Hell's Half-Acre

"Hell's Half-Acre" was a common term for the slum neighborhoods in many cities (including a possibly more famous one in Honolulu which gave its name to a 1954 film noir hit). There were even Hell's Half-Acres in the Chicago suburbs, including one in the Northwest suburb of Niles.

But Chicago's Hell's Half-Acre was the block bounded between State St. and Third Ave. (later known as Plymouth Place, and even later known as Plymouth Court), and south of Polk, down to around Taylor. in the 1870s and 1880s, Hell's Half-Acre was one of the city's toughest blocks, adjacent to Custom House Place, and primarily serving the transient population that arrived at Dearborn Station, around the corner on Polk. "Serving" might not be the right word -- "robbing" was more accurate. It is said that there was not a single building on the block that was not a gambling den, a bordello, a saloon, a brothel, or some combination of these. Police never traveled into the area, except in pairs, so dangerous were the residents.

The name for the block is first noted in the Tribune in 1871, in a report about a group of drunken Swedes who were assaulted in a Hell's Half-Acre saloon by a gang of Know-Nothing nativists who resented the immigrants' revelry.

Another similar (and politically incorrect) report from 1877 described a common practice among the denizens of this depressed area -- seeking sympathy by claiming more children than they really had:

In a certain district on the South Side where the colored people, the Italian padrones, Polish Jews, and the mixed nationalities predominate, the custom of borrowing children is quite extensive as a means of eliciting the sympathy of the visitor. The trick has been quite successful among the Poles and colored people, who have repeatedly passed their offspring up and down the alleys in the rear of State street and Third and Fourth Avenues. It must be said that the Poles are the heaviest dealers in this kind of business. The art of concealment seems to have developed into a profession among these people.

After the city's dismantling of Custom House Place in 1903, Hell's Half-Acre's position as a vice district diminished, but it continued as a slum for another seventy years. The entire block is now filled by The Terraces, a townhome and condominium complex built in 1983.

The 'Raiding Pastor' takes on Capone

Reverend Henry C. Hoover, a Berwyn minister, was the leader of a vigilante group known as the West Suburban Ministers' and Citizens' Association, and a constant thorn in Al Capone's side. As early as 1925, Hoover had identified Capone as a menace to society, and, together with his Association, paid off a rival group of gangsters to burn down one of Capone's brothels in Cicero, near the race track. These actions led Hoover to acquire the moniker, "The Raiding Pastor."

On May 16, 1925, Hoover set his sights on the Hawthorne Smoke Shop, a Capone-controlled gambling house, located here at 4818 W. 22nd St., in Cicero. His group raided the house early in the morning and toted out an array of gambling paraphernalia. When Capone heard about the raid, he personally marched over to the Smoke Shop (still dressed in pajamas) to find out what all the fuss was about. When he confronted Hoover, Hoover turned to a police officer who had accompanied him on the raid and asked, "Who is this man?"

Capone answered for him, using his common pseudonym: "I'm Al Brown, if that's good enough for you."

Hoover mocked the bootlegger, "Oh, I thought it was someone like that, someone more powerful than the president of the United States."

Hoover re-enacted this scene word-for-word on the stand at Capone's tax evasion trial in 1931, offering the jury the sacred word of a man of the cloth describing Capone's wickedness, and linking him to a known gambling operation. After this confrontation, Hoover explained that Capone had tried to cut a deal with the Raiding Pastor:

"Why are you fellows always picking on me? Reverend, can't you and I get together - come to an understanding? If you will let up on me in Cicero, I'll withdraw from Stickney."

Hoover responded righteously: "Mr. Capone, the only understanding you and I can have is that you must obey the law or get out of the western suburbs."

Damning as the testimony was, it never should have been heard in court. The raid was over five years old at the time of the trial, and Capone's attorneys could have had it excluded on statute of limitations grounds, had they realized it.

Rev. Hoover continued his crusades against organized crime until his passing in 1955.

Capone's Soup Kitchen

By late 1930, the U.S. attorney's office had obtained income tax-related convictions against Ralph Capone and Frank Nitti, two of Al Capone's right-hand men, and it was obvious their next target was going to be Big Al himself. The famous racketeer decided it was time to manufacture some good publicity for himself, and the onset of the Great Depression offered him the perfect opportunity.

With thousands laid off from their jobs and the economy worsening, Al Capone turned himself into a one-man relief operation, feeding over 1,000 of Chicago's hungry every night at his own soup kitchen, located here at 935 S. State St.

The building was located deep in one of the city's poorest and most crime-ridden neighborhoods (a hardboiled 1921 Tribune article describes a valorous police officer who shot and killed a transvestite who had tried to to attack the officer and steal his gun at this address), and on Thanksgiving Day, 1930, Capone triumphantly fed 5,000 of the neighborhood's neediest.

The press ate it up, and those who dined on Capone's dime supplied the newsmen with plenty of quotes about how this bootlegger was doing more for the impoverished than the entire U.S. government. Capone's federal pursuers were furious at the development, and ordered even closer watch on his activities, raiding the Cicero hangout the week after Thanksgiving.

While Capone received an enormous amount of positive publicity for his efforts, Bergreen notes that much of the food may have come from local merchants who were blackmailed or otherwise coerced into supplying it. Then again, does the government do it any differently?

Nevertheless, it was all to no real avail. By June, 1931, Capone had been indicted for income tax evasion, and by October, he was in prison, where he stayed for the next eight years.

The building remained a flophouse for the next 25 years, until the city shut it down for fire code violations in 1955. Today, all that remains is a parking lot.

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.

Victoria Moresco's Childhood Home

Victoria Moresco was born in Italy, one of eighteen children, and came to New York with her family in the 1880s, but eventually settling in Chicago in 1891. She became wife to "Big" Jim Colosimo, taught him the prostitution racket, and their stormy relationship may have been the cause of his death.

When the Moresco family arrived in Chicago, they settled at 526 Division St., around the location of Mother's Original Night Club, pictured here. At the time, the area was a majority Italian slum known as "Little Hell" for the myriad crimes that took place here. Dion O'Banion was another product of Little Hell.

After Victoria (or "Vittoria" as the newspapers sometimes called her) became an adult, she moved to the Southside and opened a small brothel in the 22nd St. Levee. In 1902, she married a fellow Italian immigrant with ambition in criminal enterprises, Big Jim Colosimo. Together, they reigned over the vice district, and Victoria was in charge of running the couple's several large mid-price brothels.

In his latter days, Big Jim fell in love with a cabaret singer from his cafe, Dale Winter. After an acrimonious divorce, he left Victoria, and she moved west to Los Angeles, where she became involved with, and eventually married, Antonio Villiano. Victoria lived in Los Angeles until her death in 1964.

At the time of Colosimo's murder in 1920, only a short time after the divorce, Victoria (or possibly Villiano or one of Victoria's brothers) were considered prime suspects, but no evidence ever surfaced against them. Colosimo's murder has never been solved, but the most likely theory is that Johnny Torrio, Colosimo's second-in-command, was unsatisfied with his boss' personal life (Torrio was a strict Roman Catholic and disapproved of divorce), and especially with the way it was distracting Colosimo from the business the two men ran. Torrio may have hired Frankie Yale or another New York-based hitman to come to Chicago to take down Colosimo, allowing Torrio to take command of the organization.

Joseph Stenson, Torrio's "Silk Hat"

Joseph Stenson was a leading brewery owner in pre-Prohibition Chicago, the co-owner, with thre brothers, of the Stenson Brewing Company. After the start of Prohibition in 1919, Stenson went into business with Johnny Torrio, the famed leader of the Chicago Outfit, who took over after the death of "Big" Jim Colosimo, and who first brought Al Capone to Chicago.

It was a perfect combination. Torrio had years of experience and tutelage under Colosimo in paying off the police and operating outside the law; Stenson knew the brewery business inside and out. Together, they turned Chicago into the bootlegging capital of the country.

On Nov. 17, 1924, the front page of the Chicago Daily News first introduced the world to Torrio's low-profile business partner, though circumspectly:

John Torrio and a Chicago brewer are the twin kings of commercialized crime in Cook County today...And the brewer is so completely above the law, so thoroughly protected from prosecution, that it is unsafe to mention his name, though the police and the prosecutors know quite well who he is.

The Chicago Tribune had no such misgivings about mentioning Stenson's name, and they did so in the following day's edition. They referred to Stenson as Torrio's "silk hat," the scion of wealth living in the heart of the Gold Coast, whose fortune (which it is estimated, came to $12 million) came from vice.

Stenson's home was at 1218 N. Astor (pictured above), the most prestigious street in the city to this day, and could not have been more different than the 22nd st. Levee district that Torrio ran or the middle-class Southside building Torrio lived in. Stenson's home still stands, and recently changed hands for a sum of $3.5 million.

A Footnote on Street Numbering

This is not really a crime scene, but relevant for Chicago historical research. Although Chicago 's city planners developed the city on an orderly grid of streets, the naming and numbering of those streets was haphazard until the 1880s. There were many cases of multiple streets with the same name, streets that changed name between blocks, and the numbering system was idiosyncratic to each street.

In the 1880s, North-South streets on the Southside were renumbered according to the street numbers. For example, 5200 S. Blackstone would be located at the corner of Blackstone and 52nd St. Later, in 1909, Northside streets were uniformly numbered as well. Finally, in 1911, State and Madison was declared the "origin" -- the zero North/South and zero East/West point -- for the city, and Loop streets were renumbered as well. This numbering system, developed and tirelessly lobbied for by Edward P. Brennan, remains today, making Chicago perhaps the easiest large city in the U.S. to navigate.

The photo above is at 915 N. Dearborn. Before 1909, this property would have been numbered 285 Dearborn, and the remains of that old number are still visible.

A directory of the 1909 and 1911 changes can be found through the Chicago Historical Society here (1909) and here (1911). Changes to street names can be found here.

The Arena

In the 1880s and 1890s, 1340 S. Michigan Ave. was a three-story mansion set fifty feet off the street, the home of millionaire president of the Chicago Brick Company, Patrick J. Sexton. Mr. Sexton and his wife hosted a number of important social events throughout the late nineteenth century, during which 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 after his death they moved out of the home.

With the new automobile industry growing in Chicago, the south Michigan area became home to a number of showrooms, but the mansion at number 1340 remained a private residence, with the windows 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 Everleigh Club, and all other forms of open vice trade. 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 divorces and family court in the 1980s and 1990s. The building is empty today, but there are plans to remake it as a condominium complex in the near future.

Andy Craig's Life of Crime

Between 1880 and 1925, Andy Craig was consistently at the center of Chicago's underworld. While he owned many saloons, brothels, and gambling dens over the years, his most famous hang-out was the Tivoli, located at 383 S. State St. (in today's street numbering system, this would be 645 S. State), in the middle of this parking lot by the elevated tracks. The Tivoli was in operation between 1898 and 1903.

The Tivoli was known as the meeting place for most of the South side's pickpocket crew. In return for spending their money on the Tivoli's amenities, which besides the saloon included a sports book in the basement and prostitutes upstairs, Andy Craig served as the general bail bondsman for the group, always ready with a loan when one of them ended up in the Harrison Street police station. It was said that Craig, who became known as the "bail bond king", could be found serving bail at the police station every single day in the year, and for this reason the patrolmen came to refer to pickpockets as "Craig's people."

The Mayor ordered the Tivoli closed in 1903, after a sweep on Thanksgiving Day morning found the saloon open at 1:15 a.m., well past the midnight closing hour. The Tribune described the Tivoli at that time as home to all type of "disreputable persons," including "pickpockets, thieves, women, confidence men, and other law breakers." Not just thieves, but women!

This did not end Craig's career. Like hundreds of other Custom House Place and Whisky Row residents also swept out of business in 1903 by popular demand, he moved his operations south to the new Levee district centered around 22nd and Dearborn Streets, and continued operating as a pander, loan shark, saloon-keeper, and bookie for the rest of his life. Newspaper articles as late as 1925 name the old-time saloon keeper as a material witness in a case in which he loaned $2,500 to a known heroin addict, as the owner of the Northern Lights Cafe at Devon and Broadway, where a policeman shot a gangster in a firefight, and as a well-known book-maker operating out of Capone's Hawthorne Race Track.

Fred Ries, or How Cockroaches Brought Down Scarface

Fred Ries was the cashier at several Capone-controlled gambling operations, including the "Subway", at 4738 W. 22nd St., in Cicero, located where the building pictured above now stands. In large part because Ries was entomophobic (afraid of insects), Jake Guzik, Frank Nitti, and Al Capone ended up in federal prison.

Ries' job as cashier involved collecting the house's winnings each night, converting them into cashier's checks, and then passing cuts of these checks to the Capone Outfit's leadership, including "Scarface" himself. This laundering scheme kept any evidence of income (and thus, tax liability) safely separated from Capone and company. The feds knew Al had plenty of money -- they had seen him lose $20,000 in a night of gambling, plus his substantial real estate holdings -- but they had no way to prove he had earned it as income. Until, that is, they found out that one of Capone's cashiers was deathly afraid of cockroaches.

At the time of his arrest as a material witness, federal agents found Ries hiding out in St. Louis. They threw him into a specially-made cell in Danville, Illinois, which had previously been prepared with roaches, spiders, rats, and bedbugs. After five days in the cell, Ries was ready to talk. He would have done anything to escape that cell.

Based on his grand jury testimony, Guzik, Nitti, and Al Capone were indicated for tax fraud. Of course, during the time between the indictment and the trial, Fred Ries became the #1 mark for Capone's henchmen, which is why the feds sent him on an all-expenses-paid vacation to South America for a month. At trial, Ries' testimony was the coup de grace, the government's final and most convincing witness, tying Al Capone directly to substantial sums of income on which he had never paid taxes.

Capone went to prison for eight years, effectively ending his racketeering career. Ries went into hiding, and apparently was never heard from again.

Fred Ries' operation, the Subway, sat on property which is now the location of a Dunkin' Donuts store (currently being renovated).

Capone's Horse Track

As with pretty much everything else in Cicero, Al Capone took control of the Hawthorne Race Track early on, and the fix was frequently in.

Lawrence Bergreen quotes a photographer for the Evening American, who claims that Capone used the fix to bribe him:

Assigned to cover a horse race at the Hawthorne track Capone controlled, Berardi was surprised to find Al himself at the race that day, accompanied by his usual retinue of five bodyguards. "Kid, how you doing?" he called out.
"I'm doing fine," said Berardi.
"Why don't you bet on number 6?"
The odds against the horse Capone recommended were exceedingly long: ninety-nine to one. Before Berardi could reply, one of Capone's attendants rushed over and stuffed a slip of paper in his jacket pocket. "I looked at it," Berardi rememberd, "and it was a five-dollar ticket on this number 6 horse....Well, he broke out in front and stayed out in front, and I don't think anyone dared catch him. The goddamn horse won by a block....Capone didn't bribe me; he just put $300 in my pocket.

(Bergreen, Lawrence, 1994, Capone: The Man and the Era. New York: Simon & Schuster, pp. 150-151).

Most of the Hawthorne track burned down in 1979, and a larger track was rebuilt afterwards.

Gangster Peace Conference at the Sherman House

Autumn of 1926 saw Chicago's gangsters involved in a dangerous and bloody cycle of violence. In late September, Schemer Drucci and Bugs Moran and Hymie Weiss had shot up Capone's Cicero headquarters. Within days, Capone had ordered the assassination of Weiss on the street in front of O'Banion's Flower Shop.

On October 20, Capone arranged a peace conference with the Northsiders, held at the Hotel Sherman, at Clark and Randolph. "Big" Bill Thompson, the former Chicago mayor who was planning a political comeback, served as the impartial mediator.

The Northsiders demanded that O'Banion's assassins, Scalisi and Anselmi, be punished by Capone. But even they seemed to have been impressed with Capone's earnestness for peace. He argued:

I couldn't stand hearing my little kid ask why I didn't stay home [in Chicago]. I had been living in the Hawthorne Inn [in Cicero] for fourteen months....If it wasn't for him I'd have said, 'To hell with you fellows! We'll shoot it out.' But I couldn't say that, knowing it might mean they'd bring me home some night punctured with machine gun fire.

The conference led to a general amnesty between the gangs, in which all murders performed in the past were considered closed with no further repercussions. Drucci and Moran would control the Northside areas of the city near the lake, and Capone would control the Southside below Madison, plus Cicero. There was not a single gangland murder for 70 days after the conference, the longest period without gang violence in years.

The Sherman House, which was originally built in 1837 by Francis Sherman (father to William Tecumseh Sherman, the famed Civil War general), had been rebuilt after the Great Fire as the poshest hotel in town, and was one of the first establishments in Chicago to offer jazz entertainment to white audiences. The hotel remained open until 1973, and was razed in 1980 to make way for the State of Illinois Center, later renamed the James R. Thompson Center, pictured here. Possibly Chicago's most unusual building, the Thompson Center is either an architectural masterpiece or a hideous spaceship/toilet, depending upon who you ask.

"Schemer" Drucci Killed by Police Officer Healy

Vincent Drucci was a teenage pickpocket and thief when he became close with the Northside gang, run by Dion O'Banion. Eventually, he became their leader.

Besides being a racketeer and notorious criminal, Drucci was a first-class goofball. He earned his nickname, "Schemer", for the wild, harebrained ideas he was constantly dreaming up for stealing the crown jewels, bringing down the U.S. government, running for Mayor, or some other equally ridiculous plan. As a practical joker, he was unparalleled among gangsters, and was famous for walking around dressed as a priest, while making mischief among those he happened to come across.

He rose through the O'Banion organization, becoming second in command under "Hymie" Weiss after O'Banion's death, and taking over the leadership when Weiss was assassinated. A ruthless killer, he held the distinction of murdering two consecutive presidents of the Unione Siciliana, Angelo Genna and Sam Smoots Amatuna.

He made countless attacks on the lives of Al Capone and other members of the Torrio-Capone syndicate. During 1926, while Capone was sequestered away from Chicago in Lansing, Michigan, waiting for the heat from the Bill McSwiggin murder to pass off. The Northsiders took this opportunity to expand the reach of their gang. When Capone returned to the city, he decided to send a message to Drucci and company. One of Capone's loyal deputies, Louis Barko, engaged Hymie Weiss and Drucci in a firefight through the streets of the Loop, leading to Drucci's arrest. It was this event that triggered the Northsiders' revenge attack upon Capone's Cicero headquarters, the Hawthorne Inn.

Schemer Drucci's run of luck ended in a rather inglorious way. April 4, 1927 was mayoral election day in Chicago. "Big" Bill Thompson, the Republican candidate who had previously served as second ward alderman and whose career was guided and mentored by the corrupt vice king-aldermen of the first ward, Hinky Dink Mike Kenna and Bathouse John Coughlin, was running on a "wet" platform against "Decent" William Dever. For his anti-prohibition stance and general amenity to corruption, Thompson was gangland's choice, and Drucci decided to help his man in the best way he knew -- by kidnapping Dever's supporters. After breaking into the office of Dever's biggest supporter on the City Council, Lincoln Park Alderman Dorsey Crowe, Drucci managed to get arrested and, after some legal wrangling, ended up in a police car headed for the Criminal Courts building downtown.

His police escort included one of Chicago's toughest cops, Dan Healy. Healy's description of what took place during that car ride follows:

Drucci said, "You -- I'll get you. I'll wait on your doorstep for you." I told him to shut his mouth. Drucci said, "You take your gun off me or I'll kick hell out of you." He got up on one leg and struck me on the right side of the head with his left hand, saying "I'll take you and your tool. I'll fix you," grabbing hold of me by the right hand. I grabbed my gun with my left hand and fired four shots at him."

Drucci was shot in the back of the police cruiser while stopped for traffic on the Clark Street bridge over the Chicago River, pictured above. Despite pleas from his attorney, Healy was never seriously investigated for the killing, since the police were more than happy to see Drucci gone. Even Drucci's widow found her self less than distraught over the decease of the gangland leader. Inheriting his half-million dollar estate, she is reported to have said at his funeral (organized by John Sbarbaro, of course), "We sure gave him a great send off."

Allan Pinkerton Sets a Sting Operation

The Sauganash Hotel, named after a famous Illinois Potawatomi chief, was Chicago's first frame building, erected by "Jolly" Mark Beaubien in 1831, here at the corner of Lake St. and Market St. (the latter now known as Wacker Dr.). Of its comforts, Herbert Asbury quotes a Chicago visitor in 1833, who described the Sauganash as a "vile two-storied barrack," where "all was in a state of most appalling confusion, filth and racket." Nevertheless, the Hotel was one of Chicago's only public houses and served for several years as a central meeting grounds for the town's hoi polloi.

It was at the Sauganash that Allan Pinkerton first made his name as a detective, running a sting operation that rounded up a local counterfeiting ring.

Pinkerton came to Chicago from his native Scotland in 1842, and worked in the Northwest suburb of Dundee as a successful barrelmaker. One day, seeking a new source of wood for his product, Pinkerton floated to a small island in the middle of the Fox River, where he happened upon the campsite of a group of local counterfeiters. Returning to town, Pinkerton informed the sheriff, who returned with him to the island, and arrested the criminals. However, the leader of the gang was still at large, and the town council, sufficiently impressed with Pinkerton's earnestness, deputized him to find and arrest the ringleader. They gave him $125 with which he was to buy counterfeit bills as evidence.

Pinkerton quickly found his man, striking up a conversation with him in a local saloon, and offering the $125 as down payment on over $4,000 worth of bills, which he proposed to buy at $0.25 on the dollar. The men agreed to execute the rest of the transaction at the Sauganash in Chicago one week hence.

On the specified date, Pinkerton entered the hotel restaurant, and as two plainclothes officers looked on, bought the bills. As the money changed hands, the officers revealed the sting and arrested the counterfeiter. It is said that no counterfeit money was seen again in Cook County for over a year.

Impressed with Pinkerton's abilities, the sheriff hired the barrelmaker as a full-time investigator, from which he went on to great fame and success. He founded the Pinkerton National Detective Agency in the 1850s, and was involved in foiling an assassination plot on President Lincoln, performing military intelligence during the Civil War, and arousing strife within labor unions that kept them from successfully organizing against business interests. His Detective Agency still exists today.

The Sauganash Hotel burned in 1851, and the site was later used for the Republican convention that nominated Abraham Lincoln in his 1860 campaign. Today, the Chicago Lantern Building at 191 N. Wacker covers the spot where the Sauganash once stood.

Capone's Cicero Headquarters

Al Capone's Chicago headquarters were the Four Deuces, the Metropole Hotel, and later, the Lexington Hotel. But in Cicero, the town his syndicate owned, from the Mayor to the streetsweepers, business was chiefly transacted at the Hawthorne Inn, at 4833 W. 22nd Street.

After Capone's violent takeover of the town of Cicero in the election of 1924, he set up shop at the Hawthorne, fitting it with bullet-proof shutters and surrounding every entrance with battalions of armed guards. This was the true city hall in Cicero, the center of power, and when orders emerged from the Hawthorne Inn, even the mayor, Joseph Z. Klenha, jumped.

It was at the Hawthorne that Dion O'Banion began his double-crossing scheme, telling Capone and Johnny Torrio that he planned to leave the bootlegging game for greener pastures out West, leading to Torrio's arrest at Sieben Brewery, O'Banion's assassination, and Torrio's brush with death.

Having failed to kill Torrio, O'Banion's henchmen attempted to avenge their slain leader's life with a direct frontal attack on the Hawthorne Inn on September 20, 1926. On that date, Al Capone was eating lunch on the first floor of the Hawthorne. At 1:15 p.m., the sound of machine gun fire echoed through the restaurant, sending the waiters and patrons running out the back. Capone and his bodyguard hit the deck as a car passed by and the sound of bullets intensified.

Once the gunfire ceased, Capone arose unharmed and ran to the door, ready to get a good look at his assailants. Suddenly he noticed something odd: despite hundreds of bullets, not a thing was broken in the restaurant. The apparent drive-by shooting was a decoy, and only blanks had been fired, in an attempt to draw Capone out of the restaurant to his death. With this sudden realization, Capone's bodyguard tackled him, just as a caravan of seven Lincolns, headed by Schemer Drucci, Bugs Moran, and Hymie Weiss, passed by the Hawthorne, practically razing the hotel with machine gun fire. Almost 1000 shots were fired into the establishment, but again the Northsiders were frustrated: not one person, and certainly not Capone, was killed.

In retaliation, Capone ordered the hit on Hymie Weiss at O'Banion's flower shop, and the cycle of violence between the Capone Outfit and the North side gang continued to intensify.

The Hawthorne Inn remained open until 1970, and during much of that time, it remained a mob hangout. Today, the location is the parking lot for a bank.

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).

Dead Man's Corner

Between 1880 and 1920, the most violent spot in "Bloody Maxwell," the most violent neighborhood in Chicago, was the corner of 14th place and Sangamon, otherwise known as Dead Man's Corner.

Conveniently near the Maxwell Street Police Station, Dead Man's corner was continually the site of gun battles between police and criminals.

Long past its heyday of criminality, but still a slum, this photograph from the Cushman collection at Indiana University shows the southeast corner of Dead Man's Corner, in 1949. The photo following it shows the corner as it looks today.

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.

Colosimo's Home

James "Big Jim" Colosimo was the first great Chicago mobster, considered by many to be the founder of "the Outfit." He lived in a large home at this location, 3156 S. Vernon.

Born in Italy, Colosimo came to Chicago as a teenager and, in 1897, became a sweeper with the "white wings," a city-funded group that cleaned manure out of the streets. Big Jim was a natural leader and soon organized the streetsweepers union. He parlayed that job into political power, which he used to become the city's king of vice for over 20 years.

Colosimo married into the vice business, his wife Victoria being a brothel owner, and together with Maurice Van Bever, the gang ran a profitable white slavery ring in the 1910s and 1920s. Van Bever was imprisoned in 1909. Together with the Mona Marshall case, Van Bever's trial brought public opinion to bear on interstate prostitution traffic, leading to the passage of the Mann Act in1910. Van Bever's absence opened up a top position in the gang for Johnny Torrio, who at that time was in charge of Colosimo's biggest brothel, the Saratoga. It was Torrio who later brought Al Capone to Chicago to help him run the gang after Colosimo's death.

Colosimo's house was not far from his chief place of business, Colosimo's Cafe, which for many years before and after Big Jim's death, was a place to be seen for the city's power elite. It was to this home that Colosimo brought his second wife, the beautiful young singer and actress Dale Winter, whom he loved dearly and hoped to retire with from the vice trade. Unfortunately for Big Jim, he died within a month of his marriage, shot by an assassin, most likely Frankie Yale, working on behalf of his friend and Colosimo's protege, Johnny Torrio.

The site of Colosimo's home is now a quiet South side park.

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.

Capone's Chicago Home

Al Capone had been in Chicago only about a year when he purchased this home at 7244 S. Prairie Ave in the summer of 1922. Capone was finding success in the Johnny Torrio organization, and had earned enough to afford this middle-class house in a sleepy South side neighborhood, about eight miles south of downtown Chicago, and 13 miles from his business operations in Cicero. It remained Capone's official address for the rest of his life, and the deed remained in the family until the 1950s.

Here, Capone installed his long-suffering wife, Mae, his only child, Sonny, plus his widow mother Teresa, and younger siblings Albert, Mimi, Matthew, and Mafalda. The home, fortified by iron bars in the basement windows (still visible today) and a massive brick garage with a car always at the ready, remained a safe place for the Capone family for thirty years. Teresa continued living here until her passing in 1952, after which the house was sold.

Starting in the 1950s, the Irish and Italian immigrants who had previously populated the neighborhood, were replaced primarily by African-Americans. Other than that, the neighborhood remains a quiet, family-oriented area to this day.

Walsh School

The John A. Walsh School was founded in Chicago's "Bloody Maxwell" district in 1866. Between 1880 and 1905, it served as the primary battleground for two vicious street gangs of boys, the Irishers and the Bohemians. The school sits on Peoria St., then known as Johnson St., which was the border line between the Irishers' territory to the east, and the Bohemians to the west. During the 1880s and 1890s, blackjacks, clubs, and pistols were frequently used, both inside and outside the school, leading to the death of several students, and leading up to the final battle in December of 1905.

In that month, around 50 Irishers and Bohemians faced off in a gun battle at the school in which between forty and fifty shots were fired. When the police arrived, they found no boy older than 15, and many as young as ten.

Following the battle, no one was allowed to enter the school without a thorough search.

The building of the Walsh School has since been rebuilt.

Lincoln's Coffeehouse

No, not that Lincoln. In the summer of 1835, Solomon Lincoln, who had up until then made his living principally as a tailor in Chicago, opened the city's first saloon at this location on the corner of Lake and LaSalle Streets, known as Lincoln's Coffeehouse. The coffeehouse quickly became the most popular drinking establishment in the city, which wasn't saying much since Chicago's population was under 4,000 people at the time.

Unlike the tattooed and pierced barista at your nearby Starbucks, Lincoln was a noted hunter of wolves, which at that time were a persistent nuisance in Chicago. In fact, the area around the confluence of the Chicago River, just three blocks west of the Coffeehouse, was known in the 19th century as "Wolf Point," for the ubiquitous animals. In Gem of the Prairie, Herbert Asbury quotes an "old-time Chicagoan" as saying: "Many a time, I have seen Mr. Lincoln mount his horse when a wolf was in sight on the prairie toward Bridgeport, and within an hour's time come in with the wolf, having run him down with his horse and taken his life with a hatchet or other weapon."

No wolf sightings at this Bank of America, which currently occupies the site.

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.

Johnny Torrio Shot

After Dion O'Banion double-crossed him at Sieben Brewery, Johnny Torrio's south side organization came into constant conflict with the North side gang. With encouragement from the Genna brothers, Torrio had assented to O'Banion's murder.

In retaliation, O'Banion's followers targeted Torrio. After the bust at Sieben, Torrio had turned over his major operations to Al Capone, making him think he was safe from rival gangsters. However, Hymie Weiss and Bugs Moran, two of O'Banion's lieutenants, were motivated by revenge, not business matters, and about 4:30 p.m. on a cold January morning in 1925, they ambushed Torrio in front of his home, pictured here, at 7011 S. Clyde Ave.

Torrio and his ever-loyal wife, Ann, had spent the day shopping in the Loop, and had just returned to their South Shore home. Accompanied only by their driver, they walked up to the front door, with Torrio carrying a load of packages, unaware of the blue Cadillac that had arrived moments after them. Weiss and Moran jumped out and unloaded a hail of bullets, first at the Torrios' car (wounding the driver, who was still inside), then at Johnny Torrio himself. One bullet in the arm, another in the groin, both at point blank range. Finally, Bugs Moran put his pistol to Torrio's head for the coup de grace. Click. No bullets left.

Torrio survived the hit, though barely. After four weeks in the hospital, protected by Al Capone personally at his side day and night, Torrio served his nine-month sentence for the Sieben bust at Lake County Jail, then departed immediately for Italy, where he lived for several years before returning to New York. He never set foot in Chicago again, and Al Capone took over the leadership of his organization.

Al Capone's Cicero Hangout

Al kept his wife, mother, and son at the family home in Chicago, but also kept this apartment building at 1600 Austin Blvd., in Cicero, as a crash pad for late night parties. Not far from his Cicero business headquarters, this unassuming home was protected by a heavy steel door (which appears to have been replaced -- see below), a 8 foot backyard fence, underground escape tunnels, and two or more bodyguards prowling the grounds at all times.

The block is one of the most well-kept in Cicero, but the current owners seem to have purposely allowed the shrubbery to obscure the entry and windows.

The Holmes Castle

Herman Mudgett was a New Hampshire-born medical student with an interest in the macabre. Mudgett, or H.H. Holmes, as he began calling himself (among a number of other aliases) came to Chicago in 1886 and quickly charmed his way into work at a pharmacy in Englewood on the South side of Chicago, at 63rd and Wallace. After the widow who owned the pharmacy mysteriously disappeared, Holmes took over the business and grew it successfully, largely by charming the neighborhood women, who took pains to visit and patronize his business.

With the money from his drug store, Holmes purchased the lot across the street (pictured above) and designed and built his "castle," which included retail shops on the first floor and rooms on the second. It wasn't until much later that the interesting aspects of the castle came to public notice: the rooms with locks on the outside and gas nozzles on the inside, the vats of acid, the corridors that led to nowhere, the kiln hot enough to disintegrate flesh in the basement.

Before, and especially during, the World's Fair of 1893, Holmes tortured and killed scores of visitors, especially women, to whom he was preternaturally irresistible. He became Chicago's first serial killer, the "Jack the Ripper of America." Holmes married several times (usually without divorcing the previous wife); during the Fair, he moved his wife to an apartment in Lincoln Park.

He was eventually caught, and hanged in 1896.

Holmes was no architect nor engineer, and his castle was neither well-designed nor built to particularly high standards. In addition, in order to conceal his misanthropy, the building was erected by a continually changing cast of workers. Holmes' practice was to hire a crew one week, then refuse to pay them, then hire a new group of workers when the last ones gave up. The castle would not have stood long, but its demise was hastened by an unknown arsonist, and it burned to the ground shortly after Holmes was arrested. The location is now a U.S. post office.

UPDATE: Based on information from a commenter, it appears that, after the fire, the building was largely rebuilt, and continued to be used until January, 1938, when it was purchased by the city for use as a post office. The photo below shows the building as it looked in 1938, when the address was 601-03 W. 63rd. Thanks to Adam Seltzer for the tip.

Maxwell Street Police Station

The Maxwell Street district, termed "Bloody Maxwell" by the Chicago Tribune, was the chief breeding ground for criminals during the 19th and early 20th century in Chicago.

Most of those criminals ended up at one time or another, here, at the 22nd precinct police station at the corner of Maxwell and Morgan St. During its heyday as a terror district, the station was surrounded on all sides by "corners, saloons, and houses that have seen the rise, the operations, and often the death of some of the worst criminals the land has ever known," according to the Tribune.

Likely the newspaper had in mind Dead Man's Corner, located just two blocks away from the station.

Built in 1888, the station was in continued use by the Chicago police for over 100 years. Fans of the 1980s hit television series Hill Street Blues will recognize the station from the opening credits.

Today, the station is still in use by police as the headquarters for security at the University of Illinois at Chicago.