Paddy Whacked: The Untold Story of the Irish American Gangster (24 page)

The cops never came up with enough evidence even to charge O’Banion, though they had a good idea what happened. Later reports were that Deanie and two accomplices had driven Duffy out of town on Nottingham Road. On the dark, deserted road, they pulled over so that Duffy could urinate. While Duffy and O’Banion both stood relieving themselves, Dean pulled out a .38, put it to the back of Duffy’s head, and pulled the trigger. After the victim went down, Dean shot him twice more, just to be sure. That was O’Banion—thorough, professional, and to the point.

He was also a helluva practical joker. Most of Dean’s jokes were of the hotfoot, whoopee cushion variety, but occasionally he could be truly demented. His biggest whopper of all was the joke he pulled on Johnny Torrio.

Silver-haired “Papa John” Torrio was the Italian mob boss of Chicago. He was originally from Naples, by way of Brooklyn. As a youth in New York City, he’d been a member of the Five Points gang under Paul Kelly (Vaccarelli). In 1915, Torrio packed up his wife and kids and moved to Chicago. He had been summoned there by his uncle, Jim Colosimo, who was at that time the most powerful Italian criminal in the Windy City.

Torrio’s uncle, known to his family and friends as Big Jim, got along with most people, including aldermen Bathhouse John and Hinky Dink. They gave Colosimo his start by making him a precinct captain in the First Ward. Through various gambling, extortion, and labor rackets, Colosimo rose to become a major power in the underworld.

The fact that Big Jim Colosimo remained loyal to Coughlin and Kenna did not sit well with some in the city’s Italian underworld. The Unione Siciliane—a quasi-legitimate cultural organization that would eventually become a key player in the city’s gang wars—distrusted Colosimo’s affiliation with the city’s two preeminent Irish American ward bosses. The Unione Siciliane’s consiglieri, or legal counsel, was Joseph Bulger, formerly Guiseppe Imburgio, whose Sicilian-born father had been lynched to death in New Orleans following the Chief Hennessey murder trial. Bulger/Imburgio did not countenance appeasement with the Irish, whom he felt represented a faction of the establishment that could never be trusted. The position of the consiglieri and the rest of the Unione Siciliane was underscored dramatically on May 11, 1920 when Big Jim Colosimo was gunned down in the vestibule of his cafe. His killers were never caught, but it was generally believed that he had been taken out in an internal Italian American coup.

Johnny Torrio inherited his uncle’s rackets, and he further enhanced his underworld standing by becoming an early supplier of booze on the city’s South Side. A soft spoken man with a placid surface demeanor, Torrio saw himself as the great accommodator. He had spent the early years of Prohibition negotiating a division of territory throughout the city’s many wards, the result of which was an unwritten non-aggression pact that had held, more or less, for four years. For Torrio, the most difficult aspect of keeping this peace treaty in place was appeasing his fellow Italians, who wanted to go after Dean O’Banion. Some of them disliked the man simply because he was “an Irish bastard.” Others wanted Deanie out of the picture because they coveted his territory, for O’Banion’s North Side domain included Chicago’s Gold Coast, a strip of mansions and estates along Lake Shore Drive that was home to bankers, judges, politicians, real estate moguls, and other members of the financial elite. O’Banion supplied booze for some of the most highfalutin soirees in the city, which made him rich and well-connected.

The Italian bootleggers’ covetous dislike for Deanie was mutual. O’Banion had grown up in a part of the city known as Kilgubbin when it was an Irish working-class neighborhood in the process of becoming Italian. Gangs of Irish and Italian youths routinely clashed, and O’Banion, in particular, was known as a young hooligan who was more than willing to stand up for his neighborhood against “the dark people.”

By the time the Irishman had emerged as a major player among the city’s vast bootlegging underworld, he was shrewd enough to realize that he would not last long without some form of understanding with the Italians. In the early decades of the twentieth century, Chicago had seen a phenomenal population growth among Italian groups. Some, like Johnny Torrio and his young sidekick, Alphonse “Scarface” Capone, came from the East Coast; others came up the Mississippi and Missouri rivers from New Orleans; and still others arrived directly from Sicily, as immigrants of modest means looking to plug into one of America’s most thriving Italian American communities. There were probably more new Italian immigrants than Irish immigrants in Chicago, although the Italians had nowhere near the strength the Irish had in politics, the police department, the unions, and other spheres of municipal power.

While O’Banion may have accepted the idea of appeasement with the Italians because it made good business sense, he didn’t necessarily like it. He was frequently heard grumbling about the dagos. He was especially aggrieved because Torrio and his organization were big in the prostitution business. “I don’t peddle flesh,” said the avid Catholic. “And I never will. It goes against God and the Mother Church.”

One day in early May 1924, O’Banion approached Torrio with an astounding proposition. He was looking to get out of the bootlegging business, he said, and he wondered if Torrio wanted to buy out his interest in the Sieben Brewery, an extremely profitable beer manufacturing operation jointly owned by him, Torrio, and a few others. The brewery had been producing quality beer in O’Banion’s North Side territory for three years, under the protection of the precinct police. For half a million dollars, said O’Banion, he would divest his share; he explained that he wanted out because the bootlegging business had become too dangerous. Torrio would be doing him a favor by buying him out. As a parting gesture of goodwill, he’d even assist in the turning over of one last shipment. Torrio jumped at the offer, even though his second in command, Capone, cautioned that he smelled a rat.

O’Banion and Torrio, along with two members of Deanie’s crew and under the watchful eye of two uniformed police officers who were on the payroll, met at the Sieben Brewery on the morning of May 19. There Torrio delivered his payment of $500,000. In return, O’Banion escorted Torrio around the facility, showing him the recently concocted shipment of beer ready for delivery to speakeasies throughout the city. He showed him the financial ledgers listing the various bootlegging organizations that were scheduled to receive product. After Torrio had fully assessed the operation and the last of thirteen trucks was loaded by a crew of teamsters, he asked O’Banion, “So what will you do with yourself now that you’re out?”

Deanie smiled. “I’m retirin’ to Colorado to become a gentleman farmer.”

Before Torrio had even finished chuckling at that remark, from all directions, blocking all exits, came a troop of blue uniforms led by none other than the chief of police himself, Morgan Collins. “You’re all under arrest for violation of the Volstead Act,” announced Chief Collins. He personally ripped the badges from the two uniformed officers on the premises. 130,000 gallons of beer were confiscated and thirty-one bootleggers arrested, including Torrio and O’Banion. Torrio went into a panic. He knew that a second offense for bootlegging could mean jail time. This would be his second offense, while it would only be O’Banion’s first.

At the Federal Building downtown, O’Banion was chipper as hell. He paid his $7,500 bail and whistled on his way out of the courtroom, knowing that even if he were convicted of the offense, it would bring no more than a fine. Torrio, however, was sullen. He, too, was released on bail that day, but with the knowledge that if he were found guilty of a Volstead violation, he would be serving time in prison.

A few days later, Torrio learned an even more disturbing fact. A police informant told him something that his sidekick Al Capone had suspected all along. The Sieben Brewery bust had been a setup. The “Irish bastard” knew about the police raid from the beginning and had made sure Torrio would be on the premises to be arrested. “I guess I rubbed that pimp’s nose in the mud all right,” O’Banion reportedly said about his little joke on Papa John.

O’Banion did go to Colorado for a few months (he even bought property, paying cash for a 2,700-acre ranch), but he did not retire from the bootlegging business. He was soon back in the city demanding his share of the spoils and pissing off Italian criminals throughout the underworld. The fact that John Torrio and Al Capone did not immediately go after the capricious Irishman, leaving his corpse riddled with bullets in a roadside ditch, was a testament to O’Banion’s status as the most popular hoodlum in Chicago.

The Merry Prankster

In Kilgubbin, the neighborhood where Charles Dean O’Banion
¹
was raised from the age of nine, they had a saying: “You can lead a dago to water, but you can’t make him drown himself.” It was meant as a joke, but the racial denigration behind this nasty little aphorism was a pointed reminder of the hostility that existed between the Irish and Italians—part of an ethnic tribalism that defined street life in most East Coast and many Midwestern American cities in the early years of the century.

Despite the ethnic animosities that were part of his inheritance, Dean O’Banion was not raised to be a gangster. On the contrary, his upbringing was classic Norman Rockwell Americana. Born on July 8, 1892, in Moroa, a small town in Central Illinois surrounded by cornfields, Deanie remembered this tree-lined hamlet with fondness throughout his life. In later years, when he had acquired his wealth, he made financial donations to the town and was always ready to help out its inhabitants. He made an arrangement with Chicago hospitals that if anyone from the village of Moroa were ever admitted, he would be notified immediately so that he could send flowers. While this may have been the gesture of a proven sentimentalist, it’s also likely that, as his life became increasingly dangerous, he found solace in maintaining ties to a more innocent time and place.

O’Banion’s father, also named Charles, was a hard-working Irish immigrant plasterer and part-time barber who scrambled for any kind of work he could find. He and his wife, Emma Brophy, labored long and hard to support their family, which included Deanie’s older brother, Floyd, and younger sister, Ruth. The children’s upbringing was stable enough until a dark day in 1901, when their mother died suddenly from tuberculosis. Shortly thereafter, Deanie’s heartbroken father moved him and his brother to Chicago to stay with their grandparents (sister Ruth was left with an aunt in Decatur).

Located on the city’s near North Side, Kilgubbin had once been a respectable Irish enclave, but the area’s tenement housing and local traditions had deteriorated; with the predictable upsurge in robbery, prostitution, and violence, the neighborhood lost its Celtic designation altogether and became known as Little Hell.

In Little Hell, Deanie O’Banion was often truant from school and eventually fell in with a gang known as the Little Hellions, the juvenile division of the Bloody Market Streeters, a gang known primarily for the marketing of stolen property. The Little Hellions were an ethnically mixed bunch. Among them were Earl Wojciechowsky, a Polish Catholic who later changed his name to Hymie Weiss; George “Bugs” Moran, who was half Polish and half Irish; and Vinnie Drucci, an Italian whom O’Banion nicknamed Schemer because he was good at devising schemes for boosting the merchandise that the gang would sell to the Market Streeters for a modest profit.

Even at a young age, O’Banion was known as a prankster whose desire to have a good time, more than anything else, singled him out as leader of the Little Hellions. One of his good-natured stunts left him crippled for life: Attempting to show off to his friends by sitting on the fender of a moving streetcar, he was thrown to the road when the vehicle suddenly lurched. Before he could get out of the way, the streetcar backed up and crushed his left leg. An operation saved his leg but left one leg shorter than the other; forever after he walked with a noticeable limp.

The accident did nothing to subdue Deanie’s wild streak. He quit school altogether at the age of fourteen and shortly thereafter found work in McGovern’s Saloon and Cabaret, a notorious dive at 666 N. Clark Street. Years before, Deanie had honed his voice in a short stint with the Holy Name Church choir; now he was a singing waiter, hustling around the tables with trays of beer steins and whiskey glasses while belting out traditional Irish crowd pleasers like “Danny Boy” and “Too-Ra-Loo-Ra-Loo-Ra (An Irish Lullaby).” He also served as a bouncer. Though only five-foot four, Deanie was solidly built and never afraid to mix it up with drunken and unruly customers when duty called.

One McGovern’s regular who took a liking to O’Banion was Gene Geary, an older Irish American racketeer from Canaryville, a district in the city known for producing highly skilled gunmen. What Geary loved most was whiskey, Irish ballads, and the sound of a pistol being fired off. He took young Deanie under his wing and schooled him in the art of ambidextrous gunplay. From rooftops and in tenement basements, he and the much younger O’Banion conducted target practice. Geary even showed Deanie the best way to hide various weapons on his person by sewing special pockets into the interior lining of his clothing—a tactic that would later become one of mobster O’Banion’s most well-known trademarks.

The disciple-mentor relationship between Deanie and the elder gangster was the sort of alliance that was at the heart of many burgeoning careers in the Irish American underworld. The two men remained close friends until 1921, when Geary was committed to a mental institution as a homicidal maniac.

Prohibition was made-to-order for Dean O’Banion. He served a gangster apprenticeship as a slugger during the city’s brutal newspaper circulation wars (he first cracked heads for Hearst’s
Herald-Examiner
then switched sides when the
Tribune
offered more money) and later as an expert safe cracker and second-story man. He and his North Side gang then pulled off two early coups that helped establish their bootlegging supremacy. One night in late 1923, they invaded a West Side railroad yard and transferred $100,000 worth of Canadian whiskey from a freight car to their trucks. A few nights later, they broke into the Sibley Warehouse, trucked out 1,750 barrels of bonded liquor, and, to conceal the robbery as long as possible, left in their place an equal number of barrels filled with water. Lieutenant Michael Grady of the detective bureau and four detective sergeants on O’Banion’s payroll escorted the trucks to his North Side storage depot.