Skulls & Shackles
Mistress of Quent and captain of the sloop-of-war Luck of the Draw, a popular figure throughout the Shackles. Widespread rumor holds that she will be the next Hurricane King, either by acclaim or by force.
Tessa Fairwind is a slender woman with long red hair worn in a no-nonsense braid. She wears a figure-hugging combination of fashionable finery and practical sailor’s clothes with a tricorne hat at a jaunty angle.
Her fine features and delicately pointed ears accent her exquisite looks, and she moves with lithe fluidity and graceful efficiency evident in her every motion.
While the exact details of Tessa’s past are the subject of much speculation and several tragic ballads among the islands of the Shackles.
Her career as a pirate began as a young adolescent when she stole a yacht from Cassomir’s docks and used it to burglarize a smuggler’s secret stash. By the age of 15, Tessa was captaining her first ship, sailing it up the Junira River to lead an audacious midnight robbery of a Thuvian pleasure barge. Within 3 years, the price on her head had become so high that Tessa sailed through the Arch of Aroden and into the Arcadian Ocean to avoid capture by bounty hunters. Her successful raids on Chelish shipping near Khari as she voyaged westward were an indication that the young pirate had no intention of changing her wild ways. Sailing down the Garundi coast, Tessa attacked Rahadoumi trading vessels and coastal villages until she arrived in the Shackles, finding the pirate isles much to her liking.
Tessa soon set about making a name for herself and carving out a place in the dangerous pirate confederacy, which quickly put her into conflict with several Free Captains and pirate lords. Through all the skullduggery and treachery, those who underestimated Tessa Fairwind soon learned that meddling with the half-elf captain was an exceedingly painful mistake, and often a fatal one.
Over time, she became a powerful pirate Free Captain, gathering a loyal following of scoundrels and a large fleet of ships
under her banner, including her personal ship, the sloop-of-war Luck of the Draw. Tessa Fairwind is now Mistress of Quent on Motaku Isle—one of the Shackles’ most important ports—and one of the leading lords of the Pirate Council. She is a shrewd player in the game of politics, but her rebellious and carefree attitude has won her popular acclaim in the Shackles. She prefers the freedom of the open sea, with the wind in her hair and the sway of a good ship beneath her to time in port. Most of all, she loves the thrill of the hunt when seeking merchant ships to plunder, though she views wealth as simply a means of keeping score.
Tessa is an unconventional worshiper of Calistria, for while she truly believes in the hedonistic pursuit of pleasure and the freedom to live as she pleases, she finds seeking revenge for petty slights a waste of time, and games of trivial intrigue a distraction from the joys of living. Nevertheless, bawdy songs of Tessa’s exploits are known throughout the Shackles, though
Tessa herself neither confirms nor denies the veracity of these tales.