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[Pex]

Sounds like Gangsters: Organized Crime to me. There was second part as well, called Gangsters II.

[The Fifth Horseman]

The only 1980's title that seems similar to your description is this: http://www.mobygames.com/game/king-of-chicago

Others are all in the mid to late 1990's rather than 1989 as you're posting. The use of colors (VGA? SVGA?) and CD-ROM medium suggests 199x as a more likely time frame.

Mob Rule in particular sounds similar to your description: http://www.mobygames.com/game/mob-rule

http://www.mobygames.com/game/legal-crime
http://www.mobygames.com/game/beatdown
http://www.mobygames.com/game/dos/dime-city/

[mitchellA]

Originally Posted by Pex

Sounds like Gangsters: Organized Crime to me. There was second part as well, called Gangsters II.

Thank you Pex.
Judging from the screenshots I've seen, this is indeed the game I am looking for (or its successor). Funny thing is that this is a Windows game, and I never looked at it because the game I played was definitely a DOS game.

PS: The Fifth Horseman may be right, it could have come out any time before 1994 when I bought the Wing Commander Privateer CD.