With Al Capone out of the picture, Chicago's prohibition-era profit is up for grabs. Are you merciless and cunning enough to gain it by whatever means are required? Every action you take has complex long-term consequences which are not always obvious at the time.
You must keep your people on your side, watching what you say and do, knowing that an overthrow could be hatched at any moment. Look after your woman as well - who's going to respect a single mobster? The money has to be juggled in these ways, not forgetting to reach an 'understanding' with the Mayor to avoid any negative attentions.
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The different endings are triggered depending on how you overrun Chicago.
The obvious ending can be seen of course by taking over Chicago one by one, until you kill Santucci in the South Side.
Another way however is through Lola, your girl-friend! You can either treat her really bad or use her as a bait; in both cases, you'll end up finding her in Santucci's residence, where you get to kill him - regardless of what other parts of Chicago you already run. However, if you did treat Lola badly, you're in for a very bad surprise!
The third ending is still unknown.