A mammoth city on the prairie, Chicago brought together urban corruption and Wild West lawlessness, resulting in a volatile and deadly compound. Decades before Al Capone set foot in the city, a large, well-organized, and deeply entrenched syndicate already had its hand in running many aspects of civic life. Its presence was no secret, and it bred social malaise and fierce resentment. “First in violence, deepest in dirt; loud, lawless, unlovely, ill-smelling, irreverent, . . . the ‘tough’ among cities, a spectacle for the nation,” scolded the muckraking journalist Lincoln Steffens, in his popular exposé, The Shame of the Cities (1904). “I give Chicago no quarter and Chicago asks for none. ‘Good,’ they cheer, when you find fault; ‘give us the gaff. We deserve it and it does us good.’ They do deserve it.” Chicago confirmed Steffens’s thesis that the alliance of politics and business—which Capone would soon learn to manipulate to great profit—guaranteed civic corruption. Yet even this sternest of critics failed to predict the level of violence this situation would create.
In his exhaustive retrospective of Chicago corruption, Organized Crime in Chicago, John Landesco, writing from the vantage point of 1929, observed:
For many years Chicago has been under the domination of the underworld. For many years Chicago has tolerated vice, and now the underworld and vice have it by the throat. We have complained of crime . . . , yet we have exhibited to our youth the spectacle of a policeman in full uniform acting, not only as customers of, but often as partners in, our brothels, our gambling houses, and our liquor selling. . . . This is the dark side of Chicago. The measure of crime in Chicago is the measure of its social selfishness, of its public indifference, and of its public corruption.
Landesco said what everyone in Chicago acknowledged to be the case, and he explained it as folks in Chicago did, ascribing the pervasiveness of corruption to the fact that the city was, for all its size and apparent sophistication, still a frontier boomtown at heart. “The prevalence of crime in Chicago is in large measure due to our very newness and to our very democracy,” Landesco observed. “Crime is the problem of adolescent youth and the failure properly to deal with crime is nearly always a weakness of an adolescent city and of an adolescent nation. There has always been crime upon the frontier. The main trouble with Chicago is that it is too young and that it has grown too fast.” Like many early students of Chicago, he offered mesmerizing statistics to make his point. “With the exception of New York,” he claimed, “Chicago furnishes the richest field for plunder that is to be found in the United States. In ninety-three years Chicago has grown to be the third largest city in the world. The bank clearings of the Chicago district for the year 1927 amounted to the enormous sum of $35,958,216,000. Is it to be wondered at that the robber is to be found among us?”
Indeed, criminal organizations had been a fixture of civic life in Chicago since the beginning of the century, fully two decades before Capone’s arrival. The term gangster was already part of the American tongue and initially denoted organized attempts to stuff ballot boxes and rig local elections; later the term came to include street gangs and groups of criminals of every sort. In a 1927 study of Chicago’s neighborhoods, Frederic Thrasher found no fewer than 1,313 active gangs comprising 25,000 members, and this was, in Thrasher’s words, a “conservative estimate”; no doubt hundreds of other gangs eluded his painstaking research. The gang, Thrasher demonstrated beyond dispute, was an integral part of Chicago, too entrenched to be eradicated by reform, prosperity, or other panaceas. Another, related term, racketeer, came into use in the mid-1920s, when Chicagoans suddenly began to discuss, and their newspapers to cover, the city’s more sophisticated gang members. Within several years the term became popular throughout the country, and the Chicago Journal of Commerce devised a definition as precise as that slippery expression allowed:
A racketeer may be the boss of a supposedly legitimate business association; he may be a labor union organizer; . . . or he may be just a journeyman thug. Whether he is a gunman who has imposed himself upon some union as its leader, or whether he is a business organizer, his methods are the same; by throwing bricks into a few windows, and incidental and perhaps accidental murders, he succeeds in organizing a group of smaller business men into what he calls a protective association. He then proceeds to collect what fees and dues he likes, to impose what fines suit him, regulates price and hours of work, and . . . to boss the outfit to his own profit. Any merchant who doesn’t come in, or who comes in and doesn’t stay in and continue to pay tribute, is bombed, slugged or otherwise intimidated.
Racketeers and gangs controlled the other Chicago: the city’s flourishing demimonde, to which the Capone family naturally gravitated. Throughout the Midwest, in fact, mention of Chicago conjured two images. First came the wealth, excelled only by New York, and then, close behind, the city’s reputation for licentiousness. In churches and in revival meeting tents, preachers tirelessly warned of the plight of innocent farm girls who went off to Chicago in search of a better life and higher wages, and quickly fell prey to the nets and snares of the modern (and godless) age. Alone, subject to temptation on all sides, desperate for money, these young women, so the preachers said, wound up in Chicago’s white slave trade; in other words, they became prostitutes. One of the best-known jeremiads directed against Chicago was Samuel Paynter Wilson’s book, Chicago and Its Cess-Pools of Infamy (1910), in which the author railed against the manifold snares of Chicago’s vice trade. “Sexual commerce may be purchased almost anywhere in the South State street and West Side alleys for the remarkably low price of ten cents,” he warned. “The street boy hunting these underworld sections of our city is first led into sexual sin by one of the crippled, half rotten, yet painted vampires of the street whose only care or hope is a crust of free lunch and enough whisky or ‘dope’ to drown for a time.” Another popular broadside of the day, William T. Stead’s If Christ Came to Chicago! condemned Chicago’s flesh trade in tones of biblical wrath, but at the same time his book helpfully included a map of all the city’s best-known brothels, ostensibly to warn the unwary of what streets to avoid. The guide disguised as a diatribe caused a sensation and sold briskly. With a copy of If Christ Came to Chicago! in hand, a tourist could find his way to a brothel and later return to the book to understand how terrible the experience had been.
• • •
At the moment Al Capone arrived in Chicago, the city’s vice trade was undergoing a rapid transformation, emerging from its sordid and celebrated Victorian past. Along with the stockyards, railroads, and other major businesses invoked by Carl Sandburg, vice had long been intertwined with the city’s history and political structure, and like those other important businesses, vice had its own district, in this case the infamous Levee. As most Chicagoans knew only too well, the Levee covered the blocks between Clark Street and Wabash Avenue, from Eighteenth to Twenty-second Streets. Brothels honeycombed the streets, pickpockets flourished, and youth gangs caroused. Pimps were so numerous and brazen that they formed their own union, the Cadets’ Protective Association, and the madams, not to be outdone, formed theirs, the Friendly Friends.
To those who came to the Levee in search of pleasure, price determined everything. Indeed, the Levee was organized into a rigid caste system determined by the cost of sexual services. At the bottom of the ladder was Bed Bug Row, where black prostitutes sold their bodies for twenty-five cents a throw, and at the top, the celebrated Everleigh Club at 2131 South Dearborn Street. To the rest of the United States, the little prairie towns, and even New York, the Everleigh Club was Chicago prostitution; everyone knew about it, including the city’s most influential police and politicians, who were regular customers, and who were paid off handsomely to permit it to function, indeed, to thrive. Two sisters, Ada and Minna Everleigh—proper, Kentuckyborn daughters of a lawyer—presided over the club, which boasted fifty palatial rooms, a gourmet kitchen, and the most refined women to be found in the entire Levee. Beginning in 1900, the Everleigh Club operated twenty-four ho
urs a day, and the Everleigh sisters became celebrities in Chicago; their picture appeared in the paper, and they went about the city together in their horse-drawn carriage, dressed in splendor. Eventually the forces of reform caught up with the Everleighs, and Chicago’s Mayor Carter Harrison, who had vowed to rid the city of vice, shut the place down. The Everleigh sisters had no choice but to comply, but they proved so accomplished at their trade that they retired as millionaires, still in their thirties. Thus they became another Chicago success story.
With the departure of the Everleigh sisters in 1912 and the waning of the Levee as the focus of prostitution, organized syndicates took over the prostitution business, giving rise to a new type of vice lord. James Colosimo was by far the best known of the new breed. He had emigrated from Consenza, Italy, in 1895 and gotten his start in Chicago as a Levee pimp who attracted the backing of two hopelessly corrupt aldermen whose names were always mentioned in the same breath: Michael “Hinky Dink” Kenna and John “Bathhouse” Coughlin. Colosimo made himself useful as their “collector,” a euphemism for extortionist. All the while, he maintained a parallel legitimate career as a street sweeper. Within a short period of time, he organized other street sweepers into a union, and he had the beginnings of a power base. In exchange for delivering the union’s vote, he won an appointment as a precinct captain. Now part of the city’s power structure, he had nothing to fear from the law, and he returned to his first love: prostitution. Big, jolly, handsome, careless, popular, Rabelaisian, Colosimo attained a celebrity of the first rank. His flagship was the gaudy Colosimo’s Café at 2128 South Wabash Avenue, one of the most popular nightspots in Chicago. Patrons came to drink at the renowned mahogany-and-glass bar, and to eat in its dining room, whose walls were covered with green velvet and gold filigree. Beneath chandeliers made of solid gold, racketeers mingled with society figures and famous performers. Colosimo adored the opera, and his pal Enrico Caruso regularly patronized the café, as did Clarence Darrow, the distinguished lawyer, and a good part of the city’s power elite. “Here they could rub elbows with demimondaines and their pimps, with gamblers, prize fighters, liquor agents and out-and-out sex perverts,” wrote former mayor Harrison in disgust, “enjoying the experience as a new fling at life!” In addition to his café, Colosimo maintained “cribs” (minibrothels) all over town; the cribs skimped on luxury, but they brought their services closer to the customers. Despite their dreariness, Colosimo’s brothels generated vast profits a trick and a shot of whiskey at a time. Newspapers estimated that Colosimo reaped more than $50,000 a month from his “resorts.” Out of this income he built opulent homes for himself and his father, staffed by liveried servants. With his outsized appetites and huge girth, “Big Jim” was very much a product of the Gilded Age; he wore diamonds on every finger, a diamond horseshoe on his vest, and diamond studs in his shirt. Even his belt and suspender buckles glittered with diamonds. He came by his diamonds cheaply, since he acted as a fence for jewel thieves, and the diamonds he did not wear he carried loose in his pockets like so many marbles, which he magnanimously dispensed to grateful policemen and other guardians of the sacred public trust.
Colosimo’s partner in love and crime was his wife, Victoria Moresco, a successful madam in her own right. As their family business grew, Colosimo sought a capable, unassuming man who could manage the enterprise without attracting attention. A man who could be trusted. After rejecting dozens of potential candidates in Chicago, Colosimo began hearing about the fine reputation of a low-keyed pimp and racketeer in Brooklyn: Johnny Torrio. In some versions of this tale, Torrio is described as Colosimo’s nephew, but in the absence of evidence to confirm the relationship, it is more likely their kinship was spiritual rather than familial. When the two men finally met—Colosimo huge, obvious, and carefree, Torrio slight, subtle, and worried—Colosimo came away impressed, and he offered Torrio the job. Torrio accepted, and from then on he was the driving force behind Colosimo’s success. Although he came to exercise great political influence in Chicago, Torrio never flaunted his status. He lived as unobtrusively here as he had in New York. In contrast to the garish excesses of his boss, Torrio, the classic insider, lived in an unpretentious apartment at 101 West Twenty-first Street with his wife, Ann, to whom he remained devoted. Unlike so many other men in the vice trade, including Colosimo and Al Capone, Torrio resisted any temptation to engage in sexual relations with his prostitutes. He made it a point to be home at six o’clock each evening, and he went about the city unarmed, despite the constant threat of danger. Neither did he smoke, drink, or swear. As he entered middle age, he looked exactly like what he was, a prosperous and entirely private businessman.
Even as Torrio assembled an empire of vice, his boss, consumed by a reckless passion, squandered it all. Colosimo’s undoing was, not unexpectedly, a woman. Her name was Dale Winter, and she had come to Chicago, like so many other girls, to seek her fortune as an actress and a singer. Unable to find work, she resorted to singing at Colosimo’s raffish café, and it was there that “Big Jim” saw and fell in love with her. From that time forward he was infatuated with her and left the running of his business to Torrio, who tirelessly soldiered on. Finally, in March 1920, Colosimo made the decisive break and in the process set the stage for the first modern gangland slaying. He divorced his wife and business partner, Victoria Moresco, and within three weeks he and Dale Winter were wed; at the beginning of May he installed his new bride in his home on Vernon Avenue. The courtship, divorce, and May-December marriage were the talk of Chicago—and beyond. From his vantage point of the Harvard Inn in Brooklyn, Frankie Yale closely followed Colosimo’s folly. Still an exceedingly dangerous, vicious man, Yale had watched his former ally, Johnny Torrio, progress from Brooklyn to Chicago, with great success. With the advent of Prohibition, Yale was doing a booming business running bootleg whiskey out of his Harvard Inn, but Yale wanted more. It appeared that Colosimo, old, fat, and hopelessly in love, was vulnerable. So it was that Frankie Yale decided to visit Chicago.
On the last day of his life, May 11, 1920, Jim Colosimo said good-bye to his new bride and rode in his chauffeured car to the café, where he planned to catch up on business he had neglected during the previous months. He went to his office, talked with the secretary and the chef, called his lawyer but failed to get through, and passed the time of day. He seemed impatient and ill at ease that afternoon, for he had an appointment—with whom he did not say—and the man was late. At 4:30, he stepped into the lobby on his way to the street, but he never made it. Pistol in hand, Frankie Yale had concealed himself in an adjoining cloakroom, and when his target came into view, Yale fired twice. The first bullet struck Colosimo at the back of the head; the second shattered the glass of the empty cashier’s cage and disappeared into the wall. “Big Jim” Colosimo, Chicago’s popular vice lord, fell on his back, dead, assassinated. His hair was soon matted with blood, which seeped into the floor. He was forty-three years old. Covered by a gray tweed suit, a red rose fastened to the lapel and a pearl-handled revolver in the pocket, his massive bulk was truly impressive; in death he somehow seemed larger than he had in life. Yale immediately fled the scene of the crime, but not before at least one witness, a terrified waiter, got a good look at him.
News of Colosimo’s assassination astonished all Chicago, and it was immediately seen as a watershed event for the city. The day after, the seriousminded Chicago Daily News commented, “The murder of James Colosimo, vice lord on the south side since 1912, . . . marks the ending of one epoch and the beginning of another in the history of vice in Chicago. . . . The old Levee was never dead; it was simply slumbering. With its awakening came the war for power—power to collect money from disorderly houses, to give jobs to henchmen, to gain immunity.” Had Colosimo lived out his natural life span, he would have been just another racketeer pursuing his inglorious career, but the assassination conferred a significance on him that he had lacked in life. His funeral on May 15 became a gaudy demonstration more appropriate to the
last rites of a powerful political figure or a popular entertainer—both of which he had been, in his own way. In fact, the last rites of James Colosimo became the first of Chicago’s great gangster funerals, an event that priests and police captains alike attended to pay their last respects to the sort of man they were supposed to condemn. Colosimo was universally recognized as Chicago’s premier pimp, yet his honorary pallbearers included three judges, a congressman, an assistant state attorney, and no less than nine Chicago aldermen—all of them marching in step with racketeers such as Johnny Torrio and Jakie Adler as well as an unsavory assortment of smalltime pimps and white slavers. Torrio, who never displayed emotion, wept in public and told the press, “Big Jim and I were like brothers.” A procession of 5,000 of the faithful followed the hearse bearing Colosimo’s body to Oak-wood Cemetery. “It is a strange commentary upon our system of law and justice,” remarked the Chicago Tribune of the spectacle, which accurately reflected the close alliance between the city’s racketeers and political establishment.
Once the body was laid to rest the questions began. The first concerned the disposition of his estate. At the time of his death, “Big Jim” Colosimo, who left no will, was rumored to be worth at least half a million dollars, diamonds included, but in the end, only $75,000 could be located; because of legal technicalities surrounding the circumstances of his marriages, the money went to his father rather than to Victoria Moresco or Dale Winter. The second, and far more troubling, question concerned the identity of his assassin. Since Colosimo had died with his pockets full of money and the jewels he habitually carried, and his seven-carat diamond ring still on his finger, it was apparent that robbery was not a motive. The precise, methodical execution suggested that the culprit was a professional on assignment. The list of suspects included corrupt politicians with whom Colosimo had quarreled; his ex-wife, Victoria Moresco (whose brothers, it was said, were out to avenge her honor); an early lover of Dale Winter’s; and even Johnny Torrio. Suspicion also fell on the Black Hand, the freelance blackmailers who sent elaborate letters to extort money on pain of death. Wealthy and visible, Colosimo was a prime target of Black Hand threats, but his method of dealing with blackmail was simple: he paid the money. One faint clue did turn up: a note someone had scrawled on the back of a blank check in Colosimo’s dining room that day. It read, “So long, vampire. So long, lefty.”
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