Five Things You Didn’t Know About 1920s Gangsters in Chicago

A new book offers some surprising glimpses into the city’s early 20th century underworld.

BY HANNAH NYHART  This article appears in the June 2017 issue of Chicago magazine.


ONE: Cicero, not Chicago, was dubbed the “wettest spot in the United States.” Agents discovered 20 separate large-scale stills in a single series of raids, reports John J. Binder in Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition (June 6, Prometheus Books). Crackdowns had forced the alcohol underworld into the western suburb, where the Torrio-Capone gang roughed up voters to sway the 1924 election and keep certain friendly politicians in office, thus securing itself free run of the town.

TWO: A sign of how cozy gangsters were with elected officials: After Capone’s mentor, James “Big Jim” Colosimo, was killed in 1920, his pallbearers included eight aldermen, three judges, and a U.S. congressman (shown above).

THREE: Gangsters weren’t all to blame for the murderous era. Of the 729 homicides in Cook County between 1919 and 1933 classified as “gang-style” killings by the Chicago Crime Commission, Binder found that 43 percent were actually not related to organized crime but to personal feuds and other private matters. A 1932 newspaper ad for a local textile shop read: “Bullet Holes Rewoven Perfectly in Damaged Clothes—Low Price.”

FOUR: Chicago’s 6,000 illicit slot machines temporarily disappeared in the late 1920s after a vigorous state’s attorney was elected, but gambling as a whole never really died down. By 1930, there were roughly 10,000 illegal locations, from barbershops to newsstands, to wager on horses or place other bets. You could find a spot to lose money about as often as you can find a bus stop today.

FIVE: Capone’s gang was pulling in “tribute” payments—a cut of profits for protection—from two-thirds of the city’s labor unions, but the milk wagon drivers refused to be controlled, even after Capone affiliates kidnapped their union’s president for a $50,000 ransom. Instead, they bombproofed the union office and bought a bulletproof car. Plan B: Capone opened a rival dairy, staffed trucks with his own men, and sold milk two cents cheaper. Read more

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Alcatraz 1934

On this day in 1934, the first federal prisoners arrived on Alcatraz Island

By Katie Dowd Thursday, August 11, 2016

Eighty-two years ago today, Alcatraz went from a rock to The Rock.

On Aug. 11, 1934, the first boat loads of federal inmates arrived at Alcatraz Federal Penitentiary, entering American lore in the process.



Alcatraz had been a military prison since the turn of the century, but it wasn’t until 1933 that it was purchased by the Department of Justice to serve as a maximum security facility for America’s worst criminals. It was, officials and newspapers declared, utterly escape-proof.

Most of the first inmates were transferred from Leavenworth in Kansas. They were bank robbers, murderers and counterfeiters. “Although the total population of Uncle Sam’s new fortress for incorrigibles will run into the hundreds, the 47 now ‘on hand’ will be sufficient to give Attorney General Homer S. Cummings an idea of the situation,” the Chronicle wrote upon their arrival.

Among the first shipment of prisoners was “Red” Kerr, a Chicago gangster who stole over $200,000 from a Sacramento post office and John M. Stadig, a “counterfeiter and escaper.” Its most famous inmate, unbeknownst to him, was being prepared for a similar move.

“Unusual precautions, it was learned, will be taken to safeguard several nationally known figures in the world of crime from Atlanta and Leavenworth penitentiaries to the prison in San Francisco bay,” the Chronicle revealed.

Nationally known was an understatement: On Aug. 20, the Chronicle found out that none other than Al Capone was on a heavily guarded train from Atlanta.

Capone had been secretly packed onto a custom steel-barred train car in the dead of the night, but word quickly spread that the Chicago mobster was traveling across the country.

The Chronicle reported that an onlooker called out to the other prisoners, asking if Capone was on the train. Another inmate pointed to a coach window. “The man in that window, who resembled Capone, grinned when asked whether he was Capone,” wrote the Chronicle.

Early on the morning of the 23rd, the train arrived in San Francisco. Capone and 52 other convicts were loaded onto a barge in Tiburon. Accompanied by an armed Coast Guard cutter, they sailed to Alcatraz.

“Al Capone, who iron nerve he boasted would never break, quailed when he viewed the escape proof ramparts of Alcatraz yesterday,” proclaimed the Chronicle.


Indeed, Capone never attempted an escape from Alcatraz. His health declining, he spent much of his last year in the prison hospital. He finished his sentence at Alcatraz on Jan. 6, 1939. READ MORE.

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Chicago Crime 1925 – 1932

Scarface, Tommy guns and Chicago’s gangster mystique in film

by Michael PhillipsChicago Tribune

Al Capone 1931 at a football game AP

Al Capone 1931 at a football game AP

In a a few, bloody years — 1925 to 1932, from the rise of Al Capone to the release of the film borrowing Capone’s nickname for a title — Chicago cemented its image in the popular imagination. The Cubs come and go; Chicago’s gangster mystique remains steadfast.

Here are six stops on the timeline of those key years in the making of Chicago’s corrupt, violent popular image.

1925: Brooklyn-born Alphonse Capone, later nicknamed “Scarface” by a Tribune reporter, takes over the Chicago activities of New York racketeer Johnny Torrio. By 1927, Capone is the world’s most revered and famous gangster, coddled by Chicago mayor Big Bill Thompson until Thompson considers Capone a drag on Thompson’s political advancement. By 1928 Capone relocates to Florida and spends most of the ’30s behind bars.

1926: Ex-Tribune police reporter Maurine Dallas Watkins writes a comedy about a couple of Chicago killers. Originally titled “Play Ball,” the play is renamed “Chicago” and opens on Broadway. Cecil B. DeMille produces a silent film version in 1927; Ginger Rogers stars in a 1942 film adpatation, “Roxie Hart”; Bob Fosse directs and choreographs the 1975 stage musical; the movie version of the musical wins the Academy Award as best picture of 2002.

1927: Another Chicago crime reporter, Bartlett Cormack, writes “The Racket,” a play set in a police precinct on Chicago’s outskirts, about an honest cop beset by corrupt superiors and pliable politicians in league with local bootleggers. The character of underworld kingpin Nick Scarsi is a thinly disguised Capone stand-in. Edward G. Robinson plays the role on stage; when the touring production of “The Racket” is banned from Chicago, reportedly at Capone’s urging, it travels instead to LA and the movies discover Robinson, who stars in “Little Caesar” in 1930, after the medium learns to talk and spit lead at high volume.

Read More.

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Al Capone’s Brother May Have Invented Date Labels For Milk

Huffington Post by Casey Williams


FILE - In this 1938 file photo shows Ralph " Bottles" Capone, Brother of Al Capone. A descendant of Al and Ralph Capone says in a new book that the two gangsters played a much bigger role in creating Nevada’s gambling empire. Historians are skeptical because the claims are based on information passed down to author Deirdre Marie Capone by her grandfather, Ralph Capone, who was the older brother and business partner of the infamous Al Capone. (AP Photo/file)

FILE – In this 1938 file photo shows Ralph ” Bottles” Capone, Brother of Al Capone. A descendant of Al and Ralph Capone says in a new book that the two gangsters played a much bigger role in creating Nevada’s gambling empire. Historians are skeptical because the claims are based on information passed down to author Deirdre Marie Capone by her grandfather, Ralph Capone, who was the older brother and business partner of the infamous Al Capone. (AP Photo/file)

In the early 1930s, mobster Ralph Capone, Al Capone’s brother and Chicago’s Public Enemy Number 3allegedly convinced dairy producers in Illinois to stamp dates on milk bottles. Ralph knew a man whose son grew sick after drinking spoiled milk, the story goes, prompting the gangster to demand that the dairy industry beef up its health and safety standards.

Read more

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1929 Al Capone’s Cell

In May 1929, Capone was sentenced to a prison term in Philadelphia’s Eastern State Penitentiary where he spent a year. His reach at the local and state level was shocking as a picture of his luxury accommodations will affirm.

Al Capones cell

Aside from the egregious lodging, something else is wrong. It is located just below the center of the picture  next to the plush chair.


The following is an article clipped from the Philly Inquirer News dated May 31, 2016

by Stu Bykofsky

What was wrong in Al Capone’s cell?

AT A glance, seventh-grader Joey Warchal knew something was very wrong. He loved everything he saw during a tour of Eastern State Penitentiary – Al Capone’s cell most of all, but something was very wrong.


A tour guide said the Prohibition-era gangster was incarcerated in 1929 and 1930.

“The radio featured in the display is historically inaccurate,” Warchal politely emailed Eastern State Penitentiary senior vice president Sean Kelley after his tour.

“As an antique collector specializing in radios,” Warchal said “the radio displayed is a Philco A-361, made in January 1942,” after Capone had departed Eastern State. It could not have been his radio.

Warchal offered to help Kelley find a historically accurate radio for the display. And he did… READ MORE

Al Capone’s Rigged Roulette Wheel Used by the Mob

The Sun

May 5, 2016

Revealed – Al Capone’s rigged roulette wheel: Table used by the Mob in 1920s Chicago uncovered.


ONE of Al Capone’s rigged roulette wheels used to fix games and rob gamblers has been uncovered after being dismantled for restoration. Alexander Walder-Smith, from Guildford, bought it in Iowa from a man who had stored it in a barn for decades.


Mr. Walder-Smith said: “I just thought it was a very nicely made roulette table from the 1920s or 1930s. It was only when my restorer called to say he’d found batteries that we realized there was anything unusual.” The restorer discovered a series of concealed wires leading to two push buttons disguised as screw heads. The hidden buttons interrupted the spin of the ball, allowing crooked croupiers to fix games. When activated, two tiny pins shot out which could guide the ball towards a particular number or colour.


“The batteries were concealed in one of the legs and changing them would have been a major operation. They had used newspaper to pad them. They were all local Chicago papers dated between 1928, when we think the table was built, and 1931 when the batteries were last changed.”  Read More