The Pirates who don't do anything
The Free Captains united under the Hurricane King in 4674 AR to harass shipping north of the Shackles. Their recent success spurred the so-called Glorious Age of the Free Captains that began in 4681 AR and represents the unprecedented era of prosperity that the Free Captains currently enjoy.
Free Captains are leaders among the Shackles Pirates. To become one, they have to build a certain level of fame and power, as well as pay tribute and pass a test for the Hurricane King. Upon passing, they are handed a Shackles Letter of Marque, authorizing them with official, sanctioned support from the nation to raid the shipping lanes and towns of other nations for greater plunder.
While Free Captains are not often on the friendliest terms with each other, nearly all of them respect and support each other as a group when called upon by the Pirate Council or its leader, the Hurricane King. Free Captains have built a network for themselves, and are surprisingly organized when they need to be, which has made them more prosperous and lasting on a scale few other criminal nations have ever accomplished. Free Captains can and often will call upon each other to team up in a raid, or back each other up against a larger threat. In some more extreme cases, fleets of pirates have been formed to fend off full-scale naval retaliations from more civilized countries.
Free Captains have many contacts to call upon for all sorts of tasks, can enter most ports in the Shackles without worry, and have access to information that most sailors would kill for. Free Captains can earn their trade hunting privateers, looting innocents, taking (or freeing) slaves, exploring ancient ruins, smuggling, monster hunting – the possibilities are endless for these few who practically worship freedom. By far the most popular and fearful legend of Free Captains is the ability to ride the winds of the Eye of Abendego - it is almost a rite of passage that all Captains eventually try this feat, and although many perish in the attempt, those that survive become true Free Captains.
Each year since 4677 AR, independent Free Captains can attempt to increase their status by entering the Free Captains' Regatta. The winner gains a seat on the Pirate Council – the most powerful of the Free Captains, lordship of an island, and a hefty purse.