Origins Settled by United States Army in 1803 and annexed in 1837
Area Central Chicago

Chicago River on the north, Roosevelt Road on the south, Lake Michigan on the east, Chicago River on the west

After Jean Baptiste Point Du Sable became the first non-Native American settler to settle what would be Chicago in the 18th century, the area was now on the map for the United States government.

In the year 1803 the United States Army came to this land near Lake Michigan and built a military fort directly south of the current Michigan Avenue Bridge (at Michigan Ave and Lower and Upper Wacker Drives) which puts the original site of the fort just within the boundaries of the Loop neighborhood.  The name of the fort was “Fort Dearborn” and it became a society of its own.  The fort did not last long; by 1812 it was attacked by Pottawatomie Native Americans on August the 15th of that year.  The United States was at war once again with Great Britain and the British loved to recruit Native Americans to attack U.S. troops and burn down military posts and that is exactly what happened to first Fort Dearborn during the War of 1812.

The war ended in 1815 and it was not until 1816 that the Army rebuilt Fort Dearborn.  The purpose of the Fort was to defend trade routes up Lake Michigan with Canada from Native Americans.  Eventually the trade route became so complex and flourishing that a decision was made to convert the fort into a town in 1833.

By 1833 the United States had just about won the war on Native Americans and there was not as much of a need for military ran societies like Fort Dearborn.  There were already a few hundred civilians living in the fort so now the area became a town, a town called “Chicago.”

By the year 1837 the town of Chicago had exploded in size to over 4,000 inhabitants, this brought the need for this town to become a city, the City of Chicago.  Many immigrants poured into the city in search of a better life and the Loop was the first Chicago neighborhood and the first area to offer jobs and industry.  White collar jobs became affluent as early as the 1840s bringing about several upper classes that built mansions and lived in expensive quarters.

In and near the fort Dearborn walls, farmers-built houses and reaped the land while hotels, outposts and saloons catered to travelers.  Many traders of all walks of life passed through Fort Dearborn and many needed recreation after enduring such grueling travels.  This gave way to the opening of gambling parlors and small brothels serving the frontiersmen as they traveled west in search of fortune.  I am not sure if vice and gambling was widely practiced before Chicago incorporated in 1833 but there is much speculation it was because just five days after Chicago’s incorporation the Board of Trustees was empowered the deal with the nuisance of gambling which is solid evidence gambling was widely practiced when Chicago was Fort Dearborn and was already a big problem (Fact source: Gambling–Should it be Legalized Virgil W. Peterson).  Chicago indeed was already a gambling colony right after incorporation in 1833 and most of that activity was in the Loop neighborhood.

The earliest Board of Trustees was also busy trying to put an end to the earliest vice in this new city.  In the year 1835 the Board imposed fines of $25 to any known brothel owners, proving Chicago had issues with brothels in operation.  The first settlement of Chicago in the 1830s was in the northern part of the Loop neighborhood where the Chicago River forks, and this is where the oldest settlement was made with the oldest buildings.  Sure enough, with the Loop being the oldest majorly built-up part of Chicago means the first criminal element was biggest here in this community.  In the year 1838, there were complaints being filed with the city about an open-air strip of brothels operating along the present-day strip on Wells Street between Jackson Boulevard and Congress Expressway.  Complaints stated “houses of ill repute” were operating in this area in the present-day Loop neighborhood.  This was the first evidence of a section of the city that became designated to crime (Fact source: Digital Research Library of Illinois History Journal, Neil Gale PH.D).

As Chicago’s earliest criminal element was in development in the 1830s the rest of this country was battling a scourge of gambling rackets primarily in the southern states near the Mississippi river.  Legislation soon was in order by the end of the 1830s that banished gambling dens in these southern states and some Midwest states.  This left the big-time money-making gamblers needing a place to set up new operations.  The fancy gamblers boarded boats that traveled up the Mississippi river stopping at many cities and towns offering high stakes games to many that came aboard while these gambling sharks remained immune from law enforcement as they sat comfortably on their boats where the law couldn’t reach them.

By the year 1840 these riverboat gamblers landed themselves in Chicago and saw the potential for big business in this already shady looking city.  Brothels, several saloons, and cheap hotels made for a perfect environment for a gambling racket to settle in the city situated on a swamp.  Scores of traveling seafaring men and westward travelers would make ideal customers especially after enjoying several spirits at local saloons.  These clever gamblers noticed Chicago already had a gambling colony it just wasn’t well organized in the 1830s and there were no big-time gamblers organizing these games and no big gambling dens.    This new city also lacked law enforcement as the city only had up to three police officers for another nearly 15 years after these gamblers arrived.  This slew of early gamblers was George C. Rhodes, George Smith, Charles Smith, John Sears, Cole Martin, Walt Winchester, Bill Mcgraw, Dan Oaks, and Dan Brown.  These men came from cities like Cincinnati, St. Louis, New Orleans, Vicksburg, and an assortment of others all escaping local laws that were falling in alignment with President Andrew Jackson’s war on gambling in the 1830s.  These gamblers were “skin gamblers” which means they basically rented saloon rooms, hotel rooms or any other parts of businesses and paid 10% of the profits to the proprietors of these establishments. Skin gambling allowed these gamblers to move about the city from location to location.  (Fact source: Fools of Fortune; or Gambling and Gamblers.)  Many of these early gamblers hailed from Cincinnati which was once regarded as the gambling capital of the country.  This city was the home of the “Wolf Trap.”  This area was home to thieves and killers and professional gamblers who used every trick and tactic to cheat their way into reaping large profits (Fact source: Commission on the Review of the National Policy
Toward Gambling, 1974).

By 1844, a few men stood out among these early gamblers as they organized the game better than ever before.  Bill “Dutch House” Mcgraw and Dan “Little Dan” Brown created the first gambling bookmaking.  These men were the first to operate a roulette wheel and the first to handle wagers on horse races (Fact Source: Journal of Criminal Law and Criminology Volume 40, issue 3).  These men laid out how to organize a racket even though they were not kingpins of the racket.  Around this time when bookmaking for gambling was invented soon several gambling houses popped up in the Loop area, some were quite exquisite for the time.

During this same 1840s decade many wealthy elites were building grand mansions along Monroe Street especially by Monroe and Wabash.  This brought about the “Garden City” area by Monroe and Wabash.  During the 1850s decade this area saw a decline as the wealthy elites began to move out.  Lumberyards at the very west end of Monroe near Monroe and Wacker brought pollution.  The opening of the Chicago Gas Light and Coke Company in 1850 also brought more pollution from Monroe and Wacker.  Then came North’s National Amphitheater in 1856 at Monroe and Lasalle which hosted many carnivals and circuses which drew many drunken unsavory types that often added to the crime elements as they indulged in heavy drinking, thievery, gambling and contributing to vice.  Property values soon tumbled as elites moved out quickly and impoverished Irish immigrants-built shantytowns at Monroe and Wells in an area known as “Mrs. Conley’s Patch.”  As the elites left this area it became much worse in the later 1850s as crime was rampant (Fact source: The Chicago Crime Scenes Project).

A strip of land located in the present day Streeterville area in the Near North Side neighborhood was always home to several saloons and cheap motels for dock workers and travelers along the Chicago River banks (Fact source: Digital Research Library of Illinois History Journal, Neil Gale PH.D).  To give you an idea of where this area was located, it was right where Rush Street meets the River on the north side of the river.  The Wrigley Building and Chicago Tribune building currently sit in this area.  As this area aged it became a haven of the impoverished and for the gambling and vice rackets of the city.  Soon much of the worst criminal element moved to this part of the city famously known as “The Sands,” named after the white sands along this river front.  Many of the residents here built poorly constructed shacks that often-caught fire or just collapsed.  Some lived in the old buildings that were decaying.  Almost all these thirty some odd structures were gambling dens and brothels.  Crime was rampant after this area took shape in the early 1850s. Very dark crimes were committed here, and murders were a normal occurrence.

In the year 1855 the city at last organized an adequate police force but it was far too late as the underworld in Chicago had already grasped organized crime, although absent of an organized crime group, the underworld was learning scattered organized crime type practices as they were taught by gamblers, pimps and wild packs of criminals imported from other states and other countries.  This was the foundation and the backbone for the beginning of organized crime that would lead to our first gang elements in this city.  Chicago was already becoming well advanced in the business of crime before this city had more than three police officers and the money potential was exponential, all that was needed was for someone or some group of people to take control of it.

In the year 1857 Mayor John Wentworth had enough of the Sands and now wanted to see it eradicated from this earth.  The Sands became the hub of pimps, prostitutes, gamblers, and many wanted and dangerous criminals.  Many of the criminals hiding out in the Sands were stone cold killers and very dangerous.  Some of these criminals attacked citizens at will and were known for being quick with the trigger. This became a serious criminal and sociological problem in early Chicago society and the only way to get rid of this element was to do something extreme because even the new police force was too scared to go in and enforce laws.  approximately thirty ran down shacks were in the sands full of brothels and gambling dens as fights, extreme intoxication and filth plagued this neighborhood.  Plenty of murders happened almost daily here and violence was very common (Fact source: Digital Research Library of Illinois History Journal, Neil Gale PH.D).  This was the first dangerous area of the city and the first area of the city where criminals gathered which laid foundation for this city’s future of organized crime and gangs.  When several criminals operate in an area alongside each other organizations eventually develop.

In April of 1857 William Ogden now legally purchased all the land that comprised of the Sands.  He was able to do this because the criminal element living there were just squatters, no one on the Sands had legal right to this land and were only entitled to squatter’s rights.  William Ogden had big plans to be the landlord to several big businesses and to have a big part in the construction of the new Randolph Street bridge.  Ogden was in the process of doing business with lumber yards, The Great Sugar Refinery, the ice houses of Messrs, Joy and Frisbie and a J.H. Reed warehouse (fact source Chicago Tribune August 13, 1859).  Ogden ordered the squatters to leave the land he just purchased but of course they refused to leave.  Ogden then complained the Wentworth and Wentworth was all too happy to help.  On the day of April 20, 1857, Wentworth arranged for a dog fight between Sands brothel owner Dutch Frank and the Market Street butcher William Gallager’s dog at the Brighton Race Track located at Archer Avenue and Western Avenue in the McKinley Park neighborhood on the south side of the city.   The advertisements were posted all over the Sands and boasted of a $500 cash prize.  As the men of the Sands flocked to this event leaving most of the Sands vacant, Wentworth and Ogden came to the Sands with a team of thirty police officers and firemen.  They had large iron hooks attached to the end of tackles on horse drawn carriages.  They placed the hooks at the base of the foundations and tore the shacks to the ground.  The ones that were sturdier were set on fire and burned to ash (Fact source:  Gleanings of Archer Road by Joseph Hamzik).  When the inhabitants returned they started a violent riot looting their neighbors and setting fires causing destruction and mayhem through the rest of the district but in the end Wentworth and Ogden won successfully wiping out the first criminal neighborhood in Chicago history (Fact source: Digital Research Library of Illinois History Journal, Neil Gale PH.D).

Chicago was plagued by standing water because of the severe lack of a draining system that caused pockets of standing water to breed bacteria that infected thousands of Chicagoans with Typhoid fever, Dysentery and Cholera.  The city struggled to enact a plan to curb this issue until the idea was created in 1856 to raise the entire city near the lake on jackscrews and put the buildings, sidewalks, and streets on stilts.  This allowed engineers to create an entire sewage system and a drainage system.  Beginning in January of 1858 this was done the entire year until the city was put on stilts.

The criminal element of Chicago that was mostly wiped away when the Sands came down once again returned in the same Loop neighborhood this time further west at the grim intersection of present-day Monroe Street and Wells Street. This time this new element had a leader, an organizer, a man that created a new criminal community known as “Under the Willow.”  Roger Plant was an Englishman born out of Yorkshire England.  Legend has it that he committed a serious crime in England and his sentence was to be deported to Australia where other convicts were sent at that time.  Legend has it that Plant escaped custody in 1857 and headed for Chicago.  Once he arrived, he got in with the criminal underworld in the Loop and took it by the reigns.  Plant also took advantage of these new underground barracks built by the city in 1858 and borrowed his way under the stilts at Monroe and Wells building a saloon with three brothels and white slave holding rooms.  He installed purple window shades that had writing that said, “Why Not.”  This hideout was named “Under the Willow” due to the sad looking slumped willow tree at the intersection where Plant and others dumped trash.  Prostitutes would lure their clients into rented cubicles to conduct business while some clients were then held up at knife point.  Many of times Kitty Plant, the 250-pound towering wife of Roger partook in the holdups alongside gangs of hoodlums.  As they rendered their victim’s unconscious they tossed the bodies in the alleys, Kitty herself even scooped up grown men to be tossed away.

Roger Plant was the first crime kingpin in Chicago’s history and was the first man to have enough power to tell hoodlums to do his bidding.  He originally named his establishment “The Barracks” but later it was Under the Willow.  These shacks under the stilts were decrepit hell holes with dirty cubbies/cribs for men to engage with prostitutes.  Kitty ran the brothel business while Roger ran the saloon and any other rackets.  Roger was a tiny man standing barely above five feet tall and weighing around one hundred pounds, yet he was a vicious fighter and skilled with just about any weapon.  The only person that was reported to be able to beat him down was his wife Kitty that towered him.  Plant inadvertently taught the Chicago underworld how to engage in organized crime as he paid off police to stay out of his affairs.  In one such incident in October of 1866 Plant helped bail a man out of Bridewell jail (now Cook Country Jail) for $25 then he turned around and robbed the man when released.  Plant was then released a few days later with no charges which caused anger.  Plant was summoned to testify before a committee about police corruption but Plant refused to cooperate and was let go by the committee as an uncooperative witness (Fact source: Digital Research Library of Illinois History Journal, Neil Gale PH.D).  Plant had shown the underworld that the city could be bought, and that crime can be organized.  He operated among the worst area of the city at the intersection of Monroe and Wells and as the Civil War played out his empire grew further down Monroe and Wells.  As immigrants poured into the Monroe and Wells area in the 1850s and 1860s it brought more prospects for the Plants as more impoverished immigrant girls came to work as prostitutes.  More thieves and killers escaping their native country’s laws immigrated and became henchmen of Plant.  More customers flocked in as the nearby shacks and slums filled with more potential gamblers and drunks. In 1868, Plant retired and left the city as he still rented his property to other hoods until his death in the 1890s.

Let us not forget about the area that once contained the legendary “Sands.”  Even after the removal of the Sands the far north side of the Loop was still a dangerous place, in fact, the area down Randolph Street between State Street and Clark Street was known as “Hair Trigger Block” due to many shootings and violence.  Most of the shootings were attributed to gun battles between two big time gamblers Samuel H. “Cap” Hyman and George Trussell.  These men had a rivalry and at the time became the biggest gamblers in the city at the advent of the Civil War.  Trussell used to be a businessman serving as bookkeeper for the banking firm George Smith and Company until he lost it all.  Through business he met seedy characters and even a very young teenage prostitute named Mollie.  Trussell soon discovered big money in gambling and just like Hyman he was a former businessman that knew how to maximize profits and organize the game.  This brought intense rivalry between the two men as they each claimed Randolph as their own as they fired upon each other.  They never shot each other and Trussell was killed by Mollie whom he married then neglected.  Mollie murdered him in a fit of jealously in September of 1866.  Hyman fell into a similar fate as he was attacked by his soon to be wife Annie Stafford, a notorious Sands prostitute that went on to open her own brothel in the neighborhood.  After the attack in 1866 the two moved to Lakeview and started their own business until Hyman died after going mentally insane in 1876.  Hair Trigger Block was also burned down during the fire of 1871 but was the first block in Chicago where many shootings would happen.

Roger Plant, Cap Hyman and George Trussell were the first gangsters in this city to amass fortunes from organized crime.  They did not last long in the business but as their exploits continued during the Civil War years another was rising to power in their shadows that would become bigger than they could achieve.  The neighborhood they haunted along Randolph Street was the earlier of gambling districts known as Hair Trigger Block and this is where a young gambler first learned the big game and became all too inspired.

In the 1860s Irish organized crime was formed in Chicago thanks to the arrival of Michael Cassius Mcdonald who became the city’s first crime boss.  Mcdonald worked hand in hand with crooked politicians to help keep vice and gambling operations moving smoothly.  Most of the vice business was right in the Loop or in the “Little Hell” area of the Near North Side.  The roughest sections of the Loop were “Whiskey Row,” “Gamblers Row” and the “Vice District.”  Whiskey Row and the Vice District were located all along State Street just south of Van Buren Street.  This area was dangerous full of cheap saloons and brothels.  Underground and dangerous criminal elements hung out in the cheap saloons on Whiskey Row and very often several crimes would happen here.  The brothels in the Vice District further south were filled with dangerous elements and pimps that were quick to take you out if you threatened their business.  Gamblers Row was a small section right nearby the Vice District and Whiskey Row that was bounded by Harrison Street on the north, Polk Street on the south, State Street on the east and Dearborn Street on the west, this area is now known as “Printer’s Row” today.

Gamblers Row is where the first African American organized crime gangster John “Mushmouth” Johnson had his beginnings working in the shady gambling dens in Gambler’s row in the 1880s until he was able to open his very own saloon/Gambling den on State Street in Whiskey Row in 1890.  Mushmouth along with Big Jim Colosimo jointly operated another gambling hall in the Loop in 1906 until Mushmouth’s death in 1907.

After the Great Chicago Fire of 1871 much of the shady saloons, brothels and gambling dens were destroyed in the fire.  This caused the organized criminal element to mostly migrate south into the South Loop/Near South Side neighborhood where the notorious Levee District would operate.  Michael McDonald had a large stake in the gambling business in this neighborhood.

In the later decades of the 19th century and earliest decades of the 20th century criminal elements and gambling syndicates would still operate in the Loop especially in the poorer sections of the neighborhood until the city vested more interest in making the Loop more appealing for tourism and for upper classes to reside here.  Even after more of the impoverished were pushed out of the Loop and criminal elements began to vanish the Loop area still had many shabby areas and unkept buildings.  Many areas still housed the poor and many of these streets were still shabby and rather ran down.

In the late 1940s Puerto Rican families settled in shabby apartments and sleazy motels as they worked in some of the most exquisite downtown hotels nearby.  These buildings were eventually torn down by the end of the 1950s forcing the Puerto Rican people to migrate further west in the city.  This was often how many of the impoverished lived in the Loop, taking up residence in the shabby buildings while working for exquisite hotels and restaurants.

During the 1950s the city clamped down on poverty and blight in the Loop as rents were raised and property values skyrocketed.  The impoverished were mostly moved out by the end of the 1950s and many of the buildings they once resided in were razed or heavily renovated.  For the next few decades, the Loop still struggled with some seedy parts, blighted buildings, and unsavory businesses but by the 1980s the Loop became completely re-invented as simply a tourist area where people come to either work or live in very expensive living quarters.  To afford to reside in the Loop one must have deep pockets.

All the organized crime and gang life of Chicago can be traced back to this neighborhood as this was the original home of criminals, gangsters, mobsters, hoodlums and thieves.  On these streets is where the organized crime life of Chicago was born before Al Capone was even born this was where the gangs and mobs dwelled.