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Charles Dion O’Banion

Gang Leader and Capone Rival

Charles Dion “Deanie” O’Banion

He was Al Capone’s toughest competitor in the latter’s struggle for power in Chicago, the gangster capital of the world. Even after he was assassinated in 1924 in a Capone–Johnny Torrio coup, O’Banion’s ghost continued to haunt Capone. O’Banion supporters, enraged by his murder, refused to give in and for the balance of the decade the carnage on Chicago streets reached unparalleled levels.

O’Banion had a kind of perverse charisma; he was as charming a psychopath as one could find. And he would do anything for a laugh. His sense of humor was legendary, although best appreciated by the criminal mind. Among his more innocent practical jokes was giving a friend Ex Lax and telling him it was sweet chocolate. Really thigh-slapping fun was his shotgun challenge. He would surreptitiously fill both barrels of a shotgun with hard-packed clay and then bet some friend or acquaintance that he could not hit the side of a barn some 30 feet away. With the money down, O’Banion made a ritual out of loading both barrels and handing the shotgun to the sucker. He moved back out of the way of the inevitable recoil as the patsy pulled the trigger. The backfire would cause him to lose an arm or an eye or even three-fourths of his face. Dear Deanie would still be howling about it the following day.

Chicago chief of police Morgan Collins labeled O’Banion “Chicago’s archcriminal” and said he killed at least 25 men. Others said Collins was less than half right, that O’Banion had at least 60 murders to his credit as he cheerfully made his appointed murder rounds, always with a rosary in his pocket and a carnation in his buttonhole. He also had three pistols tucked away in special pockets of his expensive made to order suits. For years O’Banion had been the darling of the Democrats for his skill at getting out the vote, until he switched to the Republicans at higher pay. The oftquoted joke of the time was: “Who’ll carry the Forty-second and Forty-third wards?” The answer was, “O’Banion, in his pistol pocket.”

O’Banion grew up in the Little Hell district on Chicago’s North Side. He lived a double life as an acolyte and choir boy at Holy Name Cathedral and as a street punk in a tenement jungle jammed with saloons and whorehouses. Thanks to his training in the church choir Deanie became a singing waiter in the tough dives on Clark and Erie. He brought tears to the customers’ eyes with sentimental Irish ballads, and when they were deep in their cups, he’d pick their pockets.

After-hours, O’Banion labored as a street mugger, becoming partners with a young Lou Greenberg, destined to become the multimillionaire owner of the Seneca Hotel on the city’s Gold Coast. One midnight, each without knowing the other was present, they had pounced on the same victim in an alley, and then over his prostrate body contemplated bashing the other for the loot. Instead, wisdom prevailed. They split the take and became partners. The arrangement continued for several months until in 1909 Deanie was imprisoned three months for robbery. In 1911 he did another three months for carrying concealed weapons. Although he was arrested many times thereafter, it was the last prison time O’Banion did in his life. He quickly learned that Chicago was the city of the fix and always spent the money required to cool the ardor of policemen, prosecutors and judges.

He graduated from street mugging to a form of journalism as a slugger for Maxie Annenberg, Moe Annenberg’s brother. Maxie at the time was in charge of promoting sales of the Chicago Tribune, and O’Banion was used mainly to bop newsdealers to convince them that the Trib was not only the world’s greatest newspaper but for their purposes Chicago’s only newspaper. Later on O’Banion transferred his loyalties to the newer Hearst papers in town. At the same time O’Banion learned the safecracking art under one of the racket’s foremost practitioners, Charlie “the Ox” Reiser. From Reiser he learned the theory that convictions were impossible without witnesses and dead witnesses made for terrible testimony. It didn’t always come to that. On one occasion an executive of Hearst’s American put up $5,000 bail to secure his release on a safecracking charge. There were newspapers to sell, after all.

George Clarence “Bugs” Moran

Henry Earl J. Wojciechowski aka Hymie Weiss

By the time Prohibition came, and with it the enormous new opportunities for criminals, O’Banion was the leader of a mighty gang on the North Side. Among the senior members were Bugs Moran, Hymie Weiss, Schemer Drucci (the only Italian O’Banion ever trusted and vice versa), Dapper Dan McCarthy, Two-Gun Alterie and Frank Gusenberg. The O’Banions, almost completely Irish in lowerlevel manpower, formed an alliance with many Jewish gangsters of the old 20th Ward, especially those working with Nails Morton, and the gangs more or less merged. When Morton was killed in a horseback riding accident, the grief-stricken O’Banions exacted the proper underworld revenge by executing the horse.

Vincent “The Schemer” Drucci

Frank Gusenberg

O’Banion’s approach to Prohibition, even before it went into effect, was to stockpile supplies by hijacking booze from legitimate sources. He tried to continue the same method when the 18th Amendment became effective. “Let Johnny Torrio make the stuff,” he was quoted. “I’ll steal what I want of it.” However, even a consummate thief like O’Banion could not steal enough to meet the needs on the North Side, and he started taking over some of the area’s top breweries and distilleries.

This switch in tactics removed a major source of conflict between the Torrio-Capone mob and the North Siders, although Torrio and Capone were deeply upset that O’Banion would not let them operate whorehouses in the North Side, which would have added millions to their income. Deanie’s religious inclinations simply would not allow dealing in bodies—although he seemed totally untroubled about filling bodies with lead. Still, if they won O’Banion’s forbearance about hijacking, Torrio was more than content to let the Irish keep the North Side.

Johnny Torrio

Torrio was more concerned with syndicating the booze and other rackets in the city so that the various elements could function without harassment from other gangs. Given the makeup of the various gangs, the concept in at least some cases bordered on the utopian. In the first place O’Banion couldn’t give up hijacking booze forever; the principles of stealing were too strongly ingrained in him. Then too the Terrible Gennas could not be controlled. A murderous Sicilian family, they had organized moonshining in Little Italy into a veritable cottage industry, with the manufacturing of bathtub booze the chief source of income for many families. Since such rotgut was produced so cheaply, the Gennas could and did invade other areas and undersell other bootleg gangs.

O’Banion for one was not going to stand for that. Neither would Torrio. The O’Banions and the Gennas believed in direct action and warred on each other. Torrio, more cunning than either of them, solved his problems by secretly helping Gennas knock off O’Banions and O’Banions knock off Gennas.

Then O’Banion pulled a swindle that victimized Torrio and caused him to lose face in the underworld. He informed Torrio he was quitting the rackets and was heading West as soon as he could sell off an illegal brewery for a half-million dollars. Torrio jumped at this opportunity to be rid of the unpredictable O’Banion and eagerly put up the money. Almost instantly after the deal was closed and Torrio took possession, federal agents swooped down and seized the brewery and charged Torrio with violation of the Prohibition law. Torrio discovered O’Banion had learned in advance of the upcoming raid and dumped off the property on Torrio. Even when Hymie Weiss, O’Banion’s loyal lieutenant, urged him to make amends to Torrio, the gang chief rejoiced contemptuously, “Oh, to hell with them Sicilians.”

Now all-out war was inevitable although Mike Merlo, a power in politics and the head of Unione Sicilana, the now bootlegger-corrupted fraternal organization, kept the peace for a time. Then in November Merlo died of natural causes and Torrio was free to act. O’Banion knew an attack was coming but figured his enemies would wait until Merlo was in the ground. He was wrong.

Deanie ran a florist shop on North State Street, directly opposite the church where he had once been a choir boy. The place was partly a dodge to provide him with a legitimate front, but it also satisfied his love for flowers. And O’Banion got a perverse joy out of making a small fortune from selling his blooms for the many gangland funerals. He did a land-office business for the Merlo affair, some of his creations selling for thousands of dollars. On the evening of November 9, he got a special order by telephone for a custom wreath to be picked up the following morning. At the appointed time three men appeared. “Hello, boys,” O’Banion greeted them. “You from Mike Merlo’s?”

The man in the middle nodded and grabbed O’Banion in a firm handshake. It was an old trick but O’Banion, given the solemnity of the occasion, fell for it. He could not escape the handshake and reach the guns he had on him at the time. The other two men pulled out guns and started firing. O’Banion took a bullet in each cheek, two through the throat at the larynx, and two in the right breast.

Albert Anselmi

John Scalise

They gave O’Banion one of the most flowerbedecked funerals Chicago had ever seen. Naturally the murder was never officially solved, although the killers were later identified as Albert Anselmi and John Scalise. The handshaker was Frankie Yale, a big-shot gangster imported from New York especially for the job by Torrio and Capone.

Francesco Ioele aka Frankie Yale

St. Valentine’s Day Massacre

The death of Deanie did not end the war, as the remaining O’Banions sought savage revenge for their chief’s death. Weiss and Drucci who in turn succeeded to leadership met lead-filled ends, and Johnny Torrio as well was nearly assassinated. Recovering from his nearfatal wounds, Torrio decided he’d had enough of Chicago and retired back to Brooklyn, taking $30 million with him in consolation. In the meantime Capone took charge and continued the war to win control of Chicago, masterminding the infamous St. Valentine’s Day Massacre which wiped out all the top North Siders except for Bugs Moran.

The importance of the fight with the O’Banions was that it kept Capone off-balance for years. He too thought of organizing crime nationally, but, unable to do what had to be done in Chicago, he was forced to leave that promising field open for the New York mobs under Lucky Luciano and Meyer Lansky.