The Outfit (3 page)

For the gangsters, this translated as “we’ll get you elected, and we don’t even want jobs. Just look the other way when we do our thing.” And that’s just what the pols did. The hoods used muscle and money to turn out the votes for their handpicked candidates, many of whom operated gang-controlled saloons. Chicago would become infamous for “vote slugging” and “graveyard votes.” It was the Windy City that coined the expression “Vote early and vote often.” The city was essentially for ransom.

Among the earliest architects of political corruption in the Second City was First Ward committeeman Michael “Hinky Dink” Kenna, also known as “The Little Fellow.” Working in partnership with alderman John “Bathhouse” Coughlin, Kenna set the standard and constructed the template for all the official chicanery that would follow.

The sons of Irish immigrants, Kenna and Coughlin rose to power as the twentieth-century dawned, writh Chicago’s population now swelling to more than two million. Their partnership was fixed when Kenna, the owner of the city’s most popular saloon and an influential Democrat, pulled out all the stops in fixing the vote in favor of Coughlin’s election. In a short time, with both pols in office, the duo devised a foolproof, if inelegant, scheme that would guarantee them great wealth.

Through black committeemen such as William Dawson, protection payoffs for the “policy” game were made directly to City Hall. However, Kenna-Coughlin predictably took aim at the city’s Levee district for their main financial fix.

Like Baltimore’s “Block” or New York’s “Eighth Avenue,” the Levee district of Chicago’s First Ward was the epicenter of vice and vulgarity but on a gargantuan scale. By the 1920s, there were more than one hundred bookie and gambling joints in the Levee area alone, with eight hundred more scattered throughout the city. Houses of prostitution spread like wildfire. These brothels took on monikers rich in connotation: The House of AH Nations, The Bucket of Blood, and the low-end Bed Bug Row, where action was available for a mere two dollars.

Since Kenna-Coughlin’s control of the First Ward (and its jobs) was total, no one - not cops or inspectors - would make a move that went counter to Kenna-Coughlin, who were now bringing in sixty thousand dollars a year each above their annual official salaries. However, it was the dynamic duo’s chosen “collectors” who would go on to become the patron saints of the Outfit, the men who would extend organized crime’s tentacles beyond anything as parochial as the vision of Bathhouse and the Little Fellow. They were known in the Italian ghetto as Big Jim and The Fox.

The Outfit’s Forefathers

Giacomo Colosimo was born in Calabria, Italy, around 1880. Some seventeen years later he and his parents emigrated, eventually arriving in Chicago. Americanizing his name to Jim, the youngster followed the lead of the countless Italians who had arrived before him and started at the bottom - literally. Jim Colosimo first earned money in America as a ditchdigger. But this type of servitude did not suit Jim, who soon discovered that easy money came to a young man with his peculiar talent for pickpocketing. From there the now muscular “Big Jim” graduated to Black Handing, moving quickly up the crime evolutionary ladder to the far more lucrative position of
ruffiano:
a pimp.

Initially, Jim’s new vocation flopped. After a confrontation with Chicago’s finest, Colosimo laid low, returning - albeit briefly - to a life of honest work. Working for two dollars per day as a “white wing” (the shoveler who followed horse-drawn wagons) would seem to offer upward mobility to only the most enterprising laborer. Such was Big Jim. He quickly rose through the ranks to foreman and went on to organize his own social club. Soon he was elected to the leadership of the Street Laborers Union and the City Streets Repairers Union. Kenna-Coughlin were not unaware of Colosimo as a rising star.

Kenna-Coughlin, constantly on the lookout for votes outside the Irish strongholds, saw Colosimo as their ticket to support in the burgeoning Italian ghettos. In short time, Kenna-Coughlin made the momentous decision to adopt the first Italian-American into corruption, City-Hall style. It was a critical juncture in the history of the Outfit, assuming mythic status in future underworld folklore.

Big Jim’s success in delivering the vote prompted Kenna-Coughlin to place him in the “protected” post of Democratic precinct captain. In effect, this made Big Jim immune to police harassment. More important, he was reacquainted with the world of the
lupanare,
or whorehouses, from where he collected Kenna-Coughlin’s payoffs. The Kenna-Cough lin-Colosimo enterprise became referred to as The Trust, and for a time it hummed along effortlessly. For Big Jim, the role of graft collector for Kenna-Coughlin was indeed life-defining, since in that capacity he made the acquaintance of the Levee’s premier madam, Victoria Moresco.

After a whirlwind two-week courtship, Big Jim and Victoria, who was twice his age, made it legal. Soon, another dimension was added to their marital relationship: a business partnership. By 1912, they owned more than two hundred brothels. This translated to $600,000 per year in “under the table” income for the Colosimos. When the First Ward was redistricted in a show crackdown in preparation for Chicago’s first World’s Fair, Kenna-Coughlin lost their power base and soon drifted off the scene. Not so Colosimo. The Trust was now so powerful, it no longer needed to court the corrupt pols; the pols had to court
them.

As his empire expanded, Big Jim pioneered a style that went on to become de rigueur for the stereotypical twentieth-century pimp, sporting diamond rings on each finger, diamond cuff links, diamond studs, diamond-encrusted belt and suspenders, a diamond horseshoe brooch, all accenting a garish snow-white linen suit checked with (what else?) diamonds.

Colosimo’s ostentatious style made him an obvious candidate for Black Hand extortion - the same thuggery he had himself once espoused. Although Big Jim had personally murdered three Black Handers who had previously threatened him, one particular threat seemed beyond his capacity to ameliorate. On this occasion, he was being extorted for the unthinkable sum of $50,000. When Colosimo decided he needed outside help to cope with the situation, his wife, Victoria, suggested her cousin from New York. In placing the call, Big Jim would paradoxically save his life in the short term and guarantee his own extermination eleven years later. More important for history, the man Colosimo brought in for damage control placed Chicago gangsterism one giant step closer to the creation of the Outfit.

In Brooklyn, New York, Johnny “the Fox” Torrio answered the call of his cousin Victoria’s husband, Big Jim Colosimo. Born in Italy in 1882, Torrio was the leader of the Lower East Side’s notorious James Street Gang. By the age of twenty-two, he owned a pool hall, a saloon, and a brothel, in addition to his gang of burglars, hijackers, and extortionists.

One of Torrio’s most important traits was his willingness to forge alliances with rivals. In New York, Torrio brokered an important coalition between his James Street Gang and the powerful Five Points Gang, strong-armed by a professional killer and Black Hander named Frankie Yale (Uale). Like Torrio, Yale would also play a pivotal role in the twists and turns of the Chicago crime world.

Torrio possessed still another skill that would prove indispensable in his future Windy City home: an appreciation of the importance of controlling the political system. While still in his early twenties, Torrio led his gang in a total war on the electoral process. In 1905, with Torrio’s help, the Five Points Gang ensured the election of their mayoral candidate by systematically stealing ballot boxes and mugging (or “slugging” as it was known in Chicago) their opponent’s supporters.

Although Torrio was the undisputed brains of the gang, he never personally dirtied his hands in the commission of a crime. As the brilliant capo, he was too important to be placed in jeopardy. Years later, near the end of his life, he bragged - probably honestly - that he had never fired a gun in his life.

This would not be the first time that Torrio had traveled to Chicago to extricate Colosimo from the clutches of the Black Handers, but this time his ticket to the Second City would be one-way. On this occasion, Torrio, as per his style, attempted to negotiate with the Black Handers who now threatened Big Jim. Failing in this, Torrio agreed to meet the extortionists and deliver the money. On meeting the trio of Black Handers, Torrio brought guns instead of gold. Two of his gunmen emptied their clips into the extortionists, and Johnny instantly ascended to the role of Big Jim’s right-hand man.

In short time, Torrio found himself running Colosimo’s empire. But Torrio clearly viewed his stewardship of Colosimo’s businesses as merely a stepping-stone. He had big dreams that orbited around the central concept of a limitless crime empire. Colosimo gave Torrio the go-ahead to build his own organization, and the new crime baron set up headquarters in the Four Deuces, a four-story office building named for its address, 2222 South Wabash. Above the first-floor saloon, Torrio installed gambling dens and, on the top floor, a brothel. Chicago historian Herbert Asbury described Torrio’s typical day at the office in his keystone book,
Gem of the Prairie:
“There he bought and sold women, conferred with the managers of his brothels and gambling dens . . . arranged for the corruption of police and city officials and sent his gun squads out to slaughter rival gangsters who might be interfering with his schemes."

Flush with success, Torrio rapidly expanded his vice trade into the compliant Chicago suburbs. His personal empire now numbered over a thousand gambling joints, brothels, and saloons. One suburban club, the Arrowhead, employed two hundred girls and netted $9,000 per month. Torrio was grossing over $4 million per year. And prohibition’s windfall had yet to arrive.

During the graft-ridden mayoral term of William “Big Bill” Thompson, Kenna-Coughlin-Colosimo-Torrio were given free reign to plunder the city.
³
In Chicago, the term
underworld
was now but a humorous oxymoron, since there was no longer a need, or attempt, to conceal the wanton criminality.

The Second City Meets the Eighteenth Amendment

When Volstead passed, Chicagoans reacted swiftly: On December 30, two weeks before prohibition became law, infamous Second City gangster Dion O’Banion single-handedly hijacked a truckload of whiskey in anticipation of the exorbitant prices it would fetch on the last “wet” New Year’s Eve. “In twenty minutes we had buyers for the whole load,” Dion later boasted. “We sold the truck separately to a brewery in Peoria.” On January 16, 1920, six hours before the bill took effect, a West Side gangster crated off $100,000 worth of medicinal liquor from freight cars parked in the Chicago railyards. On the other side of town a liquor warehouse was looted. Still others utilized printing presses and forged phony withdrawal slips for presentation at government-bonded warehouses.

In short time, some fifteen thousand doctors and fifty-seven thousand druggists applied for “medicinal” liquor licenses. In prohibition’s first year, sacramental wine sales increased by eight hundred thousand gallons. This in addition to the illegal trade, which eclipsed the officially sanctioned variety. Windy City “speakeasies” popped up on every corner. Breweries operated in plain sight, with at least twenty-nine in Chicago alone. Countless more were established in suburbs such as Joliet, Cicero, Waukegan, and Niles. As Dion O’Banion said at the time, “There’s thirty million dollars” worth of beer sold in Chicago every month and a million dollars a month is spread among police, politicians, and federal agents to keep it flowing. Nobody in his right mind will turn his back on a share of a million dollars a month.’ Roger Touhy, a former car dealer who seized bootlegging’s brass ring, wrote, “There wasn’t any stigma to selling beer.
It
was a great public service.” Touhy continued, “Clergymen, bankers, mayors, U.S. senators, newspaper publishers, blue-nose reformers, and the guy on the street all drank our beer.”

Meanwhile, Colosimo was falling in love with a lissome young woman named Dale Winter. From the first moment Big Jim eyed her singing in his bistro, Colosimo’s Cafe, located at 2126 South Wabash, he was smitten with the girl less than half his age. Colosimo’s primary objective now was, to the astonishment of his friends, quiet domestic bliss.

Johnny Torrio, by contrast, had visions of the streets of Chicago paved with gold. He, like Touhy and most other businessmen, grasped the obvious. At last there was a clear road map to riches for the immigrant entrepreneur. When Torrio approached Big Jim with his master plan, Torrio must have been stunned by the response: a vehement no.

In a sad irony, it was now Torrio’s sponsor (and relative) who stood in his way. The Fox made what must have been an agonizing decision: his “uncle” had to be eliminated.

On May 11, 1920, three weeks after marrying Dale, and a scant four months after Volstead became law, Big Jim Colosimo was murdered in the lobby of his own restaurant. Official sources let it be known that their prime suspect was Torrio’s New York associate Frankie Yale. Although police questioned thirty suspects, including Torrio, no one was ever charged in the crime. One witness, a porter, who had initially described an assailant who fit Yale’s profile, refused to ID him in a lineup. Although never charged, Torrio was widely believed by police to have paid Yale, or
someone,
$10,000 for the rubout of Big Jim.
⁴

As Big Jim’s second-in-command, Torrio took charge of the Colosimo empire at a time when the Chicago crime world was in chaos. Rough-and-tumble gang warfare was out of control, with opposing sides clearly divided along racial and ethnic lines: Irish vs. Italians, Greeks vs. Poles, Jews vs. gentiles, and blacks vs. whites. In a frantic effort to establish turf in the newborn high-stakes business of bootlegging, countless gangs flexed their collective muscle. The period was characterized by continual intergang terrorism featuring bombings, truck hijackings, and kidnappings. In a sixteen-month period, 157 Chicago businesses were bombed. Taking their cue from the Black Handers, the bootleggers, led by bomb masters such as Jim Sweeney and Joe Sangerman and their experts, Soup Bartlett and George Sangerman, detonated more than eight hundred bombs between 1900 and 1930, dynamite and black-powder bombs being the weapons of choice. (Before the prohibition wars, the explosives were used in labor union struggles.)