As is well known, pirates founded the great city of Freeport. Although Sea Lord Drac gave Freeport the veneer of legitimacy, the city retained its buccaneer spirit. While modern day Freeport is a port of call for merchants the world over, it remains a haven for those living outside of the law.
The Freeport Pirate is the inheritor of a great legacy. He maintains a code passed on from captain to captain since the founding of the city. While the Captain’s Council plays politics and makes grand alliances, the pirates live life as they always have. A fast ship, a stout crew, and sharp steel is all a pirate needs.
That being said, piracy these days is a quite a bit different than the days of yore. The well-organized navies of the continental nations are dangerous opponents, and few pirate captains have more than one ship under their command. These days Freeport Pirates must range further afield, and take longer voyages, to find ripe pickings. Many head east, fueled by tales of spices and riches, while others harry the humanoid coastlands in the distant south. No one on the continent sheds any tears for the kuo-toa, orcs, or lizardfolk who fall to pirate cutlasses.
Fighters and rangers are most likely to become Freeport Pirates, closely followed by rogues and barbarians. Bards and sorcerers are unlikely pirates, but their high Charismas make can make it work. Clerics of maritime gods sometimes become pirates, as do druids that focus on the element of water. Monks and paladins never become Freeport Pirates, due to their lawful natures.