|Release date(s)||November 2003|
|Genre(s)||Organized crime, RPG|
The game is based in the American city of Chicago in the 1930s, an era heavily associated with gangsters. The RPG style game allows players to choose to be the mafia, headed by Don Carmine Falcone, or a special unit of the police, headed by Edward Nash.
- Mafia: If the player chooses to play as the Mafia, they will play as Jack Beretto, a member of the local Mafia and right-hand man of Don Carmine Falcone. Playing as Mafia, your goal is to destroy all of your enemies and take over Chicago. The powerful Irish organized crime leader, Hank O'Neil is head of Chicago and there's this mysterious character "Baron" who is apparently stealing money from Don Falcone. When it's revealed that O'Neil is not the Baron, new character will get into plot: District Attorney Dan D. Dougherty. But, it will be also revealed that Dougherty isn't the Baron after all.
- Police: If the player chooses to play as the Police, they will play as Edward Nash, an FBI agent. The FBI head will give the player missions. The antagonist is Don Falcone, the king of Chicago. The player will have to slowly take over Falcone's territories as you proceed to ruin his empire. The traitor Beretto will help you a little, but he is also an enemy. At the end of this chapter you will find out who is hiding under the Baron name.
- Henchmen: These are people that help the main protagonist (Jack Beretto or Edward Nash). They are also playable characters and can be used for different tasks (for example, a gangster or officer with high shooting skill can be sent to kill by shooting.). Game will not be over if a henchman dies.
- Don Carmine Falcone: The brutal Mafia boss from New York, shows up in Chicago. If you play for his Mafia empire, you'll have to beat bunch of enemies on your way to top. Notice, that his name and story are a parody on Al Capone. Also shares name with a Mafia boss from the DC Comics universe.
- Jack Beretto: Right-hand man of Don Falcone, Jack is the protagonist of the first chapter. In second chapter he will help you a little with info's against Falcone, but you will still have to put him behind bars. Responsible for killing Hank O'Neil and Dan D. Dougherty, two antagonists.
- Edward Nash: Protagonist of second chapter, FBI agent. Notice that his name and story are similar to that of Eliott Ness.
- FBI Head: Man giving you orders in second chapter.
- District Attorney Dan D. Dougherty: Man who was supposed to be Baron, but it is revealed he's not. Kidnapped and interrogated by Don Falcone, and later killed on his orders. If you play as police, your first mission will be to investigate the death of Dougherty.
- Hank O'Neil: Irish mobster, ruler of Chicago before Don Falcone and second antagonist in first chapter (the other being District Attorney Dan D. Dougherty). Killed on Don Falcone's orders, last mission in first chapter.