I'll always hold Cinemaware games close to my heart - Defender of the Crown, Rocket Ranger, even SDI (it's rubbish, but the box art is great) - but none of them come close to King of Chicago.
You had to retire your old boss - via bullet or intimidation - and then you took over as head of the family, expanding your influences to the four corners of the city, balancing the books to get 'safe' politicians in your hood, but not without drive bys or reprisals... Or you could just date your moll until you got shot in the back of the head by the boss of a rival family.
Or you could take over the city. Your choice. Choice is good. The game never played out the same time.