"We’re all alone,

No chaperone can get our number..."

"-- Let’s Misbehave"

C. Porter

Mr. O’Banion found the rents in the city higher than expected and out of desperation chose a flat in an area affordable to a tradesman. Never having experienced firsthand the dangers of a large metropolis, he naively carted his family into probably one of the worst spots in turn-of-the-century Chicago. Its name might have lured his ancient blood; it was called Kilgubbin. Once a heavily Irish area, and even though its population was giving way to other nationalities, the name stuck. But, the burgh of brownstone tenements and rambling townhouses had earned another name, too -- one that, had Charles heard it beforehand, might have recoiled him: "Little Hell."

Along its streets were the elemental ingredients of crime, temptations for a boy like Deanie wanting fun -- saloons, honky tonks, billiard parlors, gambling dens, pawn shops selling anything, tawdry vaudevilles and, as poet Carl Sandburg described, "painted ladies under the gas lamps". Tin Pan Alley pianos tinkled and hurdy-gurdies bellowed long under the stars, drowning out the sanctus bells of Holy Name Cathedral. The attitude was one for the opportunist: to grab whatever came along now because it might mean a fast buck before morning. Kilgubbin had no curfew, too few policemen, and plenty of vice. The corner of Oak and Milton, only a legshake from where the O’Banions had moved, was coined "Death Corner," obviously because of its penchant for collecting bodies knifed or shot in one of its shadowy dives.

Deanie was, for a short time, an altar boy; he also sang in the church choir at Holy Name. He possessed a lilting Irish tenor and, as so believed, was encouraged by his conductor to pursue vocal training. But, the arts held no interest, nor did the somber glow of vigil lights stir a religious devotion.

He had grown restless, had seen his pals who didn’t attend school partaking of the trinkets and prizes offered with the street life. His eyes bright, his pulse racing, he would listen to their adventures -- adventures he was missing -- picking pockets, jackrolling drunks, sometimes followed by a thrilling chase down Clark Street inches in front of a cussing policeman’s billy club. A lot of fuss, perhaps, for nickels, dimes and quarters, but the scamps were having more fun and were jingling more coinage than his empty pockets carried. His father barely eked out a living with whatever job came his way through the painters’ union and Deanie was sick of week-old bread and tattered knickers.

Earl Wojciechowsky, aka as Hymie Weiss (POLICE)

The gang was often called upon to serve as "sluggers" by vying major newspapers in town, the Chicago Tribune and the Chicago Herald and Examiner. In the lawless first decade of this century, sluggers literally beat newsstand owners who refused to sell the competitive paper, as well as scoot street corner barkers who hustled the wrong banner.

Deanie launched this "career" with the Tribune, but when mob boss Moses Annenberg offered him more money he switched allegiance. John Morgan’s Prince of Crime states that, at sixteen years old, Dion O’Banion seemed to be "the principle exponent of thuggery in newspaper selling," outfighting and outwitting other boys who would later blossom into top-ranking gangsters, including Murray Humphreys, the future union organizer for the Capone mob.

One afternoon, Deanie was roustering with some friends near the streetcar tracks that transversed State Street. Distracted, he didn’t hear the motorman’s bell clanging from an approaching Chicago Surface Lines trolley. He ran in front of it. Thrown onto the cobblestones, he was knocked unconscious and mangled; passersby rushed him to a hospital where doctors at first thought he would die. He survived, but his splintered left leg never quite healed correctly, leaving him with a rolling gait that, reporters later determined, "added character" to his already jaunty aire. If other kids laughed and called him "gimpy," it wasn’t to his face. The O’Banion sense of humor, they figured, might stop there.

Annenberg, who got a percentage of every Examiner sold, and for whom Deanie continued to work once he was back on his toes, watched the little bantam rooster with delight. This O’Banion, he noted, seemed afraid of no one and managed, at the same time, to actually earn respect from those he accosted. That Irish charm beneath the Hottentot. Annenberg’s praise for Deanie drew the boy into the trust of other underworld denizens, including Charles Reiser, a safecracker who was looking for apostles. From Reiser, Deanie and his friends learned the basics of the art, and both for Reiser and separately, they went about testing their accrued knowledge on the back room safes in neighborhood shops. Sometimes, the boys’ eagerness outdid them, like the time they blew out an entire wall of a factory -- while the safe they charged remained locked. Deanie picked himself up from the rubble, brushed the mortar dust from his face, and thought it was the best laugh he had had in years.

During one of these soirees with a safe in early 1909, Deanie was apprehended and served three months in the city’s House of Correction. Two years later, he did another brief sentence for assault with a blackjack. These two terms "in the hole" were enough for Deanie, who liked the open streets; he vowed he would never do jail time again. He never did.

In between and afterwards, he continued to bloody noses for Annenberg and the Examiner. Because his tough guy image had escalated and he was considered a presence to beware -- after all, he was now a "jailbird" -- younger and less experienced sluggers would scoot at his sight. The opposition didn’t like that. Threats become common and Deanie thought it best that he carry a revolver as well as the brass knuckles he visibly wore. On rooftops, he and his friends -- in particularly, Wojciechowsky (who had shortened his name to Weiss), Drucci and Moran -- skilled their aim on pigeons and rats.

Deanie became an excellent marksman. He began carrying his favorite gun, a .38, with him as he wandered the streets of the North Side. He probably used it for more than show. His bankroll increased with each job he performed for Reiser, Annenberg and others. Car jackings, warehouse robberies, here and there an occasional busted head. He severed his ties with the Market Street Gang; he enjoyed the life of the freelancer. And, for laughs, invited only the best of them to follow.

Weiss. Drucci. Moran. Everything their Deanie did and every place their Deanie went, they followed suit. The schoolboy who had once followed now led. And his "Kilgubbin lads" were happy to emulate his walk and his talk.

Vincent "Schemer" Drucci (POLICE)

Vinny Drucci, despite Deanie’s adopted dislike for most of the other Italian kids in Kilgubbin, proved himself to be an invaluable and loyal partner. This dark, deep- pondering and silent Chicagoan, a native of Little Hell (1895), is said to have masterminded most of the heists they pulled, to the point of strategizing extra precautions to pull them off safely. For this, Deanie named him "Schemer."

George "Bugs" Moran

Their favorite hangout was McGovern’s Liberty Inn at Canal & Erie streets. Here, Deanie spent off-hours as a singing waiter, rendering popular ballads in his fine Irish voice. And, while he sauntered from table to table, "Molly Malone" on his lips, his hands picked the pockets of many patrons. He counted each wallet’s contents in the kitchen, kept the green, and tossed the billfold in the incinerator. Out front, at the bar, his hangers-on waited anxiously to help Deanie spend it when McGovern’s closed.

Through Annenberg, the boys were introduced to the political decision-makers throughout the 42nd and 43rd wards who called upon the mobs to help "steer" the outcomes of elections. The means by which this occurred often involved intimidation, ballot-box stuffing and murder. Deanie’s easy-going verbose boyishness -- and willingness to play ball -- proved time and again to be his ticket to many a lawmaker’s private mahogany office where deals were made and money for "services rendered" flowed quicker than the Chicago River.

The 42nd and 43rd wards, located over many linking blocks north of the river, contained within their boundaries a diversity of life, from the rich to the poor. While the infamous Little Hell was part of the package, the cash that its assorted illicitness brought in was a pleasant factor, eyesore or not. Most of the vice, Deanie learned quickly, went unmolested since the politicians and police were getting a percentage of every penny earned. But, along Lake Michigan, only several streets east, lay the "Gold Coast," a mile-long row of mansions and swanky apartment buildings housing the judges, the lawyers, the businessmen and the philanderers who oiled the daily gears of Chicago. These were the men who sought the aid of Deanie and his rascals.

And they paid well. As the lads of Kilgubbin would drive their chrome-striped automobiles up and down the old neighborhood -- no more walking for them -- the people would wave and smile at the lovable "ward boys"; the cops, either on horseback or in squad, would give them right-of-way. Deanie, especially, became almost an icon; the familiar sight of his limping gait at any saloon’s doorway meant free beers on the house; it meant a fine a warm hello and a pat on the back and the pleasure of being seen in his company. His dad, Charles O’Banion, believed his son had found an honest City Hall job and boasted to anyone who listened wryly that his offspring "never forgets his dad". He would flash the new wristwatch or the diamond ring his son had just bought him.

In effect, Charles was correct. Deanie and his pals were still, indeed, City Hall "ward boys," wandering from one job to another. They yearned for -- but couldn’t figure out what -- something bigger.

Then came Prohibition.