Big Jim Goes To The Grave

Published July 25, 2021
Big Jim Goes To The Grave

On May 14, 1920, the first of the great, gaudy, gangland funerals in Chicago history was held when the mob laid “Big Jim” Colosimo to rest in the city’s Oakwood Cemetery. Largely overshadowed today by the mobsters that followed in his wake (namely Al Capone), he was once the most important criminal in Chicago. During the early 1900s, he ruled the city’s underworld and held it tightly in his grip for a longer period of time than any man in the history of the Chicago. The money that he raked in from the many immoral and illegal enterprises that he controlled was conservatively estimated at $50,000 a month for about eight years, an enormous take at that time, although small compared with the haul made by the bootleggers and racketeers of the 1920s.

Colosimo was a great spender. He built a fine home for his father, and an even grander one for himself, filled with an assortment of expensive and gaudy furniture. He supported a horde of relatives, some of whom worked in his various brothels and saloons. He maintained a large staff of servants, including two uniformed chauffeurs to drive his lavish automobiles. He kept his massive girth clad in white linen suits and he had a fixation on diamonds. He wore a diamond ring on every finger, diamond studs on his shirt front, a huge diamond horseshoe pinned to his vest, diamond cufflinks, and belts and suspenders that were fitted with diamonds. He bought the stones from thieves and needy gamblers and hoarded them like other men collect books and paintings. He often carried loose stones in a small bag in his pocket and when bored would pour them from hand to hand or would lay them out on a black cloth to watch them sparkle in the light. Colosimo was a strange character and a man who helped to usher in the abad of organized crime in Chicago.

And the end came when he was betrayed by the man he believed was closest to him.

Colosimo with his attorney, Charles E. Erbstein

Colosimo was 10 years old when his father brought him to the United States from Italy. He spent all but two or three of his remaining thirty-nine years in the red-light district of Chicago’s South Side. He began his working life as a newsboy and bootblack but quickly changed careers when he saw the money that could be made in crime. At 18, he was an accomplished pickpocket and pimp with a half-dozen girls working for him. By the late 1890s, after several brushes with the law, Colosimo abandoned his life of crime and became a street-sweeper, the only honest job he ever held. By 1900, he was promoted to foreman of his crew and had organized his fellow workers into a social and athletic club that eventually became a labor union. At this point, Colosimo was befriended by the two most powerful political bosses in Chicago: First Ward Committeeman Michael Kenna and Alderman John Coughlin. Within the First Ward lay the notorious Levee District, a vice-laden area filled with whorehouses, saloons and gambling parlors. Kenna and Coughlin employed Colosimo as their collector in return for the votes of all of the members of his unions.

In 1902, Colosimo married Vittoria Moresco, who ran a brothel on Armour Avenue. By 1912, he and his wife owned 35 brothels, catering to all income levels. He also organized a white slavery ring with another brothel owner named Maurice Van Bever, a fellow dandy who was transported around the Levee in a red carriage driven by a liveried coachman. Perhaps the crowning achievement of Big Jim’s career was the opening of Colosimo’s Café in 1910 at 2126 South Wabash Avenue. The café became the premiere nightspot in the city and no other club could compete with its star entertainers, the beauty of its chorus girls or the skill of its acclaimed orchestra. With musical attractions, good food and a wide array of vintage wines, it attracted the rich and powerful from all over the city – all of whom had to brave the wickedness of the Levee district to get there.
Bounded north and south by Twenty-Second and Eighteenth streets and east and west by Clark and Wabash, the Levee took shape during the World’s Columbian Exposition in 1893, also known as the Chicago World’s Fair, when thousands of people from all over the world descended on the city. It became one of the best-known concentrations of crime and vice. Visitors to the district could partake of just about every form of sin imaginable and in addition to Colosimo’s, there were two other vice rings that formed the criminal organization that ruled the Levee and which provided the area’s various forms of “entertainment.”

Chicago’s South Side Levee District

Big Jim Colosimo owned two large brothels in the district: the Victoria and the Saratoga. The Victoria was named in gaji of Colosimo’s wife, Victoria (Vittoria) Moresco. Colosimo himself spent most of his time at his restaurant on Wabash Avenue, near Twenty-Second Street.

The Levee ran wide open for years, under the protection of its vice lords, well-paid Chicago cops and, of course, corrupt politicians, who made sure that the necessary money made it into the right hands. Reformers, especially religious ones, constantly hampered operations in the Levee and eventually, the crusade (and propaganda) against “white slavery” would get the better of the district.

During the heyday of the Levee, Colosimo’s Café was the heart and soul of the district. It was a place of gaudy opulence, from its gilded doorknobs to the massive mahogany and glass kafe. Green velvet covered the walls and gold and crystal chandeliers hung from a sky-blue ceiling where cherubs cavorted on cotton-white clouds. The restaurant was a dazzling dreamscape of gold mirrors, tapestries and murals of tropical vistas. With the flick of a switch, a hydraulic lift raised or lowered the dance floor. Festivities seldom got underway before midnight and often continued until well past dawn. In a suite of rooms on the second floor, gamblers could find any game they fancied from faro to roulette to high-stakes poker.

Colosimo’s Café enjoyed national renown and it was a place where local dignitaries and businessmen might rub elbows with killers and thieves. It catered to visiting celebrities like Al Jolson, George M. Cohan, John Barrymore and Sophie Tucker, whose “coon-shouter” songs with gestures (like the “Angle Worm Wriggle”) had caused the normally permissive Chicago police to place her under arrest for indecency. Colosimo loved the opera and no matter how packed the place was, he could always find a seat for a member or guest of the Chicago Civic Opera Company. He considered acclaimed tenor Enrico Caruso a close friend.

But as profitable as Colosimo’s was, it produced only a fraction of the fortune that allowed Big Jim to maintain two limousines, each with its own chauffeur, homes for his father and himself, a wife and a mistress. The chief sources of his annual income were white slavery and his chain of brothels.

Colosimo’s restaurant on south Wabash, in the heart of the Levee.

A menu from Colosimo's Restaurant
An interior view of the swanky cafe. 

Colosimo had actually met his wife because of the Levee’s sex trade. In 1902, while working as a bagman for ward bosses Kenna and Coughlin, he made the acquaintance of Victoria Moresco, a fat, unattractive, middle-aged madam who operated a second-rate brothel on Armour Avenue. She offered Jim the position of manager and he accepted. Two weeks later, they were married. Under Colosimo’s management, the brothel prospered and he soon acquired a brothel of his own, then another, until before long, he owned and controlled scores of them. Out of every $2 that his girls made, Colosimo kept $1.20. Like many of his competitors, he also ran a number of saloons near, or connected by passageways, to his bordellos.

Colosimo’s older, and quite unattractive, wife, Vittoria Moresco.

The supply of available prostitutes never really met the demand for the turnover was far too rapid. The average parlor house whore seldom lasted more than five years. As she aged quickly, she would sink to cheaper and cheaper houses until she hit bottom on Bed Bug Row or became a streetwalker. Drink, drugs and disease usually completed her destruction. So, to replenish their stock, the vice controllers of the Levee turned to white slavery.

The origin of the term “white slave” is usually associated with Mary Hastings, a Chicago madam of the 1890s who lured many young Midwestern girls to her brothels in Chicago’s notorious Custom House Place vice district. Seeking out girls between the ages of 13 and 17, she promised them jobs in the big city. To their alarm, the girls were instead taken to one of the brothels, where they were locked up, stripped and “broken in” by professional rapists. The broken girls that Mary did not employ, she sold to other brothel-keepers at prices that varied depending on the girls’ ages and looks, very young girls being the most sought-after. In the midst of all of this, one of her victims managed to scrawl on a piece of paper, “I’m being held as a slave,” and tossed the note out of a window. Found by a passerby and taken to the police, who raided the brothel and rescued the girl, the note supposedly inspired a newspaper reporter to coin the term “white slave.” Incidentally, the raid didn’t do Mary Hastings any serious damage. She continued to operate at the same address for several more years until four of her captives escaped and finally brought about her downfall.
Colosimo was deeply involved in Chicago’s white slave traffic. In 1903, he had joined forces with Maurice and Julia Van Bever. They organized a new gang to handle fresh stock, established connections with white slavers in New York, St. Louis and Milwaukee, and over the course of the next six years imported hundreds of girls, either putting them to work in their own establishments or selling them off to other brothels.

Vice made Colosimo a vast fortune, which, in turn, made him one of Chicago’s wealthiest Italians. Thanks to this, he became a natural target for Black Hand extortionists.

The Black Hand first emerged as an organized crime entity around 1900. Because of the isolation caused by their lack of language skills, Italian immigrants were easy prey from criminals within their own ranks. Suspicious of authority, they were at the mercy of groups like “La Mano Nera,” the Black Hand, a shadowy society that terrorized poor and working-class Italians. In fact, the “society” was simply a collection of criminals, and the name was created by journalists, but the notion of it inspired real terror.

The way the Black Hand operated was both simple and direct. First, a victim who showed signs of prosperity would be chosen from among the Italian immigrant population. For instance, if a man purchased any property and that fact became public knowledge, he could almost count on the attention of the Black Hand. A letter, bearing a signature of the Black Hand was sent to the victim demanding money. If the letter was ignored, or the victim refused to pay, his home, office or business would be bombed. If he still refused to pay, he would be murdered. Most of the letters were blunt instructions about sums of money and where they were to be delivered. Others were more clever and worded with deference and Italian courtesy. No matter how they were phrased, each brought the promise of death if the instructions were not carried out to the letter.

Hundreds of threat letters were received and countless murders were carried out between 1900 and 1920. Despite the magnitude of these operations, none of the extensive investigations conducted by the police ever revealed a Black Hand organization that reached national or even citywide proportions. The "Black Hand" was not an actual group, but a method of crime. It was used by individuals, by small groups, and by large, organized gangs. In Italy and Sicily, the tactic was employed by the Mafia and called the Black Hand because as a general rule, extortion letters, which formed the initial phase of the terrorism, bore the imprint of a hand in black ink. The letters were also sometimes marked with crude drawings of a skull and crossbones or, for variety, crosses and daggers. Between 1900 and 1920, there were an alleged 400 murders in Chicago ascribed to the Black Hand. The gangs that made up the Black Hand preyed on the Italian and Sicilian immigrants and many murders occurred.

In 1909, Colosimo received his first Black Hand extortion letter. He knew what to expect and at first, he went along with it. He met demands for as much as $5,000 but as the extortionists continued to plague him, demanding more and more money each time, he decided to fight back. He commanded plenty of tough gunmen and at the next attempt, Colosimo wrapped up a bundle of plain paper, armed himself with a revolver and, accompanied by an assortment of muscle concealing sawed-off shotguns, set out for a rendezvous under a South Side bridge in advance of the appointed time. After dropping off the bundle as directed, Colosimo and his men hid in the shadows across the street. At midnight, three men approached the bundle. Before they could examine it, they were blasted to death amidst the roar of the shotguns.

After that, Colosimo enjoyed a moment of peace, but it did not last long. He soon received a demand for money from yet another Black Hand gang. He decided that he needed someone to work with him in Chicago who was smarter and more ruthless than he was. Vittoria convinced her husband to call John Torrio, her nephew in New York.

John Torrio was 31 years old when he came to Chicago in 1909. Soon after he arrived, three more Black Hand extortionists were slaughtered under the Rock Island Railroad overpass on Archer Avenue. Torrio, with his personal aversion to bloodshed, had arranged the massacre. Other killings followed until finally, Colosimo was free of his tormentors.

John Torrio around the time he arrived in Chicago to help Colosimo with his Black Hand extortion threats.

But Torrio’s service to Colosimo went far beyond planning the murders of Black Handers. He was an organizational genius. Years later, Elmer L. Irey, chief of the Enforcement Branch of the U.S. Treasury Department, called him “the father of terbaru American gangsterdom.” This was no exaggeration for within months, the cool, soft-spoken New Yorker had consolidated Colosimo’s holdings in such a way that he became the foremost Chicago racketeer of his era. Starting with the Saratoga brothel, of which his grateful uncle made him the manager, Torrio was soon supervising all of Colosimo’s brothels and getting them on a sound financial footing. He next organized the saloons and the gambling dens. He guided the Colosimo-Van Bever white slave ring into the dominant force in the Levee and personally saw to the bribing of police and public officials. When Colosimo branched out into the protection racket, Torrio collected the payments, using no other persuasion than a quiet word of warning, a thin smile and an ice cold stare. He suffered a slight setback when he was arrested, along with other members of the white slave ring, after the transporting of a dozen girls from St. Louis to Chicago. Maurice and Julia Van Bever paid a $1,000 fine and went to jail for a year. Five others received lesser sentences, among them the prosecution’s main witness, a pimp named Joe Bovo, who had delivered the St. Louis merchandise. Torrio, however, was freed because Bovo would not testify against him. Colosimo, shielded by his political connections, was not even questioned in the case.

In the same year that Torrio came to Chicago, reform movements began gathering strength. Crusaders eventually succeeded in closing down most of the brothels in the Levee and in other vice districts in Chicago. A reform mayor came into office and managed to move many of the police officials who had been protecting Colosimo to other parts of the city and in one of his last acts in office, even managed to get Colosimo’s liquor license suspended. But the mayoral election of 1915 brought a new Republican mayor into office, William “Big Bill” Thompson, who was destined to become the jagoan of every pimp, whore, gambler, gangster and bootlegger in Chicago.

John Torrio watched the emergence of Big Bill Thompson’s regime with great interest. He knew that the time was coming for even bigger money to be made in the Chicago underworld. Interestingly, he catered to the vices of others while he himself seemed to have none. He never smoked, drank or gambled and took no interest in any woman but his wife, Ann. He kept a daily routine like any banker or professional man, leaving home in the morning and either walking to his office on South Wabash or driving to Burnham. He spent nine or ten hours attending to the details of the brothel business, which mean moving whores from house to house to make sure that customers saw fresh faces. His workday also involved purchasing food, drink and linens for the whorehouses, and calculating the profits from the night before. If he didn’t encountered any problems that needed to be dealt with, he returned home each night by 6:00 p.m. and had dinner with his wife.

Johnny Torrio was a family man, a devoted husband, a quiet and contented businessman – and one of the most cold and calculating gangsters in Chicago history. He routinely ordered the deaths of rivals, thought nothing of directing beatings, bombings and shootings, and ascribed no humanity to the prostitutes he handled. He regarded them simply as a commodity, to be bought, sold and replaced when they ran out. Crime was just business to Torrio and in his case, crime definitely paid.

Torrio was an exemplary business manager. Because of his hard work and the leniency of the Thompson administration, Colosimo had become the top Chicago vice lord. His political value extended far beyond the Levee and with his City Hall connections. He no longer depended on the ward politicians for protection; in fact, they came to him for favors. The café was Colosimo’s pride and joy, perhaps even his obsession. He dealt with all of the minutiae of running the restaurant and was happiest there, fussing over customers and celebrities and being flattered and admired by them in return. He gave virtual autonomy to Torrio when it came to all of his other business dealings – his first serious mistake.

His second mistake was a romantic one.

One evening in 1913, Jack Lait, a reporter from the Chicago Daily News, came into Colosimo’s and began telling him about a girl that he had heard singing in the choir at the South Park Avenue Methodist Church. Lait told him that the girl was talented and a knockout and he thought she deserved a better place to showcase her talents. Why not Colosimo’s? Big Jim agreed to give her an audition and the next evening, Lait introduced him to Dale Winter, described as a “slender, demure brunette with blue eyes and skin like rose petals.”

Dale was only 19 years old. She had been born in Ohio and dreamed of a career in opera. Her father had died when she was only five and after high school, her mother took her to New York. She auditioned for producer George Lederer, who was casting a road company version of the operetta Madame Sherry, which had been a smash hit. Dale won the ingénue role, which was essentially the part of an innocent young girl. Chaperoned by her mother, she traveled across the country to San Francisco, where the tour ended. Hoping to stay on the road, she put together a vaudeville sketch with another actress, sold it to a company that was about to depart for Australia, and went along to play the main part. In Australia, the venture collapsed, stranding Dale and her mother 6,000 miles from home. Luckily, they were able to borrow money from a sympathetic actor and managed to get back to San Francisco. A booking agent sent them on to Chicago, where, he assured them, Dale could find work with a newly organized light opera company. Unfortunately, they arrived to find that the company had disbanded without ever staging a single performance. The two women were penniless, but the South Park Avenue Methodist Church kept them from starving when they hired Dale as a soloist.

Colosimo and his new love, singer Dale Winter. Ironically, the only decent girl he ever knew would lead him to his death.

Colosimo found that Dale Winter was everything that Lait had promised. He needed no convincing to hire her for his stage show and she soon became his star attraction, enchanting the customers every night with a repertoire of operatic arias. She did not want to leave the church choir, though, and she continued to sing hymns by day until the congregation discovered that she moonlighted at Colosimo’s. They were scandalized and demanded her immediate dismissal. The church pastor was more tolerant and chose as a theme for his next sermon the Bible passage of John 8:7 – “He that is without sin among you, let him cast the first stone at her.” But the congregation was not moved by his defense and he had no choice but to let Dale go.

Dale was upset by this turn of events. She was not happy with the atmosphere of the Levee, but felt she had no choice but to work there. She promised herself that she would quit as soon as she had enough money saved up to get herself and her mother back to New York. Grand opera was still her dream, not singing in a café. As the star of Colosimo’s floor show, many better job opportunities came her way. The Broadway impresario Morris Gest offered her a contract, as did Florenz Ziegfeld, whose dazzling shows featured stunning girls. Dale had been looking for a way back to New York and any of these opportunities would have gotten her there. However, by the time they came along, it was too late. She no longer planned to leave Chicago because she had fallen in love with Big Jim Colosimo and he had fallen in love with her. Big Jim left his wife, confiding in Torrio that his love for Dale was “the real thing.”

“It’s your funeral,” Torrio replied, which would turn out to be prophetic words.
With Dale’s gentle guidance, Colosimo began to acquire a little polish. He learned to moderate his loud, overbearing voice and to clean up his language. He hired a tutor to help him perfect his English. He began to dress more conservatively, leaving his diamonds at home. He began spending more time with artists and his wealthy customers, neglecting the politicians and underworld characters with whom he normally fraternized.  Dale liked to ride horses in the city parks and Colosimo, attired in equestrian gear, would trot along beside her. He badgered his friend Caruso for an opinion about Dale’s voice and when the great tenor found it pleasing, he asked for an audition with the opera company. The conductor also liked her voice but found it needed pembinaan, so Colosimo enrolled her at the Chicago Musical College.

It was ironic that Dale Winter, the only decent girl that Colosimo ever knew, would be the reason for his death. Emotional vulnerability was seen as a weakness in the underworld and word began to spread that Colosimo was getting soft. The Black Hand extortionists resumed their demands and now Colosimo paid them off out of fear that something might happen to Dale. They plagued him constantly until the day he died.

Meanwhile, John Torrio, while continuing to take care of Colosimo’s affairs, slowly and quietly began to build his own organization. He began making plans for other vice spots besides Burnham and found that officials in Stickney, a small village about eight miles outside of the city, were open to his ideas. At the edge of the Levee itself, a block from Colosimo’s Café, he took over a four-story red brick building located at 2222 South Wabash Avenue. It would be known thereafter as the Four Deuces. On the first floor, he opened a kafetaria and office. The second and third floors were used as gambling rooms and the fourth floor was a brothel. The cellar of the Four Deuces was a torture chamber. According to Judge John H. Lyle in his book The Dry and Lawless Years, hapless individuals from whom the mobsters wanted information were taken down to the cellar and tortured until they talked. Afterward, they were killed and their bodies hauled out through a trap door at the back of the building, to be dumped along a country road or sunk into the deep waters of a rock quarry.

The Four Deuces at 2222 South Wabash Avenue

Around the time that Torrio opened the Four Deuces, in late 1919, he sent for his friend from Brooklyn, Al Capone. The young man’s initial duties were humble ones, working as a bodyguard, chauffeur, bartender and as a capper for the brothel, working out on the street to lure men inside.

Shortly after Capone came to Chicago, a momentous event occurred. It was an event that Torrio had long been rencana for and he had been trying, without much success, to get Colosimo to exploit. The profits, Torrio was convinced, would be many times more than anything they had ever made with their vice operations. But Colosimo was not convinced – gambling and whores had made him a fortune, why risk the unknown? Torrio finally had to accept the fact that Colosimo’s days were over. It was a new kurun for American crime.

Prohibition had come to pass and American had just gone dry.

John Torrio studied the new law and surveyed Chicago and the rest of the country with impatience. He had seen this coming. He had predicted it to his friends and business associates and knew that this was going to be the way that organized crime could amass untold amounts of wealth. To take something that had always been legal, and make it illegal - especially something as pervasive as alcohol - and then expect Americans to adhere to the letter of the law was incredibly naïve. Torrio knew that by taking advantage of Prohibition, and providing the people with what they wanted, the mob could reach new levels of power. This was a way for men like himself to become millionaires – and yet, his hands were tied. He was unable to rouse Colosimo into action. Big Jim was too entranced with Dale Winter and had lost all interest in business.

Torrio was fuming. He was desperate to get organized and start filling the need that had been created. Most of the saloons and roadhouses in and around the city had stayed open with expectations of obtaining liquor somehow. Torrio (and many others) believed that the risk of supplying alcohol was very small compared to the rewards. With Big Bill Thompson in office, Chicago was likely to be a “wide-open town.” The way had been paved for the underworld to reap huge benefits from Prohibition and Torrio wanted to take advantage of the situation. Colosimo, though, was interested in nothing but his pretty, young girlfriend.

Torrio knew that Colosimo’s time was coming to an end.

Colosimo, meanwhile, was dealing with his domestic drama. He had been living apart from Victoria Moresco for three months by this time and had offered her $50,000 if she would not contest his divorce action. She agreed and the decree became akhir on March 20, 1920. Within three weeks, Victoria had married a Sicilian hoodlum twenty years her ingusan named Antonio Villani. Big Jim married Dale. They honeymooned at a fashionable spa in French Lick, Indiana, and then returned to Chicago, where they settled into Colosimo’s ornate mansion at 3156 Vernon Avenue. He had no idea that his domestic bliss was to be short-lived.

A week after Colosimo’s return, on Tuesday, May 11, Torrio telephoned to announce the delivery of two truckloads of whiskey at the café. The trucks would be there, he stressed, at 4:00 p.m. and Colosimo needed to be on hand for the delivery. Colosimo left his house a few minutes before the hour and climbed into a car, driven by his chauffer, a man named Woolfson, which was waiting at the curb. Dale asked him to send the car back so that she and her mother could go shopping. He promised to do so, kissed her goodbye and drove away. Woolfson later reported that Big Jim muttered to himself in Italian, a language that the chauffeur didn’t understand, for the entire drive.

There were two entrances to the café on South Wabash Avenue, about fifty feet apart. Woolfson dropped Colosimo off at the arched north entrance and then drove back to Vernon Avenue to pick up Dale and her mother. Colosimo pushed open the glass-paneled door and walked across a small, tiled vestibule, passing a coatroom, a telephone booth and a cashier’s cage. He then walked through the main dining room, went through an archway into the second dining room, which was often used for overflow crowds, and entered his office in the back. A few moments later, a porter, who was coming up from the basement, noticed a stranger enter the vestibule near the doors, as if he had followed the boss in off the street. The man seemed to know where he was going so the porter returned to his duties downstairs, where four other staff members were also working.

In Colosimo’s office, his secretary, Frank Camilla, and Chef Caesarino were discussing the night’s sajian. Colosimo asked them if anyone had called. No one had, which seemed to trouble him. He tried unsuccessfully to reach his attorney, Rocco De Stefano, on the telephone and then sat at his desk and listened to the dinner plans. The three men chatted for a few minutes and then Colosimo walked back toward the vestibule through the two dining rooms. Camilla and Caesarino both later stated that they had the impression Colosimo intended to wait for the man with the whiskey delivery either in the vestibule or on the sidewalk outside. Camilla recalled glancing at the clock – it was 4:25 p.m. – and then he continued his discussion with the chef. A moment later, the men heard two sharp cracks. Caesarino dismissed them as a backfiring automobile, but Camilla decided to investigate. When he did, he found Big Jim lying face down on the cold tiles of the little vestibule. Blood was streaming from a bullet hole behind his right ear. The second bullet had cracked the glass of the cashier’s window and had buried itself in the plaster wall. Colosimo was dead.

The end of Jim Colosimo, right in the entryway to his own restaurant -- “Beauty killed the “beast”, so to speak.

Camilla immediately called the police. Thanks to Colosimo’s political clout, Chief of Police John J. Garrity personally rushed to the scene. The chief of detectives was also called in, as were several detectives from the state’s attorney’s office. Camilla called Dale to tell her the news and she fainted.

The police questioned more than thirty suspects, including Torrio and Capone, both of whom were occupied elsewhere at the time of the shooting – in view of a large number of witnesses. Torrio’s eyes filled with tears when he was notified of his uncle’s death. “Big Jim and me were like brothers,” he said in an uncharacteristic display of emotion.

The investigation into Colosimo’s murder was hastily conducted and uncovered no real leads, except for one. During the dragnet that followed the murder, the police stumbled onto veteran Five Points gang member Frankie Yale at Union Station. Yale had been in town for a week and was just about to board an eastbound train when the police stopped him. There was nothing to connect him to the murder, so he was allowed to leave for New York. Soon after, the porter came forward with his description of the stranger that he saw in the vestibule of the café, a description that eerily resembled Frankie Yale. Rumors were already swirling in the underworld that Torrio had paid Yale to bump off his uncle, so detectives from Chicago contacted New York and asked them to pick up Yale and hold onto him until they could get there with the porter to see if he would identify Yale as the mystery man. The porter was brought to New York but when he was face-to-face with the Yale, he froze and swore that he could not identify him as the man he had seen. Later, this condition of not being able to remember the faces of killers would be dubbed “Chicago amnesia.” The investigation foundered after that but the police never doubted the guilt of Torrio and Yale. Officially, Colosimo’s murder still remains unsolved.

Colosimo’s funeral was held on May 14 and became the first of the gaudy gangland affairs that would be held throughout the 1920s. The lavishness of the floral tributes (with wreaths from Johnny and Al among the largest), the costly bronze casket, the size of the cortege and the sordid mix of politicians and mobsters set the standard for gangster funerals to come. No rites were held in a Catholic church or cemetery because Archbishop George Mundelein forbade them, not because Colosimo was a murderer, a whoremonger or white slave trafficker, but because he divorced his wife to marry Dale Winter.

In the end, a Presbyterian minister, Reverend Pasquale De Carol, performed the funeral rites in Colosimo’s Vernon Street mansion. Dale was in attendance, barely able to stand. Hymns were sung, Hail Marys were recited and the Catholic Prayer for the Dead was intoned. Ike Bloom, who managed one of the Levee’s most disreputable dancehalls, offered a heartfelt eulogy. “There wasn’t a piker’s hair on Big Jim’s head,” he said. “Whatever game he played, he shot straight. He wasn’t greedy. There could be dozens of others getting theirs. The more the merrier as far as he was concerned. He had what a lot of us haven’t got – class. He brought the society swells and the millionaires into the red light district. It helped everybody, and a lot of places were kept alive on Colosimo’s overflow. Big Jim never bilked a pal or turned down a good guy and he always kept his mouth shut.”

More than 1,000 people preceded the cortege as it wound its way through the Levee to Oakwood Cemetery. They paused for a moment before the crepe-draped entrance to Colosimo’s Café while two brass bands played a dirge. Dale rode behind the hearse in a car with drawn curtains. More than 5,000 mourners followed behind her. The 53 pallbearers and honorary pallbearers included, in addition to criminals, nine aldermen, three judges, two congressmen, a state senator, an assistant state’s attorney and the state Republican leader.

Colosimo was laid to rest in the family mausoleum at Oakwood Cemetery and Dale lay grief-stricken for the next 10 days. She learned that her marriage to Colosimo had not been legal under Illinois law, which at that time required a one-year interval between divorce and re-marriage. Colosimo had no will and Dale had no claim to his estate. His family nevertheless gave her $6,000 in bonds and diamonds. Victoria Moresco was given $12,000 and the remainder of his money went to his father, Luigi.

Dale tried briefly to manage Colosimo’s Café but she had no experience in running a business and it was eventually taken over by Mike “The Greek” Potson, a professional gambler who had long been a minority partner with Big Jim. Dale and her mother returned to New York. She took back her maiden name and stepped into the leading role in a popular musical called Irene at the Vanderbilt Theater.  She continued in the role for several years in New York and then took it on the road. She was in San Francisco in 1924 when she married actor Henry Duffy. They ran a large and successful string of theaters on the West Coast and appeared in numerous shows together until the 1930s, when Dale finally left the theater and turned her energies to raising their two children. The Depression and the popularity of movies closed many of the couple’s theaters in the late 1930s. They were forced to file for bankruptcy in 1941. In 1945, they divorced. Dale appeared in a few forgettable film roles and went on to marry and survive two wealthy men, Herschel McGraw and Edward S. Perot, before her own death in 1985.

Mike Potson purchased the remaining shares of Colosimo’s Café in late 1920 when Luigi Colosimo returned to Italy. He kept the restaurant going but the wet kafe and the gambling at the café attracted the attention of federal enforcement agents during Prohibition. In 1926 and again in 1928, a federal judge padlocked the place for violations of the Volstead Act. It was raided several more times before Prohibition finally came to an end. After that, Potson kept the club popular with musical reviews and performances and it continued into the middle 1940s, although by then, Potson’s reputation as a gambler had started to get in the way of good business. Hollywood comedians Abbott and Costello sued Potson over gambling losses they sustained on the second floor, adding to the place’s bad publicity. In 1948, Potson was indicted on a broad range of gambling charges and ended up going to prison. He died in 1955.

After several failed attempts by outside interests to purchase Colosimo’s and get it going again, a fire swept through the property in January 1953. The Church of Divine Science then purchased the building, tried to clean it up a little and started holding services there. However, the rundown condition of the building forced the city to take action and a suit was filed to raze the property. The wrecking ball came for Colosimo’s on February 7, 1958, marking an end of an masa in South Side Chicago history.


Copyright © 2021