The player is the head of one of these crime organizations, whose goal is to edge out the competition and get their bosses arrested or killed. This can be achieved in many different ways, all of them illegal, but often involves copious amounts of racketeering, bribery, and midday assassinations.
During the turn-based portion of the game, the player is given a set of elaborate menus detailing everything about his/her organization. This includes a full roster of men, potential recruits, real-estate, weapons, vehicles, and even a list of the city's political figures that could be manipulated. The player can view lots of statistics about each of these, and must eventually use them all to come up with a plan for what each member of the outfit will do during the coming week. Your troops can be sent out to perform all sorts of missions, such as recruiting more men, acquiring new property and setting up illegal activities, running said illegal activities to get money, bribing or assassinating officials, and of course attempting to "hit" members of the opposing crime factions. You need to select the right men and equipment for each job, set routes and schedules, and make sure everything is in order before committing to your plan.
Once this phase is done, the week begins, and all orders are carried out by your numerous "employees" in real time (though orders may still be given, to change your plans on the fly). The city contains not only hundreds of criminals but also thousands of civilians and law-enforcement officials, who will also go about their business as the week proceeds. It can be downright chaotic at times, especially when several factions go to war with each other all over the map (making micromanagement difficult, if not downright impossible). Once the week is over you are returned to the planning stage, to rinse and repeat.
The game was exceptionally complicated for its time, and hardware-intensive to boot. Unfortunately, its execution (particularly the difficulty in staying on top of things during the real-time portion of the game) made it quite difficult to play, and the copious statistics and limited in-game instructions made the whole thing utterly confusing to newcomers. Nonetheless, it was one of the first games to delve so deep into the operations of criminal organizations during the 1920s, and one of the first games to portray such a large-scale "living world" in real time.
This game provides examples of:
- All Crimes Are Equal: Played with. Your hoods will occasionally be freed if arrested after a gunfight (seemingly for self-defense reasons) if the enemy gang started the fight. Also, heavier crimes such as gunning down officers of the law and bombings will attract more police attention than a simple protection racket.
- Artistic License – Economics: Somehow buying two Colt 1911's for dual wielding is more expensive than a single Tommy gun.
- Corrupt Politician: It's possible to bribe several key figures in the city, in order to reduce police interference in your plans and generally keep you and your men out of jail.
- The Determinator: The FBI. Beyond trying to lay low, there's nothing you can do to get them off your back. They cannot be bribed, and violence against them only makes them more aggressive.
- Enemy Mine: It's possible to ally with other gangs. If only two gangs are left and allied to each other, they both win, so it's possible to try to team up with another gang to fight the rest.
- You can send unarmed hoods to assault enemy hoods; If the enemies draw guns and start firing, the police will attack them.
- Eternal Equinox: Averted in the second installment. Nights are longer during the winter month stages.
- Every Man Has His Price: While you cannot bribe the FBI, you can bribe police officers, the Chief of Police, the jury in a trial, and even the judge — as long as the player has a lawyer and enough money.
- Gang Up on the Human: Completely averted.
- Police don't go after your crimes any more than they do the other crime bosses.
- The some-what aggressive behaviour of the AI bosses generally means they're likely to start fighting each other before going to war with the player - especially if you stay out of their way and/or declare peaceful intentions.
- Game-Breaking Bug: It's ill-advised to speed up the working week, as characters don't fully "speed up" with the clock, making it impossible to fully complete multiple orders that aren't short.
- Guide Dang It!: How stabbing a hood to death works is entirely different than the manual claims. The "kill" order is only for hoods armed with guns; A stabbing will only happen if a Hood follows an "assault" target into a building.
- Guns Akimbo: The best fire-arm in the game, with a noticeably higher price than even the Tommy Gun.
- Let's You and Him Fight: A valid tactic, if you have an unarmed hood assault an enemy who retaliates by pulling a gun, then he runs into the sightline of the police while being shot at, the police will kill the enemy hoods, this will also increase the total police attention for that gang due to their members getting in gunfights with the police.
- Molotov Cocktail: A public "Torch" order will consist of trying to throw a Molotov through the window of the building instead of starting the fire from inside it.
- One-Hit-Point Wonder: Everyone. The "Stealth" skill does influence the chance to dodge bullets, but other than that everyone goes down in one shot.
- Pacifist Run: Very difficult, but possible - even if you count extortion or intimidation as violence. You'll need to use business-minded mooks to purchase and run legitimate businesses to make money, while also trying to keep the peace with your rivals (and hoping that they start wars of attrition with one another that'll keep them busy and away from your assets). Illegitimate businesses can help make money faster, but they're bound to attract rivals and/or the police, which will typically lead to violence. Keeping hold of one's territory without violence is the hardest part, but there's usually enough territory left over to purchase and make good use of - especially the high-value blocks like the Department Stores which rivals are unlikely to buy until much later on. At the end, you have two non-violent choices to win the game: Either get elected for mayor, or simply go straight.
- Power Up Letdown: The Tommy Gun and Dual Pistols fall somewhat into this. While they are effective in the hands of hoods with high "Firearms" skill, the fact is that the shotgun/rifle are simply more practical for any hood that isn't a sharpshooter, since they have a much higher chance to hit at Close/Long range respectively. A fast rate of fire doesn't help much when everyone dies in one hit, so it's simply more practical to have a more hoods armed with shotguns and rifles than the more expensive and skill-requiring Tommy Gun/Dual Pistols.
- Ranged Emergency Weapon: The Revolver is this. It's way cheaper than other weapons, but without a very high firearms skill your Hoods will miss multiple times before killing a single enemy, even at point-blank range.
- Simultaneous Turn Resolution: A rare case, where the "planning" phase is very long and involved, and is followed by a similarly-long "execution" phase that could last many minutes. It also allows giving additional orders during the "execution" phase, though they are much more limited.
- Stupid Surrender: Any wanted hoods (Or hoods that were caught doing a crime and escaped in the same working week) will automatically surrender if an un-bribed police officer spots them — even if they have a Tommy Gun and have just gunned down several cops that same week. The surrendering hood won't even go free if another hood guns down the arresting officer.
- Take a Third Option: It is possible to win the game by running for Mayor or going straight.
- The Roaring '20s: The setting for this game. It portrays at least the criminal element of that period with some degree of accuracy, regarding how criminal organizations carried out their business (with illegal activities, such as numbers rackets and extortion, financing expansion, and resorting to violence only when push comes to shove).
- Unexpectedly Realistic Gameplay: The Bosses of crime families particularly the Italian Mafia Families don't really go out and shoot or hurt enemy hoods themselves, they got people for that, I guess you could say this is unexpected for those who are both uninitiated or initiated in how The Mafia works or operate, they are mainly like a Corrupt Politician, they do this for fear crimes could be traced back to them, the hoods are just Plausible Deniability, useful for getting "Problems" out of the way.
- Villain Protagonist: The player controls a crime boss trying to remove rival gangs.
- Wide-Open Sandbox: The city is pretty large, and you can start off doing almost anything you want in it. There are so many options for things you can do, it's easy to get lost (and eventually lose the game) on your first few attempts. This is probably one of the reasons the game failed commercially, despite having a very good replay value.