Capone’s Foes: Dean O’Banion
John Torrio’s most formidable foe was a peppery, diminutive Irishman named Dean O’Banion, the fearless, heedless leader of the North Side Gang. Though he was not the mad dog killer he is often made out to be, he personally dispatched upwards of 25 men: exponentially more than Capone ever did. Impulsive and not unusually intelligent, he was a street tough in the toughest neighborhoods of Chicago: one of William Randolph Heart’s head-crackers in Chicago’s newspaper wars, a petty thief, a burglar, and a singularly incompetent safe cracker, before — and even after — he became a racketeer.
But he was also a devout catholic and generous to his territory’s downtrodden, handing out cash and foodstuffs in much the same way the political bosses of the time distributed their largesse, and in the same manner Capone himself would adopt. Add to all that O’Banion’s charm, audacity, and Irish tenor, and you have a man who inspired deep devotion.
He was at least as prescient as Torrio about Prohibition’s potential for spawning a massively profitable criminal enterprise. While Torrio was still vainly begging his boss, Diamond Jim Colosimo, to go into the bootleg racket, O’Banion’s North Siders were already hijacking thousands of bottles and barrels of booze from trucks, trains, and warehouses. In fact, it was the North Siders’s rapid success that induced Torrio to knock off Colosimo and jump into bootlegging lest the North Siders overpower him.
For brains, he relied on his second-in-command. Clever, ruthless, Hymie Weiss was said to have been the only man Capone feared (though Wild Bill Lovett and Joey Aiello must have also kept him up at night.) What made him an especially dangerous adversary was that because he was dying of cancer, he had little or nothing to lose.
The North Side Gang wasn’t Irish — none of O’Banion’s successors were Hibernian — but its culture was. They were less disciplined than Torrio’s men. Even as O’Banion’s boys were raking in millions from Prohibition, they remained true to their penny-ante origins: mugging, burglarizing, and safecracking.
O’Banion oversaw a looser confederation than John Torrio. Anyone joining Torrio’s gang was in it for good or else. But the Irish and their allies could duck in and out of O’Banion’s service without reproach, let alone receiving a bullet to the back of their heads.
O’Banion hated Italians, especially the Sicilian Genna Brothers who dominated what was once his old neighborhood. He referred to Torrio himself as “that dago pimp.” To get his bootleg operation up and running, Torrio had turned to the Gennas and the gangs that vied for dominance in central Chicago to supply him with the raw materials he required: sugar, hops, alcohol, and a miscellany of extenders, some of them toxic.
Torrio took it upon himself to try to act as an arbitrator and guarantor of the confederacy he persuaded the others to join, including a half-hearted O’Banion. But he was unable to ease the rising tension between the reckless North Siders and the ambitious Gennas.
Suspecting Torrio of siding with the Gennas, he and Weiss hatched a plot to get rid of him. By now Torrio had already been convicted of bootlegging, for which he had paid a negligible fine, but O’Banion had never even been indicted. Armed with this intelligence, he met with Torrio at one of his breweries, announced he was retiring to the sticks, and offered to sell the brewery to Torrio for half a million dollars.
Rejoicing at the prospect of O’Banion’s withdrawal, Torrio agreed to O’Banion’s price. The next day he returned to the brewery to finalize the deal. But unbeknownst to Torrio, O’Banion had arranged that this second meeting coincide with a police raid. Stunned by a sudden invasion of boys in blue, initially Torrio did not suspect O’Banion of tricking him, since the Irishman, after all, had also been arrested.
But this being O’Banion’s first arrest for bootlegging, he only faced paying the same negligible fine Torrio had paid, whereas this being Torrio’s second bust, he faced doing time. Outraged, humiliated, Torrio and Capone swore vengeance, but, oddly enough, what stood in their way was a Sicilian: peaceable Mike Merlo, the head of the Unione Siciliana, who dismissed O’Banion’s treachery as an Irish prank.
Soon thereafter, Merlo conveniently died of cancer, to be replaced by Angelo Genna, who joined Torrio and Capone in a plot to exterminate the little Irishman, giving the contract to a couple of Sicilian gunmen and the redoubtable Frankie Yale, who agreed to do the job for his old Brooklyn pals albeit for $10,000.
Many a gangster employed legitimate businesses to shield themselves from scrutiny, but few were as conspicuous as Schofield Company, O’Banion’s flower shop, where the boss could be seen most mornings in an apron, preparing wedding bouquets and gangland funeral wreaths for all and sundry.
One November morning in 1924, three men turned up at O’Banion’s shop, ostensibly to fetch a large wreath. But when O’Banion put out his hand to greet them, the lead man would not let go, and as O’Banion struggled to reach for his pistol, they opened fire, killing him instantly.
Apparently, a great many other gangsters had a role in O’Banion’s assassination: the Gennas’ boys and Torrio’s men — possibly including Capone — blocked the streets with their cars, and, according to one witness, a woman drove the getaway car.
Torrio may have calculated that with O’Banion gone, a chastened Hymie Weiss would prove more reasonable. But, perhaps because he had never elicited the same deep loyalty that O’Banion did, Torrio underestimated the North Siders’ lethal grief. When word spread that Hymie and his boys were out to get him, Torrio pleaded guilty to bootlegging and sought the safety of a prison cell.
But two months after the hit on O’Banion, as Torrio was preparing to serve his one-year sentence, his successors gunned him down in the street. After a phenomenal recovery from multiple wounds, Torrio announced from prison that he was done with racketeering and left his criminal empire to Capone.
Copyright © 2018 by Andrew Ward. All rights reserved.
