If you haven't heard of the game Gangsters, you should check it out. You create a boss and start with a few gangsters in a large 1920s city. Before each week of gametime starts, you assign jobs to your crew, such as recruiting more gangsters, extortion, collecting protection from citizens, bombing enemies, and lots of other tasks. You can even set up legitimate businesses or ones that just fronts for the real money-makers. Once you become powerful enough, you can win the game by killing your rivals or by a few other ways.

I highly recommend this game. If you want to buy it, you might have some trouble finding it, because it is several years old and only on pc. There's also a Gangsters 2, but that game is inferior in my opinion because the structure of the game is changed.