Charles Dean O'Banion: Part 1

The son of Irish immigrant Charles O'Banion, Charles Dean O'Banion (who crime writers often refer to as Dion) was born on July 8 1892 in Maroa Illinois. In 1901 his mother Emma died of tuberculosis and Charles Sr. took his two sons to Chicago. Dean's father, who was a painter by trade, brought the boys up in Chicago's Kilbubbin district, known as Little Hell because of it's high crime and unemployment rates. As a child, Dean attended the Holy Name Parochial School and served as an alter boy in the Catholic Holy Name Cathedral.

The Bloody Market Streeters were a gang of muggers and shoplifters who sold the Chicago Tribune. Anyone who refused to sell the Tribune exclusively became the target of the gang's assaults and vandalism. Dean O'Banion was a member of the Little Hell Gang, the youth branch of the Market Streeters. Through the gang, he met the three teenagers who would become his lifelong friends: Earl "Hymie" Weiss, Vincent "the Schemer" Drucci and George "Bugs" Moran.

Throughout his life, Dean always displayed a wild sense of humour. In his days as a Little Hell gangster, he enjoyed riding on the back bumper of the street cars. On one occasion, a car he was sitting on suddenly stalled and then rolled backwards. Dean was thrown to the ground and the car ran him over. In hospital, doctors were convinced that the unconscious boy would die, but he survived. However, his left leg was an inch shorter than before, and he walked with a limp for the rest of his life.

O'Banion left school at the age of 16 and worked in McGovern's Saloon and Café. Dean, apparently a superb tenor, was a singing waiter and took full advantage of this job by picking the pockets of the drunken customers. One of McGovern regular was Gene Geary, a psychopathic Irish gangster from the Canaryville section of Chicago, a place renowned for it's gunmen. Geary had his own brand of cigars that were forcibly sold to shopkeepers all over the city. He took the young O'Banion under his wing, giving him shooting lessons and advice on how to run criminal rackets. Dean was a dedicated student who spent much of his spare time on the roofs of Kilgubbin buildings, practicing his gunslinging skills on rats and pigeons with his friend Hymie Weiss. O'Banion and Geary remained friends right up until 1921 when Geary was diagnosed with homocidal mania and committed to an asylum. With Gene Geary as his role model, it is not surprising that O'Banion gained a reputation as one of Chicago's craziest gangsters.

O'Banion, Weiss, Drucci and Moran were so successful promoting the Chicago Tribune for the Bloody Market Streeters that they were recruited by newspaper racketeer Moses Annenberg. Annenberg offered them more money to compete against their old gang by selling the Chicago Examiner. Soon, the Examiner had a strong monopoly on newspaper sales in Kilgubbin. The four boys were also trained in the art of safecracking by Annenberg's friend Charles Reiser.

In 1909, O'Banion was arrested by a night watchman while stealing postage stamps from a drug store. This resulted in his first criminal conviction and he served a 3-month sentence for burglary in a house of correction. He also served a short prison sentence in 1911 for assault (with a blackjack) and possession of deadly weapons. This was the last prison sentence he ever received.

Annenberg appreciated that the abilities of his four underlings were wasted in the newspaper business, and he set them to work as political "sluggers" for the Democrat Party. They supported politicians by intimidating voters, stuffing ballot boxes and attacking opposition campaigners. The public soon recognized that Dean controlled the appointments of all ward bosses and aldermen in Chicago's Northside. At election time, people would sing "Who holds the 42nd and 43rd wards, O'Banion in his pistol pockets."

O'Banion's men also operated a car-jacking ring, and sold stolen cars to mechanic Sam "Nails" Morton. Morton then disguised the cars and sold them at his garage in Maxwell Street. But only with Prohibition did the real money come in. When the Northside Gang (as they were known) discovered that the government was banning alcohol, they set up bootleg breweries to supply the underground speakeasies with beer. Even before January 1920 when the Prohibition came into effect, the Northsiders were selling their tax-free product to Kilbubbin taverns.

On Febraury 5 1921, Dean married 18 year-old Viola Kaniff. According to Viola, he was a loyal and caring husband who never left home without telling her where he was going. The two were married at the Holy Name Cathedral on North State Street, and bought an apartment at 3600 North Pine Grove Avenue, in one of Chicago's more upmarket areas. He also made the effort to get a legitimate job, buying a half share in Schofields Flower Shop at 738 North State Street (opposite the Holy Name). Dean, who had a passion for flower arranging, worked long hours in the shop and often brought a bouquet home to his wife. Business-wise, sharing his shop with a gangster like O'Banion was one of the best things William Schofield ever did. Schofields supplied the flowers for just about every gangster funeral in Chicago (and during the Prohibition, such funerals were not infrequent). When a powerful crime figure died, local mobsters seemed to compete with each other over the size and quantity of their funeral wreaths, and this practice made for huge profits at Schofields. The flower shop also became the Northsiders headquarters, and was the place bartenders phoned when they wanted to order more beer or whisky.

Despite the fact that he now ran organized bootlegging and political rackets, Dean never gave up on old-fashioned theft. Police and historical records show that he was indicted four times in 1921; once in March (for burglary), twice in May (burglary and possession of burglary tools) and once in June (procuring explosives). He was never convicted on any of these charges. He is also credited with Chicago's first liquor hijacking. On December 19 1921, he spotted a truck on a whisky delivery round. The truck halted at a stop sign and O'Banion opportunistically drew his gun and jumped into the cab, pushing the driver out. He drove the truck to Morton's garage and made a few phone calls. Within 20 minutes, the whisky was sold.

After that first heist, hijacking became a major earner for the Northsiders, but it also got O'Banion in trouble. The biggest booze supplier at the time was Johnny Torrio, who had just taken over "Big Jim" Colosimo's Outfit and set up the new Chicago Crime Syndicate, a partnership between the main gang leaders in Chicago. Torrio and his lieutenant Al Capone met with O'Banion and Weiss to discuss the robberies. 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. As leader of the syndicate, Torrio received a portion of the profits from the other gangs, but in order to keep the peace, he was willing to make an exception in the case of the Northsiders. O'Banion agreed to join and to consolidate their new partnership, the two sides exchanged shares in each other's rackets. Torrio got shares in some of O'Banion's breweries, including 50% of the Sieben Brewery (probably the biggest one in the city). In return, O'Banion was brought in on some distilleries and gambling dens belonging to the Torrio Outfit.

With their new syndicate membership, the Northsiders carried on as before. O'Banion and his men continued to hijack trucks as opportunities arose, and the fact that some of them belonged to Torrio did not seem to matter. The casual nature of these heists is illustrated in a story regarding Dean and one of his men, Dan McCarthy. One morning in May 1922, the two gangsters were ordering breakfast at the Sherman Hotel when a bartender arrived from a speakeasy across the street. Dean always made it known that anyone who tipped him off about a potential hijacking target would receive 10% of the profits from the job. This bartender saw O'Banion enter the hotel and came to tell him that a shipment of whisky was westbound from a nearby truck depot.

O'Banion asked the waitress to hold their food while he and McCarthy rushed off to intercept the delivery. Having pulled off a successful hijacking they parked the stolen vehicle nearby, leaving thousands of dollars worth of cargo, and returned to the Sherman. Only when they had finished breakfast did they take their plunder to Morton's garage. The rig contained 5,400 pints of genuine American whisky, dating back from the early 1910s, before the Prohibition. "Nails" Morton bought the whole lot for $22,500.