Big Jim O'Leary

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"Big" Jim O'Leary, Chicago's greatest gambler and the man who held that number for many years, was born into the city's most infamous and unfortunate family. It was Mrs. O'Leary's -- his mother's -- cow who started the Great Fire of 1871 -- or so the story goes. Big Jim was only two at the time, but that event set the course for the rest of his life in the underworld.

After the fire, the family was decimated financially and their reputation in the city was shot, so they moved to the South side stockyards district, where Jim grew up on the rough streets, among the slaughterhouses. With his infamous name, legitimate work was hard to find, and a large chip grew on his shoulder as he aged. In his 20s, he opened a saloon on Halsted St. near the stockyards, soon adding a handbook and other gambling enterprises.

With the profits from that enterprise, he opened the city's most palatial gambling mecca at 4183 S. Halsted, which included a billiards room, several bowling alleys, a saloon, a barbershop, and a sauna. The name "O'Leary" in giant electric letters (pictured below), proudly emblazoned the front door as a sign of Big Jim's pride.


Big Jim was "the man who would bet on anything." He had agents working in every downtown hotel, ready to take wagers on every sporting event imaginable. A daily set of odds quotes was distributed to office employees at the nearby stockyards. Ninety years before Intrade made it fashionable, O'Leary offered odds on the 1908 presidential election (4-to-1 on Taft, 5-to-1 on Bryan).

Big Jim's motto was:

There are three classes of people in this world - gamblers, burglars, and beggars. Nearly everybody gambles. Sometimes it's with money, sometimes it's with time, sometimes it's with jobs. Nearly every fellow is willing to take a chance. Other folks are burglars. They make their lives by stealing. The second-story man, the safe cracker, and the dip are not the only burglars. You'll find a lot of others in offices in the loop. A fellow that won't gamble or steal is a beggar.

Whatever that meant, O'Leary became the top gambler in the city, with a reputation for fair dealing. Chicago's longtime alderman-vice lord, Michael Kenna, said of him, "He was a square shooter. Big Jim never welshed on a bet. He was a good loser and his patrons had confidence in him that he would always pay off if he lost. His home life was ideal."

O'Leary's success attracted unwanted attention, both from rival gambling operations and the police. The resort at 4183 S. Halsted was constantly raided by the cops for twenty-five years, beginning in 1899, but Big Jim was always one step ahead, and though indicted four times, he was convicted for gambling only once, at the age of 53, three years before his death, and was fined $100 for the first offense. In 1906, the Mayor briefly revoked O'Leary's saloon license, but before long, O'Leary "sold" his gambling house to an employee, who reapplied for, and was granted, a new license, putting Big Jim back in business for good. Some of O'Leary's success in evading the police was political: his son, James, Jr., married the daughter of the city's top police inspector. Also, police officers, like most other men, enjoyed gambling, and frequently tipped off O'Leary if a raid was planned.

A bigger problem were rival gamblers. During the gambling wars, Big Jim's place was bombed with dynamite in 1907 (possibly as retribution for the bombing two months earlier at Blind John Condon's place), and twice in 1908. Each time, he rebuilt.

Late in life, O'Leary mused to a reporter about his success: "How much have I cleaned up? I'm satisfied with the results. I've got enough to take a trip around the world when I sell my shop. Then I'm going to settle down in some live little town."

Big Jim never got to do that, as he died in 1925. After his death, the O'Leary gambling house continued to be run by a business partner for a few years, until, somewhat ironically, the place burned down in the second-biggest fire in Chicago history, the 1934 Stockyards fire.

The lot stood empty for a decade, then was occupied by the Burlington Diner (pictured below), built inside an old train car, which was decorated inside in the "pop art" style, with every window a different color. The Burlington advertised "The best coffee in town. We never close." But in the early 1970s, with big demographic changes affecting the old "Back of the Yards" neighborhood, the Burlington did close. The site is now again an empty lot, as pictured at the top.

Johnny Torrio and Al Capone's Accounts Receivable Department

The Torrio-Capone Outfit could have been entirely rolled up in 1924, if not for some behind-the-scenes legal wrangling and judicial payoffs.

After Chicago mayor William "Decent" Dever, the "dry" Democrat, shut down Capone's headquarters at the Four Deuces, the gang moved all their accounting operations to the second floor of a nondescript brick shopping center on the northwest corner of 22nd and Michigan, at 2146 S. Michigan. The photo above shows the location today (taken from the perspective of Michigan Ave.); see below for a newspaper photo of the scene at the time of Capone's residence (taken from the perspective of 22nd St.).

The shopping center was busy most of the time, and featured restaurants, offices, and dry goods, so for awhile, no one noticed the unusual activities in the physician's office on the second floor, where hung a sign reading "Dr. Frank Ryan" (some accounts claim the sign used Capone's favorite pseudonym, A. Brown, but this seems unlikely, given the gang's expertise at discretion) . A peak inside Dr. Ryan's office revealed an ordinary waiting room, furnished with various vials of medicines.

But beyond the waiting room were file cabinets upon file cabinets, containing the gang's accounts receivable records. There, Jake "Greasy Thumb" Guzik, the Outfit's chief accountant, kept ledgers detailing the assets, income and trade secrets of the largest bootlegging and prostitution ring in the world.

When Chicago police raided the doctor's office in April, 1924, and arrested Guzik, Frank Nitti, and Johnny Patton (the latter two were top lieutenants in the gang), they found ledgers showing major beer customers, locations of all speakeasies under Torrio-Capone control, details of the gang's liquor supply chain from Canada and the Carribean, corporate control documents for breweries owned and operated, and detailed T-charts for the suburban brothels in Stickney and Burnham. Embarrassingly, they also uncovered a list of police officers and federal agents receiving hush money.

The incredible findings were enough to shut down Torrio and Capone for good. As Mayor Dever told the newspapers, "We've got the goods now." Not only Chicago and Cook County authorities, but the Bureau of Investigation and the IRS in Washington prepared to examine the seized documents. William McSwiggin, the county attorney, was ready to empanel a grand jury.

Capone's men worked furiously behind the scenes. In Judge Howard Hayes, they found their man. Shortly after the raid, he summoned all seized records to his courtroom. The following day, without notifying McSwiggin, he returned all of these documents to Capone's attorneys, on the basis that the police had no search warrant for the accounting records, only for illegal liquor. A few weeks later, he dismissed all charges against the arrested men.

McSwiggin and the feds were infuriated at being outmaneuvered by Capone and undercut by Judge Hayes, but Capone remained a free man until 1931. After the raid, he relocated his headquarters to the Hotel Metropole across 22nd street.

Bob Mott and the Pekin Theater

Robert T. "Bob" Mott was born in 1861 and arrived in Chicago in the 1890s, when he began operating a gambling house in the Custom House Place levee district on S. Clark St. He gained political power and used his success as a gambler to open a saloon in 1903 at 2700 S. State St., in the heart of the "Black belt," the segregated strip of city blocks running along S. State below 22nd St.

Gambling continued in the back rooms of the saloon, where it was well-known that police officers could have any drink they wanted on the house, in return for turning a blind eye. Mott's continued success and political influence allowed him to open the famous Pekin Theater at this location in 1906.

The Pekin became Chicago's leading African-American institution in the first decade of the 1900s, and its performances were widely renowned, as it was at the time the world's only Black-managed and operated playhouse. Luminaries including the Russian ambassador to the U.S. and Mrs. Potter Palmer enjoyed the performances of the Pekin players. Below is an advertisement for the Pekin from its peak years:


The Pekin's success (plus the death of "Mushmouth" Johnson, a rival underworld leader, in 1907) made Mott the city's leading Black power broker. When Chicago native Jack Johnson won the title of heavyweight champion of the world in 1910 (before celebrating at the Everleigh Club), it was Mott who led the celebratory welcoming parade and held a banquet in Johnson's honor at the Pekin.

After Mott's death in 1911, the Pekin was sold to Dan Jackson, and its reputation sank. Jackson turned the Pekin into a burlesque, and opened a scandalous "black-and-tan" cafe, the Beaux Arts, on the second floor, where racially-mixed customers danced to Jazz music. Hundreds attended on weekend nights. A 1917 police report states:

Lieut. Loftus...visited the "club" on the night of April 8 and found the dancing "very disgusting." There were 300 white and colored couples on the floor, the majority of whom were doing an underworld dance.

One can only imagine what an "underworld" dance would look like, but we get more details from a February, 1920 report published in the Tribune. The letter was clearly intended to raise an uproar, and uses every racially-insensitive term in existence, yet one can't help thinking the Beaux Arts sounds like a pretty fun place:

Lawless liquor - sensuous "shimmy" - solicitous sirens - wrangling waiters - all the tints of the racial rainbow - black and tan and white - dancing, drinking, singing - early Sunday morning at the Pekin cafe, 2700 South State street.

Those pleasure bent figures carousing about the gaudy second floor were not the ghosts of the long gone days of Chicago's roaring levee. They were real - the society man, the chorus girl, the gangster, the lawyer, the jazzbo - all heading the call of the bright lights.

It was a bit after midnight when the adventurers stopped under the soft red lamp that marks the Pekin. Half way up the stairs was a door with a peep hole, which framed a chocolate eye. At the top of the stairs the big brown man asked to see the card of admittance....

In came a mighty black man with two white girls. A scarred white man entered with three girls, two young and painted, the other merely painted. Two well dressed youths hopped up the stairs with two timid girls. Seven young men - they looked like the back o' the yards - came with two women, one heavy footed, the other laughing hysterically. Two fur coated "high yaller" girls romped up with a slender white man....

Meanwhile a syncopating colored man had been vamping cotton field blues on the piano. A brown girl sang.

"I'd take mos' any kind of chance," she screamed. Then she shimmied. A dollar turned the "shimmy" into a muscle dance that put the old time "hootch" to shame. Two black boys moaned and screamed on saxophone and clarinet....

Dancing "across the table" was in vogue. A painted girl would "give the eye" to a man across the hall and then they hurried to the dance floor. Once there, they picked a spot and wiggled. One girl returning from the floor found her chiffon waist disarranged and her hennaed hair was falling about her shoulders.

The fun ended in August, 1920, when two Irish police officers, who were being paid off by Jackson to allow the Beaux Arts to remain "wet" and in business, became involved in a physical alteration late one evening at the club, and ended up being shot and killed. In the ensuing political scandal, the Beaux Arts was closed, and the building was sold to the congregation of the Zionist Baptist Church (Rev. A. M. Martin, pastor), who held services there for several years.

In 1925, the old Pekin Theater became home to a district police station, which remained there until the building was demolished in the late 1940s to make way for a public housing project, Dearborn Homes, which still stands at the location of the Pekin today.

Al Capone Murders Joe Howard

Al Capone arrived in Chicago in 1921, working as a street-level thug for Johnny Torrio. Capone's business acumen led to quick promotion through the ranks of the gang. His capacity for violence didn't hurt either. An incident that occurred here, at 2300 S. Wabash, on May 7, 1923, proved early on Capone's willingness to employ the gun. The following day's Tribune reported:

Another murder in the liquor and crime serial was accomplished last night. Alphonse Capone, vice lord of the south side bad lands where he is better known as Al Brown of "Four Deuces" fame, is sought as the slayer.

The order to capture Capone went out thirty minutes after the body of Joseph L. Howard, beer runner and burglar, credited with three notches on his gun, was found lying in front of the cigar counter of "Hymie" Jacobs' saloon at 2300 Wabash avenue. Howard had been shot six times, four times in the face and twice in the right shoulder.

Howard was a low-level neighborhood hoodlum, and after one too many drinks, became involved in a physical altercation with a leading Torrio-Capone associate, Jake "Greasy Thumb" Guzik. When Guzik told Capone about the confrontation, Big Al hunted Howard down at Hymie Jacobs' bar, just a half-block from Capone's Chicago headquarters at the Four Deuces. When Capone arrived, he demanded an apology from Howard, and Howard replied by calling Al Capone a pimp -- a moniker he despised (though it was true). Thus, Capone's rage and violence.

After the command to find Capone went out, the police immediately checked the Four Deuces and Capone's home on Prairie Ave., with no success. Capone went into hiding for a month (probably in Cicero), while sending word through his lieutenants that any witnesses with loose lips had better think twice before talking to the police. In fact, though there were several eye witnesses in the saloon who say the murder, strangely it seemed that everyone just happened to be looking away at the exact moment of the killing.

"I'll bet 50 cents Al Brown didn't kill him, and I'll bet $50 they never convict him of the murder," was the word on the street.

Eventually, realizing the coast was clear, Capone walked into the police station one day, saying, "I hear you're looking for me. What's this all about?" A young assistant state's attorney, William McSwiggin, continued the investigation earnestly for a few more months, but was never able to put together enough evidence to prove Capone's involvement. A couple of years later, in 1926, McSwiggin himself met his end at the hands of Capone's henchmen, though accidentally, it seems.

Nevertheless, even years later, in 1931, Capone feared he might be prosecuted for the Howard murder, and sent Louis "Little New York" Campagna to "take care of" any remaining witnesses. But by that time, tax evasion was the more pressing problem for Big Al, and it doesn't seem that anything came of the order.

Interestingly, this wasn't even the first gangland murder to take place at this address. In 1913, Jimmie Kelly (nee James Fletcher -- for a time in the early 20th century, it was common for gangsters to change their names to sound more Irish) was found murdered in a hallway in the residence above the bar. Kelly was the leader of the Archer Avenue Gang, and was killed by rival gangsters.

The building that housed Hymie Jacobs' bar remained until the 1960s, when it was demolished. The lot currently serves as an industrial storage yard.

Arbeiter-Zeitung and The Alarm

"Workingmen, are you armed?"

The Arbeiter-Zeitung was the newspaper of the German Working-Men's Party, and the leading Anarchist newspaper in the country during the 1870s and 1880s. Along with a similar publication, The Alarm, it was edited and published here, at 107 5th Ave. (now 41 N. Wells). Both publications played a crucial role in the Haymarket affair of May, 1886.

August Spies, editor of the Arbeiter-Zeitung, and Albert Parsons, editor of The Alarm, used their publications to constantly agitate for workers' rights -- in particular, the eight-hour workday. Some of their rhetoric, especially that praising dynamite, was certainly intended to incite. A letter published in the Feb. 21, 1885 Alarm waxed philosophical:

Dynamite! of all the good stuff, this is the stuff. Stuff several pounds of this sublime stuff into an inch pipe, gas or water pipe, plug up both ends, insert a cap with fuse attached, place this in the immediate neighborhood of a lot of rich loafers, who live by the sweat of other people's brows, and light the fuse. A most cheerful and gratifying result will follow. In giving dynamite to the downtrodden millions of the globe, science has done its best work. The dear stuff can be carried around in the pocket without danger, while it is a formidable weapon against any force of militia, police or detectives that may want to stifle the cry for justice that goes forth from the plundered slaves....A pound of this good stuff beats a bushel of ballots all hollow, and don't you forget it.

This passage was quoted by the prosecution at the Haymarket trial, in which Spies, Parsons, and five other anarchists (several of the others were also linked with the newspapers published at this location) were convicted and sentenced to death. Spies claimed to have kept 9,000 dynamite bombs in his office at the Arbeiter-Zeitung (although this was probably more of a boast than a reality).

In the days leading up to Haymarket, the two anarchist newspapers attempted to rouse their fellow workers against their oppressors. On May 1, 1886, The Alarm editorialized, "Make your demand for eight hours with weapons in your hands to meet the capitalistic bloodhounds -- police and militia -- in proper manner."

On May 3, Spies drafted the famous "Revenge" circular in his office at the Arbeiter-Zeitung, which strongly suggested that the Haymarket meeting would be a violent one, and that attendees should bring weapons (although Spies attempted to delete the incendiary elements of the circular before it was published, a number of the unedited copies went out).

The afternoon edition of the Arbeiter-Zeitung on May 3 included two signals which were widely known to be signs of the start of The Revolution: a letter "Y" and the word "Ruhe" (rest) in the "Letter-Box" column on the front page.

The promotion of violence by the Arbeiter-Zeitung and The Alarm, plus the tension associated with a general strike for the eight-hour day in Chicago at the time, brought events to a head on May 4 at Haymarket Square, where an unknown assailant brought dynamite, and threw it into a crowd of police, who were attempting to disrupt the meeting. The police began firing their weapons, and an all-out riot began, in which ten died.

Spies and Parsons were hanged for their role in the riot, although neither threw the bomb. Their violent publications turned public opinion against them, and their trial, though a travesty, reflected the hatred of the populace towards these rabble-rousers. The Arbeiter-Zeitung continued publishing after Haymarket, in a new location on 12th St., but The Alarm never again appeared.

A sketch of the old building on Wells St. is below:

Minnie Shouse and Henry Foster

Minnie Shouse was the leader of a Southside gang of robbers, and one of Chicago's first great female criminals. Her practice was to lure men into an alley in Hell's Half-Acre, running longways between Polk and Taylor between State and Plymouth. This dirty alley, always piled high with offal, became infamously known as Dead Man's Alley, an estimate of the likelihood of emerging from it alive. The middle of Dead Man's Alley would have been about here (pictured looking north from 9th St. above, and south from 9th below).

Shouse worked with a strongarm named Henry Foster, better known as the Black Bear, for his propensity to overwhelm his victims with his powerful grip. Shouse was arrested over 300 times in the early 1890s, but typically paid off the police to intimidate the victim, or else did it herself. The Tribune of Aug. 17, 1893, describes one such incident:

Officer Frank Kalb was dismissed from the police force by Chief Brennan yesterday. Kalb is charged with bribery. Minnie Shouse, a notorious woman whom the police have been desirous of lodging behind the bars, stole $42 and a revolver from Napoleon Barland of Kankakee County April 29. She was arrested and Barland appeared as prosecuting witness. The woman left the courtroom and the trial was postponed. At the next hearing, Kalb paid Barland $20 to leave the city and the case fell through.

Shouse finally went to prison in 1895. Later that year, Henry Foster was working alone to rob a man in Dead Man's Alley at 4:00 a.m. one morning when a local saloon-keeper, George W. Wells, ran out in an attempt to stop the crime. Foster shot Wells twice dead. The Black Bear was hanged in January, 1896.

Dale Winter's Home

Dale Winters was born in 1891 in Ohio, and became a teenage beauty and singing talent. She arrived in Chicago in 1915 and auditioned as a singer at Colosimo's Cafe, by which time she was going by the singular, Dale Winter. Big Jim was impressed with her talent and he hired her on the spot at a rate of $40 per week.

Over time, Colosimo found himself increasingly attracted to this beautiful young woman, and her innocence awakened in him a desire to quit the rackets. A local clergyman, for whose congregation Dale sang, said, "she has the image of goodness written in her face." Colosimo paid for her to take singing lessons and attained for her a college scholarship to study music. During this time, Dale lived with her mother here, at 5716 South Parkway (now Martin Luther King Dr.).

Big Jim's wife, Victoria, was none too happy having her husband fawning over a teenager, and did everything in her power to separate the two. Finally, she could read the writing on the wall, and decamped for Los Angeles in 1920. Colosimo and Winter became more and more closely intertwined, and they were married on April 16, 1920 at the West Baden Springs Hotel in Indiana. After a short honeymoon, Dale moved into Colosimo's home on Vernon Ave.

Less than a month later, on May 11, Dale Winter was a widow. Colosimo was assassinated, probably at the behest of his lieutenant, Johnny Torrio. Dale Winter renounced all claim to Colosimo's money (no one else ever got much anyway), saying "All I want of Jim is the memory of him. I don't want his money or the things he gave me. I'm going to sing again. Maybe I'll sing better. I know now there isn't much to life except giving something to others. There'll never be anything in my life except singing and remembering and singing."

Dale Winter went on to a moderately successful career on Broadway, and occasionally, in film. She married again in 1924 and moved to California, where she and her husband operated a chain of theaters. Her husband died in the 1960s, and she remarried again twice, each time becoming a widow.

Dale Winter passed on in 1985 at Santa Barbara, California.

Blind John Condon

John Condon was born in Indiana, and became one of Chicago's great gambling kings. An early associate of Mike McDonald, Condon later developed major gambling innovations, including the world's first gambling boat, the City of Traverse, which he operated together with Big Jim O'Leary.

Condon's business was diminished somewhat by his declining eyesight, by which he earned his moniker. But he was still able to purchase a very large Victorian home here, at 2623 S. Michigan, which had previously been occupied by one of Chicago's foremost families. He was an avid art collector, once outbidding J.P. Morgan in 1905 for the works of an old master.

After McDonald's decline from power, Condon and Mont Tennes slowly monopolized the handbook business in Chicago, based from Condon's race track, the Harlem, in Forest Park. Monopoly is a dangerous business though; in 1907, a gamblers' war broke out between the Tennes operation and a Loop syndicate run by Tom McGinnis. The first shot over the bow was a bombing on July 9, 1907, here at the Condon family home. No one was hurt. Throughout the remainder of 1907 and 1908, dynamite was a common occurrence at the homes of the city's top sports, including three times at Tennes' home alone. Condon's favorite slogan was a gamblers' creed: "Every man has his price, somewhere between a cigar and a million dollars."

Blind John Condon died at age 61 in 1915.

Marshall Field, Jr., Shot

Marshall Field, Jr., heir to the department store fortune and holder of the most famous name in Chicago history, died here at his home of a gunshot wound on November 22, 1905. Who fired the shot? There are three theories.

The official inquest concluded that Field had accidentally shot himself while cleaning his gun. Practically everyone saw this as an unlikely story from the start.

A number of witnesses claim that Field was a guest of the famous Everleigh Club brothel that evening, and was shot during foreplay with one of the residents. Fearing public embarrassment, he asked to be driven home, where his wounds proved more serious than expected. However, some of these supposed witnesses cannot be considered reliable, as they stood to benefit from selling their stories to the press.

A third theory -- and possibly the most likely -- is that, regardless of whether Field was at the Everleigh Club that evening or not, he was severely depressed and committed suicide in his bedroom. On the other hand, no suicide note was ever discovered, although it is possible that a note may have been suppressed by his powerful family to avoid embarrassment.

Field's mansion on S. Prairie Avenue still stands, and is currently being renovated into a six-flat condominium. It's not clear whether buyers would find Field's history a positive attribute in a home, but the developer certainly seems to be making it a keystone of the advertising campaign.

Haymarket Square

Haymarket Square is a widened portion of Randolph Street, between Des Plaines and Halsted, which once served as a common market area for the surrounding working class neighborhood. On May 4, 1886, it became synonymous with one of Chicago's most famous incidents, in which at least ten men died, four were hanged, and another committed suicide in jail -- the infamous Haymarket riot between police and anarchists.

The riot did not take place in Haymarket Square, but instead around the corner, north on Des Plaines. The incident took place following a socialist/anarchist rally which was originally intended to take place in Haymarket Square, but since the weather was so poor that evening, the turnout for the rally had been underwhelming, and the organizers thought it best to move to a smaller venue.

Despite the fact that none of the action in the Haymarket affair actually took place in Haymarket Square, the city ordered an heroic 9-ft statue of a policeman built in the middle of the Square to honor the policemen who lost their lives there.

This obviously displeased anarchists and radicals who felt the police had been the chief cause of the violence. A disgruntled streetcar driver mowed down the statue in 1927 on the anniversary of the riot. The statue was rebuilt. Weather Underground terrorists blew up the statue in 1969. The statue was rebuilt. The Weathermen blew it up again in 1970. The state was rebuilt, and given its own 24-hour police retinue to ensure its safety. After a few years, the irony in using actual policemen to protect a statue of a policemen dawned on someone, and the statue was removed to police headquarters.

Pictured here is the eastern half of Haymarket Square. The western half, closer to Halsted, was demolished in the 1960s to make room for the Kennedy Expressway. Note the diagonal parking areas on both sides of Randolph, a highly unusual feature for a Chicago street, but evincing the original "square".

Myrick's Race Track

Williard F. Myrick was one of Chicago's original settlers, building a house on Vernon Ave., in what was then the open prairie. He was one of the city's leading citizens and a substantial philanthropist. He was also a master horseman, and in 1844, he developed Chicago's first horse track at this location, between 26th St., 31st St., and east of Indiana Ave.

Chicago early on was a gamblers' haven, drawing Mississippi River riverboat sharpies who fled prosecution in the South during the 1830s. Betting on horse races was a favorite pastime for many of Chicago's earliest residents.

Myrick died in 1889, and his race track has long since been developed, although Dunbar Park, pictured here, recollects the area's original use. The park was created in 1965, named after African-American author Paul Dunbar.

Hinky Dink's Place

Michael "Hinky Dink" Kenna opened his first saloon at this location, 105 W. Van Buren (then 120 W. Van Buren) in 1881. He used the position to move into gambling, protection rackets, and politics. He was elected Alderman for the 1st Ward in 1897, a position he held until 1923, when he retired to become ward Committeeman, a position he kept until his death in 1946.

Kenna grew up on Chicago's west side, and earned the label "Hinky Dink" for his short stature -- he was only 5'1" tall, but tougher than most men a foot taller than him. After a adventure to the American West during the mining boom, Kenna earned enough money to buy a tiny, 5'x8' room here, which he operated as a crude saloon. He came to be known as a friend to those who needed cash for bail, an occupation that put him into contact with "a class of men who are extremely useful at primaries, in conventions, and at elections", as the Tribune put it.

Over time, Kenna opened up the second floor of his saloon as a gambling house, and despite some harassment from the police, his political power grew until he could operate unmolested. He expanded the bar, and started serving higher quality drinks, which attracted the patronage of some of the city's power elite. He changed the name of the saloon to the more rarefied "M. Kenna's Sample Room."

In 1895, he first ran for Alderman, losing to the Republican nominee, but he returned to win in 1897. Together with John "Bathhouse" Coughlin, he presided over Custom House Place, and later, the 22nd street Levee district, collecting protection money and allowing those businesses that paid to stay in business.

Upon Kenna's death, he left over $1,000,000 to his heirs.

The location of Hinky Dink's Place is still a bar, the Sky Ride Tap, which the Sun-Times describes as a "little-known but comfortable dive where day traders rub elbows with construction workers."

Manhattan Brewing Company

The Manhattan Brewing Company was incorporated in 1892. Producing suds at 3901 S. Emerald, in Chicago, it always seemed to have an locational identity crisis.

For the first 27 years of its existence, it was a large, but otherwise ordinary brewery (one exception was an accidental explosion in 1908 that killed two workers, and could be heard throughout the South side).

In 1919, at the start of national Prohibition, Joseph Stenson, a top Chicago brewer, along with South side gang leader Johnny Torrio, bought the brewery, changing its name to Fort Dearborn Products -- although it continued to make beer. After Torrio's departure from Chicago, the brewery fell into the hands of Al Capone, and it became one of the largest manufacturers of alcoholic beverages during Prohibition.

In the early 1930s, with Capone in prison and Prohibition ended, the brewery came to be held largely by Capone's chief accountant, Louie Greenberg. Greenberg changed the name back to Manhattan, and later began producing a sister brand, Canadian Ace. That the brewery remained in the hands of organized crime is evident from the continued attempted bombings of the factory throughout the 1930s. In the 1940s, Greenberg attempted to open a sister brewery in New York with business partners including prizefighters Joe Lewis and "Sugar" Ray Robinson, but was turned down by state authorities due to his connections with the Outfit in Chicago.

In the 1940s, the Federal Trade Commission successfully sued the brewery on false advertising charges, since Canadian Ace was produced on the South side of Chicago, not in Canada (or in Manhattan!). Both Manhattan Beer and Canadian Ace were highly successful brands in the 1940s, 50s and 60s.

After Louie Greenberg was assassinated in 1955, the brewery continued to operate, but faced with increasing competition and a lack of gang muscle, it finally shuttered in 1968. The factory was demolished in the mid-1970s. The lot is empty and overgrown with brush today.

For more about the Manhattan Brewing Company, including historic photos, see this fansite.

Capone Brewery Raided by Untouchables

Due to his penchant for self-aggrandizement and talent for publicity-seeking, Eliot Ness and his gang of "Untouchables" has come to be seen as a larger part of the effort to take down Al Capone than, in fact, it was.

Nevertheless, one of Ness' most successful raids took place here, at 2108 S. Wabash. Capone ran a brewery at this location, and on June 13, 1930, federal agents crashed through the doors with a battering ram attached to a ten-ton truck, atop which sat Eliot Ness himself. Five workers were arrested and 200,000 gallons of beer and mash were captured. The evidence was later used as part of the indictment that took down Capone.

The brewery was operated as a tire shop for many years after the bust. Today, it houses a bar and restaurant, "Room 21", which proudly advertises its historic relationship with the Capone brewery. Supposedly, the property houses a number of secret passages meant for quick getaways.

Black Hand Gang Eliminated -- by Johnny Torrio?

Late in the evening on November 22, 1911, three men were shot in the Rock Island Railroad underpass at Archer Street. Two died at the scene, the other was seriously injured and sent to the hospital. Why? There appear to be two theories.

The dead men were Pasquale Damico and Francisco Denello. According to the next day's Tribune, Damico was shot at close range nine times in the back, while Francisco Denello was shot twice, once in the head and the other through his left side. Denello's brother, Stephano, who was also shot, was discovered by a policeman dragging himself down the sidewalk a block away, and rushed to the hospital.

Under police questioning, Stephano refused to reveal any clues about his attackers. He did, however, ask that Levee big shot and Chicago Outfit founder "Big" Jim Colosimo be brought to his bedside. When Colosimo showed up, however, Stephano refused to talk with him.

Police identified the Damico and the Denellos as a Black Hand gang, sending extortion threats to prominent Italian businessmen in the neighborhood. The police captain interviewed by the Tribune said,

The city is rid of a bad gang. It is my belief that the three men were lured to the scene of the shooting by men whom they have blackmailed or were attempting to obtain money from through Black Hand letters. The Denello brothers and Damico have done most of the black hand work in this police district. We have known for a long time that they were black handers, but it has been impossible to get their victims to rap against them. Fear of death has kept them from giving the police information that might have sent the gang to the penitentiary.

As an important Italian businessmen, Colosimo was likely the frequent target of Black Hand gangs. Some historians believe that the fact that practically nothing was left of Colosimo's fortune upon his assassination indicates that he paid heavily to the Black Hand, although as the gangster king of the city, it is difficult to imagine that he would have suffered such indignities.

Instead of paying up, Colosimo may have dispatched his right-hand man (and his successor in leadership of the Outfit), Johnny Torrio, to "bump off" any would-be extortioners. The extreme manner in which Damico was riddled with bullets may have been a warning to other hoodlums that Big Jim was not to be taken advantage of.

Two weeks later, however, the Tribune advanced an alternative theory of the killings: they were part of a classic Italian love triangle. Police theorized that Mary Palaggi, a Levee saloon-keeper's daughter, was engaged to one man, but desired by another. The Denello brothers, it is claimed, were friends of the fiance (though he denied it), and Damico was an associate of the would-be paramour. The shootout under the railroad tracks, then, arose from a dispute among the parties, not an attack from assassins. The question of why the surviving Denello would have called for Colosimo in the hospital is left unanswered.

The underpass separates the Levee area, now dominated by the Hilliard Towers apartments and the Harold Ickes Homes housing project, from Chinatown, visible at the end of the road in the photo below.

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."