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Two men in suits seated with hands clasped, in a room with wooden furnishings.

Match the Chicago Mobsters and Associates to Their Nicknames

Chicago gangster James Colosimo sits with attorney Charles E. Erbstein in 1914. Credit: DN-0063234, Chicago Daily News collection, Chicago History Museum

Match the Chicago Mobster to His Nickname

You’ve got your Jimmys. You’ve got some Johnnys. And then you’ve got men like “Greasy Thumb” or “Hinky Dink.” In the 1920s gangster scene, Chicago was full of interesting and dangerous characters and even more interesting nicknames. Sometimes, nicknames were used to conceal the identities of gangsters from the authorities – or anyone else who may have wanted to whack a fella. See if you can guess the nickname that belongs to each mobster or gang associate below featured in the show. You can practically hear the brassy jazz and smashing beer bottles.

Matching Game

Drag and drop the nickname onto the correct name below.

Scarface
The Fox
Bugs
Big Jim or Diamond Jim
Greasy Thumb
Machine Gun
Bathhouse John
Hinky Dink
Al Capone As “Public Enemy No. 1,” Capone was one of the country’s most notorious gangsters and was boss of the Chicago Outfit from 1925 until 1931.
Johnny Torrio Torrio helped establish the Chicago Outfit and was a mentor to Capone. He was known to be cunning.
George Clarence Moran Moran led the North Side gang, the rival to Capone’s South Side gang.
James Colosimo Colosimo helped establish what would become the Chicago Outfit. He was later possibly betrayed by Torrio and Capone and murdered by Frankie Yale.
Jake Guzik Guzik was a member of the Chicago Outfit and a trusted Capone lieutenant.
Jack McGurn McGurn was an Italian boxer-turned-trigger-man and a member of the Chicago Outfit.
John Coughlin Coughlin was the 1st ward alderman who led the “Gray Wolves,” a corrupt group of aldermen who partnered with the gangsters for financial gain.
Michael Kenna Kenna was another alderman who worked with Coughlin to lead the Gray Wolves.