The age of jazz and speakeasies, shorter hemlines, and bigger parties was also a time of gangland violence in 1920s and ’30s Chicago. As the infamous Al Capone took over as the boss of a major South Side gang, a series of violent mob disputes called the Beer Wars erupted. Hundreds of gangsters were killed as Al Capone’s mob, the North Side gang, and various other groups fought over money, territory, and control over bootlegging operations. In the end, the Chicago Outfit emerged as the largest group in organized crime.
Prohibition and Chicago’s Bootleggers
Organized crime had a robust history in Chicago long before Prohibition made bootlegging a big source of income for the city’s gangs. Gangsters such as James “Big Jim” Colosimo – who led a gang that would eventually become the Chicago Outfit – earned their profits from gambling, prostitution, and labor racketeering. With the support of corrupt aldermen John “Bathhouse” Coughlin and Michael “Hinky Dink” Kenna, Colosimo became a precinct captain, protecting his network of brothels in the city’s seedy Levee District from police raids. Colosimo eventually brought Johnny “the Fox” Torrio into the fold, and Torrio later hired a young man named Al Capone as a bouncer at one of his gambling and prostitution joints. It was a relatively humble beginning for a man who would soon make a fortune and lead an expansive criminal enterprise.
On January 16, 1920, Prohibition took effect in the United States. While consuming alcohol was still legal during Prohibition, the production, transportation, and sale of alcohol was banned.
“Johnny Torrio, perhaps more than anyone in Chicago, sees the potential and recognizes that this could be a huge business, that they could make more money than they’ve ever dreamed of. This is like Microsoft,” Jonathan Eig, author of Get Capone, told Chicago Stories. “One of the biggest industries in America had just been declared illegal. So if you are willing to try to step in there and take it over, people still want this product. There’s demand. All you have to do is create the supply.”
But Big Jim Colosimo was “standing in [Torrio’s] way,” when it came to entering the bootlegging industry, said Eig. And when Colosimo left his wife – who also happened to be Torrio’s aunt – to be with a singer, Torrio’s loyalty to Big Jim waned. Torrio had Colosimo killed, and he took over the operation and expanded into bootlegging. Al Capone served as his right-hand man.
Chicago was a “very, very, very good place to be a bootlegger” during this period, John Binder, author of Al Capone’s Beer Wars told Chicago Stories. “It’s a hard-drinking town,” Binder said. And the level of political corruption allowed the underground business to run rampant, made easier with William “Big Bill” Thompson – Chicago’s infamously corrupt mayor at the time – turning a blind eye to the crime.
“Beer tended in many cases to be produced locally,” Binder said. “Look at the explosion of microbreweries today around this country. It’s not that hard to do it. The bootleggers had some people who knew how to make beer. They’d rent or buy some space. They’d put up some copper kettles. They’d start churning out beer and [they’d] keep doing it there until [they were] raided.”
In addition to beer, bootleggers also produced pure alcohol, and the output of the Torrio-Capone gang’s operation was shipped all over the country.
“Chicago was the center of the railroad industry. It had access to the Great Lakes,” Paul Durica, director of exhibitions at the Chicago History Museum, told Chicago Stories. “There were the resources here in the city that made an operation like Capone’s capable of flourishing.”
The Torrio-Capone gang’s territory stretched over a large swath of the city’s South Side, extending from roughly 71st Street into the parts of the Loop, “which was the best bootlegging province in the city given the multitude of hotels, bars, and nightclubs,” writes Binder in Al Capone’s Beer Wars. Torrio and Capone were effective, savvy leaders, managing an estimated 500 gang members at the group’s height. There were a large number of Italian Americans in the group, though, contrary to popular belief, many of the city’s gangs, Torrio-Capone included, were ethnically diverse.
The Torrio-Capone gang was hardly the only gang in town. They were one of at least a dozen bootlegging groups in the city of Chicago. One of the other major players was the North Side gang, led at the time by Dean O’Banion (sometimes incorrectly called Dion O’Banion). The North Side gang controlled much of the city north of the Chicago River, extending up through Rogers Park. It was O’Banion’s North Side and Torrio and Capone’s South Side gangs that would be the key players in a years-long mobster war.
The Beer Wars
The problems began in earnest around 1923. The Genna gang, who operated on the Near West Side, started selling their liquor in territory controlled by the North Side gang.
“When Johnny Torrio was leading the [gang], there was always an effort to smooth over any differences or any conflicts that arose, and that led to, more or less, a kind of code of conduct among different people involved in the outfit and among their rivals,” Durica said. For example, as long as someone didn’t steal a beer truck, steal a supply coming in through the Great Lakes, sell in another gang’s territory, or kill a member of a rival group, “you were more or less fine,” said Durica. But violating these terms, particularly financially or in terms of territory, “could often result in severe repercussions.”
Unhappy with the Genna gang’s violation, Dean O’Banion and the North Siders approached Torrio for help, but Torrio declined. So the North Side gang began hijacking the Genna gang’s booze trucks.
“O’Banion seems to not only be mad at the Gennas,” said Binder. “He decides Torrio is also at fault, and he sets Torrio up.”
O’Banion invited Torrio to close on a brewery sale, knowing that the police were going to raid the place. At the time, the law required prison time after two bootlegging offenses. Torrio already had one offense, so he would serve time. Torrio realized it was a set-up. “At that point, I think O’Banion is a dead man walking,” said Binder. A few months later, O’Banion was shot to death in his flower shop, leaving Hymie Weiss as head of the North Side gang.
“The North Siders come back with a vengeance. And that’s then the real start of the difficulties,” Binder said. In retaliation, Torrio was then shot up and wounded, though he survived. An attempt was made on Al Capone, too. “That then sets off the big gang war that runs through much of Chicago's history for about the next six years.”
Torrio eventually left Chicago in 1925 after his prison term to return to New York and left 26-year-old Capone to lead the gang. The city’s other gangs allied themselves with Capone’s South Siders or Weiss’s North Siders. There were a number of retaliatory killings back and forth over the next few years. “The number of killings and the amount of violence is quite large. Some of it’s very, very spectacular,” Binder said.
One such event was a drive-by shooting at the Hawthorne Hotel, Capone’s headquarters for a time in Cicero. (Before “Big Bill” Thompson was elected for a third, non-consecutive term as Chicago’s mayor in 1927, Mayor William Dever attempted to crack down on gang violence, and the Capone gang moved its base of operation to Cicero.) In 1926, North Side gang members and their allies loaded up their machine guns and opened fire on the Hawthorne Hotel. According to Binder’s book, 1,000 rounds were fired into the building. Capone apparently escaped out the back of the building after possibly being tipped off. In further retaliation a few weeks later, Weiss was killed by machine-gun fire from Capone’s men, now leaving George “Bugs” Moran in charge of the North Siders.
How the St. Valentine’s Day Massacre Unfolded and Shocked America
What is now a parking lot adjacent to a senior living center on Clark Street in Lincoln Park was once the location of a shocking, violent event at the height of Chicago’s gangland wars of the 1920s.
Go deeperIt was this kind of sensational violence that earned the city of Chicago an international reputation. “Al Capone is world famous in the 1920s already, and Chicago is world famous for organized crime during the 1920s. That’s not something that comes later, like when Hollywood started to do all those gangster movies in the early 1930s. No, no, no. In Capone’s day, around the world, people knew who he was,” Binder said. The fact that Capone talked to the press and was a very visible figure, the use of Thompson submachine guns (or “Tommy guns”), and dramatic shootouts made for splashy headlines.
One such splashy conflict was one of the deadliest. The Beer Wars came to a dramatic crescendo with the St. Valentine’s Day Massacre on February 14, 1929, when seven members and affiliates of the North Side gang were killed. While there is still a question of certainty as to who was behind the killings, it is most often suggested that Capone at least pulled the strings.
It was a shocking event that made headlines. There were a few instances where a few gangsters were killed at the same time. “But there’s no case where four are killed. There’s no case where five are killed. There’s no case where six are killed,” said Binder. “Then it jumps all the way up to seven in very spectacular fashion using machine guns.”
The Chicago Outfit
The St. Valentine’s Day Massacre marked a shift in public opinion. In 1929, Capone was arrested in Philadelphia for carrying a concealed weapon and sentenced to a year in prison. Not long after his release, the Chicago Crime Commission came out with its first “public enemies list.” Atop the list, at Public Enemy Number 1, was Alphonse Capone. He was also facing increasing heat from President Herbert Hoover, who, said Eig, was the first president to run on an anti-crime platform.
“He tells his men every morning in the cabinet meetings, ‘What are we doing about getting Capone? We’ve got to get Capone,’” Eig said.
Ultimately, authorities would get Capone on a tax evasion charge. In 1931, Capone was sentenced to 11 years in prison, though he would be granted an early medical release in 1939.
But Capone’s criminal organization was well established by then, woven into the fabric of Chicago crime. It would continue to operate in some form, under various leaders, through the present.
While some violence persisted in the early 1930s, the Beer Wars more or less came to an end when Prohibition was lifted in 1933. In the end, Capone’s gang emerged on top. It began to control most organized crime in the city, and it had created allies out of the other gangs. That’s when the gang got a new name.
“After Capone goes to prison and Prohibition is over,” Binder says, “I would say that’s when the Chicago Outfit is created.”
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