banion’s share and gave him half a million dollars.
Shortly after the night of O’Banion’s last shipment, the police raided the brewery. They arrested Torrio who had to bail out himself along with six other associates. They all faced jail time while O’Banion was in the clear. Torrio demanded O’banion return the money and he refused. Torrio eventually realized he had been double-crossed. He had lost the brewery, $500,000 in cash, been indicted, and been humiliated. The Genna;s had wanted to kill O’banion for some time and Torrio had previously refused permission. After the brewery scam, Torrio finally agreed and granted permission to the Gennas’ earlier demand to kill O’Banion.
On November, the 3rd 1924 O’Banion sat in with Al Capone and other bosses like Frank Nitti, Frank Rio and others to tally the week’s profits. Nitti claimed that Angelo Genna had was short and had dropped a large amount of cash, plus a sizeable marker. Capone recommended that they cancel the marker as a professional courtesy. O’Banion refuseed to agree and called Genna demanding that he pay his debt within a week.
The Gennas sent a killer named 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 November 9th of 1924, O’Bannion got a telephone order for a custom wreath to be picked up the following morning.
On the morning of November 10, 1924, O’Banion was arranging chrysanthemums in the back room. His bodyguard, Louis Alterie, had claimed he was sick with a hangover and did not come to the flower shop that morning. Frankie Yale entered the shop with John Scalise and Albert Anselmi. “Hello, boys” greeted O’Banion, “You from Mike Merlo’s?” and stuck out his hand in greeting. Yale nodded and returned O’Banions handshake in a clasped 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.
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