Paddy Whacked: The Untold Story of the Irish American Gangster (17 page)

Elsewhere, the rest of the nation read about the goings-on in Chicago with astonishment and, in some cases, envy. One person who steadfastly followed the activities of the Kenna-Coughlin organization from afar was a man named Richard Croker, grand sachem of New York’s Tammany Hall.

It wasn’t just the First Ward Ball that caught Boss Croker’s attention; it was also the manner in which Kenna and Coughlin aligned all the necessary forces to make the Ball possible. First and foremost among the Chicago Machine’s benefactors was Carter Harrison, Jr., son of Our Carter. Just four years after his father’s death, Carter Junior ran for mayor on the principle that under a new Carter Administration, Chicago would forever be a “wide open town,” just as it had been under his father. Hinky Dink and The Bath rallied around their own version of “Our Carter,” securing his election and reelection for an unprecedented twelve years in office.

In New York, Boss Croker had a mayoral election coming up and had put forth a non-Irish, non-Catholic candidate not unlike Carter Harrison. Curious to learn from his colleagues in Chicago, Croker invited Bathhouse John and Hinky Dink Kenna to visit New York as his guests. The two aldermen were delighted to take him up on the invitation.

Coughlin, Kenna, and a contingent of politicos known as the Cook County Democracy arrived by special train in Manhattan and were feted at Tammany’s main wigwam, a stately building on East Fourteenth Street. Croker, a tough former gang member with bulging muscles and a full beard, towered over the two men, especially tiny Hinky Dink. But Tammany Hall’s “Mister Big” was exceedingly solicitous of his political brethren, stating to the press, “We are honored and gratified to have in our presence a group of men known to be political wizards in their own fair city, men of great accomplishment and civic virtue, masters in the science of political persuasiveness. We will show them a fine time here in New York and edify ourselves at their behest.”

A special Tammany parade was arranged. Many of the New Yorkers who turned out to see the Chicagoans march down Broadway were especially eager to get a glimpse of the inimitable Bathhouse John and Hinky Dink. Dressed in their usual marching attire of long frock coats, pinstriped trousers, starched white shirts, silk top hats, white gloves, and umbrellas that served as walking sticks, the two alderman cut quite a figure.

After the parade, the contingent from Chicago retired to the Hesper Club on the Bowery, a Tammany district headquarters operated by Paddy Sullivan, brother of Assemblyman Big Tim Sullivan. Big Tim himself was on hand to welcome the Chicago crowd and give them an impromptu tour of the legendary Sixth Ward, which included what used to be known as Five Points. This storied neighborhood, once the home and incubation center for a generation of post-famine Irish street gangs such as the Dead Rabbits and the Whyos, was now divided into a series of smaller ethnic enclaves, including Chinatown, Little Italy, and the predominantly Jewish Lower East Side. All that remained to remind residents of the old days was a large gang that managed the area’s still thriving vice rackets, the Five Points gang. This gang, of course, operated under the aegis of the local political boss, Big Tim Sullivan.

There is no record of what was discussed at this historic meeting of the minds between the nation’s two preeminent political organizations. Given that the Chicago and New York Irish political leaders saw themselves as being engaged in a similar struggle, and had developed remarkably similar methods to achieve their goals, they might well have viewed this gathering as a meeting of the brain trust. At the turn of the new century, Chicago and New York were the Rome and Athens of the underworld, dominant practitioners of an up-from-the-gutter brand of politics that incorporated sluggers, shoulder hitters, and vice mongers of every variety. As the leaders of this movement, Boss Croker, Big Tim, Bathhouse John, and Hinky Dink were part of what the press sometimes referred to as an “Irish American cabal.” The men themselves would have approved of that designation. For these municipal masters, there seemed to be no end in sight.

When all was said and done, the various political bosses exchanged hearty handshakes and went their separate ways. Coughlin, Kenna, and the others returned to the city of Chicago, energized by the deification bestowed on them by the preeminent Irish American political power, the vaunted Tammany Hall.

A few years later, the Chicagoans reciprocated by inviting Big Tim Sullivan to the First Ward Ball, where, among the whores, gamblers, political grafters, and mobsters of the Levee district, the assemblyman from Manhattan was honored as a special guest.
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Chicago Gambling Wars

In the first two decades of the new century, gambling remained the mother of all criminal rackets. Card games, craps, and roulette were as popular as ever, but the gambling business had truly made revolutionary strides with the Sport of Kings—horse racing—which was transformed in the early years of the twentieth century by the invention of the electronic wire service. Western Union and other corporate forces had created the telegraph wire as a means of transferring money. The modern bookmaker used it for the transference of illegal funds through off-track betting into their own pockets.

Before the wire service existed, you actually had to go to the racetrack to place a bet or at least to a betting parlor adjacent to the track. Now a gambler could place his bet with a bookie anywhere in town. Usually, this was done at a poolroom, originally a place where lottery tickets were sold. A lottery was called a pool because of the manner in which winnings were paid off. Since lottery tickets were sold all day and the drawings were not held until late in the evening, proprietors of poolrooms installed billiard tables to occupy their customers during the waiting periods. Now they installed betting boards as well, which posted odds on the races and a myriad of other sporting events.

Bookmaking operations now became an adjunct of the gambling parlors. The gambling czars employed a legion of bookies who worked the district. The bookies, many of whom were themselves degenerate gamblers, took bets from dozens of clients. The bookies might then lay off a portion of their action through sizable wagers of their own with their boss, the gambling czar. The bookies figured that, even if they lost their bets, they were covered by gambling proceeds they’d taken in through their own losing clients. It didn’t always work out that way, of course. Bookies and their pigeons, or marks, became the bottom feeders of the underworld. When their financial ledgers dipped too strongly in a losing direction, sluggers were called in, and the bookmaker wound up in a world of hurt.

Given the newly dispersed, far-reaching nature of the business, a centralized gambling overlord like King Mike McDonald was no longer practical. Thus, the city’s gambling empire broke down into mini-fiefdoms that were constantly encroaching on each other’s turf.

One of the most powerful gambling czars to emerge in the new century was Big Jim O’Leary. O’Leary was a jowly, barrel-chested son of the South Side whose family had become social pariahs after his mother’s prized cow allegedly touched off the largest single disaster in the city’s history. Growing up, the O’Leary boys were taunted endlessly. The oldest of the brood, Con “Puggy” O’Leary, was so haunted by the family’s stigma that he became a brawling, hard drinking ne’er-do-well who, in 1885, killed a woman and injured his own sister for refusing to give him a dollar to buy a pail of beer. Jim O’Leary was less tortured by the family’s past; he merely chose a profession where having a tainted history was not necessarily bad for business.

O’Leary got his start as a bookmaker in the McDonald organization. By the late 1890s, he had become a financial participant in a highly successful casino run by Blind John Condon in Hot Springs, Arkansas, which in one season took in a nifty $250,000. O’Leary used his portion of the proceeds to open a gambling parlor on South Halstead Street near Chicago’s famous Stockyard district and began to organize a series of poolrooms and handbooks. He also had an interest in numerous saloons, racetracks, and a gambling boat.

Big Jim’s Halstead Street gambling parlor was the most elaborate establishment the city had seen since the days of King Mike’s place, the Store. Not only did it provide facilities for all sorts of gambling, but there was also a bowling alley, a billiard room, a Turkish bath, and a restaurant. The main attraction, however, was the poolroom, with its luxurious chairs and sofas, servants to bring drinks, and chalkboards that gave the odds and results for every horse race in the United States and Canada. In this room, and in his outside handbooks as well, Big Jim took bets on everything from prize fights and baseball games to elections and even crops and the weather.

Unlike most gambling czars, O’Leary steadfastly refused to pay off the coppers. “I could have all kinds of [police protection],” he once proclaimed,

“but let me tell you something. Protection that you purchase ain’t worth nothing to you. A man who will sell himself ain’t worth an honest man’s dime. The police is for sale, but I don’t want none of them.”

Instead, Big Jim turned his Back o’ the Yards gambling house into a veritable fortress. It had secret passageways, trap doors, a fake chimney with a ladder that could be drawn up, a steel-plated front door, and inner walls constructed of heavy oak and covered with zinc—making the place, according to Big Jim, “fire-proof, bomb-proof, and police-proof.” Still, coppers did sometimes raid his establishment, gain entry, and seek to destroy the place. O’Leary was usually ready for them. On one occasion he even lined the walls of the gaming room with a toxic red pepper; when raiding police took their axes to the place, they unleashed a blinding powder.

When O’Leary wasn’t battling with officers of the law, he was under assault from rival gambling organizations. Of the three main gambling combines in the city, the largest—even larger than O’Leary’s—was run by Mont Tennes, the son of German immigrants and a former saloon keeper who had the backing of Kenna-Coughlin, among other friends in high places. In July 1907, a bombing war erupted among the city’s gambling factions. The first to be hit was Blind John Condon, one of O’Leary’s partners and a link to the McDonald syndicate of the past. Condon was relaxing in the rear of his home at 2623 Michigan Avenue when a bomb was tossed into the front yard. Lucky for Blind John, the bomb was time-fused and only caused partial damage to the façade.

Two days later, on July 25 at nine o’clock at night, Mont Tennes’s home was hit with a steel-cased bomb that landed in a paved alley directly behind the house. Tennes, who was enjoying a bath at the time, was rattled to his feet by an explosion that shattered numerous windows in the house. The German gambling boss was not hurt. To the police he claimed ignorance of who might have wanted to do such a thing. “It must have been the work of some mischievous boys with a cannon cracker,” Tennes said.

After this, the bombs kept flying. Jim O’Leary’s Halstead Street gambling emporium was hit with what proved to be the biggest bomb of all. Buildings a block away shook from the explosion, and people ran madly down the street. O’Leary, who was not on the premises at the time, told the police that the explosion was the result of a cap on a gas pipe that blew out. The cops didn’t believe him, but they had little in the way of details or evidence to determine the truth.

Over the next few years. Chicago’s tit-for-tat bombing war raged unabated. There were dozens of bombings that took place in saloons, poolrooms, gambling parlors, residences, and even a South Side police precinct. The pattern was always the same. A home-made explosive device would go off, creating a deafening blast. Helmeted police blowing calliope whistles and toting night sticks would arrive on the scene after the dynamiters had fled. There were occasional arrests, but no one was ever convicted for a single bombing. Amazingly, no one was ever killed either.

The city’s gambling wars were an unnerving escalation of underworld competition, and they added to a growing weariness on the part of the general population. The days of the gentleman gambler, it seemed, were being replaced by a more menacing reality. Faced with frequent disruptions, destruction of property, and the threat of serious violence, political and social reformers stepped up their counter-efforts with almost daily rallies against the saloon keepers, gamblers, and vice mongers.

One of the first underworld figures to sense the turning of the tide was Big Jim O’Leary. O’Leary had gotten into the game as a way of possibly salvaging his family’s name and reputation. He had even once hired a public relations firm to put a positive spin on his gambling operations. The bombing war and the wild nature of the city’s commercialized vice in general convinced Big Jim that the time had come to move on. To the surprise of many, O’Leary sold off his operations and publicly announced his retirement from the underworld on December 1, 1911.

The gambling wars raged on, with Tennes strategically bombing Big Jim’s many successors until a few years later, when Hinky Dink Kenna allegedly stepped in and mediated a peace settlement. A police informer claimed that Kenna had received forty thousand dollars for his efforts. Hinky Dink denounced the informant as a “big liar.”

The cessation of the city’s long bombing war did nothing to pacify the growing reform movement. When a cop was killed on July 13, 1914, during a wild shoot-out on West Twenty-second Street in the Levee district, the Board of Fifteen, a powerful citizens organization comprised of ministers and temperance leaders, announced to the public “We declare war on the Levee and all commercialized vice in the city. It’s a war to the finish!”

The do-gooders and church leaders were not the only ones who had grown tired of the city’s long accommodation with the underworld. The very nature of the wide open town was a commercial mandate that had created a world in which young men of violence were tolerated, if not openly encouraged. Among the Irish American lower middle class, which was the first generation of Irish Catholics to rise above the poverty level, a pervasive gang culture had spread and became institutionalized. A well-known study on gangs in Chicago by academic Frederick Thrasher claimed that there were 1,313 gangs in the city. The number was misleading in that Thrasher designated virtually every street corner gathering of young men—whether it was a politically-affiliated group or just four guys having a smoke together—as a gang. But the overall point was undeniable; the gang lifestyle was pervasive, and it fueled a culture of aimless violence that was “put to good use” by the mobster and political bosses.
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