It does not take money to make money, at least not when you're a pirate. In "Tropico 2: Pirate Cove," a new game for PCs from Take 2, you can gin up money from thin air. That is if you have a mighty ship and a blood-thirsty crew.
In "Tropico 2," players assume the role of a pirate king. You are not the captain of a ship leading raids. Your job is more administrative.
In this game, pirate kings do not plunder innocents, they hire sailors for such menial tasks. Pirate kings remain in port planning cities. While you may build ships and commission captains, the big sea battles all take place off screen.