With mob hits, booze smuggling, and violent turf wars, the Windy City of the 1920s and '30s was a chaotic and dangerous place.
The 1920s transformed Chicago into one of America’s most notorious ganglands, where organized crime thrived during the Prohibition era and corruption ran so deep it reached the highest levels of government. This decade witnessed the rise of infamous criminal figures, brutal violence, and lawlessness that would define the Windy City’s reputation for generations.
Despite a similarly powerful criminal network in New York City and other cities, however, Chicago’s organized crime syndicate arguably helped define what made a gangster a gangster. As such, Chicago became increasingly infamous for its prevalence of the mob and its bloody turf wars.
See what life was really like in Chicago’s gangland of the early 20th century in our collection of vintage photos below.
Colosimo and Torrio's relationship allegedly devolved after a number of disagreements, including Colosimo's reluctance to dive into the bootlegging business, which would prove extremely profitable during Prohibition.The Mob Museum
Dillinger rose to prominence during the Great Depression, when he became infamous for bank robberies, murders, and prison breaks. Dubbed "Public Enemy Number One" by the FBI, he was ultimately ambushed and gunned down by federal agents in front of Chicago's Biograph Theatre in 1934.FBI
Her husband, Rick Manzie, was a Chicago Outfit associate, and he was found fatally shot in their Las Vegas home in 1976. The case remains unsolved, though Chicago Outfit figures were suspected.The Mob Museum
Moran was a prominent Chicago gangster during Prohibition, leading the North Side Gang. He was also a bitter rival of Al Capone, leading to a violent turf war that culminated in the St. Valentine's Day Massacre in 1929, where seven of Moran's men were killed.
Moran narrowly escaped, as he was running late to that fateful meeting with his doomed associates, but his power soon waned, and he died while in prison for robbery in 1957.Everett Collection Historical/Alamy Stock Photo
He was convicted of the attempted murder of Etting's new love interest, Myrl Alderman, but he was ultimately released on appeal after just one year behind bars.Public Domain
Old Log Cabin was actually just Canadian Club whiskey, illegally imported into the United States by Al Capone. Kirn Vintage Stock/Alamy Stock Photo
Lombardo served as the consigliere to Al Capone and was involved in a violent gang war. He was ultimately assassinated by rival gangsters in 1928.NY Daily News Archive/Getty Images
Jack "Machine Gun Jack" McGurn was a Sicilian American mobster in Al Capone's Chicago Outfit during Prohibition. Known for his ruthless efficiency as a hitman, he was a key figure in the gang wars and is widely believed to have masterminded the St. Valentine's Day Massacre. He was murdered in 1936, ironically on the seventh anniversary of the massacre, by unknown assailants.Everett Collection Historical/Alamy Stock Photo
O'Banion was shot and killed in his flower shop in 1924, sparking a brutal gang war.Public Domain
Nitti died by suicide beside railroad tracks near North Riverside after learning that he had to face trial and possible prison time on extortion charges. March 19, 1943. Everett Collection Historical/Alamy Stock Photo
Accardo, also known as "Joe Batters" and "Big Tuna," was a long-reigning boss of the Chicago Outfit. Rising from Al Capone's bodyguard, he expanded the Outfit's influence and rackets, becoming one of the most successful mob leaders in U.S. history.
Notably, Accardo died of natural causes at the age of 86 in 1992, having never spent significant time in jail. Digital Commonwealth Massachusetts Collection Online
O’Hare was a lawyer and businessman, involved in dog racing ventures, who had ties to Al Capone in Chicago during Prohibition. O'Hare later became an informant for the IRS, providing crucial evidence that helped lead to Capone's conviction for tax evasion.
Later on, O'Hare was shot and killed in 1939, likely in retaliation for his cooperation with the authorities, though this was never proven and his killers were never caught.Bettmann/Getty Images
These members of the Touhy gang were arrested and awaiting trial for the kidnapping of mobster John Factor in 1933.Everett Collection Inc/Alamy Stock Photo
She was connected to various underworld figures and at one point served time in prison for attempted murder.Everett Collection Inc/Alamy Stock Photo
Prohibition And The Dawn Of A New Criminal Era
When the 18th Amendment took effect in January 1920, banning the manufacturing, sale, and transportation of alcoholic beverages, it inadvertently created one of the biggest criminal opportunities in American history, especially in bustling urban centers. Chicago, as a strategic transportation hub with an already-established tradition of political corruption, soon became a hotspot for illegal alcohol distribution as a result.
The city's railroad networks and its proximity to Canada made it ideal for smuggling operations, while its large population provided many customers eager for alcohol and recruits who were willing to risk everything for money.
The demand for alcohol remained enormous despite its illegality. Secret bars called speakeasies proliferated throughout the city, with estimates suggesting Chicago had over 10,000 illegal drinking establishments during Prohibition. These venues required a steady supply of liquor, creating a massive underground economy that organized crime syndicates dominated.
The profits were staggering — bootlegging could lead to proceeds of millions of dollars per week, making it more lucrative than other criminal enterprises.
How Al Capone Became The Notorious King Of Chicago Crime
Bettmann/Getty ImagesAl Capone smoking a cigar in the train that took him to federal prison.
No mobster was more prevalent in 1920s Chicago than Al Capone, who arrived from New York in 1919 to work with crime boss Johnny Torrio. When Torrio retired in 1925 after an assassination attempt, Capone inherited control of the South Side crime syndicate and expanded its operations.
Capone's organization was remarkably sophisticated, operating almost like a corporation, with different divisions handling different aspects of the illegal alcohol trade. His massive empire included bootleg breweries, distilleries, speakeasies, gambling houses, brothels, and more.
At its peak, Capone's organization employed over 1,000 people, and he eventually reached a net worth of $100 million (about $1.5 billion today).
What set Capone apart was his public persona. Unlike other crime bosses who shunned publicity, Capone cultivated his image as an almost Robin Hood-like figure, claiming he was "just a businessman, giving the people what they want." He attended public events, granted interviews to the media, and even operated a soup kitchen during the Great Depression.
This carefully crafted image helped him maintain public support even as his organization engaged in increasingly violent activities.
In the end, Capone's downfall came not through his violent crimes but through tax evasion. Federal agents, led by Eliot Ness and his police division known as the "Untouchables," couldn't make bootlegging charges stick due to corruption and witness intimidation. But authorities could prove that Capone failed to pay income taxes on his illegal earnings.
In 1931, he was convicted and sentenced to 11 years in prison. Though he didn't serve his full sentence, he was forced to retire from his former life of crime due to an increasingly severe case of syphilis that ravaged his brain.
Rival Gangs And Territorial Wars Reshaped The Windy City
University of Wisconsin MilwaukeeA map outlining the early 20th-century gangland of Chicago.
Chicago's gangland was far from unified under Al Capone's rule. The city was divided into territories controlled by various gangs, leading to constant warfare over everything from bootlegging operations to protection rackets.
The North Side Gang, led first by Dean O'Banion, and later by Bugs Moran, maintained a fierce rivalry against Capone's South Side operation. O'Banion's assassination in 1924 sparked a series of retaliatory attacks that would culminate in one of the decade's most infamous acts of gang violence.
Other significant players in the city's gangland included the Genna Brothers, who controlled Little Italy's operations, and various Polish, Irish, and Jewish gangs that carved out their own territories throughout the city.
These territorial disputes weren't always only about business — they often represented deeper ethnic and cultural divisions within Chicago's immigrant communities, many of whom were competing for lucrative economic opportunities and wider social acceptance in American society.
The Brutal St. Valentine's Day Massacre
The most infamous event of Chicago's gangland era happened on Feb. 14, 1929, when seven members of Bugs Moran's North Side Gang were gunned down in a warehouse on North Clark Street. The St. Valentine's Day Massacre, which was widely attributed to Al Capone's organization though never officially proven to be Capone's doing, shocked the nation and marked the beginning of the end for Chicago's open gang warfare.
The killings had been meticulously planned. The gunmen, some disguised as police officers, approached their victims in the warehouse (which was owned and operated by Moran). Once the gunmen were inside, the seven victims were lined up against a wall and executed with Tommy guns.
Bettmann/Getty ImagesThe St. Valentine's Day Massacre was one of the most infamous mob hits in history.
The brutal efficiency of the murders demonstrated the sophisticated organization and ruthless determination of Chicago's criminal syndicates.
Public outrage over the massacre led to increased federal intervention in Chicago's gangland. The federal government, previously reluctant to involve itself in local crime issues, began treating organized crime as a more national security threat that required federal resources.
Rampant Corruption And Political Connections With The Mob
The success of Chicago's gangsters depended heavily on their ability to corrupt public officials. Police, judges, and politicians were routinely bought off, creating a system where organized crime operated with virtual impunity.
Mayor William Hale "Big Bill" Thompson, who served during much of the 1920s, was widely suspected of having ties to criminal organizations and later gained infamy for his specific protection of Al Capone.
The corruption extended beyond individual officials to entire institutions. Entire police districts sometimes even had informal agreements with local gangs, if the criminals had enough money to buy them off. This systematic corruption made it nearly impossible for honest law enforcement officials to combat organized crime, as investigations were routinely compromised.
Keystone-France/Gamma-Keystone/Getty ImagesEdward J. O'Hare — a lawyer who once collaborated on business ventures with Al Capone but later helped put him away for tax evasion — pictured at the wheel of his car after he was fatally shot in 1939.
The peak era of Chicago's gangland era arguably came to an end with the repeal of Prohibition in 1933. However, it left a lasting impact on the city. The decade established patterns of other forms of organized crime, including gambling, and political corruption that would plague Chicago for decades.
The gangster era also contributed to Chicago's cultural identity, inspiring countless books, movies, and television shows, some of which romanticized the period's violence and lawlessness. This cultural legacy has been both a burden and an asset for the city, attracting tourists fascinated by Chicago's criminal history while perpetuating stereotypes about the city's character.
The 1920s proved that in the right circumstances, organized crime could grow powerful enough to challenge legitimate government authority. The lessons learned from Chicago's gangland era influenced federal law enforcement strategies and contributed to the development of modern organized crime-fighting techniques that remain relevant even today.
Gangland Chicago is, in a way, a cautionary tale about the unintended consequences of certain forms of legislation and the importance of maintaining a level of honor in public offices across American society.
Next, dive into the brutal history of the New York Mafia's Five Families. Then, read about some other infamous Mafia bosses who defined mob history.
