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Chicago Gangster History: Chicago's Gangster Era


Legendary tough guys such as Al Capone made Chicago the home to America's first gangsters. These hardened hooligans left a permanent mark in the history books of this bustling city by coining the Windy City as their center of operations for organized crime.

Chicago gangsters as we now know them sprung up in Chicago in 1920 right after the passing of the 18th Amendment prohibiting the sale of alcohol in the United States. The overwhelming demand for "hootch" led to the formation of groups of Chicago gangsters that trafficked illegal alcohol and managed prostitution and gambling rings. The most well-known gang was the Chicago Outfit, which was headed by scandalous gangsters such as "Scarface" Al Capone and Johnny Torrio.

On Valentine's Day, 1929, the gang wars in Chicago culminated with the St. Valentine's Day Massacre. Seven members of Bugs Moran's Northside gang (in competition with the Outfit) were found grotesquely gunned down in a garage. Although there was no supporting evidence to accuse Capone of the murders, it is highly suspected that he and his cohort, Jack "Machine Gun" McGurn, were the masterminds behind the slaughter. After Prohibition ended, the groups of gangsters slowly dissolved in Chicago, but there are remnants of these gangs still active today.

Besides being social deviants, Chicago's gangsters were highly active in politics. By interfering with elections, threatening the police, and pulling other illegal maneuvers, gangsters succeeded in influencing the greater Chicago area.

For a closer look at Chicago’s gangster history, try visiting the locations listed below. They are sure to excite the aura of the early 1900s in any emerging historian.

Mount Carmel Catholic Cemetery
For truly motivated 1920s gangster aficionados, the Mount Carmel Catholic Cemetery located in a nearby Chicago suburb is a must. The cemetery can be found about 25 minutes outside of Chicago in the town of Hillside. Holding over 400 family mausoleums, the largely Italian cemetery draws visitors from around the world. Gangster legends such as Al Capone, Deanie O’Bannion, Hymie Weiss, Jack "Machine Gun" McGurn, and the Genna brothers along with other big-time criminals are all laid to rest at this historic plot. Besides gangsters, Mount Carmel Catholic Cemetery also holds the graves of the bishops and archbishops of Chicago in the noted Bishops’ Mausoleum.  

Holy Name Cathedral
This beautiful Catholic Cathedral in the heart of Chicago retains a deep connection to the city’s gangster past. Many bootlegging criminals in the 1920s held strong to the Catholic faith and often attended mass at Holy Name Cathedral on Sunday. In 1926, the North Side Gang leader Hymie Weiss was gunned to death steps outside of the Cathedral. The submachine gun that ended his life left a permanent bullet mark in the white stone that visitors still can fit their finger in today. Enter the Gothic-style church to view the intricately carved bronze doors, heavenly bronze statues, and the Cathedral alter adorned with Catholic relics.