The Gangs of Chicago

In Wise Guys you will be taking over operations of one of four gangs, competing with your rivals to be the most successful and wealthiest in Chicago!

The Chicago Outfit


When Al ‘Scarface’’Capone took over the Chicago Outfit from his mentor, he inherited a well-oiled machine. The Outfit has the right connections in the Italian-American Mafia, city politics, and the police, to keep things above board and business-like. Capone takes the same professional approach to his syndicate, divvying up the turf to other gangs and avoiding unnecessary warfare. That doesn’t mean he’s a pushover. Mess with an ally and you’ll feel his wrath. Mess with the Chicago Outfit and ‘Machine Gun Jack’ will make you wish you hadn’t.

“You can go a long way with a smile. You can go a lot farther with a smile and a gun.”



North Side Gang

The O’Banion Gang runs the North Side, an Irish-American stronghold. The youth gangs there all report to O’Banion and his lieutenants, providing a useful source of income and recruits. O’Banion’s Irish contacts in the police force make their aggressive style of operations, including literal daylight robbery, possible and profitable. Having put several rival gangs out of business, open warfare with Capone’s Chicago Outfit will cost the gang dearly in the St. Valentine’s Day Massacre.





Saltis-McErlane Gang

‘Polack Joe’ Saltis was a Slovak, but to Chicago he was a ‘Polack’, a Pole, just like any other Eastern European. When Prohibition came into force, he started up business with the city politician ‘Dingbat’ O’Berta in the Back of the Yards neighborhood on the South Side. The small but fiercely independent gang quickly found itself in conflict with its neighbors. However, the addition of the murderous Frank McErlane to the gang and a series of vicious ‘hits’ on their rivals increased their notoriety, making other gangs wary of crossing them

“I’ll take care of it.”




Sheldon Gang

Ralph Sheldon had a simple plan — sell cheap booze. This plan quickly made his gang the major supplier on the Southwest Side of Chicago, even supplying Capone’s Chicago Outfit. Unfortunately, the low quality of their product and their unorthodox methods of sourcing product — they weren’t above hijacking other gangs’ shipments — put them at war with the Saltis-McErlane Gang and other South Side gangs. When that happened, they got creative, even using an aircraft to bomb a rival operation





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