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.