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.

Dion O'Banion's Birthplace

This is the location where the founder of the North Side Mob, the man who dared turn against Johnny Torrio and Al Capone, the great singer, floral arranger, and bootlegger, was born. The site, 841 N. Wells, currently belongs to the Moody Bible Institute.

Sbarbaro's Funeral Parlor

John Sbarbaro's funeral parlor, at 708 N. Wells, was the parlor of choice for gangland royalty. After his death, Dion O'Banion "lay in state" here in November, 1924, in a casket said to be worth over $10,000, before his famously lavish funeral, which included a mile-long procession, three bands, a police escort from Stickney (Chicago police were strictly ordered not to attend), and over 10,000 well-wishers.

Sbarbaro himself was a double agent, serving both as funeral director to gangland and assistant district attorney in Chicago. In fact, he was the lead prosecutor investigating the shooting of Johnny Torrio. Later, Sbarbaro served as a cook county judge. At the same time he was pronouncing the law from the bench, he was also a racketeer, and his home served as a storage unit for illegal liquor -- until it was bombed by rival gangsters.

McGovern's Saloon

Dion O'Banion, the renaissance man of crime, was the founder of the North Side Mob. Besides floral arrangement, one of his other great talents was singing. He performed at McGovern's Saloon, 661 N. Clark, located where the parking lot above is now, as a singing waiter during his misspent youth while growing up in Little Hell.

Carrie Watson and Sig Cohen

After Annie Stewart's brush with the law, she retired from Madamhood and sold her interest in 441 S. Clark to Carrie Watson in 1868. In league with her boyfriend and financier, Sig Cohen, Watson upgraded the decor and quality of the women working within, and operated it as one of Chicago's finest brothels before and after the Fire, into the 1890s, during that time becoming one of the city's richest women. A businesswoman with an excellent eye for publicity, her house's supreme gimmick was a trained parrot who sat in a cage outside the door and constantly repeated, "Carrie Watson. Come in, gentlemen."

Sig Cohen's gambling operation, which provided the startup capital for Carrie Watson's business, operated at this location in the 120 block of S. Clark St., which at the time would have been 194 S. Clark. A sign above the casino read, "Diamond Broker -- Open Day and Evening".

Mike McDonald

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

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

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

Waterford Jack

Francis Warren, a.k.a. "Waterford Jack," the so-called "millionaire streetwalker," operated out of this location at 120 W. Monroe (then 146 E. Monroe) in the 1870s. One of Chicago's first great entrepreneurs of sin, Waterford Jack organized and managed a troupe of streetwalkers who were individually assigned to locations throughout the city each night. A local publication in 1877 wrote of her, "It is said to her credit that she never stole a cent and was never drunk in her life. She is a pug-nosed, ugly-looking little critter, but for all that she has prospered in her wretched business, and now stands before the world the richest street-walker in existence."

Having banked over $30,000 by 1880, she quit the business and retired out of sight. Where streetwalkers once schemed, Chinese food is now served.

The Mansion

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

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

South Wells St.

Wells St. was Chicago's oldest and longest-running red-light district. Prostitution was likely present in Chicago even before the city's incorporation in 1833, as suggested by the fact that the Board of Trustees imposed a $25 fine on known brothel owners in 1835. In 1838, record was made of complaints that several houses of ill-repute were operating openly on S. Wells St., between Jackson and Congress (originally known as First St.). The location pictured above is at Van Buren and Wells, halfway between Jackson and Congress.

The area became so infamous that, between 1870 and 1900, the street was renamed First Avenue out of respect to the memory and family of Billy Wells, a noted Indian fighter of the War of 1812, after whom the street had been named. Later, the western tracks of the downtown Loop were located above Wells, no doubt in part due to the lack of organized civic opposition leadership among Wells' entrepreneurs.

The street continued to be a skid row up until the 1980s, and a few hints of its former seediness remain here and there, mostly ignored by the businessmen on their lunch breaks and upscale condo-dwellers who populate the area today.

The location pictured below is Wells St., between Adams and Quincy, once the home to a group of Black-owned brothels collectively known as Shinbone Alley. Today, it holds a parking garage for the Sears Tower, located one block west.

Pacific Garden Saloon

During the 1870s, a tough saloon operated at this location just west of State St., which would then have been 67 E. Van Buren. The bar is better known for its subsequent occupant, a religious group which changed the name of the building slightly to "Pacific Garden Mission," and preached the gospel to the poor and hungry who found themselves on the tough streets of the near South side for the next 130 years. The great baseball player-turned-evangelist Billy Sunday was converted to Christ at this location.

Operating since 1880, the shelter moved from this location to 646 S. State in 1923, where it became civic fixture with a prominently displayed neon sign reminding everyone that "Jesus Saves." That location is currently being demolished to make way for an extension to the high school next door, while Pacific Garden Mission has relocated a new building a few blocks South and West. The photo below shows the demolition site on S. State:

Custom House Place

Custom House Place ran south from Jackson St., and between the Great Fire of 1871 and 1903, was the largest and most depraved red light district in Chicago. Home to a number of "panel houses," brothels in which secret doors in the walls allowed a thief in the next room to reach in and steal from a client's coat or pants when they were hung over a chair or in a closet, Custom House Place was located just across Polk St. from Dearborn Street Station, where most of the train traffic arriving into Chicago from St. Louis and other southern cities disembarked. Thus, Sears, Roebuck & Co. advised farmers arriving in the city to go immediately to their offices and not speak to anyone on the street. The wild stories of innocent girls arriving in Chicago, being romanced by a seductive stranger and shortly finding themselves drugged, beaten, and bound into forced prostitution were mostly exaggerated, but not totally.

Madame Mary Hastings said of her brothel that if a girl was good enough to be accepted at an ordinary brothel, then she was too good for her own. She also boasted that there was no act of perversion that could be imagined which her girls would not perform. In 1895, Madam Hastings was indicted on white slavery charges for holding girls aged 13 to 19 against their wills at 128 Custom House Place, and forcing them into brutal lives of prostitution. She managed to escape prostitution by fleeing to Canada until all of the witnesses against her had left Chicago or forgotten the details of her crimes.

Most of the bawdy houses in the area were shut down by the city in 1903-04, the road was renamed Federal St., and many of their proprietors and residents moved south to the Levee district between 18th and Cermak, which became the segregated vice district until the mid-1910s. The Dearborn Street Station continued in operation until 1976, when train traffic was consolidated into Union Station on the city's west side. The ticket house was converted into a retail shopping center and the rest of the train station was developed as a strangely suburb-like park area with white brick townhomes.

Whisky Row

Whisky Row was the name given to the string of cheap and dangerous saloons that lined the west side of State St., south of Van Buren., in the 1880s and 1890s. John V. "Mushmouth" Johnson, Tom McGinnis, Al Connolly, Johnny Rafferty, Sime Tuckhorn, Andy Craig, and Bob Duncan all ran joints in this skid row where thieves and robbers drank and caroused at all hours.

By far the most famous resident of Whisky Row, however, was Mickey Finn, who tended bar at the Lone Star Saloon near State and Harrison. His famous knock-out drinks, promoted by the ladies who worked the barroom, allowed him to rob and do violence to unsuspecting men while they lay unconscious in the back room. The next day they would find themselves missing their clothes, their money, and usually their memories of the previous night. To this day, the practice of drugging a victim with a poisoned drink is known as slipping a "mickey".

O'Banion's Flower Shop

The first great North side gangster was Dion O'Banion, who ruled from this location at 736 N. State St.

O'Banion was the Renaissance man of crime, a professional singer who was a talented pickpocket and safe-cracker. But the great love of O'Banion's life was floral arrangement, for which he had a passion and talent. In the halcyon days of gangland, it was customary to send flowers to the funeral of a man you shot, and O'Banion supplied the goods for most of the underworld's needs. In was at his flower shop that he ran his gang, and it was at the flower shop, while working late at night on arrangements needed for the next morning, that he was assassinated by Mike Genna, and the famous assassins, Scalisi and Anselmi, in November, 1924., at the behest -- or at least with the indifference of -- Al Capone and Johnny Torrio. O'Banion was Torrio's North Side operative, but was restless and eventually betrayed Torrio to the police in an elaborate scheme. It was O'Banion who coined the famous gangland phrase, "To Hell with the Sicilians." Men like O'Banion did not last long in those days. After his death, O'Banion's gang was later led by Bugs Moran, who moved the headquarters north to a garage on N. Clark Street, the site of the famous St. Valentine's Day Massacre.

Despite the value of this property, located in Chicago's Gold Coast just two blocks from the tourist meccas of N. Michigan Ave., the location of O'Banion's flower shop is a strangely nearly empty block which serves largely as a parking lot for the Holy Name Cathedral, the seat of the Roman Catholic Archdiocese in Chicago, which was built in 1874. O'Banion had served in this church as a choir boy, and due to his infamy, the rector refused to allow his funeral service to be held there.

Little Hell

After 1880, the area on the North side bounded by La Salle St., Division St., and the Chicago River became known as "Little Hell" for the pernicious criminality that prospered there. It is said that, in the first 51 days of 1906, the police made over 900 arrests. Every sort of depravity, including brothels, saloons, robbery, cocaine and morphine sales could be found in Little Hell. The North side's first great gangster, Dion O'Banion, was a product of this district.

Since most of the vice districts in Chicago were on the South and West sides of the city, this area was more or less ignored for many years in the city's fight against crime. Today, it is still a notorious ghetto, though only a few blocks removed from the Gold Coast, one of the most concentrated areas of wealth in the world. The Cabrini Green housing projects, which became a symbol for failed public housing nationwide, were built in the 1940s-1960s in Little Hell, and while many of the major high-rises have been demolished during the last 10 years, many of the low-rise projects (including the one pictured above at Crosby and Larrabee) remain. The area is, possibly by force and certainly by city incentives, becoming gentrified, although slowly.

The Black Hole

After the Great Fire (and long before the astronomical term was coined), the slum area around Washington and Halsted streets became known as the Black Hole, both for the devious activities that took place here and for the near West side's growing African-American population.

The most infamous establishment of the Black Hole was "Noah's Ark," located at this intersection, which housed a number of saloons, brothels, and cubicles which were rented for use by streetwalkers as they entertained their clients. It was a regular client of Noah's Ark who started one of Chicago's first race riots. Bill Allen, the husband of one of the brothel owners, was a thief and murderer, who shot a police officer, Clarence Wright, who had tried to arrest him. On the run, Allen himself was shot and killed by the police during hot pursuit.

Community members surrounded the police station, believing Allen still to be alive inside, and demanded his body for lynching. The crowd, which threatened to storm the police station, was only sated when the police captain laid Allen's body out on a mattress, in the window, displayed like a mannequin at Marshall Field's, so that all could see he was, in fact dead.

Several respectable establishments crowd around this quickly gentrifying area today, which is convenient to the central "loop" business district, including a local television station, a bank, and a wireless telephone store. Oprah Winfrey's Harpo Studios is located in the Black Hole, five blocks west of this location.

Gentle Annie Stafford

"Gentle" Annie Stafford, the "fattest brother-keeper in Chicago," ran a brothel here at 155 N. Wells St., just north of Randolph, in the 1860s. Gentle Annie started her career as a prostitute in a house at the Sands in the 1850s, and was a notorious fighter, winning the affection of her madam when she led a battle against a rival madam who had recently stolen one of their best girls.

Later, Gentle Annie won the heart of Cap Hyman, the infamous gambler of Hairtrigger Block, who bought her this location, although she had to force him into marriage at the end of a bullwhip.

After the renumbering of houses in 1911, 155 N. Wells became 27 S. Wells. Currently, this location is a restaurant.

St. Valentine's Day Massacre

After Dion O'Banion's death, his gang passed through the hands of several leaders, including most famously, George "Bugs" Moran, who headquartered the dominant North side gang in a garage at this location, 2122 N. Clark St. It was here that the most infamous gangland hit in history took place, the St. Valentine's Day Massacre, on February 14, 1929.

On that evening, men believed to be from Capone's gang entered the garage, concealing machine guns under their coats, lined their victims up against the wall, and began shooting, killing seven. Moran was not killed, but his gang was decimated, and public outrage over the killings led to greater law enforcement response to organized crime.

The garage was torn down in 1967. Today, the site is a garden and parking lot abutting a home for the elderly.