Colosimo and Mushmouth Work Side by Side in the Levee

Number 239 Twenty-second street (now numbered 41 W. 22nd) was a virtual who's who of the underworld in the first decade of the 1900s, an interracial mixing of Chicago's once and future vice kings in the midst of the Levee.

The building appears to have housed a first-floor saloon, with various gambling, billiards and off-track betting operations on the second floor. It was on the second floor that "Big Jim" Colosimo, future titan of the Levee and founder of the Chicago Outfit later run by Johnny Torrio and Al Capone, founded his first establishment, the Colosimo Billiard and Pool Room Parlor, sometime about 1904. The Parlor was connected by telephone, a sure sign in those days that a horse racing handbook was operating within, as race information needed to be distributed quickly to bookmakers (see, e.g., the Mont Tennes operations).

(pictured: James "Big Jim" Colosimo)

In his authoritative volume on Colosimo, Arthur Bilek claims that Big Jim hired two of his brothers-in-law, Joseph and John Moresco, to work at the Parlor (this was before Colosimo divorced his first wife, Victoria, for a new love interest), and that these two eventually took over the business while Colosimo concerned himself with his Cafe and various brothels.

The second floor was also the site of the Frontenac Club, a joint operation between three of the city's top gambling lords: policy (lotto) king John "Mushmouth" Johnson, dice-man Bill Lewis, and Tom McGinnis, who was at times an independent bookmaker and at other times associated with the Mont Tennes and Jim O'Leary syndicates. The Club opened May 1, 1906. Notably, though Johnson and Lewis were black, the Frontenac Club catered exclusively to white customers of means (a gambler had to flash at least $10 -- roughly a week's wages for a typical laborer -- in cash at the door to be admitted). The name of the Club evoked 17th Century Quebecois leader and Indian fighter Count Frontenac, and so symbolized old world wealth and aristocracy in a city short on both. Reports at the time indicated the Frontenac Club turned profits of $200 per day (nearly $5,000 in 2008 dollars), which was split in thirds between the owners.

The building's popularity among the Levee's elite kings of vice may have been due to its central location. 22nd and Dearborn was ground zero for the red light district, and some of the better establishments, catering to a higher class of sinner, such as the Everleigh Club, were just across the street.

After Mushmouth Johnson died in 1907, it's not clear what became of the Club. A report in 1908 indicates the police raided operations on the second floor of the building and discovered a big craps game run by Bill Lewis, with mostly black players, a fact which suggests the Frontenac had either closed or changed substantially in character, although it's possible the Lewis game took place in a separate room.

That the building was still a major gambling resort in 1909 is certain from the fact that it suffered a dynamite attack in the Gamblers' War that year. The owner of the first floor saloon, old-time Satan's Mile barkeep John Morris, claimed there was no gambling currently in the buildilng (highly unlikely), though he admitted the second floor housed poker rooms at some time in the past.

As late as 1920, Colosimo's old billiards room, apparently consolidated by Bill Lewis, was still in operation. After the closure of the Levee in the mid-1910s, most of the big names in vice had moved either into the suburbs or further south (for instance, Lewis was by that time headquartering at a notorious mixed-race craps game on 35th street), but many gambling and vice resorts were still operating surreptitiously at that date.

The buildling was demolished in the mid-1950s as the entire Levee district was slowly redeveloped by the Chicago Housing Authority for low-income residences. The CHA's headquarters building between 1961 and 1974 was located on the southwest corner of Dearborn and 22nd (by then renamed Cermak Rd.), right where the Colosimo-Johnson building once stood. Ironically, the CHA left in 1974 citing crime in the nearby Ickes and Hilliard projects they managed. Robert Loeffley, information director for the public housing agency, told reporters

Because the present office location is in the midst of a string of public housing developments, people have the idea, whether it's true or not, that the neighborhood is unsafe.

The site is now part of the campus of the "National Teacher's [sic] Academy," a public magnet school opened in 2002.

Harry Cullett Bribes Morals Squad Inspector Dannenberg

In early 1914, Second Deputy Superintendent Funkhouser and his Morals Inspection Bureau squad leader, William Dannenberg, were finally cleaning up Chicago's famed segregated vice district, the Levee. Between December of 1913 and February, 1914, Dannenberg's squad had made over 1,000 arrests and shut down scores of brothels, saloons, and call flats in the area surrounding 22nd and Dearborn. The leaders of the vice gangs who ran the Levee knew something had to be done. Their first approach was to bribe Dannenberg into keeping the heat off, and on February 26, 1914, their man, "Chicken" Harry Cullett, met Dannenberg in front of MacLean's Central Drug Store at 1000 W. Wilson (site pictured above), to hand over the money.

The Morals squad was created in 1913 during a reorganization of the Chicago Police Department ordered by Mayor Carter Harrison, on the recommendation of the Civil Service Commission, which had led a major investigation of vice conditions in 1911 and 1912. The Commission's report detailed what almost everyone knew -- that the 22nd street police station, which held jurisdiction over the Levee district, was completely corrupt. The captain and all of the officers of the station were under direct orders from First Ward aldermen Michael "Hinky Dink" Kenna and "Bathhouse" John Coughlin to turn a blind eye to disorderly conditions in the district, in return for political patronage. So long as the 22nd street cops were in charge, the Levee would never close.

In order to break the hold of Kenna and Coughlin, Mayor Harrison created the special position of Second Deputy Superintendent, and appointed the thoroughly uncorruptible Maj. Metellium Funkhouser to the post. Funkhouser, in turn, created a citywide agency, the Morals Inspection Bureau, which would have authority to raid vice resorts when the 22nd street station police would not. Funkhouser appointed Inspector William Dannenberg to lead the Morals squad; Dannenberg was a vice veteran, having played a prominent role in the Maurice van Bever white slavery case in which van Bever was sent to prison, opening up a role in the Colosimo organization for Johnny Torrio.


(pictured: Inspector William C. Dannenberg)

Despite antagonism from the 22nd street station police, Dannenberg's men began closing the Levee district, ending the era of tolerated segregated vice in Chicago. Their raids put hundreds of prostitutes and their handlers in jail, and profits for the major vice rings plummeted. On January 8, 1914, the Morals squad shut down the Rhinegold Cafe, a saloon and house of ill-repute operated by the King of vice, "Big Jim" Colosimo.

Soon after, Colosimo called a meeting of major underworld figures at his Cafe to discuss strategy. Besides Colosimo, those present included Johnny Torrio, "Polak Ben" Zellen, owner of the Vestibule, an infamous resort that later was the site of an organized labor hit by "Mossy" Enright, "Beck" Moriarty, who owned a saloon at Harrison and State Streets, and the Marshall Brothers -- Joe and Bill -- who ran a call hotel at 21st and State. It was decided that a bribery attempt would be the first option, and if that failed, then violence. Even the possibility of murdering Inspector Dannenberg came up.

The man selected to approach Dannenberg with the money was a crooked cop from the 22nd street station named Harry Cullett. Cullett had been on the force for over a decade and had consistently been involved in high-profile cases, including a white slavery/murder case in 1910 and another case involving an international ring of thieves operating through the U.S. Navy. It was his fellow officers who gave him the playful nickname "Chicken Harry". In September 1913, Cullett left the police force after accusations of corruption surfaced, but he was still well-known and liked in the Department.

After leaving the police force, Cullett joined a private detective agency, the American Secret Service Bureau. From his days in the 22nd street station, he would have been familiar with the major characters of the Levee, and he apparently was willing to help them in their time of need.

(pictured: "Chicken" Harry Cullett)

On January 31, 1914, Cullett left a telephone message at the home of Dannenberg's second-in-command, Assistant Inspector for Moral Conditions Edward Altz, asking to meet that evening. At 7:00, Cullett and Altz met face-to-face at Perkins' Saloon at Monroe and Clark Streets. Cullett informed Altz that 11 Levee saloon-keepers were willing to put up $200 each in order to stop the raids on their establishments. As Dannenberg later described the deal,

To lull the public mind I was to raid a list of "fall houses," with which they provided me. Each night the divekeepers agreed to give me the name of a house to raid. From it I was to take two girls. The other places were to be immune.

Cullett asked Altz to liaise with Dannenberg to find out his attitude toward the possible deal.

The following Monday, February 2, Altz informed Dannenberg about the meeting, and Dannenberg immediately contacted his superior, Maj. Funkhouser. Dannenberg asked Funkhouser for permission to play along with the bribery scheme in order to find out who was behind it, and Maj. Funkhouser assented.

It is impressive that Dannenberg was able to so quickly pass up Cullett's offer. $2,200 in 1914 would be roughly the equivalent of $48,900 worth of purchasing power in 2008. Essentially, Dannenberg gave up a $586,000 per year salary in order to enforce the law. The bribe was probably five or ten times Dannenberg's official salary at the time.

On Tuesday, Feb. 17, 1914, Cullett and Dannenberg met face-to-face for the first time, in the corridor outside the Morals squad leader's office at City Hall. The two ducked into a quiet room nearby, where Cullett laid out his plan directly to Inspector Dannenberg. The $2,200 was only a start: brothel owners who opened resorts in the future would also add to the payoffs. The revenue potential was endless. Dannenberg agreed to the plan, and Cullett said he would get in touch when the financial arrangements were in order.

It seems the vice kings of the Levee might have gotten cold feet, for during several subsequent meetings in the mezzanine of the Hotel Sherman, Cullett had to admit he had been unable to procure the agreed-upon sums. However, finally, on February 26, everyone was convinced that Dannenberg was ready to go on the take, and a meeting at Sheridan and Wilson was planned where Cullett would hand over a $500 down payment on the first month's payoff.

Before the designated meeting time, Inspector Dannenberg was thoroughly searched by four of his men to insure he had no money on his person before leaving, and two Chicago Tribune reporters were tipped off to the story. At 8:40 p.m. on Feb. 26, Dannenberg arrived at MacLean's Central Drug Store at 1000 W. Wilson Ave. to await the arrival of Cullett. His fellow officers and the reporters hid nearby in doors and entryways.

Five minutes later, a taxicab dropped off Harry Cullett on the opposite corner. Cullett told the driver to run the meter and wait for him, while he walked briskly across the street to where Dannenberg was standing in front of the drug store window. He touched the Inspector on the shoulder, and the two began walking north on Sheridan Rd. up to Leland Ave. Then they walked back towards Wilson. Four times, Cullett led Dannenberg back and forth on the block, checking to be sure no one was following or watching. Finally, Cullett and Dannenberg darted across Sheridan to an alley behind the Grasmere hotel across the street from the drug store.

Cullett handed the money over to Dannenberg, and the two reappeared and walked back toward the corner of Sheridan and Wilson. When they reached the corner, Dannenberg removed his hat, a predetermined signal, which brought the four Morals squad officers out into the street, surrounding the pair.

"What the hell?" gasped Cullett. "I don't know what this means."

What it meant was that Cullett was under arrest for bribery. A phone call was immediately put in to Maj. Funkhouser, informing him of the successful operation, and a press conference revealed the details of the scheme to the public.

Cullett posted $2,000 bail, and a trial date was set, but never came. With the support of his detective agency, as well as Aldermen Kenna and Coughlin, Cullett's attorneys successfully made the argument that since the ordinance that created Dannenberg's office did not fully specify the duties of the Morals Inspection Bureau, he was not amenable to bribery under the statute.

Cullett never served a jail term for his role in the scheme, nor were his financial backers prosecuted. Nevertheless, Dannenberg kept up the heat on the Levee, and kept it closed tight throughout 1914.

It appears that Harry Cullett continued in private detective work, and in that, he was joined in 1915 by Inspector Dannenberg himself. The latter became one of the nation's most famous "private dicks", making his name in divorce and election fraud cases until his death in 1955.

The Central Drug store at Sheridan and Wilson changed hands several times, becoming a Liggett's, then a Ford Hopkins, then a Rex-All Drug, until it was demolished in the 1960s. The location is now a McDonald's restaurant.

Colosimo's First Brothel

"Big Jim" James Colosimo started his first brothel at this location, 2001 S. Archer, known as "The New Brighton". Interestingly, at around the same time, Paul Kelly, the famed leader of New York City's Five Points gang, also opened his headquarters on the Lower East Side under the same name. Both men began long-lived criminal empires: the Five Pointers were later absorbed into the New York mafia, while Colosimo founded the Chicago Outfit, which would continue major crime operations in Chicago, Florida, and Las Vegas through the 1970s and into the 1980s.

Big Jim's career began in 1897, when he found a job working as a street sweeper, cleaning horse manure out of the alleys in pre-automobile Chicago. He quickly moved up from this lowly job to alley inspector in 1901, a position that gave him substantial ability to extort business and home owners. He also began unionizing the street sweepers, working together with Italian political power Tony D'Andrea and "Dago Mike" Carrozzo to create a powerful voting block of immigrant voters who could be purchased for the right price.

Colosimo had always dabbled in the underworld, working briefly in the business of writing Black Hand extortion letters, and pimping a group of streetwalkers in the old Custom House Place red light district. By 1902, however, he had left low-level criminality behind and was charting a path to becoming the city's first king of vice. He opened a pool room with gambling apparatus, renting space above one of "Mushmouth" Johnson's later resorts, the Frontenac, on 22nd and Dearborn. He also met and married a young madam in the Levee named Victoria Morseco.

Moresco grew up in the Northside Italian conclave known as Little Hell or Little Sicily, but as a teenager became involved in prostitution, and rose quickly to the position of madam at the brothel at 2001 S. Archer. In 1902, at age 20, she married Colosimo, who was three years her elder, and taught him the business of running a "disorderly hotel". He quickly took over the management of his wife's brothel, renaming it "The New Brighton".

Later, he opened a second brothel next door on Armour, which he named in honor of his wife, who operated the business for the remaining years of their marriage, "The Victoria" (Armour Ave. was vacated south of 20th St. to make way for the Hilliard Towers housing project in the 1960s; also, the rest of Armour was renamed Federal Street). He also opened a restaurant, the Brighton Cafe, on the first floor of the New Brighton.

By 1909, Colosimo had convinced Johnny Torrio (coincidentally, a member of Paul Kelly's gang) to move to Chicago from New York and take charge of his prostitution operations, headquartered at the New Brighton. Upon Colosimo's death in 1920, Torrio took over the entire organization, leading it into the Prohibition era.

Thus, it was Torrio who was cited as the proprietor for the New Brighton in 1914, when Chicago mayor Carter Harrison, Jr., was finally forced by public acclaim into closing down the Levee, and on May 30, 1914, the New Brighton's business license was revoked. The Tribune noted that Harrison's reason for shutting down the brothel "was not so much the activities of women as the character of the man habitues," an indication that the New Brighton was no peer of the Everleigh Club in class or amenities.

Through Colosimo's deep influence with aldermen Michael "Hinky Dink" Kenna and "Bathhouse" John Coughlin, he was finally able to reopen the New Brighton, though most of his other gambling houses, drug dens, and brothels were closed as public pressure on the police forced the end of open vice in Chicago, forcing him to expand further into the suburbs, a process which Torrio and Al Capone continued in the 1920s.

The spot where the New Brighton stood -- and where most of the major Levee institutions stood -- has been completely vacated and turned into parkland surrounding the Hilliard Towers apartment buildings.

Marie Kerrigan Sues Colosimo

Marie Kerrigan was a cigarette girl at Colosimo's Cafe in 1919 when she was assaulted by a waiter and manager at that establishment. She subsequently sued Colosimo, making the tough characters who populated his restaurant a news item, and leading the city's biggest gangster to retreat from his life of crime. Kerrigan lived here, at 627 W. 46th St. Her home is gone, but has been replaced by another on the same lot. In her lawsuit, she claimed to live with her sister, and to be the only breadwinner for the family, which included her lame father and mother.

Kerrigan was working after midnight on May 19, 1919 when she saw a drunken woman stumble into the employee dressing room. As she went to assist and redirect, Marie Kerrigan was grabbed and manhandled by one of the cafe's waiters and one of Colosimo's business partners, Mike "The Greek" Potson. The two thugs dragged the hapless girl through the restaurant and threw her out into the alley.

Kerrigan sued the Cafe's owner, "Big Jim" Colosimo and Potson for $5,000, and her story made the papers. At this time, the Prohibition movement was sweeping the country, and soon to become federal law. At the same time, Colosimo's activities in Cook County, especially his suburban brothels in Burnham, were attracting the attention of law enforcement. This was not the kind of publicity "Big Jim" needed.

In fact, Kerrigan was not quite the angel she appeared to be, as one might expect given her employ at Colosimo's. Despite her sad story and her $5,000 demand, she settled for only $125. She signed the settlement papers at her other place of work, an exotic night club called the Midnight Frolic.

Nevertheless, Kerrigan's story made for good press, and brought public attention to Colosimo's vice empire and the continuing red light district in the old Levee. Reporters, investigators, and law enforcement agents increased their surveillance of Colosimo's businesses, eventually leading the gangster to try renouncing crime to live a life of virtue with his honest and pure new bride, Dale Winter.

Once in the underworld however, it is nearly impossible to leave, and Colosimo was assassinated in May, 1920.

Those not familiar with Chicago in the winter may wonder about the furniture strewn around the front yard in the photo above. This is a unique form of extra-legal property rights, in which Chicago residents lay claim to parking spots they have dug out after a big snow storm by placing old pieces of furniture in the spot during the day. City government perpetually threatens to shut down this informal system, but without it, there would be little incentive to dig out spaces on the street in high-traffic areas.

Mossy Enright

Maurice "Mossy" Enright was one of Chicago's foremost hitmen, and led a gang of enforcers for the plumbers' union. When he pulled up in his trademark fog-colored "gray ghost" sedan, trouble was soon to follow. By late 1919, he was leaving behind his life of petty plunder for a career as a labor leader, and purchased this beautiful home at 1110 W. Garfield Blvd. He didn't enjoy it long, as just two months later, he was assassinated at the wheel of his automobile in Chicago's first recorded drive-by shooting.

Mossy Enright was born in Ireland in 1886, but came to Chicago as a toddler. He attended school intermittently for a few years, then became a plumber's apprentice, eventually joining the local 520 of the United Association of Steamfitters. He was popular and successful -- and was willing to crack skulls when necessary -- characteristics which led to his election as union secretary, an honorary position, but one that carried political influence. He also became known as an enforcer, and man who could "do a job" when needed.

Economic theory teaches that labor unions operate essentially like OPEC, DeBeers, or any other cartel, cutting the supply of their product -- labor -- in order to raise prices (wages). A crucial element in the success of a labor union, then, is limiting the number of workers available to employers by keeping nonunion labor off the job. Thus the need for "sluggers" or enforcers, who intimidate and incapacitate nonunion workmen. The Tribune described the Enright gang's modus operandi:

Their duties would be to pick out one or two of these nonunionists working on a job, waylay them on their way home, and beat them to such an extent that they would not be able to return to work the next day. Their fate would act to scare the rest of the nonunion workers.

In 1911, Enright's steamfitters' union was involved in a major dispute with another plumbers' union over the rights to work in a number of new buildings under construction in the Loop. Each union sent their enforcers to intimidate the other side into submission. Thus did Mossy Enright kill Vincent Altman, a slugger working for the rival labor group. Fleeing the scene of the crime, an onlooker grabbed Enright, who shed his overcoat in the man's hands and escaped.

The overcoat, which had identification in the pockets, led to Enright's arrest and indictment for the crime. Released on $7,500 bail (paid for by the steamfitters), he worked assiduously to pay off jurors and to kill and intimidate witnesses. After the prosecution's chief witness disappeared mysteriously, it appeared "The Moss" might walk out of court a free man, but in a dramatic turn, the witness reappeared the day before jury deliberations began, having recovered of a pistol wound to the shoulder. The jury returned a verdict of 11-1 in favor of the death penalty, the one holdout saving Enright's life. In late 1911, Mossy began serving a life sentence at Joliet for the Altman murder.

At roughly the same time, six members of the Enright enforcer squad were tried, convicted, and sentenced to serve between five and eleven years in the penitentiary for the death of a nonunion worker they had killed.

But the story of Mossy Enright does not end in 1911, for in 1913, Governor Edward Dunne released him on a pardon. One of the state's main witnesses admitted perjuring himself that year as he lie on his deathbed, and 40,000 union members signed a petition to Dunne to secure his release.

After walking out of Joliet in 1913, Mossy Enright moved into higher levels of union intrigue, attempting to consolidate power over several Chicago unions. He achieved some success in this business, becoming wealthy enough to purchase the large Garfield Blvd. home pictured here. But he also attracted powerful enemies, including rival gangster and union man, "Big Jim" Colosimo.

One of the unions under Enright's control was the First Ward Streetsweepers' union, known as the "white wings" for their uniforms. This was the union where Colosimo had gotten his start in politics, and the Levee vice lord maintained a close affiliation throughout his life. In 1919, Colosimo managed to make his personal bodyguard, Michael "Dago Mike" Carrozzo, president of the union, displacing the Enright-supported man who had held the position previously.

In early 1920, Enright and two henchmen proved they would not accept this action lying down, and attacked Carrozzo and members of his faction at the Vestibule Cafe in the Levee district. Their bullets missed, and Enright was a marked man.

At a secret meeting at Colosimo's Cafe, Carrozzo and two allied union heavies, Frank Chiaravaloti and "Big Tim" Murphy, plotted Enright's murder. They hired "Sunny" Jim Cosmano, a colorful figure who, in 1912, had taken a bullet from Johnny Torrio while trying to extort Colosimo through "Black Hand" letters, to be the assassin. Since they didn't fully trust Cosmano, they also hired an expert hitman from Buffalo, New York, known only as "Tommy the Wop". This group followed Enright for a week to learn his habits and to wait for the right moment.

That moment came on the afternoon of February 4, 1920. Mossy Enright left his office in the Loop at 5:30 and drove the gray ghost down to his favorite saloon at 54th and Halsted, where he lingered, chatting with friends over beers. When the bar telephone rang, it was Enright's devoted wife, Etta, telling him dinner was on the table.

Enright got into his car and drove home, tailed by a rare Chalmers sedan carrying his assassins. As he parked in front of his home, the sedan pulled up next to his car. Cosmano fired twice from a sawed-off shotgun and Mossy slumped over the steering wheel.

His wife, Etta, heard the shots and ran out to the street, only to find her husband dying in the car. "Moss, in the name of God, speak to me!" she cried.

"Oh, Et--." Enright couldn't finish the thought and expired.

After the shooting, the police found the Chalmers sedan, and rounded up Cosmano, Carrozzo, Murphy, and the car's driver, James Vinci. Vinci confessed, and was put on trial first. Though he later renounced his confession, claiming that the state's attorney drugged him, he was convicted. In the mean time, the other three managed to make two key witnesses disappear, and the state's case against them fell apart entirely. They were never tried, and on the day of their release from jail, a celebration was held at Colosimo's. Vinci managed to appeal his conviction, and without the convictions of his partners in the crime, he too was exonerated on appeal.

This was the last known criminal act in which Big Jim Colosimo was involved, as he was assassinated just a few months after Enright, in May, 1920. Vinci and Murphy got theirs in the end, too, dying in beer wars gang shootouts in 1925 and 1926, respectively.

Several of Enright's followers went on to great success in crime. Tommy Maloy, Enright's chauffeur, became head of the fledgling movie projectionists' union , and was the first to realize the profit to be had in extorting theater managers to avoid strikes. He was the inspiration for the famous Bioff-Browne Hollywood extortion case in the 1940s. Walter Stevens, one of Enright's top hitmen, who killed 12 in his employ, went on to an even higher body count as a hitman for the Torrio-Capone syndicate during the 1920s.

Mossy's son, Tommy, who was 12 when his father was shot, also became a union leader, and ran (unsuccessfully) for Cook County Superior Court clerk in 1940.

The home on Garfield Blvd. remained in the Enright family until the 1950s. It is still a private home today.

Maj. Funkhouser and Inspector Dannenberg Put the Lid on the Levee

The Victorian concept of vice accepted that men were imperfect creatures and that gambling, prostitution, and liquor could never fully be eliminated from society. Therefore, it was best that these "social evils" be segregated into a restricted area of the city, where they could operate outside and apart from decent society.

This doctrine was implemented in Chicago throughout the 19th and early 20th century. Although prostitution and gambling were de jure illegal under city and Cook county ordinances, their practice in segregated vice districts was de facto tolerated. Major attacks on vice districts only occurred when city boundaries or neighborhoods changed, as was the case with the Custom House Place vice district when streetcars began bringing residents into downtown along Clark Street in 1903.

The Third Great Awakening upended the Victorian view of vice, and ended forever Chicago's toleration of its open practice. This upswing in religious fervor started after the Civil War, and included a strong paternalistic impulse, in which the poor and downtrodden were thought to be uplifted by driving saloons and pimps out of their neighborhoods by force of law.

By 1910, social and religious pressure had mounted to a degree that even Chicago's relatively lax politicians felt impelled to eliminate the open vice districts. Attention naturally focused on the 22nd street Levee, the wildest and most open segregated vice district the world had ever seen. The federal Mann Act was passed in 1910, based on a purported case of white slavery in the Levee. Even the Levee's lords and protectors, the first ward aldermen, Michael Kenna and John Coughlin, played along, feigning outrage at police indifference to unlawful saloons and brothels, and promising to act. At the same time, they convinced former Mayor and "wet", Carter Harrison Jr., to return from California to again seek the city's mayorship, which he did.

But even Mayor Harrison was eventually forced to accept the will of the city's moral majority. He forced the closure of the Everleigh Club in 1911, and in 1913, formed the city's first specialty police vice squad, led by Major Metellium Funkhouser and Inspector William Dannenberg.

These two incorruptible crusaders for the public weal aggressively pursued vice in the Levee throughout 1913 and 1914, forcing the final end of open vice districts in Chicago. First, old-time saloon keeper Andy Craig and his gang of pickpockets were rounded up. Then, in January, 1914, raids on a wide variety of Levee bars and hotels began, including one on Jan. 8 at the Rhinegold Saloon and Cafe, a bar and house of ill repute at 1939 S. Dearborn (pictured above) owned by vice king "Big Jim" Colosimo, was raided by Funkhouser and Dannenberg's morals unit. Twelve women were arrested for vagrancy, plus the saloon's keeper, Johnny "the Fox" Torrio (or "John Turio", as the newspapers called him) -- who was later to take over the gang from Colosimo and lead it into the bootlegging era of Prohibition.

Colosimo and other vice entrepreneurs attempted to bribe Funkhouser and Dannenberg, they tried to obstruct their work, they even brought a lawsuit against them -- all to no avail. By the end of 1914, all major vice operations either moved into the suburbs or underground, where they remain to this day. The closure of the Levee eliminated advertisement of liquor, drugs and prostitution, but of course, did not eliminate these evils. Outside the realm of the courts, vice entrepreneurs turned to violence to settle disputes and enforce contracts -- thus, the murderous 1920s under the leadership of Torrio and Al Capone.

Most of the Levee is gone today, with even the streets vacated. The South Loop School's Early Childhood Center, a Chicago Public School, sits on the spot where the Rhinegold once stood.

Dale Winter's Home

Dale Winters was born in 1891 in Ohio, and became a teenage beauty and singing talent. She arrived in Chicago in 1915 and auditioned as a singer at Colosimo's Cafe, by which time she was going by the singular, Dale Winter. Big Jim was impressed with her talent and he hired her on the spot at a rate of $40 per week.

Over time, Colosimo found himself increasingly attracted to this beautiful young woman, and her innocence awakened in him a desire to quit the rackets. A local clergyman, for whose congregation Dale sang, said, "she has the image of goodness written in her face." Colosimo paid for her to take singing lessons and attained for her a college scholarship to study music. During this time, Dale lived with her mother here, at 5716 South Parkway (now Martin Luther King Dr.).

Big Jim's wife, Victoria, was none too happy having her husband fawning over a teenager, and did everything in her power to separate the two. Finally, she could read the writing on the wall, and decamped for Los Angeles in 1920. Colosimo and Winter became more and more closely intertwined, and they were married on April 16, 1920 at the West Baden Springs Hotel in Indiana. After a short honeymoon, Dale moved into Colosimo's home on Vernon Ave.

Less than a month later, on May 11, Dale Winter was a widow. Colosimo was assassinated, probably at the behest of his lieutenant, Johnny Torrio. Dale Winter renounced all claim to Colosimo's money (no one else ever got much anyway), saying "All I want of Jim is the memory of him. I don't want his money or the things he gave me. I'm going to sing again. Maybe I'll sing better. I know now there isn't much to life except giving something to others. There'll never be anything in my life except singing and remembering and singing."

Dale Winter went on to a moderately successful career on Broadway, and occasionally, in film. She married again in 1924 and moved to California, where she and her husband operated a chain of theaters. Her husband died in the 1960s, and she remarried again twice, each time becoming a widow.

Dale Winter passed on in 1985 at Santa Barbara, California.

Black Hand Gang Eliminated -- by Johnny Torrio?

Late in the evening on November 22, 1911, three men were shot in the Rock Island Railroad underpass at Archer Street. Two died at the scene, the other was seriously injured and sent to the hospital. Why? There appear to be two theories.

The dead men were Pasquale Damico and Francisco Denello. According to the next day's Tribune, Damico was shot at close range nine times in the back, while Francisco Denello was shot twice, once in the head and the other through his left side. Denello's brother, Stephano, who was also shot, was discovered by a policeman dragging himself down the sidewalk a block away, and rushed to the hospital.

Under police questioning, Stephano refused to reveal any clues about his attackers. He did, however, ask that Levee big shot and Chicago Outfit founder "Big" Jim Colosimo be brought to his bedside. When Colosimo showed up, however, Stephano refused to talk with him.

Police identified the Damico and the Denellos as a Black Hand gang, sending extortion threats to prominent Italian businessmen in the neighborhood. The police captain interviewed by the Tribune said,

The city is rid of a bad gang. It is my belief that the three men were lured to the scene of the shooting by men whom they have blackmailed or were attempting to obtain money from through Black Hand letters. The Denello brothers and Damico have done most of the black hand work in this police district. We have known for a long time that they were black handers, but it has been impossible to get their victims to rap against them. Fear of death has kept them from giving the police information that might have sent the gang to the penitentiary.

As an important Italian businessmen, Colosimo was likely the frequent target of Black Hand gangs. Some historians believe that the fact that practically nothing was left of Colosimo's fortune upon his assassination indicates that he paid heavily to the Black Hand, although as the gangster king of the city, it is difficult to imagine that he would have suffered such indignities.

Instead of paying up, Colosimo may have dispatched his right-hand man (and his successor in leadership of the Outfit), Johnny Torrio, to "bump off" any would-be extortioners. The extreme manner in which Damico was riddled with bullets may have been a warning to other hoodlums that Big Jim was not to be taken advantage of.

Two weeks later, however, the Tribune advanced an alternative theory of the killings: they were part of a classic Italian love triangle. Police theorized that Mary Palaggi, a Levee saloon-keeper's daughter, was engaged to one man, but desired by another. The Denello brothers, it is claimed, were friends of the fiance (though he denied it), and Damico was an associate of the would-be paramour. The shootout under the railroad tracks, then, arose from a dispute among the parties, not an attack from assassins. The question of why the surviving Denello would have called for Colosimo in the hospital is left unanswered.

The underpass separates the Levee area, now dominated by the Hilliard Towers apartments and the Harold Ickes Homes housing project, from Chinatown, visible at the end of the road in the photo below.

Victoria Moresco's Childhood Home

Victoria Moresco was born in Italy, one of eighteen children, and came to New York with her family in the 1880s, but eventually settling in Chicago in 1891. She became wife to "Big" Jim Colosimo, taught him the prostitution racket, and their stormy relationship may have been the cause of his death.

When the Moresco family arrived in Chicago, they settled at 526 Division St., around the location of Mother's Original Night Club, pictured here. At the time, the area was a majority Italian slum known as "Little Hell" for the myriad crimes that took place here. Dion O'Banion was another product of Little Hell.

After Victoria (or "Vittoria" as the newspapers sometimes called her) became an adult, she moved to the Southside and opened a small brothel in the 22nd St. Levee. In 1902, she married a fellow Italian immigrant with ambition in criminal enterprises, Big Jim Colosimo. Together, they reigned over the vice district, and Victoria was in charge of running the couple's several large mid-price brothels.

In his latter days, Big Jim fell in love with a cabaret singer from his cafe, Dale Winter. After an acrimonious divorce, he left Victoria, and she moved west to Los Angeles, where she became involved with, and eventually married, Antonio Villiano. Victoria lived in Los Angeles until her death in 1964.

At the time of Colosimo's murder in 1920, only a short time after the divorce, Victoria (or possibly Villiano or one of Victoria's brothers) were considered prime suspects, but no evidence ever surfaced against them. Colosimo's murder has never been solved, but the most likely theory is that Johnny Torrio, Colosimo's second-in-command, was unsatisfied with his boss' personal life (Torrio was a strict Roman Catholic and disapproved of divorce), and especially with the way it was distracting Colosimo from the business the two men ran. Torrio may have hired Frankie Yale or another New York-based hitman to come to Chicago to take down Colosimo, allowing Torrio to take command of the organization.

Colosimo's Home

James "Big Jim" Colosimo was the first great Chicago mobster, considered by many to be the founder of "the Outfit." He lived in a large home at this location, 3156 S. Vernon.

Born in Italy, Colosimo came to Chicago as a teenager and, in 1897, became a sweeper with the "white wings," a city-funded group that cleaned manure out of the streets. Big Jim was a natural leader and soon organized the streetsweepers union. He parlayed that job into political power, which he used to become the city's king of vice for over 20 years.

Colosimo married into the vice business, his wife Victoria being a brothel owner, and together with Maurice Van Bever, the gang ran a profitable white slavery ring in the 1910s and 1920s. Van Bever was imprisoned in 1909. Together with the Mona Marshall case, Van Bever's trial brought public opinion to bear on interstate prostitution traffic, leading to the passage of the Mann Act in1910. Van Bever's absence opened up a top position in the gang for Johnny Torrio, who at that time was in charge of Colosimo's biggest brothel, the Saratoga. It was Torrio who later brought Al Capone to Chicago to help him run the gang after Colosimo's death.

Colosimo's house was not far from his chief place of business, Colosimo's Cafe, which for many years before and after Big Jim's death, was a place to be seen for the city's power elite. It was to this home that Colosimo brought his second wife, the beautiful young singer and actress Dale Winter, whom he loved dearly and hoped to retire with from the vice trade. Unfortunately for Big Jim, he died within a month of his marriage, shot by an assassin, most likely Frankie Yale, working on behalf of his friend and Colosimo's protege, Johnny Torrio.

The site of Colosimo's home is now a quiet South side park.

Colosimo's Cafe

"Big Jim" Colosimo, the first of the great Chicago gangsters, operated a cafe here on the west side of Wabash Ave., between 21st and 22nd streets. Big Jim ruled the underworld for longer than any other single man, including Al Capone, from the mid 1890s until his death in 1920. He owned two brothels and was known to operate a white slavery ring, kidnapping women and forcing them into prostitution. The ring was associated commercially with similar rings in New York, St. Louis, and Milwaukee, and is thought to have imported over 200 girls into Chicago, selling them for between $10 and $150 to Levee brothels. His cafe was the recognized social and political power center of the Levee, where aldermen, vice lords, and other powerful community members met and divvied out the spoils of the "contributions" made by First Ward business owners for protection.

It was Colosimo who invited Johnny Torrio, a gangster from Brooklyn, to come to Chicago and join his enterprise, in 1908. On May 11, 1920, Colosimo was assassinated here at his Cafe. The crime was never solved, but many believe Torrio ordered the hit in order to consolidate power over Colosimo's gang, in which he had risen to be the number two man. Frankie Yale, an associate of Torrio's from New York and head of the Unione Siciliane there, is the most likely gunman.

After Colosimo's death, his heirs sold their interest in the cafe to the restaurant manager, Michael Potson, who continued to run the restaurant successfully into the 1940s, when he was first sued by the famous comedy duo, Abbott and Costello over a gambling dispute, then indicted for gambling by the FBI. The cafe was seriously damaged in a fire during 1953, after which a Church of Divine Science congregation renovated the building and held services for several years, until 1958. In that year, the city condemned the property and destroyed it.

Today, the location of Colosimo's Cafe is occupied by "Tommy Gun's Garage," a gangster-themed restaurant and show where you can order "Big Jim's Lasagna" as an entree.