The player assumes the role of Jimmy "Machine Gun" DeMora who is an up and coming thug in the Al Capone family. Set in Chicago at the height of the prohibition era, the player shoots his way through the mean streets on various missions for Al Capone. Chicago Enforcer is mulitplayer with system link (2-8) or Xbox Live.
As a first person shooter, there are several different weapons to use, including a Tommy Gun, Firework Rocket Launcher, pistol, shotgun, lead pipe, sniper rifle and more. The title has several different missions, ranging from roughing up store owners by destroying their stores, to killing snitches who talk to much, to saving Al Capone from certain death.
- "Я, гангстер" -- Russian Windows title
- "Chicago Enforcer" -- Xbox title
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Game Informer Magazine (Issue #153, Jan. 2006) named it #1 of the Top 10 Worst Games of 2005.