Made Men (2004)

From the archived website:

Made Men takes place in the late 1920's, and is centered in a fictional city by the name of Port Rapture. In Made Men, players have the choice of joining large Mafia syndicates, scrounging the streets with a small gang, or even acting as law enforcement agents attempting to take down these crime empires.

Large families allow beginner players to experience life in the Mob through collecting extortion, roughing up a gang moving in on your territory, intimidating jurors, or guarding a speakeasy. Perform these tasks for the Don and you'll be taking steps towards becoming a Made Man; the untouchables of the Mafia and the highest members of a Family. Just don't become a snitch! Large Mafia Families are there for their people when they get in trouble, but if one of them becomes a rat, they are quickly silenced.

Small gangs provide a great opportunity for struggling campaigns. You'll need to recruit a gang, start up businesses, establish territory and hold it, all the while staying one step ahead of your rival gangs and out of the way of larger families. Business management, people skills, quick thinking and creative planning are all essential to turning your small gang into a thriving, respected Mafia.

Made Men is a game of strategy, role play, and wise guys.