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.

"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).

Ralph Capone's Home

That is not Ralph Capone's 1996 Dodge Grand Caravan. That is, however, Ralph Capone's house behind it, at 1924 S. 49th Ct., in Cicero.

Born Raffaele Capone in Naples, he immigrated to New York with his parents in infancy, and came to Chicago about a year after his brother, Al. For awhile, he helped Al run a call flat in Rogers' Park, working for the Johnny Torrio syndicate. Later, Ralph became the right-hand man of that organization when Al took over, and ran the entire organization during period when Al was in jail or otherwise away from Chicago. During the salad days of the Capone bootlegging operation, "Bottles", as Ralph was known, organized the distribution of liquor, and also ran several speakeasies and brothels, including the famous Cotton Club in Cicero.

Ralph also became the government's test case in prosecuting racketeers for income tax evasion. Never as smart as his brother, government prosecutors noticed that practically all of Ralph's bank deposits were in multiples of 55, notable since the going rate for a barrel of beer was $55. In addition, after his indictment, Ralph continued operating his distribution business, never considering that his telephones might be tapped. Ralph Capone was the first racketeer to serve a prison sentence for tax evasion. He spent three years at McNeil Island Corrections Center in Puget Sound before being released in 1934.

After release, Ralph continued his job in the Capone organization, working for Frank Nitti, since Al was, by that time, in prison. The government continued to dog Ralph throughout the rest of his life, primarily on income tax charges, although he never went back to prison, and eventually retired to Mercer, Wisconsin, where he died in 1974.

Mafalda Capone Maritote

Mafalda, named after an Italian princess, was the youngest Capone sibling and the only sister. Born 13 years after Al, she grew up spoiled, and retained a reputation as a profane and sharp-tongued woman throughout her life.

Born in New York, Mafalda arrived in Chicago with the rest of her family as a toddler. She attended the old Lucy Flower Vocational High School on the West side, once one of the city's best (it was closed in the late 1990s).

On December 14, 1930, she was married at the church pictured here, St. Mary's of Czestochowa, at 3010 S. 48th Ct., in Cicero. Located in the family-run town, but safely in the Polish section of town, near the Chicago border, St. Mary's provided a safe locale for the wedding event of the year. Mafalda wore a satin gown with a 25-foot train and carried a bouquet of 400 flowers down the aisle, where she was given away by her brother Ralph. At the time, Al feared arrest in Chicago and so did not attend.

The groom was John Maritote, the younger brother of a Capone organization affiliate Frank "Diamond" Maritote, who later went to prison in the Bioff/Brown Hollywood extortion case in 1943.

Mafalda was a loyal Capone family apologist throughout her life, although she was never directly known to be involved in any racketeering. Later in life she ran a successful bakery and catering service. She passed in early 1988.

O'Banion Homes

448 W. Surf (above), and 2800 N. Pine Grove (below) were among the homes occupied at various times by the founder and leader of the North Side Mob, ex-singing waiter and floral artist, Dion O'Banion, in the early 1920s. 2800 N. Pine Grove stands opposite the Commonwealth Hotel, where, a few years later, entertainer Joe Lewis was brutally attacked after he switched venues from a Capone-controlled bar to a North Side Mob saloon.

The Pony Inn

Harry Madigan ran an Al Capone-controlled bar called the Pony Inn at this location, 5613 W. Roosevelt, Cicero, in 1926. In Spring of that year, the sidewalk in front of the saloon became the scene of a famous crime that haunted Capone throughout the rest of his career. The building still stands, now known as Sarno's Restaurant.

William McSwiggin was Assistant State's Attorney in Chicago, and had vigorously pursued an indictment against Al Capone in 1924 for killing Joe Howard in a South side bar. While unable to successfully prosecute Capone (despite the presence of several eye-witnesses), McSwiggin became known as a "hanging" prosecutor. But there was more to him than met the eye.

McSwiggin was also a card player, gambler, and drinker, and that naturally brought him into close contact with Capone and his associates on a regular basis. In fact, with the passage of time, Capone began to consider McSwiggin a friend. One night in late Spring, 1926, after dinner at his parents' house, McSwiggin and a few close friends went out for a night of gambling and drinks. Shortly after leaving the house, their car broke down and they ended up joining a couple of other friends in their car. These friends were the O'Donnell brothers, rival bootleggers who had a growing feud with Capone.

The O'Donnells' shiny new Lincoln went cruising through Cicero with McSwiggin and friends, hitting bar after bar, until they ended up here, at the Pony Inn, not far from Capone's Cicero headquarters. When word came to Capone that his rivals were encroaching on his territory, he sent a convoy of lieutenants, armed with machine guns, to make his displeasure known. No one told him his friend McSwiggin was with the group.

As the drinking party left the Pony Inn, bursts of gunfire sent fifty rounds into the group, killing three, including McSwiggin (the O'Donnells, the targets of the attack, escaped unharmed).

Public outcry at the gangland death of a state prosecutor pushed the police into action. Chicago police invaded Cicero, arresting Ralph Capone and raiding several Capone-owned joints. Al fled the city, spending the summer of 1926 among friends in the Italian community in Lansing, Michigan, until the heat died down enough for him to return to the Chicago area.

Never again, however, was Capone completely unmolested by the police. Though he had never intended to hurt McSwiggin, he had lost his standing with the public, who began to put increasing pressure on the police to shut down gang operations.

The Cotton Club

In league with his younger brother, Ralph Capone ran a number of bars and speakeasies, the most famous of which was the Cotton Club, at this location, 5342 W. 22nd St., Cicero.

The mayor of Chicago, "Big Bill" Thompson, was especially fond of the nightlife here, where prohibition, despite being the official law of the land, seemed not to exist. The Chicago Crime Commission described the Cotton Club as "a 'whoopee' spot where liquor flowed freely."

The Capones were notable for their color-blind policy with respect to entertainment, and the Cotton Club played host to most of the top Black acts of the 1920s (for an all-white audience, of course), and many of the performers grew to appreciate and respect Al and Ralph. Milton Mezzrow, Judge Hinton, Jelly Roll Morton, Duke Ellingon, King Oliver, and Louis Armstrong were among the luminaries who played here, making Al Capone one of the most important figures in the development of Chicago jazz. Comedians, including Milton Berle, were also a common act.

There could hardly be less remaining of the Cotton Club or any of its famous entertainers at this location today.

Joe Lewis, the Rendezvous Cabaret, and the Commonwealth Hotel

Joe E. Lewis was a popular comedian and singer from New York, who became a favorite at "Machine Gun" Jack McGurn's speakeasy, the Green Mill in Uptown. In August, 1927, a rival saloon, the Rendezvous Cabaret, located at 622 W. Diversey, where this Panera Bread currently stands, lured Lewis away from the Green Mill with a big raise and a share of the business.

McGurn was an associate of the Chicago Outfit, while the Rendezvous was operated by their mortal enemies, the North Side Mob. Lewis had committed treason. McGurn was a close associate of Al Capone, and a loyal lieutenant of the Torrio-Capone Outfit. Worse yet, on opening night at the Rendezvous, November 2, 1927, Lewis played to a packed audience and ridiculed McGurn as a part of his act. Perhaps he thought he was safe since gangsters only killed other gangsters.

A few days later, November 9, Lewis awoke in his room at the Commonwealth Hotel, 2757 N. Pine Grove (pictured below), to three armed men, who proceeded to bludgeon Lewis with a revolver and slice his face and neck with a hunting knife.

Jack McGurn, who later masterminded the "Crime of the Century," the St. Valentine's Day Massacre, was a one-man bad publicity machine for the Capones. In this case, his men failed to finish the job.

Unbelievably, Lewis survived the attack and, after some time, regained the ability to speak (his attackers had paid special attention to his jaws, the source of his income). He even returned to entertain an overflow audience at the Rendezvous, taking on the moniker "The Man the Mob Couldn't Kill."

After gaining fame in this unfortunate way, a star-studded group of entertainers, including Al Jolson, held a benefit for Lewis and raised $14,000 (most of which Lewis, an alcoholic, managed to drink away). Sensing the growing bad publicity for his group associated with the hit, Al Capone offered Lewis his old job at the Green Mill at terms matching those the Rendezvous had offered him, and made sure he and McGurn never tangled again.

The Commonwealth Hotel, where Lewis was attacked, still stands, though its days as a posh hotel are long over. It currently serves as a home for the elderly.

Minnie Holmes' Flat

Having a wife around is such a pain in the neck for a serial killer.

Henry Holmes, born Herman Mudgett, was the most famous Chicago criminal of the 19th century. During the World's Fair of 1893, he hosted hundreds of travelers at the "hotel" he built on the South side at 63rd and Wallace. An unknown number of those travelers never checked out, tortured and killed by Holmes in any number of fiendish ways at that location.

Like many serial killers, Holmes was quite the ladies' man, and he met, romanced, and married a series of beautiful women, usually without divorcing the previous one. In 1893, Holmes, going by the name Harry Gordon, was married to Minnie Williams, a woman he had met years earlier in Boston, and who he had successfully seduced upon her arrival in Chicago. Later, he killed her and her sister Anna as well, presumably to take advantage of the sisters' real estate holdings in Fort Worth, Texas, but probably also just for the fun of it.

However, Holmes' murderous schemes in 1893 mainly involved out-of-town visitors to the Fair, and having Minnie around was likely to interrupt the fun. So he rented an apartment at 1220 Wrightwood (now 1140 W. Wrightwood), about as far from 63rd and Wallace as possible, and left Minnie to keep house there while he tended to the hotel and murdering business on the South side.

The building has been demolished and replaced with a new one, but you can still rent an apartment at this location (prices have risen a little).

Sieben Brewery

Besides his numerous other talents, Dion O'Banion was an excellent businessman. After the Torrio-Capone gang took over the Cicero city government in 1924, they assigned a small strip of that suburb to O'Banion, who had helped them in the conquest. He immediately quintupled bootlegging revenues in the area and began to extend his sphere of influence into the West side of Chicago, convincing saloon owners currently working with other gangs to buy their goods from him. Johnny Torrio demanded a cut of the new revenues, but O'Banion refused. O'Banion also made a habit of being a thorn in the side to a group of Torrio associates, the Genna brothers, who ran a large and vicious bootlegging enterprise centered in the West side. It was of the Gennas that O'Banion coined one of the most famous phrases in gangland history: "To hell with the Sicilians!"

Never cross a Sicilian.

Finally, in late Spring, 1924, Dion O'Banion could no longer contain his contempt for Torrio and his associates, and a plan to double-cross his boss took place at this location, currently the Near North Career Metro High School, but previously the site of the Sieben Brewery, jointly owned by O'Banion, Torrio, and Al Capone, located at 1464 N. Larrabee.

O'Banion had heard through the grapevine that the Sieben was scheduled for an upcoming police raid. Before that happened, he called a conference with his co-owners in the enterprise, Torrio and Capone, and announced that he was leaving the rackets, retiring to Colorado. Would they be interested in buying his share? Torrio and Capone readily agreed -- they were sick of the trouble and infighting O'Banion created, and would happily buy his train ticket out of the city.

There was just one more convoy of liquor to be delivered to the Brewery, on May 19, 1924, and after that, O'Banion was scheduled to hand over his interests in the business. Of course, O'Banion knew that that night was the planned evening of the raid. The police showed up and arrested both O'Banion and Torrio. Torrio was eventually sentenced to a nine-month prison sentence. O'Banion was murdered soon after, probably at the behest of Torrio, by Mike Genna and two other Sicilians, the famous assassins, Scalisi and Anselmi.

Thus began the great Beer Wars between the North Side Mob, under Dion O'Banion and his followers, and the Torrio-Capone Syndicate.

Death Corner

The corner of Oak St. and Cleveland St. (previously Milton St.) was known as "Death Corner" for a reason. Situated in the heart of Little Hell, it was a famous murdering ground in the 1910s, and the favorite dumping site for a number of professional assassins, including the famous "Shotgun Man," who is said to have killed over 15 men, including 4 in a single three-day spree.

The corner was a hangout for many of Chicago's "Black Hand" gangs, extortionist Italian groups , following an ancient Sicilian tradition, who preyed on entrepreneurs or anyone else believed to have money. A gang would proceed by sending a letter which invariably began with ingratiating tones, but proceeded to demand money and threaten the life or wealth of the recipient. The letter closed with various cryptic symbols, including a handprint in black ink. Anyone failing to pay was risking his life, and Black Hand gangs committed many murders. Though despised by the Italian community, the practice of Black Hand survived all attempts to destroy it until it died out slowly in the 1920s.

The area is still crime-ridden, situated in the middle of a housing project in the old Cabrini Green district. Empty lots stand on two of the four corners.