Paddy Whacked: The Untold Story of the Irish American Gangster (18 page)

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 inexplicable 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.

The anti-vice movement was about to succeed beyond its wildest dreams. Along with protecting the virtue and saving the souls of America’s wayward sinners, the movement’s success would also bring about an unintended result: an infusion of dirty money, black market commerce, and venality that would reshape American society and catapult the Irish American mobster into new realms of political influence, social ascendancy, and violence.

In the war for control of the underworld, the worst was yet to come.

CHAPTER
#
Four

4. delirium tremens or new clothes on an old dame

I
t is perhaps a minor quirk of history that Big Tim Sullivan, boss of what used to be the Five Points, benefactor of the Whyos, dispenser of shoes to the homeless, five-time assemblyman, state senator, and U.S. congressman, never made it to the glory days of Prohibition. He went crazy and died under mysterious circumstances in September 1913. The irony was that Big Tim, as much as anyone, had established the network of relationships that made it possible for the underworld to flourish during the years of “The Noble Experiment.” Journalist Lincoln Steffens, in his seminal 1903
McClure’s
magazine series, “Shame of the Cities,” used the word “System” for the first time with a capital “S” to describe Sullivan’s creation. Today, it would be referred to as a racketeering enterprise and prosecuted under the Racketeer Influenced and Corrupt Organization (RICO) laws.

The whole enterprise was based on muscle and patronage; you used muscle to get yourself into a position of power, then used patronage to take care of those who got you there. If you were a card-carrying member of the tribe, it was a beautiful arrangement. At a time when wealthy industrialists like Commodore Cornelius Vanderbilt were quoted in the press saying “let the public be damned,” street-level political bosses like Tim Sullivan were there to look out for the common man.

“I’ve never professed to be more than the average fella,” Sullivan once told a crowd of adoring constituents at a political rally. “I was born in poverty, one of six children, four boys and two girls. The boys used to sleep in a three-quarter bed, not big enough for two, and the girls in a shakedown on the floor. Some nights there was enough to eat and some nights there wasn’t. And our old mother used to sing to us at night and maybe it would be the next day that we would think she’d been singing but that she had gone to bed without anything to eat.

“That’s the kind of people we come from and that’s the kind of people who bore us down here. If we can help some boy or some father to another chance, we’re going to give it to him. The thieves we have down here ain’t thieves from choice. They are thieves from necessity and necessity don’t know any law. They steal because they need a doctor for some dying one or they steal because there ain’t any bread in the house for the children…”

Big Tim’s business was politics, the mother’s milk of patronage. His function was to bring solace to the hungry masses, and he was only as good as his ability to deliver. He once told a reporter from the
New York World
, “Every community has to have some man who can take the trouble to look out for the people’s interests while the people are earning a living. It don’t make any difference whether he’s tall, short, fat, lean, or humpbacked with only half his teeth. If he’s willing to work harder than anyone else, he’s the fellow who will hold the job…. And so, after all, there isn’t much to it to be a leader. It’s just plenty of work, keep your temper or throw it away, be on the level and don’t put on any airs, because God and the people hate a chesty man.”

Feisty, fearless, a master at the fine art of accommodation, Big Tim was a born leader, but he never would have been able to build his uncontested empire were it not for Boss Richard Croker. Born in Blackrock, Ireland and raised in Manhattan’s storied Gas House District, Croker followed Honest John Kelly as Grand Sachem of Tammany Hall after a youthful apprenticeship as a boxer and leader of the Fourth Avenue Tunnel Gang. At the age of thirty-three, he’d been arrested and tried for murder when a rival political operative was gunned down on election day. Croker denied his guilt, saying he never carried a gun and relied on his fists. He was acquitted of the crime.

As a political boss, Croker believed in letting his minions rule as they saw fit, as long as they delivered their district on election day. In Sullivan, Croker had a man whose reputation for getting out the vote was on a par with the legendary Hinky Dink Kenna of Chicago. The methods of Sullivan and other district bosses who followed his lead helped to make Croker a rich man. Although the position of Grand Sachem of Tammany Hall carried no salary, the former gang member from the Gas House District, through the standard manipulation of city contracts and municipal largesse, became a multi-millionaire. In 1903, Croker retired to Ireland to breed race horses.

Tim Sullivan was the odds-on favorite to take over as the next boss of all bosses at Tammany, if he wanted the job. He didn’t. Instead, he preferred to play the proverbial role of the man behind the man. In this case, the man was Charles F. Murphy, another product of the city’s Gas House District, who took over following Croker and, as grand sachem, cast his shadow over city government for the next twenty-one years.

The Irish triumvirate of Kelly to Croker to Murphy that steered Tammany Hall from one century into another was good for Big Tim Sullivan. He got rich beyond his wildest dreams. By the time of his death, he was part-owner of the Sullivan-Considine vaudeville circuit, a lucrative national chain of more than forty theatres that included the Dewey Theatre on Fourteenth Street and the Gotham Theatre on 125th Street. He was co-owner of the Metropole Hotel on West Forty-third Street, a popular gathering place for the sporting crowd. He was also a partner in the incipient Nickelodeon business and made successful investments in entertainments at Coney Island, including Metropolitan Racetrack, and numerous saloons and athletic clubs.
¹

Although Sullivan’s close relationship with Tammany’s various grand sachems certainly enhanced his standing and paved the way for his business successes, his true power did not come from above. It came from below—from the streets. As the Lower East Side district that he represented evolved, Sullivan learned to speak a few words and phrases in Italian, Yiddish, and Cantonese. In perhaps the most ethnically diverse district in the entire United States, he made friends among saloon keepers, businessmen, shopkeepers, and mobsters of every nationality.

Primary among Big Tim’s unofficial associates was the leader of the Five Points gang, Paul Kelly, an Italian immigrant whose real name was Paolo Antonini Vaccarelli.
²
The Five Pointers were a sprawling Italian gang that would give rise to some of the most noted mafiosi of the Prohibition era. In a testament to Big Tim’s powers of accommodation, he was also on good terms with the Five Pointers’ main rival, the Eastmans, a predominantly Jewish gang led by the indomitable Monk Eastman, a brawny, monosyllabic brute of a man. The gangsters helped Big Tim out on election day; in return, he used his influence with loyal magistrate judges to help them evade conviction. They were also allowed to run their various rackets free of harassment from local police. It was through his association with the Eastman gang that Sullivan established a relationship that would be his link with the city’s bootlegging empire of later years.