Monroe Street

Perhaps second only to Wells St., Monroe St. was the home of vice in pre-Fire Chicago.

In the earliest years of Chicago's history, Monroe street was entirely rural, with many farmhouses. It may well have been Monroe that inspired one of the earliest town ordinances, passed in 1833, which imposed a fine of $2 on anyone allowing a pig to run loose in the city "without a yoke or a ring in its nose" (pigs were forbidden on the street entirely, nose ring or not, in 1842).

By the 1840s, Monroe was home to many fine mansions, primarily country-style homes. The architectural vogue in those days was a Chicago version of Palladian, mixing the classical Greco-Roman columns with aspects more familiar to southern plantation estates. The area near Wabash Ave. was known as "Garden City", likely inspired by the city seal ("Urbs in Horto"), but also indicative of the greenery that covered the Loop in those early years. Standing at Monroe and Wabash today, with the clash and clatter of the elevated train passing overhead and darkened by the hulking shadows of steel tracks and skyscrapers, it is difficult to picture the bucolic setting in which early Chicagoans once resided.

But while Wabash and Michigan Ave. retained their large estates up until the Fire, the 1850s saw Monroe St. in decline. Lumberyards sprouted at the west end of Monroe, near the river, and just on the other side of the river. 1850 saw the city's first gas works plant, the Chicago Gas Light and Coke Company, built at the corner of Monroe and Wacker Dr. (then known as Market St.). The presence of a big, dirty, industrial factory lowered surrounding property valuesSeptember 5, 1850 saw the city lit by gas for the first time, and by the end of the year, a series of pipes connected the factory to 112 street and bridge lamps around Chicago.

Another cause for Monroe street's diminishing reputation was the establishment, in 1856, of North's National Amphitheater, one of the city's first commercial venues for amusement, on the north side of Monroe, between Wells and Clark streets. The Amphitheater played host to traveling circuses, carnivals, and other troupes, and the characters who worked in these events were considered unsavory, and frequently stood accused of drunkenness, vice, as well as more serious crimes.

One 1850s newspaper review of a show indicated the precarious position Chicagoans were still in with respect to Native Americans on the plains:

"The Iroquois Indians are a novel feature, and go through their dances, and other aboriginal barbarities, with as much unction as their white brethren of the sawdust. It is also cheering to know that they entertain a high opinion of their audiences, and are invariably in favor of peace."

Levi J. North, the proprietor of the Amphitheater, was one of the 19th century's most famous horsemen. After performing in traveling shows up and down the East Coast, the Caribbean, and in Europe, where he was famed for an act involving galloping bareback, while holding aloft an infant child, North came to Chicago and built the Amphitheater.

(Advertisement of show at North's Amphitheater, Jan. 5, 1859).

Like most great riders, North was relatively small of stature, standing less than five and a half feet, and had long, flowing blond hair, which trailed behind him as he sped around the circus ring. In his later years, one commentator wrote that "He was born on a horse, has always lived on a horse, will die on a horse, and have a horse for a monument, and will rest uneasily if the monument is not trained." He was said to have been the first rider to ever turn a somersault on horseback.

While in Chicago, North also became involved in politics, running for and winning a seat as alderman of the third ward. The election was disputed, since North had only moved into the ward ten days before the election, but he was eventually allowed to keep his seat. After some years, however, misfortune befell the great rider when the theater burned, and the insurance company simultaneously went bankrupt. North rebuilt the circus ring and began performing again, earning $50 per night, which he continued in Chicago and in touring companies for over a decade before retiring in 1870 and moving to New York City. The Amphitheater was demolished in 1864 and the property rebuilt for commercial use.

With the poverty and criminality growing on the street, wealthy residents increasingly moved away from Monroe, lowering property values and attracting even more itinerant and criminal elements, perpetuating a vicious cycle. Cigar stores and houses of prostitution, including most famously Madam Lou Harper's "Mansion" between Wells and Franklin, and Francis Warren's troupe of streetwalkers, who resided between Clark and LaSalle.

The 1850s and 1860s saw masses of poor immigrants, primarily from Ireland, building a shantytown of low, tumble-down buildings centered around Monroe and Wells St., known as "Mrs. Conley's Patch". Longtime alderman and world-renowned dandy "Bathhouse" John Coughlin, was raised there. However, "the Patch" was also notorious in its day, not only for the decrepitude of its dwellings, but also for the depravity and dark crimes of some of its residents.

Chiefest among these was the city's first -- and perhaps greatest -- king of vice, Roger Plant. I have already covered Plant's exploits to some degree in this earlier post. A Yorkshire-born Englishman, Plant arrived in the city about 1857. Legend has grown around Plant, who was always tight-lipped about his personal history, such that it is impossible today to discern fact from exaggeration, but purportedly Plant 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 Wells and Monroe. The Barracks, later known as "Under the Willow", so named after a single sad willow tree which stood on the corner, was the center for all vice in the city up through the end of the Civil War. It was Plant who 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 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 inmates, rented out cubbies on the property for use by streetwalkers, and made a trade in "white slaves".

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 knived, and discarded in the alleys (oftentimes 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 (again 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 herself 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 long-time 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 girlfriend to Billy Meadows, a successful prizefighter. But when Meadows took sick and died in 1861, Miss Woods' decline into 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 of Wells street.

Roger Plant was also 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 of $25. A few days later, the police discharged him, much to the uproar of the city's more righteous denizens. 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 city council, Plant was directly asked whether he had every 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 as allowed him to depart his vile surroundings for a country estate outside of Chicago, and by 1871, the Tribune reported that "Roger is now a member of the church in good standing, drives an elegant team, and lives like a Christian."

Plant had many children, by some counts as many as fifteen, and a number of them went on to establish 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 went on to develop vice businesses as well. 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. 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 the sum of $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 largely as a warehouse district, while business and commercial buildings arose closer to the Lake.

The Sands

The area on the north bank of the Chicago River, near the lake shore, was originally populated by saloons and inexpensive motels of the sort popular among seafaring men working the docks of the River, or passing through Chicago on some merchant vessel. By the 1850s, however, the area had developed into the toughest criminal district in the city, known as the Sands, and 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 on a regular basis.

Drunkenness, fighting, robbery, murder, and general misbehavior was the order of the day, every day, in the Sands, and the besotted residents of the district were the bane of the town's respectable population. Annie Stafford was a famous cyprian denizen of a Sands brothel. 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, of whom an important Southside thoroughfare is now named. Wentworth, an educated man of New England and a former newspaper editor, wanted the Sands razed. In April of 1857, William Ogden, who had been Mayor before Wentworth, and who was 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, but 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 Chicago race track. Most of the male residents of the Sands were inveterate 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 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, it is the Tribune Building itself (pictured above) that sits on the property that was once the Sands. The space on which sits the Wrigley building (pictured below) across Michigan Ave., would also have been part of the Sands during the 1850s.

Water Street Fire of 1857

All of Chicago's red light districts were commonly known as "Levees," even those that were nowhere near the river, such as the famous South side Levee centered around the Everleigh Club at Dearborn and 22nd. The name was adopted from the shady areas in towns along the Mississippi, typically near the river, where seaborne men would find brothels and gambling houses during a furlough.

However, from time to time, riverfront property in Chicago did become the home to houses of ill-repute, including one located on the second floor of a brick warehouse situated at 109 South Water Street (now 35 W. Wacker). As a harbinger of fires to come, in 1857, one of the women working at this location kicked over a lantern, leading to a massive conflagration in which twenty-three died, although all of the brothel employees escaped unharmed.

As a result, political pressure led to the formation one month later, of the Citizens Fire Brigade, a group of insurance and business interests who acted to remove valuables from burning buildings and prevent post-fire looting. Another consequence of the fire of 1857 was the formation, less than one year later, of Chicago's first paid fire department (previously, all firemen were volunteers).

Lager Beer Riots

Until 1855, Chicago's streets were policed by a few county constables. That was the year the Chicago Police Department was founded. It was also the year of Chicago's first riot, in which CPD played a large role.

Chicago was always a town of newcomers, and that was certainly true in the 1850s, when over 60% of the population was foreign-born. The flow of primarily Roman Catholic German and Irish immigrants raised the degree of xenophobia in the native population, embodied politically in the Know-Nothing Party, which briefly held substantial legislative power in Chicago as elsewhere. At the same time, early Prohibitionists were active in the Illinois legislature, and had passed a state prohibition ordinance, which was to be voted on in 1855.

Chicago's German population, concentrated on the North Side, enjoyed their neighborhood beer gardens, and abhorred prohibition. The newly-elected Mayor, Levi Boone (a distant relative of Daniel Boone), lobbed a bomb into this incendiary atmosphere by ordering the police to enforce the city's Sunday closing laws, which had been mostly forgotten by that time. The police, composed almost entirely of native-born Americans, forced the North side bars to obey the ordinance, but allowed American bars on the South side to stay open.

On April 21, 1855, a mob of five hundred Germans massed outside the city courthouse at Clark and Randolph (pictured above), where one of their own was to be tried for liquor law violations that day. Mayor Boone ordered the newly-formed police squad to disperse the crowd, which they did at the business end of their clubs.

A few hours later, a squadron of over a thousand Germans marched back to the courthouse to continue the battle. The Mayor ordered the ends of the Clark street bridge (pictured below) opened, trapping about half of the rioters on the south side of the river, and a few hundred more on the bridge. The mob attacked the police, who had lined up in formation to defend the courthouse, and a firefight with pistols and shotguns, as well as clubs and chains, raged for over an hour. Some of the protesters stuck on the bridge claimed the police specifically targeted them.

In the end, however, while there were many injuries, there was only one recorded death, although rumors spread quickly that a score or so of the rioters were killed, leading to additional tension between the immigrant population and the police.

The police arrested sixty during the Beer Riots, but one two were convicted, and none were ever actually imprisoned. Later that year, the prohibition law was voted down, and open taps were the law in Chicago for another 65 years.

"Bloody" Maxwell

From the mid-1850s through the 1930s, the area bordered by Harrison St., Wood St., 16th St., and the Chicago River, was the toughest neighborhood in town, and the nation's foremost foundry for criminals. Termed "Bloody Maxwell" by the Chicago Tribune in 1906 for its violence, the district was populated first by Irish immigrants, then by Germans, Russians, Greeks, Poles, Jews, and many other ethnic groups, making it Chicago's version of the "melting pot."

The Tribune wrote, "Reveling in the freedom which comes from inadequate police control, inspired by the traditions of criminals that have gone before in the district, living in many instances more like beasts than like human beings, hundreds and thousands of boys and men follow day after day and year after year in the bloody ways of crime."

The "inadequate" police operated out of the famous 22nd precinct station nearby.

In the 20th century, the area became populated primarily by Jews, then by African-Americans relocating from the South. Over the last ten years, this "terror district" has come to be populated primarily by students at the nearby University of Illinois at Chicago. New construction is prominent (while taking these photos, a real estate agent asked whether I was looking for a condo and handed me a brochure on a nearby development).

Gentle Annie Stafford

"Gentle" Annie Stafford, the "fattest brother-keeper in Chicago," ran a brothel here at 155 N. Wells St., just north of Randolph, in the 1860s. Gentle Annie started her career as a prostitute in a house at the Sands in the 1850s, and was a notorious fighter, winning the affection of her madam when she led a battle against a rival madam who had recently stolen one of their best girls.

Later, Gentle Annie won the heart of Cap Hyman, the infamous gambler of Hairtrigger Block, who bought her this location, although she had to force him into marriage at the end of a bullwhip.

After the renumbering of houses in 1911, 155 N. Wells became 27 S. Wells. Currently, this location is a restaurant.

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.