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.