The History of Chicago's "Red-Light" Vice Districts. [PG-13]

In the early days of Chicago, the area on the north bank of the Chicago River, near the lakeshore, was initially populated by saloons and inexpensive boarding houses, like the Wolf Point Tavern (opened December 1828), the Eagle Exchange Tavern (opened in 1829), the Green Tree Tavern (opened in 1833), and Miller's Tavern [brothers Samuel and John] (opened in 1830). These were popular among seafaring men working the docks on the Chicago River and merchant vessels' crews.

Fifth Avenue, today's Wells Street, was Chicago's oldest and longest-running red-light district. Prostitution was likely present before Chicago was incorporated as a town on August 12, 1833. The Board of Trustees imposed a $25 ($630 today) fine on known brothel owners in 1835. Chicago's population proliferates, and Chicago refiles to incorporation for city status. It was accepted on March 4, 1837, and became the City of Chicago. 

In 1838, records were made of complaints that several houses of ill-repute were operating openly on South 5th Avenue (Wells Street) between Jackson and First Street (renamed to Congress Parkway in 1909).

The area on the north bank of the Chicago River, near the lakeshore, was initially populated by saloons and inexpensive motels popular among seafaring men working the docks of the River or passing through Chicago on some merchant's vessel. 

By the 1850s, however, the area had developed into the toughest criminal district in the city, known as the Sands. It was composed almost entirely of gambling dens and brothels, occupying around thirty poorly constructed shacks, which had the unfortunate tendency to burn down or simply fall apart regularly.

Drunkenness, fighting, robbery, murder, general misbehavior, and disorderly conduct were the order of the day, every day, in the Sands. The intoxicated residents of the district were the misfortune of the town's respectable population. "Gentle" Annie Stafford was a famous prostitute of a Sands brothel, later running her own brothel at 155 North 5th Avenue (Wells Street), just north of Randolph Street, in the 1860s. Another resident, Margaret McGuinness, it is said, was not sober for five years straight and did not bother to wear clothes for three of those years.

Chicago's Mayor at the time was Long John Wentworth, an educated man from the New England area and a former newspaper editor who wanted the Sands razed. In April of 1857, William Ogden, who had been Mayor before Wentworth and now an important businessman in the city, managed to purchase several properties in the Sands. He immediately ordered the squatters living in these properties out. Still, when they refused to budge, he begged the help of Mayor Wentworth, who was only too happy to see an opportunity to eliminate the hated vice district.

On April 20, Wentworth organized and advertised a major horse race at a Race Track in Chicago. Most of the male residents of the Sands were habitual gamblers, so the event attracted the substantial majority of their population. While the men were gone, Wentworth and Ogden crossed over to the Sands, accompanied by a team of horses. After serving prior eviction notices, the horse team was hitched to the foundations of several of the shanties, and each was pulled down. The destruction led to a small riot, with the remaining residents of the Sands running into the streets, looting their neighbors' properties, and destroying most of the rest of the district in the process. A few hours later, what was left went up in flames. The next day's Chicago Tribune reported a fanciful hope:

This congregation of the vilest haunts of the most depraved and degraded creatures in our city has been literally "wiped out," and the miserable beings who swarmed there driven away. Hereafter, we hope the Sands will be the abode of the honest and industrious, and that efficient measures will be taken to prevent any other portion of the city from becoming the abode of another such gathering of vile and vicious persons.

The last sentence was wishful thinking, but curiously, the Tribune Building sits on the property that was once the Sands. The land the Wrigley building sits on, across Michigan Avenue, would also have been part of the Sands during the 1850s.

The 1850s and 60s saw masses of poor immigrants, primarily from Ireland, building a shantytown of low, tumble-down buildings centered around Monroe and Wells Streets, known as "Mrs. Conley's Patch." Longtime Alderman and world-renowned 'Bathhouse' John Coughlin was raised there as a child. However, "the Patch" was also notorious in its day for its decrepit dwellings and some of its residents' depravity and dark crimes. 

There were houses of prostitution, including most famously Madam Lou Harper's "Mansion" at 219 West Monroe Street (today; 228 West Monroe Street) between Wells and Franklin, and Francis Warren's troupe of streetwalkers, who resided between Clark and LaSalle.

Roger Plant was the principal king of vice, among the city's first ─ and perhaps greatest ─. A Yorkshire-born Englishman, Plant arrived in the city in about 1857. Legend has grown around Plant, who purportedly had been convicted of a felony in England and was scheduled to be exiled to Australia when he escaped and made his way to Chicago.

By 1858, Plant had built "Roger's Barracks," a set of poorly constructed shacks centered on the northeast corner of 5th Avenue (Wells Street) and Monroe. The Barracks, later known as "Under the Willow" (1858-1868), so named after a single sad willow tree that stood on the corner, was the center for all vice in the city up through the end of the Civil War. Plant popularized the catchphrase ─ "Why Not?" ─ which was emblazoned on each of the blue window shades in the complex.

Plant himself was diminutive, at just over five feet tall and no more than 100 lbs, but he was apparently a vicious fighter, skillful with a pistol, knife, and club, but especially with his fists and teeth. The only one who could ever whip him, it is said, was Mrs. Plant, a mountainous woman weighing at least 250 lbs. Plant kept order in the saloon on the premises and operated as a fence and a bail bondsman; while his wife ran a brothel with no fewer than 80 girls, they rented out cubbies on the property for use by streetwalkers and made a trade-in "white slave" girls.

During the war, Under the Willow ("that shadowy haunt of sin," as the Tribune put it) played host to battalions of soldiers and was rarely empty at any hour. It was a fearsome place, however, with many men finding themselves robbed, beaten, or knifed and discarded in the alleys (frequently by Mrs. Plant herself) after imbibing too much or falling asleep in one of the decrepit cribs.

Some of the permanent residents of the Plant complex included Mary Hodges, an apparently fantastically talented shoplifter, who it is said, in tall-tale fashion, would drive a cart into the shopping district several times a week to bring back her takings. Another was Mary Brennan ("an audacious old sinner," as the Tribune described her), who was a thief but also the trainer of thieves and pickpockets. Mrs. Brennan's two daughters were caught breaking into a home whose owner was away on business one afternoon in 1866 and, as punishment, were placed in the Catholic Asylum, separated from their mother until adulthood.

Another longtime tenant was Lib Woods. Miss Woods arrived in Chicago in 1855 and was described in 1860 as "one of the gayest, prettiest, most fascinating creatures that could be found among her class in this city…. with a splendid head of hair that made her rivals all despair. It hung down below her waist in long, glassy ringlets."

Woods was Billy Meadows's girlfriend, a successful prizefighter. But when Meadows took sick and died in 1861, Miss Woods' declined into drunkenness, and sexual dissipation was quick. She took up residence at Under the Willow as a prostitute shortly after and was then seized with smallpox, which disfigured her beautiful features. She was frequently drunk and became increasingly violent as she aged. She died a sad death in 1870, found in a gutter on 5th Avenue (Wells Street).

After the Great Chicago Fire in 1871, the Near South Side of Chicago became known for its criminal elements. The area known as "Little Cheyenne" ran several blocks along south 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 wore bodices cut so low that they did not amount to much more than a belt."

Cheyenne District Brothel Map (1870-1905)
Click the Map to Enlarge.

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

Roger Plant was notorious for paying off the police to keep the heat away from Under the Willow and his other nefarious doings. In October 1866, he was arrested for robbing a man he had helped bail out of the Bridewell[1] for $25. A few days later, the police discharged him, much to the uproar of the city's more righteous citizens. Most likely, the increasingly wealthy Mr. Plant greased a few palms on his way out of the police house. In a later committee investigation before the city council, Plant was directly asked whether he had ever paid off the police, and, displaying honor among thieves, he refused to perjure himself ─ he "took the fifth" and was eventually dismissed for being unwilling to answer questions.

Within a few years after the war, Plant had amassed such a fortune that allowed him to depart his vile surroundings for a country estate outside Chicago. By 1871, the Tribune reported that "Roger is now a church member in good standing, drives an elegant team, and lives like a Christian."

Roger Plant had many children, by some counts, as many as fifteen. Several of them established their own houses of vice in the Custom House Place district during the 1880s and 1890s, including daughters Kitty and Daisy Plant and son Roger Plant, Jr. Many other former tenants not related to Plant also developed vice businesses. He is rightly known as the father of vice in Chicago.

By the time of Roger Plant's retirement, Under the Willow extended halfway down the block on both Monroe and Wells streets, and the centerpiece of the property, rebuilt after the Great Fire, was a four-story building. The plant continued renting the property for large sums into the 1890s until it passed out of the family's hands in 1908, purchased by the city's top sporting man, J.J. Corbett, for $100,000.

After the Fire, most of the residents of Mrs. Conley's Patch, having had their homes destroyed, moved to the south side, where many of the neighborhoods to this day still have substantial Irish populations. The west end of Monroe Street was redeveloped mainly as a warehouse district, while business and commercial buildings arose closer to the Lake.

Annie Stewart owned a brothel at 441 South Clark Street (today, the 800 block of South Clark Street) 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 (a card game). 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 (a lewd or licentious person, especially a prostitute)." Nevertheless, Annie Stewart's career ended, and another madam, Carrie Watson, took over the lease. 

Carrie Watson ran one of the world's most famous houses of ill repute between 1868 and 1897. Watson took a job as a prostitute at Lou Harper's Mansion in 1866. After two years of learning the madame business at Harper's feet and saving her money, she set out with her solid man, Al Smith, to buy the two-story brick building at 441 South Clark Street from Annie Stewart.

Watson's house usually had around 25 experienced, well-mannered, and well-dressed women and various diversions for the strictly upper-class gentlemen who frequented this house, including a bowling alley, five parlors, and a billiard room. A three-piece orchestra kept the guests entertained at all hours. The house's splendor became famous during the 1893 Chicago World's Fair.

Her most famous advertisement was a trained parrot at the door who repeated: 

"Carrie Watson!    Come in, gentlemen!"

Carrie Watson's brothel was destroyed in the first decade of the 1900s to make way for expanded tracks at the Dearborn Station. After the closing of the Station, the property was redeveloped for residential purposes.

CLICK THE MAP FOR AN ENLARGED VIEW.

46 saloons, 37 "houses of ill-repute," and 11 pawnbrokers in the Levee in 1894.

Prostitution continued to thrive and expand on the southern edge of the Loop. Smaller districts were developed on the Near West Side and Near North Side. Intermittent raids through the late nineteenth and early twentieth centuries aimed not at closing the brothels but at maintaining a flow of bribes to police politicians and politically connected crime bosses. Raids also helped to preserve a modicum of public order within the districts and to control their borders. 

In 1897, for instance, Mayor Carter Harrison, Jr. ordered police to clean up a section of South Clark Street in which prostitutes were visible from a new trolley line. In 1903, he began sweeping vice away from the southern Loop while leaving the newer "Levee District" near the intersection of Cermak Road (22nd Street) and Michigan Avenue in the city's Near South Side. It consisted of twenty square blocks. Like many frontier town red-light districts, the district gets its name from its proximity to wharves in the city. It was the largest, the most notorious, and the most vicious of all Chicago's vice sections. It combined the worst features of the "Badlands" and "Little Cheyenne," which had been located in the Loop. It had saloons of unbelievable depravity. Its streets, alleys, and dives swarmed with harlots, sluggers, degenerates, dope fiends, thieves, and hundreds of pimps for the 5,000 resident prostitutes. 

The Levee District opened in the 1880s and was home to many brothels, saloons, dance halls, and similar places. These businesses ranged from rough dives, like Pony Moore's or the Turf Exchange Saloon, to prestigious, infamous clubs like The Everleigh Club. At 2120 South Dearborn, the location of Madam Emma Duvall's "French Em" brothel, the first all-mirrored bedrooms were introduced in the early 1890s. The French Em was located just a few doors north of the famous Everleigh Club. The Everleigh Club is where Marshall Field Jr. was shot by a prostitute on November 23, 1905. 

In the late 1800s, Michael' Hinky Dink' Kenna (1858-1946) purchased a tavern on Clark Street called The Workingman's Exchange, where he traded food and alcohol for votes. Kenna was elected Alderman in 1897 when he teamed with fellow First Ward Alderman (each ward had two Aldermen until 1923) 'Bathhouse' John Coughlin (1860-1938) to create a powerful political machine in what was then called The Levee District, the area just north of 22nd Street along the east bank of the Chicago River.

Levee District Brothel Map (1924)
Click the Map to Enlarge.

To receive protection, Levee inhabitants would annually attend the biggest event in the district, The First Ward Ball. The First Ward Ball was an event where Levee residents gathered to celebrate the triumphs brought to them by Michael' Hinky Dink' Kenna and 'Bathhouse' John Coughlin. 

Michael' Hinky Dink' Kenna' Bathhouse' John Coughlin 

Madams, corrupt businessmen, dance-hall owners, saloon owners, prostitutes, brothel owners, and gamblers attended the event to support their aldermen for continuing to protect them from the law. The money they raised came from purchasing tickets for the event and alcohol. 

When anti-vice reformers protested the ball, Kenna justified it as benefiting the people in the district through education and community programs. The First Ward Ball of 1908 was the most significant ball because it was the last that the most prominent figures of the Levee attended. That year, anti-vice reformers had tried to stop the ball by bombing The Coliseum, the Arena where it would be held. The ball still went on and was successful. 

The following ball would prove otherwise. The First Ward Ball of 1909 was unsuccessful because anti-vice reformers worked towards getting the city to revoke the event's alcohol license. They succeeded, and about 3,000 people attended, less than a quarter of the attendance of the previous balls. That year, reformers like the Woman's Christian Temperance Union (WCTU) worked towards stopping events like these because they felt they harmed the Levee families.

South Dearborn Street looking north from 22nd Street in the Levee district of Chicago, 1911

The lowest part of the Levee was called "Bed Bug Row." It was a group of 25-cent brothels mostly occupied by Negro girls. It had gangs of panderers and white slavers, classes in which young girls were taught various methods of perversions after they were "broken in" by professional rapists. It also provided entertainers for stag parties, peep shows for young boys and drug stores where dope addicts congregated and openly gave one another injections of cocaine and morphine. One store even provided hypodermic needles. Bed Bug Row was located between Dearborn and Federal and 19th and Archer.

Houses on Federal Street Levee District Chicago

Houses on Federal Street Levee District Chicago. 1911

The Gray Wolves were corrupt Chicago aldermen who held office from the 1890s to the 1930s. The Gray Wolves were led by First Ward aldermen' Bathhouse' John Coughlin, ' Hinky Dink' Mike Kenna, and Johnny Powers of the Nineteenth Ward.

The Chicago City Council frequently gave franchises to private businesses to maintain public services. Many companies bribed the aldermen to be awarded such contracts, a practice known as "boodling."

In 1895, the Gray Wolves awarded a franchise to the non-existent Ogden Gas Company to force the existing franchise holder to buy up the rights of Ogden Gas. This and similar schemes resulted in the formation of the Municipal Voters League in 1896 to throw the Gray Wolves aldermen off the council.

Lincoln Steffens, a muck-raking reporter from McClure's Magazine, was the first to describe these aldermen as gray wolves "for the color of their hair and the rapacious cunning and greed of their natures."

"The Paris," a saloon and brothel in Chicago's Levee district, located at 2101 Armour Street. It was operated by Maurice Van Bever until he was convicted for operating a "white slavery" ring.

President of the Chicago Brick Company, millionaire Patrick J. Sexton, owned a three-story mansion set fifty feet off the street at 1340 South Michigan Avenue in the 1880s and 1890s. Mr. Sexton and his wife hosted several important social events throughout the late nineteenth century. During that time, "P. J.", as he was known, became a pillar of the business community. P.J. Sexton died under somewhat mysterious circumstances in 1903, with rumors circulating that he had suffered arsenic poisoning, although the coroner's report came back clean. Sexton left a considerable sum of money to his wife and children, but they moved out of the home after his death.

With the new automobile industry growing in Chicago, the south Michigan area became home to several automobile showrooms, but the mansion remained a private residence. The windows were always shuttered, and no one ever remembered seeing the front door open. In fact, the home had come to be the city's most famous lovers' rendezvous, "The Arena." The management of this short-term hotel allowed customers in by the rear door only, and only men and women of the upper crust were admitted ─ absolutely no streetwalkers or dancers.

The Arena was closed in 1911 as public opinion turned against segregated vice, and the Mayor was forced to close the 22nd Street Levee. The building was demolished and replaced by a seven-story building operated as a furniture store in 1922. This building remains on the site today. It served as the Cook County Circuit Court for divorce and family court in the 1980s and 1990s. Today, the ground floor has a Giordano's Pizza Restaurant.

Jim Colosimo, a brothel and Restaurant owner, was one of Chicago's most powerful crime bosses in 1920. His Colosimo Restaurant here was famous around the world. No other place could compete with its star entertainers and the beauty of the chorus girls. Potter Palmer, Marshall Field, Al Jolson, George M. Cohan, and Al Capone were regular customers. The cafe was located at 2126-28 South Wabash Avenue, Chicago.

On the morning of May 11, 1920, when Colosimo entered the restaurant, a gunman stepped out from the cloakroom and shot him twice behind the ear. The killer was never found, but many think that the killing was ordered by Colosimo's longtime friend and partner, Johnny Torrio. 

In 1949, Colosimo's former cafe was a cafeteria for a short time, then reopened as a burlesque bar. In 1976, it housed a sign company, which was demolished shortly after. The site is currently a parking lot.

The Levee district's success in vice came to an end when reformers such as the Woman's Christian Temperance Union (WCTU) and Chicago Vice Commission CVC (established by Carter Harrison, Jr.) worked towards publicly exposing the issues of white slavery and alcohol. The WCTU had a "department of rescue" to save women forced into slavery. 

Founded in 1877 in Chicago's notorious "Levee District," the Pacific Garden Mission intended to convert the red-light district's visitors to evangelical Christianity. Pictured is a Gospel Wagon at the Mission.

They also had a "department of social purity," which raised sexual consent laws. The WCTU paid investigators to conduct studies on forced prostitution in Midwest lumber camps that would help them publish a journal of stories of women working as prostitutes in Chicago's Levee District.

The Chicago Vice Commission focused on terminating vice districts and worked towards investigating women's conditions in the Levee. The members spoke to prostitutes, police, and neighborhood organizations to examine the issue of prostitution. They published a report, The Social Evil in Chicago, which included prostitution statistics and recommendations for improvement. The report concluded that about 5,000 professional prostitutes worked in Chicago, and about 5 million men were receiving services from them, for which the women received about $25 weekly. They were mostly uneducated and unskilled, and they had little to no opportunities for economic advancement. The report was read worldwide and influenced vice commissions in 43 cities to close their vice districts.

Closing down the entire Levee District was a long, laborious process. It began on January 9, 1910, when Nathaniel Ford Moore died in Vic Shaw's brothel. She wanted to frame Minna Everleigh for the death, but Everleigh found out about Moore before Shaw got the chance. Thus, Shaw was forced to call the police to report the death, after which her brothel was closed. 

A year later, on October 3, 1911, the state's attorney issued warrants for 135 people associated with the Levee, including Big Jim Colosimo, Ed Weiss, Roy Jones, and Vic Shaw. The warrants shut down halls, saloons, and brothels. Many people were arrested within the brothels; in Marie Blanchey's brothel, 20 women and 30 men were arrested. Word spread about corruption in the government so on October 24, 1911, Mayor Harrison ordered the closure of the Everleigh Club, which was shut down the next day, allowing the famous brothel to throw a huge party. Many businesses in the Levee District closed in 1911, but the district held on for two more years. One of the last brothels to close was Freiberg's Dance Hall, which celebrated its last night on August 24, 1914.

When the Levee was closed in 1911, the Chinese living in the original Chinatown at Clark and Van Buren in the Loop began moving south to Armour Square. Some historians say this was due to increasing rent prices. Others see more complex causes: discrimination, overcrowding, a high non-Chinese crime rate, and disagreements between the two associations ("tongs") within the community, the Hip Sing Tong and the On Leong Tong. 

The move to the new South Side Chinatown was led by the On Leong Merchants Association, who, in 1912, had a building constructed along 22nd Street that could house 15 stores, 30 apartments, and the Association's headquarters. While the building's design was typical of the period, it also featured Chinese accents, such as tile trim adorned with dragons.

In 1921, after expanding Chinatown and association membership, the On Leong Merchant's Association purchased the property at 2216 South Wentworth Avenue, Chicago, for a new, more majestic building to reflect the vitality and traditions of this rapidly growing community.

19th CENTURY SEX BUSINESS

It's crucial to remember that these nicknames were derogatory and demeaning. It reflected a deeply contradictory view of prostitutes in the 19th century. It objectified women involved in prostitution. Their lives were typically filled with hardship, hunger, exploitation, poverty, hunger and no options for escaping their circumstances. It's important to understand that these nicknames, while euphemisms for prostitutes carry a complex mix of judgment, pity, and sometimes even a degree of romanticization. The underlying tone of most terms is one of disapproval, despite some hinting at pity or romanticization. Some nicknames imply a degree of choice in their lifestyle, while others suggest fallen victimhood. 

DAUGHTERS OF SIN: Emphasizes the moral condemnation of their profession within a highly religious society. It views prostitution as stemming from inherent sin, placing blame on the women themselves. It plays into religious associations with sin and its consequences.

DOVES OF THE ROOST: A deceptively gentle term, as doves often symbolize peace and purity. This acts as both a euphemism and a stark contrast to the harsh reality these women faced.

FAIR BELLES: A euphemism focusing on the physical attractiveness of these women, masking the desperation often underlying their work. Focused on physical attractiveness, a woman of desire is an object obscuring the underlying social and economic realities.

FALLEN ANGELS: Conjures images of purity lost. This term highlights the perceived tragedy of women who have fallen from grace while still retaining an element of pity.

LADIES OF THE LINE: A blunt term likely referring to how prostitutes might line up or position themselves within certain areas known for their services.

NYMPHS DU PRAIRIE: This French term means "Nymphs of the Prairie." Nymphs in mythology were beautiful nature spirits, often associated with desire. Mythologizes them as figures of the wild, natural beauty and sexuality, creating a sense of exoticism. It romanticized the harsh realities of their lives. 

PAINTED CATS: Acknowledges artificial beauty through cosmetics. This has a dehumanizing effect and could also imply danger or predatory behavior. This unflattering term focuses on the idea that prostitutes often wore heavy makeup, drawing a demeaning comparison to animals.

SCARLET LADIES: References the biblical figure of the Whore of Babylon, invoking notions of sin and moral corruption. The color scarlet was associated with brazen sexuality and a lack of shame. References the "scarlet letter," a symbol of adultery and immorality. The color scarlet was associated with sin and prostitution.

SOILED DOVES: Doves represent purity and gentleness. This image contrasts the purity traditionally associated with doves with the concept of being "soiled," a perceived loss of innocence and tarnished reputation due to their profession.

SPORTIN' WOMEN: Presents prostitution as a frivolous activity associated with pleasure and entertainment. This term obscures the often exploitative nature of their work and the economic necessity that may have driven them to this point. A more casual, euphemistic phrase aimed at softening the harsh reality of sex work and suggesting it was paid entertainment.

Compiled by Dr. Neil Gale, Ph.D.

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[1] Bridewell - Offenders arrested in Chicago for crimes like public drunkenness, fighting, and disturbing the peace were not held at the county's jail. Instead, the City of Chicago was responsible for detaining them at the city "Bridewell" (an old English word for a jail used to house inmates on a short-term basis). Built in 1852 at Polk and Wells Streets, the Bridewell was located near the city's vice district. Inmates were rarely held there for more than several weeks.