On a raw November morning in 1924, a lengthy funeral procession moved with stately dignity along Chicago’s North Wells Street. People surged along the sidewalks and peered from rooftops, straining to catch a glimpse of the passing cortege. Inside the hearse, a $10,000 silver and bronze casket bore the remains of one of the city’s most well-known and flamboyant individuals. During the three days the body had been available for viewing, some forty thousand visitors had filed through the Sbarbaro funeral home, which overflowed with twenty-six carloads of flowers. By the time the procession reached the Mount Carmel Cemetery, in suburban Hillside, an estimated fifteen thousand people had assembled to witness the graveside service.1
From such impressive numbers, strangers to Chicago might have assumed that the deceased had been an honored member of society—a philanthropist, perhaps, or maybe a high-ranking member of the clergy or revered public servant. They would have been wrong.
The massive crowd of Chicagoans had turned out to mourn—or secretly gloat over—the death of Charles Dean O’Banion, a kingpin in the local underworld. Before mob boss Al Capone rose to power, the short, chubby Irish American known variously as Dean, Deanie, or Dion O’Banion held sway over criminal activities throughout the city’s northeastern neighborhoods. His North Side Gang kept the illegal beer and whiskey flowing during the early years of Prohibition. A paradoxical figure, O’Banion was normally jovial and outgoing, yet he packed three “gats” in his expensive three-piece suits and was linked to the deaths of twenty-five men. The chief of police called him “Chicago’s arch criminal.”2 (In the 1931 film The Public Enemy, the jaunty mobster was a model for the character played by James Cagney—the menacing Tom Powers, a sneering psycho who famously smashes a grapefruit in his girlfriend’s face.)3
Like many a gangster, O’Banion possessed the potentially fatal traits of hubris and ambition. On November 10, 1924, he was gunned down after repeated run-ins with his rivals. His murder set off the brutal “beer wars” that plagued Chicago for the remainder of the 1920s, climaxing in the gory St. Valentine’s Day Massacre in 1929, when Al Capone’s gunsels brazenly executed seven men associated with the North Side Gang. Hundreds of Chicago mobsters died during those violent years, but Dean O’Banion stood out from all the other hoods who went down in a hail of bullets. An alcohol-shunning family man, he was known for aiding the poor and generously staking friends who were down on their luck. And he had a surprising outlook on one of the mob’s more lucrative rackets: as a devout Catholic, he abhorred prostitution. (“I don’t peddle flesh,” he said, “and I never will.”)4
Even more surprising was O’Banion’s everyday occupation. When he wasn’t rubbing out a rival, highjacking a beer truck, or stealing a warehouse full of liquor, O’Banion spent his time creating artistic bouquets at a flower shop across from the Holy Name Cathedral, the church in which he’d received his religious instruction as a boy and still attended mass. It’s said that a particularly stunning floral arrangement could make O’Banion giddy, just as the sight of a child in distress could reduce him to tears.5 Without a doubt, this softhearted lover of beauty was no ordinary rum-running killer.
O’Banion was born in July 1892 in Maroa, a postage-stamp village hidden among the cornfields of central Illinois. His life might have turned out differently had his mother not died of tuberculosis in 1901. Afterward, his father took O’Banion and his older brother to Chicago to live near their maternal grandparents. O’Banion’s new home was in the North Side neighborhood called Little Hell, an aptly named mire of poverty, crime, and desperation. Before long, the former small-town kid was running wild with the Little Hellions, one of the city’s numerous street gangs. While showing off to his buddies one day, he fell under a streetcar and nearly lost a leg. The injury left him with a lifelong limp.
O’Banion’s Jekyll-and-Hyde personality revealed itself during his early years in Chicago. Besides rolling drunks with the Little Hellions, he attended the Holy Name Parochial School, sang in the church choir, and sold newspapers on the street. After quitting school at fourteen, he put his strong tenor voice to good use in one of his few legitimate jobs—as a singing waiter at McGovern’s bar and brothel, a North Clark Street dive frequented by a rowdy mix of gamblers, thieves, and other lowlifes. Despite his limp and short stature, O’Banion was a tough little fireplug of a brawler, and he sometimes filled in as a bouncer at McGovern’s.
One of the crooks who patronized McGovern’s introduced O’Banion to the delicate art of safecracking. Like everything he did, O’Banion embraced this new activity with gusto, figuring that if a little nitroglycerin was effective for opening a safe, even more would be that much better. As a result, he occasionally set a charge that destroyed both the targeted safe and its contents. On one botched job, he placed the nitro in the wrong position and blew out the wall of the building he’d broken into, leaving its safe unopened. Still, it was a dandy explosion.
As he grew older, O’Banion joined the Bloody Market Streeters, a gang that peddled stolen merchandise on Chicago’s black market. The gang members also worked as “sluggers” during the city’s newspaper circulation wars of the 1910s. The job was simple: O’Banion and his pals visited neighborhood newsstands and advised the owners to sell no newspapers other than the one that was currently paying the gang for its services. If anyone failed to heed their advice, the Market Streeters beat the stuffing out of them—a more effective marketing technique than quoting advertising rates or reader demographics. The competition between newspapers was so intense that rival sluggers sometimes had Wild West shootouts in the streets.6
O’Banion scuffled along as a minor hood throughout his teens and early twenties, bumping up against the law from time to time. In 1909, he broke into a drugstore and was caught stealing postage stamps. In 1911, he was hauled in for beating a fellow hood with a blackjack and carrying concealed weapons. Both arrests resulted in short jail terms—the only time O’Banion ever spent behind bars.7 (He’d be indicted several times in the early 1920s, but by then he was rich and powerful enough to avoid further convictions.)
O’Banion’s big opportunity came in January 1920 with the introduction of Prohibition, the “noble experiment” that turned average citizens into lawbreakers and made criminals rich. Surrounded by his own loyal and growing gang, O’Banion was well positioned to capitalize on the new law. His lieutenants included longtime friends Earl “Hymie” Weiss, Vincent “Schemer” Drucci, and George “Bugs” Moran. Buying booze in Canada or from clandestine local manufacturers, the gang began supplying the underground speakeasies that were popping up like dandelions. O’Banion was soon running all of the bootlegging activities in Chicago’s northern lakefront neighborhoods, which took in the affluent Gold Coast. (The North Siders would also insinuate themselves into the area’s politics, stuffing ballot boxes and bashing heads as needed.)
With the boldness of a buccaneer, O’Banion built up his liquor supply by robbing the delivery trucks and storage facilities of his rivals. He pulled off his initial hijacking on December 30, 1919—one of the first in Chicago—and he continued to make news with his audacious raids. In one theft, the North Side Gang snatched $100,000 worth of Canadian whiskey from a freight car sitting in a rail yard on the West Side. At the giant Sibley Warehouse at Sixteenth and Peoria, the gang carted off a fortune in bonded Kentucky whiskey. The influence of the bootleggers was on full display in the Sibley operation: a squad of cops on O’Banion’s payroll escorted the thieves as they drove away with their horde of stolen booze.8
From their headquarters above the Schofield Company—the North State Street flower shop partly owned by O’Banion—the North Siders oversaw a bootlegging empire that raked in a million dollars a year (equivalent to more than $12 million today).9 It was enough to keep O’Banion dressed in fine tailored suits and his cuddly young wife, Viola, swaddled in furs. The couple lived in a swank apartment on North Pine Grove and owned a fleet of expensive cars. Perhaps to compensate for his hardscrabble upbringing, O’Banion loved to put on a dinner jacket and squire his wife to the latest shows.
O’Banion seemed to get along with everyone, greeting strangers with a slap on the back and a cheery “Nice to meet ya, swell fellow” (while keeping one hand hovering close to his pistols).10 The North Side boss even managed a temporary coexistence with the powerful South Side gangsters led by Johnny Torrio and his lieutenant Al Capone. At the start of Prohibition, the predominantly Italian South Siders and the Irish-dominated North Siders agreed to stay within their respective territories, but thanks to the impetuous Dean O’Banion, that didn’t last.
In 1924, the South Side Gang expanded into the neighboring town of Cicero, and O’Banion expected to get his share of the action there. Johnny Torrio ceded O’Banion some of the new territory and gave him an interest in a casino. O’Banion immediately persuaded a number of Chicago speakeasies to relocate to his part of Cicero, angering the Torrio forces. When the Sicilian Genna brothers started selling their rotgut in O’Banion’s North Side territory, Torrio was in no mood to act as peacemaker. O’Banion inflamed the situation by hijacking a Genna liquor truck. The Gennas wanted to eliminate O’Banion, but the Sicilian Union, a powerful mob-connected fraternal organization headed locally by Mike Merlo, refused to sanction his murder.
Things might have cooled off if O’Banion hadn’t kept poking the South Siders (who, some say, he lumped together as “them Sicilians” and derided as “spaghetti-benders” and worse).11 O’Banion had already tried to frame Johnny Torrio and “Scarface” Capone for a murder that he’d committed. After that, he cheated Torrio by selling him his share of a Chicago brewery the two owned jointly—knowing that the police were about to close the brewery. Torrio lost $500,000 to O’Banion and ended up facing a jail sentence.12 O’Banion’s double-cross left Torrio siding with the Gennas. When Mike Merlo died of cancer on November 8, 1924, there was no one to block the mobsters who wanted O’Banion dead. They didn’t wait long to act.
Just two days later, O’Banion was in his flower shop trimming some chrysanthemums for one of the dozens of arrangements ordered for Mike Merlo’s funeral. Chicago’s mobsters never stinted on flowers to honor the deceased—including rivals they’d bumped off—and O’Banion’s shop received most of their business. While O’Banion was busy with his flowers, three men walked into his store. O’Banion stepped into the showroom to greet them, still holding his scissors in one hand. Apparently recognizing the men, O’Banion held out his hand in greeting. One of the men seized O’Banion’s hand and pulled him off balance. The two other men drew their weapons and fired a fusillade into O’Banion’s body. Two bullets struck O’Banion in the chest, two in his throat, and one in his face. One of the gunmen fired a sixth bullet into O’Banion’s face after he fell to the floor. The florist-mobster was dead in seconds.
The police made a show of searching for O’Banion’s killers, but no one was ever convicted of the murder. It’s generally believed that the three assassins included a top New York hood and a pair of local gunmen.13 O’Banion’s death set off a wave of killings. The next five years were the bloodiest in Chicago’s history, as rival bootleggers blasted away at each other with pistols, shotguns, hand grenades, and Thompson submachine guns. Hundreds of mobsters were retired “at the insistence of bullets,” as the Chicago Tribune neatly phrased it.14
Most sources claim that O’Banion’s friends Hymie Weiss, Schemer Drucci, and Bugs Moran murdered one of the six Genna brothers in May 1925.15 Two more Gennas were killed within two months, and the three surviving brothers decided it was time to relocate. The North Siders definitely went after Johnny Torrio, gunning him down in front of his apartment building and leaving him for dead. Torrio survived, but the attempt on his life prompted him to hand over his organization to Al Capone and fade away into retirement. The North Siders made repeated attempts to kill Capone but only succeeded in shooting up his car and his Cicero headquarters.
In 1926, the Capone mob cut down Hymie Weiss in front of the Holy Name Cathedral. After the police killed Schemer Drucci in 1927, Bugs Moran took over what remained of O’Banion’s empire. The slaughter in Chicago’s streets peaked on February 14, 1929, when a Capone hit squad lined up six of Moran’s men and an unlucky hanger-on in a North Clark Street garage and riddled their bodies with dozens of bullets.
The St. Valentine’s Day Massacre heralded the imminent demise of the North Side Gang.16 Like a bloated, cigar-chomping emperor, Capone now reigned supreme over Chicago’s criminal world, and the bootlegging wars would sputter out. However, the horrific nature of the St. Valentine’s Day killings outraged the public. Afterward, federal prosecutors stepped up their efforts to bring down Capone. In 1931, he was convicted of income tax fraud and sentenced to eleven years in prison. Released in 1939, he died a few years later, his physical and mental health ravaged by syphilis of the brain.
Prohibition finally ended in December 1933, rendering the enormous profits from illegal alcohol flatter than last night’s beer. While it’s true that Prohibition increased crime throughout the country, Chicago was the epicenter of bootlegging lawlessness.17 Scarface Al Capone has gone down as the most infamous of the Chicago gangsters, but chubby, cheerful Deanie O’Banion was just as avaricious and violent. What set him apart was his dual personality. It seems impossible that a man who could find joy in arranging flowers could also hold a pistol to someone’s head and pull the trigger without remorse—as he did in February 1924 when he executed gangster John Duffy, a troublemaker who killed his own wife and made the unforgivable mistake of threatening O’Banion.18 It’s well documented that O’Banion attended church regularly, although he no longer went to confession. How could he? Just imagine what he’d have had to admit. (“Forgive me, Father, but I had to kill a mug last week.”)
O’Banion’s funeral was said to have been one of the most expensive Chicago has ever known, costing a staggering $100,000 by some estimates. His friends called it the “funeral of funerals, just what Dean wanted—simple but lavish.”19 The only thing it lacked was the blessing of the Catholic Church. Officials at the Holy Name Cathedral turned away O’Banion’s body and refused to conduct a graveside service. “A person who refuses the ministrations of the church in life need not expect to have the ministrations of the church in death,” a spokesman said.20
Even so, O’Banion’s wife insisted he was “a good man” who “never left home without telling me where he was going.”21 She said he was never late for dinner and that his greatest pleasures were sitting at home listening to the radio or to his player piano. People always seem to take a few steps toward sainthood after they pass on, but at least some of Viola O’Banion’s claims were true. Although her hubby may have brought about the deaths of more than a score of his fellow human beings, he was also a hardworking businessman with an occasional streak of compassion.
Bullets, bootlegging, and bouquets . . . those were the watchwords of Dean O’Banion’s life—a contradictory combination for a wildly unconventional crook. As the Chicago Tribune noted after his death, “He really was one hard boiled florist.”22