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.

"Cap" Hyman's Sunnyside Resort

Captain "Cap" Hyman was one of Chicago's most infamous characters before the Great Fire. An inveterate gambler, he was one of the kings of "Hairtrigger Block", a gambling mecca on Randolph St., west of State.

Hairtrigger is a word that also describes Hyman's personal character. In an inebriated state, he was well-known in the city for wandering into public places and brandishing his pistol. In 1862, he did just that in the Tremont House hotel.

On the evening of August 2, 1868, around midnight, Cap Hyman found himself at the New York Sample Room, a low saloon in Clark Street. The following day's Tribune detailed what happened next:

[Hyman] entered the saloon about midnight, meeting at the entrance a friend named James McKenna, barkeeper at the Sherman House. He invited him to drink and the two, accompanied by others, stepped up to the bar. A dispute arose between them as to who should "treat," when McKenna spiritedly accused his companion of owing a bill for liquor, etc., at the Sherman House. Hyman stepped from the barroom, which is in the rear portio of the place, to the front compartment, and, drawing a revolver, discharged it at McKenna. The contents, probably a blank cartridge, failed to do any injury. He fired again, the ball entering the groin of M. Kasprowicz, inflicting a serious but not very dangerous wound. At latest accounts the victim was doing well.

Kasprowicz, also a noted gambler, was also the son of the saloon's proprietor. The article referred to both Hyman and Kasprowicz as "[g]amblers of the worst kind and very dangerous members of society." A police search for Hyman the next day failed to find him, but eventually he turned himself in, and after lengthy legal maneuvering, he was released back into the city to create more mayhem.

During his time on the lam for the Kasprowicz shooting, Hyman laid low at his place in suburban Lake View, which was in the 1860s farmland not incorporated into Chicago. Two years earlier, in 1866, Hyman and his wife, the fat brothel-keeper and former Sands resident, Annie Stafford, had opened to the public their Sunnyside Resort in Lake View, a roadside inn on the old Evanston Road (now Broadway) near the intersection with eponymous street, Sunnyside Ave. (pictured above).

The grand opening was on a Wednesday evening in December, 1866, and reporters from the major Chicago papers were brought to the gala affair in a huge four-horse sleigh. Hyman declared to all, "I would like you gentlemen of the press to understand that this affair will be straight to the wink of an eyelash. All the ladies are here on their honor, and Mrs. Hyman will see to it that nothing unseemly takes place."

Nevertheless, opening night was portentous. Hyman and Stafford intended the Resort to cater primarily to the well-to-do country traveler, and to stand as their entree into Chicago's upper crust society. But all of the couple's friends were from a distinctly different social class. A newspaper article at the time described the opening night guest list: "[t]he list was select, embracing chiefly the women keepers of some of the more fashionable brothels, and those who contribute most liberally to their support."

Everything went swimmingly until around midnight, when a fight broke out among three rival cyprians at the party, which turned into an all-out wrestling match. In a drunken fit, Hyman shot out the lights, and several of the harlots began "entertaining" clients upstairs. By dawn, the evening's tired and mangled party guests departed, and the bad publicity associated with the evening's melee doomed the business; it shut down to the public within six months.

Hyman and Stafford continued to make trouble in Chicago for a few more years before they separated, with the Captain heading to New York in 1868. Rumor had it that the old gambler's mental health was not good, perhaps the result of too many evenings spent in brothels like Annie Stafford's. In possibly the most sarcastic editorial ever published in the Tribune, the paper wrote of news of Hyman's decline:

Report has just reached Chicago of the fall of a great man. As a gambler he stood at the head of his profession, in braggadocio he had not his equal, and as a shooter at defenceless cripples and women he stood without a rival. Of course, this means the Adonis, Captain Hyman. How his diamonds used to flash in the sunlight of our streets! With what elegance of deportment he used to pick his teeth on the steps of our hotels! How immaculate was wont to be his toilet! But, alas! he left Chicago about a year ago, and with it has come his fall. Detective Ellis, just returned from New York, met him in the great metropolis, and at first mistook him for a peddler of "hot corn." The change seemed incredible. Not even a brass band ornamented his nimble digits, and he looked as if he had not enjoyed a square meal for a week. In other words, the whilom proprietor of sumptuous Sunnyside and the hero of innumerable bouts is broke clear out of his boots. Wonder if he will ever "come up smiling" again?"

Suffice it to say Cap Hyman was not a popular figure in Chicago, and his demise in the mid-1870s was welcomed by all. Annie Stafford continued to run brothels on Federal St. (then Fourth Ave.) and Wells Street until about 1880.

Accounts published in the 1860s put the location of the Sunnyside Resort on the Evanston Road (Broadway) "about two or three miles from the city limit", at what is now Sunnyside Ave. Based on educated guesses from other sources, I believe the Southeast corner of Broadway and Sunnyside would have been the most likely location for the Resort. This is pictured above.

A later account in 1941 by an old-timer describes a place called the Sunnyside Tavern, where Chicagoans of the 1880s used to go out sledding in the wintertime on Clark Street at Sunnyside. Since Clark is just west of Broadway at this point, it's possible this is the same establishment (perhaps under the control of a later owner), but I cannot corroborate that. Also, in Gem of the Prairie, published in 1940, Herbert Asbury also puts the location of Hyman's Resort on Clark St., possibly based on the same source. Nevertheless, I have chosen to rely on the contemporaneous accounts.

In any case, the Resort was gone by the turn of the century, and the southeast corner of Broadway and Sunnyside became the site of a dull gray three-story building, which was razed in 1929 and rebuilt as an equally dull gray three-story building (pictured above), inhabited by administrative offices of the Illinois Bell company. In the 1950s, Illinois Bell quit the building, which then became the offices of the city's Department of Urban Renewal. By the 1970s, the building was under the control of the Salvation Army, which ran it as a soup kitchen and shelter through the 1980s and 1990s. It appears to be closed now, possibly slated for destruction along with the buildings across from it on Broadway, which have already fallen, to be replaced by a Target.

Al Smith's Gambing Establishment

In the late 1860s, Al Smith ran a famous saloon and gambling house at this location, 111 N. Dearborn. With his earnings from this establishment, Smith bankrolled the city's top madame, Carrie Watson, who ran the most glamorous brothel in the city until the opening of the Everleigh Club. After the Great Fire, Watson and Smith went their separate ways, with Watson becoming close with Sig Cohen, and Smith leaving town for New York City, where he spent the last 35 years of his life at the posh Gilsey House hotel. Continuing to operate in the underworld, Smith was heavily involved in prize fighting, managing many fights for John L. Sullivan, the first heavyweight champion of the world. He died in 1909.

The site of Al Smith's gambling establishment is now the CBS 2 Broadcast Center.

Tremont House Hotel

The Tremont House Hotel, first built at the corner of Dearborn and Lake in 1833, burned and was rebuilt three times. During the 1860s, when all the buildings in Chicago were lifted several feet out of the mud, the Tremont was the largest building in town, and resisted all efforts in lifting her foundations, until George Pullman, later of train car fame, managed to engineer the feat.

The second floor of the first Tremont House became home to Chicago's first billiard hall in 1836, and was the favorite hangout of an itinerant criminal named John Stone, who in 1840 became the city's first executed criminal, having been convicted of the rape and murder of a Mrs. Lucretia Thompson.

In 1862, a heavily-inebriated Cap Hyman, the famous Hairtrigger Block gambler and shotgun-spouse of Gentle Annie Stafford, invaded the lobby of the third Tremont house and used his pistol to hold everyone in the hotel hostage for an hour, until police reinforcements arrived.

The fourth and final Tremont was also the site of a shooting in January 27, 1897, according to the New York Times on that date:

D.B. Chandler of New York, agent for the Colgate Soap Company, was shot in the left hand and kicked and beaten until unconscious in Room 203 of the Tremont House at 4:45 o'clock this morning.

According to Chandler's story, he was assaulted by Edward Kirkland, manager of the house, Smiley Corbett, an ex-deputy coroner, and B. McIperson, a former ticket broker. "Early in the evening," said Mr. Chandler, "I went to the Schiller Cafe, where I remained until after midnight. Kirkland, Corbett, and McIperson were also in the cafe. They insulted me several times, and I requested them to stop. At last, I left the cafe and returned to my room. As I was winding my watch, I heard John Bruno, the night watchman, say: 'Open the door.'. I was about to do this when I heard some other person say: 'Break it in.'

The door was finally broken in, and I ran into the bathroom. Then somebody fired three shots through the door, one bullet striking me in the left hand and the others barely missing me. Then the men burst in the door. They jumped on me and kicked me on the head and body until I fainted.

The Times story concludes, "The hotel proprietor will discharge manager Kirkland," which seems awfully unfair, as only one of the bullets hit the guest.

The site of the original Tremont is now the "Theatre District Self Park," a twelve-story parking garage built in 1987, catering to the nearby Randolph Street theaters.

"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).

Mike McDonald

Michael McDonald, who started his career as a boy con artist and professional gambler, came to Chicago in the early 1860s, and reigned as the king of gambling, and perhaps the most powerful man in the city, until the 1890s. His headquarters was known as "the Store," and located here, at the northwest corner of Clark and Monroe, at the head of Gamblers' Row.

The Store operated as a saloon on the first floor, a casino on the second floor, and a flophouse on the third and fourth floors. It was here that that famous con man's motto, "there's a sucker born every minute," was first coined by McDonald. In cahoots with the famous laissez faire mayor of Chicago, "Our" Carter Harrison, Sr., McDonald grew to become the most powerful and feared man in town, receiving kickbacks and doling out political favors to friends and business associates. Anyone running a gambling operation of any sort in Chicago during the last half of the 19th century was strongly advised to "see Mike" before opening for business. Failure to operate within, and pay tribute to, McDonald's organization, was not advisable.

After Carter Harrison's political career faltered, was revived, and then ended suddenly in assassination, McDonald's power waned. His taste for women did not, however, and in 1898, he divorced his wife, renounced Roman Catholicism, and married a 23-year old siren, intending to retire and make a home for her. May-December romances, however, have their limits, and McDonald's wife took several lovers, one of which she shot and killed after a spat in 1907. The shock of the event was too much for the old man, and he died several weeks later, having returned on his deathbed to the Church.

The Mansion

in the 1860s, Madame Lou Harper ran "The Mansion" at what was then 219 Monroe (now 228 W. Monroe), the finest and most elegant brothel in pre-Fire Chicago. The "twenty beautiful young ladies" (as described on Madame Harper's business card) wore evening gowns and were never drunk. No red light illuminated the entryway, and gentlemen without proper attire and manner were not admitted under any circumstance.

The Mansion's elegance was not matched in Chicago until the opening of the Everleigh Club in the 1890s.

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.

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.

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.