Each player has 9 gangsters and 5 cards to conquer cities. The cards of the players are gradually turned over, which gives information to all players. They can therefore decide which city their henchmen should go into. With each card played, you gain more information about the loot, or sanctions, that may be yours for the taking in different American cities. Basing upon this information you send out the members of your gang to those cities -- some are pros, some are wannabes. Deduction, bluff and initiative taking will make you win millions, controlling a city, unless it happens to be less welcoming than you thought. Whoever has the most gang members in a city, cashes the loot or undergoes the sanction. When going to Chicago you have no choice but splitting your takings with the boss himself: Al Capone. The further the game progresses, the higher the stakes are getting, especially in Chicago. The Boss is essentially a card game (but comes with small game board for keeping scores) of deduction, bluffing and a lot of backstabbing.