Hairtrigger Block

One of the most notorious gambling spots in pre-Fire Chicago was Hairtrigger Block, which ran along Randolph St., between Clark and State. A local newspaper wrote that this area had "become so contaminated by these execrable vagabonds that respectable persons avoid them as they would a cesspool."

One of Hairtrigger Block's best-known gamblers was Cap Hyman, who ran his own card house at 81 W. Randolph. Hyman's mistress was "Gentle" Annie Stafford, who had recently removed from The Sands, a lowlife resort which was located where the Tribune building now stands on N. Michigan Ave., but had recently been forced to open a new establishment at 155 N. Wells. On September 23, 1866, Gentle Annie, armed with a rawhide whip, stormed into Hyman's gambling den, dragged him out, knocked him downstairs, and chased him up Wells street. A few weeks later, Cap and Annie were legally married at a wedding attended by the cream of the underworld crop, not only from Chicago, but from St. Louis, Cincinnati, New Orleans, and Louisville.

Later, Hyman and Stafford opened a road house outside the city at what in what is now the Lakeview neighborhood, the opening of which was covered extensively in the newspapers. Hyman died after a mental breakdown in 1876, and Gentle Annie continued running a South-side brothel until 1880.

I suppose it's ironic that this show is now running in the exact location where Cap Hyman's gambing house once stood.

Under the Willow

The northeast corner of Monroe and Wells was the most notorious location in pre-Fire Chicago. From 1858-1868, Roger Plant ran a brothel and resort known as "Under the Willow," due to the willow tree that stood at the corner, under which Plant would ceremoniously dump liquor and trash. The windows of Under the Willow were covered with blue shades, upon which was written the famous catch-phrase he popularized, "Why not?"

Every sort of vice and criminal behavior took place at Under the Willow, and it was "one of the most talked about if not actually one of the wickedest places on the continent." It included a saloon, three brothels where men were typically robbed at knifepoint, white slave holding rooms, and cubicles which streetwalkers could rent and use to host their clients.

Plant himself was an Englishman, not more than an inch over 5 foot tall, and was dominated by his 250 lb. wife, who ran the brothels at Under the Willow. In 1868, Plant left the place and bought a house in the country, where he reportedly lived a serene life on the fortune he had made in Chicago. Several of his many children remained in Chicago and were active in the underworld into the 20th century.

The site is today a beautiful garden in front of the Northern Trust Building. There do not appear to be any willow trees on the property.

Gambler's Row

In the 1860s up until the Great Fire, this stretch of Clark St., between Monroe and Randolph, was the home of a number of notorious gambling houses, and was known as "Gambler's Row."

Little gambling occurs at this McDonalds/Nick's Fishmarket, located at the corner of Clark and Monroe today.

Capone's Chicago Headquarters

Johnny Torrio, the second great gang leader of Chicago, ran a tough dive called The Four Deuces, located where this empty lot now stands, at 2222 S. Wabash. After taking over leadership from "Big Jim" Colosimo, Torrio consolidated prostitution, gambling, and liquor operations throughout the city. He also hired a young Brooklyn-born gangster named Alphonse Capone, who had recently arrived in Chicago. Torrio himself was from Brooklyn, and had known Capone when the latter was a boy. Thus, he trusted "Scarface" to run some of his cribs and collect protection money. So effective and brutal was Capone's reputation on the streets of Chicago, that he was quickly elevated to the post of manager of the Four Deuces, and this remained Capone's headquarters after Torrio left Chicago.

In 1924, Capone moved his headquarters a few blocks west to the luxurious Hotel Metropole at 2300 S. Michigan, currently being developed as a condominium, where Capone's gang controlled two floors and sixty hotel rooms, patrolled at all times by heavily-armed gunmen. The basement of the Hotel held $150,000 worth of wine and liquor at the height of national Prohibition.

The site of the Metropole is currently being redeveloped as a condominium.

White Slavery in Chicago

The most famous white slavery case in Chicago history took place here, at 2252 S. Wabash, now the site of a collision repair shop and an empty lot where train cars are stacked.

Mona Marshall worked at the ribbon counter of Marshall Field's department store, One day in the spring of 1907, a handsome man named Harry Balding approached her affectionately, and asked her to join him for a show at a theatre. Instead, he took her to the Prima Dance Hall on 35th St., drugged her, and the next day she awoke here, at the Follansbee Flats on Wabash. After being brutally "broken in," Mona was sold to a brothel called the Casino on Dearborn St.which was run by Vic Shaw's husband, for $30.

One night, Mona wrote "I am a white slave" on a scrap of paper and threw it from her window, where it was found and brought to the attention of the police, who rescued Mona and arrested Harry Balding and the others who had conspired to enslave her.

At least, that was Mona's story, which was used to convict Harry Balding, despite a number of inconsistencies which came out at trial. The case brought the practice of white slavery to the public's eye and began the outrage which led to the passage of the Mann Act in 1910 and eventually led to the closure of the Levee's restricted prostitution district in 1911.

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.

Freiberg's Dance Hall

Ike Bloom operated Freiberg's Dance Hall on 22nd St., between Wabash and State, infamously known as the worst business of its ilk in the city. Freiberg's offered a bar, a dance floor, and a stage where prostitutes sang and danced kept the clientele entertained. One Chicago newspaper referred to it as "notorious even among the other dens of revelry and orgy which make up the South Side Levee." The Chicago Vice Commission referred to it as "the most notorious place in Chicago," and it was a known to be a place where women were kidnapped and sold into prostitution.

Bloom himself was politically well-connected and was chiefly in charge of collecting protection money in the Levee on behalf of the 1st Ward alderman's office.

The place was operated with few interruptions until 1918, when it was finally shut down. Bloom lived until 1930.

Today it is an empty lot. White Castle is next door.

The Everleigh Club

The most famous house of ill-repute in history, the Everleigh Club, operated at 2131-33 S. Dearborn St., now the site of the Hilliard Towers. Little is known with certainty regarding the history of Minna and Ada Everleigh, the Madams of the house. At times they claimed to have been born in Kentucky or Virginia, to have been married to an abusive set of brothers in Missouri, to have been reared by their father, a famous attorney, and to have traveled the country with a vaudeville show. In later years, a woman claiming to be their niece wrote that they were sold into prostitution by their parents, having lost everything in the aftermath of the Civil War.

Whatever their history, they operated the Everleigh Club between 1897 and 1911 as the Queens of the Levee, and catered to most of the leading men of Chicago, as well as visiting royalty (literally, in one case) from abroad, including Marshall Field, Jr., who died under mysterious circumstances after being a guest here.

The Club had a sold-gold piano and one of the nation's top chefs catered meals in a replica Pullman dining car inside. The entry fee was $50, and few men left without spending three or four times that much in a night.

The location would be near the entrance to the Hilliard Towers Apartment Homes, a renovated public housing project built in the 1960s.

Vic Shaw's Brothel

Before the Everleigh sisters arrived in Chicago, Vic Shaw ran the most famous and well-equipped brothel in the Levee on Dearborn between Cullerton and 21st, today the site of the Hilliard Tower Apartment Homes, a queer-looking but well-groomed set of high rises, which has recently been converted from a public housing project.

Vic Shaw ran brothels in Chicago until 1938, but was viciously competitive with the Everleighs, and attempted to frame them or their girls for murder on several occasions in an attempt to turn public opinion against them. She may have succeeded all too well: the entire Levee was shut down by popular acclaim, including her own brothel at this location, in the 1910s.

Other well-known brothels that operated in this block during the 1900s included the "Old 92", "French Em's", the "House of All Nations," and "Dago Frank's". The House of All Nations had two entrances, one for $2.00 girls, and the other for $5.00 girls. The house was not particularly well-lit, and so few customers realized that the same set of girls served both doors.

Bucket of Blood

One of the most notorious saloons in the Levee was the "Bucket of Blood" on the Southwest corner of 19th St. at Federal. One can only imagine what went on there. Today it is a mild-looking townhome complex.

Across Federal Street from the Bucket of Blood was the cheapest group of brothels in the city, affectionately known as "Bed Bug Row," which operated until 1913. A woman could be had there for $0.25, and there were also peep shows, torture chambers, and drug dens where heroin and morphine could be purchased openly (neither was illegal until the 1910s). The "King and Queen of the Cokies," as they were known, Eugene and Lottie Hustion, operate one of these dens. Lottie Hustion was a learned woman who spoke five languages and composed music when not doing business.

Much later, there was another bar on the West side also known as the Bucket of Blood, perhaps as an homage to this one.

Satan's Mile

The most famous red-light district in late-19th century Chicago was Satan's Mile, stretching along State St., from Van Buren to 22nd St. The famous Levee segregated district was a part of Satan's Mile, as was "Coon Hollow," the two blocks south of 9th Street, where bawdy houses catering to black men congregated.

The most famous resident of Satan's Mile was Kitty Adams, a robber known as the "Terror of State Street," who operated during the 1880s and 1890s. Living in a brothel in Coon Hollow, she learned to cut men with a razor, and always carried one in her cleavage for protection. Police estimate that Kitty Adams committed on the order of 100 robberies each year between 1886 and 1893, when she was sent to prison at Joliet. Feigning tuberculosis by puncturing her gums with toothpicks until they bled, she received a pardon from the governor, and returned to Satan's Mile to continue her life of crime until 1898, when she was again sent to Joliet, where she died, of tuberculosis in fact.

The Bad Lands

The Bad Lands was an area adjacent to Little Cheyenne, on Clark Street north of what is now Roosevelt Rd. If anything, it was considered even more depraved and dangerous than Little Cheyenne. "Big Maud" ran an omnibus house of dissipation near Roosevelt Rd. called the Dark Secret during the 1880s, offering drink and women for $0.25. Another famous Bad Lands madam, Black Susan Winslow, ran a ramshackle house on the same block. When the police attempted to arrest her, they found that, at 449 lbs., Madam Winslow could not be removed through any of the doors or windows of her dive. Finally, the back door was removed from its hinges and the frame and wall sawed out. A heavy rope was fastened around the portly Madam's waist and she was forcibly dragged to the police station by horse.

Currently, the location is a Target.

Little Cheyenne

After the Great Fire, the South side of Chicago became known for its criminal elements. The area known as "Little Cheyenne" ran several block along S. Clark Street, south of Van Buren, and was described by one Chicago detective as "about as tough and vicious a place as there was on the face of the earth. Around the doors of these places could be seen gaudily-bedecked females, half-clad in flashy finery, dresses which never came below their knees, with many colored stockings and fancy shoes. Many of them wore bodices cut so low that they did not amount to much more than a belt."

Little Cheyenne was so called because it had all the lawlessness of the Old West and was lined with every sort of dive, saloon, gambing house, and house of ill-repute. In response, the residents of Cheyenne, Wyoming, referred to their own red light district as "Little Chicago."

This stretch of Clark Street, between Van Buren and Congress, may be all that's left of Little Cheyenne, the way it once was. A men-only SRO hotel, a pawn shop, a liquor shop, and a greasy spoon seem out of place in the shadow of the Sears Tower and Chicago financial district.

Annie Stewart and Carrie Watson

UPDATE: The photos previously displayed in this post were of the wrong side of the street. For accurate photos of the current location of 441 S. Clark St., see this post focusing on Carrie Watson.
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441 S. Clark St. was a brothel belonging to Annie Stewart from 1862-1868. Madam Stewart left her house in 1868 after one of the girls shot a local constable who had come to visit the resort and cheated at euchre. The girl was arrested, but exonerated after it came to light that the constable had tried to choke her first. The judge ruled that she "had not forfeited her rights to self-protection by resorting to the disreputable life of a cyprian." Nevertheless, Annie Stewart's career was over, and another madam, Carrie Watson, took over the lease. Madam Watson raised the standards of the house and catered only to men of success, continuing to operate the house into the 1890s, after which it was demolished for use as a train car yard.

Chicago's chaotic house numbering system was changed in 1909, so that this location would today be numbered in the 800 block of S. Clark.

In the 1890s, the arrival of electric trolley cars running down Clark St. caused commuters to put political pressure on the city government to clean up the area, and Carrie Watson retired.