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.7
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 y
ears. 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.8
At the lowest end of the scale were the street corner gangs, comprised mostly of punks who spent their afternoons pitching pennies, stealing apples from Luigi’s fruit stand, brawling with each other, or race-baiting, which sometimes escalated into racially tinged gang fights. A more advanced type of gang were the “social athletic” clubs, which were sponsored by a nebulous organization known as the South Side Clubs Association (SSCA). These gangs usually gathered on a regular basis in public meeting halls. In return for having their rent paid by the SSCA, the athletic clubs ran errands for the political bosses—mostly Democrats—and other members of the tribe looking to hire out their services.
By far the largest and most notorious of these groups was an Irish gang, Ragen’s Colts, whose clubhouse was in a store at 5528 S. Halstead Street. The organization was named after their leader, Frank Ragen, a tough, street-smart operator who eventually rose above the gang and got himself elected to the Cook County Board of Commissioners. Long after he was gone, the gang kept his name and continued to grow, eventually adopting the slogan “Hit Me and You Hit 2,000,” which was probably only a slight exaggeration. Ragen’s Colts proved to be a veritable breeding ground for a generation of sluggers and underworld figures, among them Gunner McFadden, Harry Madigan, Stubby McGovern, and Ralph Sheldon, who became a notorious bootlegger in the 1920s.
Ragen’s Colts first made a name for themselves during the city’s rough-and-tumble newspaper circulation wars that began in 1910. The battle for readership between the city’s various broad sheets turned ugly and ushered in an era of athletic association gangs being utilized and financed by upperworld corporations. At the behest of William Randolph Hearst and other prominent publishers, gang contracts were extended to various athletic clubs who, using a method known as bootjacking, routinely intimidated, threatened, and even killed newsdealers to get their organizations to buy more of a certain paper. The Chicago American, owned by Hearst, had the most brutal enforcement arm—Ragen’s Colts, who eventually jumped ship when a rival paper, the Tribune, offered them more money.
The circulation wars were serious business. Before they were over in 1913, twenty-seven street-level newsdealers were stabbed, beaten, or shot to death while the owners stayed securely in their ivory towers. Furthermore, the newspaper wars legitimized the practice of large business entities using the gangs in all manner of disputes, a practice that would become even more commonplace during the many labor union wars that flared up in Chicago on a semiregular basis.
Given the size of gangs like Ragen’s Colts and the air of legitimacy that upperworld forces gave them, it is not surprising that they became entangled in other kinds of disturbances as well. Race, for instance, was a hot button issue in Chicago, as it was in many big, American cities. Since the athletic associations were based on ethnic affiliations—Irish, Polish, Italian, and African American being the most dominant—they often became the shock troops in the city’s seething racial hostilities. These hostilities had grown worse since the beginnings of World War I, when thousands of impoverished southern blacks, drawn by the prospect of jobs at munitions plants and packing houses, sought the promise of a better life on Chicago’s South Side. Frightened whites abandoned the area, while those who stayed saw their property values plummet. This social upheaval brought about civil tensions that would exist in the city, to varying degrees, for man decades to come.
The most cataclysmic racial event in the city’s history was initiated on July 27, 1919, when a group of young African American swimmers accidentally strayed over an imaginary racial divide that separated the white beach at Twenty-ninth Street from the black beach at Twenty-fifth Street. A group of white boys stoned the blacks with rocks until a fourteen-year-old boy was hit in the head and drowned.
What followed was a violent race riot that flared sporadically over four days, complete with lynchings, looting, the wholesale destruction of property, and murder. The police lost control early on, and the battle was relegated—as race wars often are—to young people acting out the hatred and bigotry of their elders. In this case, the athletic associations became major players in a horrifying urban nightmare. Sections of the “black belt” were randomly torched to the ground by white gangs; prominent hotels were stormed by groups of rampaging whites looking for black porters and maids. Black snipers opened fire from rooftops on the gangs and policemen. By midnight on the third day of rioting, twenty-six Chicagoans were dead, and three hundred more were seriously injured.
Subsequent newspaper accounts of the riot singled out gangs like Ragen’s Colts. Though it had nothing to do with commercialized vice per se the riot became the implement by which reformers like the Board of Fifteen would beat down sin and avarice once and for all. Negative sentiment toward the gangs and the crooked politicians who used their services was at an all time high. Years of rampant corruption, unbridled greed, political gangsterism, and now an in
explicable racial hostility had soured the public on the very notion of the wide open town. The entire system of graft, boodling, and gangsterism was on the verge of collapsing of its own accord.
It may well have, too, were it not for the overweening moralism of the reform movement. The Women’s Christian Temperance Union and the Anti-Saloon League had declared: “It’s a war to the finish!” They were not interested in election campaign reform, tougher gun laws, or a commission to investigate police corruption. All of these methods had been tried before with only temporary results. This time, the victory would be complete. Sin and vice would be stamped out at its very source—the saloon, a place where the evil influence of beer and liquor twisted the mind, inflamed the libido, and spawned a culture of degeneracy that was tearing down all that was good about the American republic.
By 1918, this temperance movement was well on its way to success. The war in Europe had aided their cause: grain-saving limits on alcohol production were imposed, and there was a heightened concern for the moral well-being of young men in uniform. The temperance leaders and hellfire preachers crusading against liquor organized into a well-funded lobby. Nine states had already gone dry by the time the U.S. Senate passed legislation banning the use and sale of alcoholic spirits. In January of 1919, the House of Representatives was poised to do the same, which would bring about an unprecedented, nationwide prohibition of booze.
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