(Mild spoilers for the Freeport Trilogy below.)
One of my PCs was a swashbuckling fighter/rogue, constantly on the edge of doing too much bad, albeit with good intentions. He was weak-willed and impulsive.
Naturally, he's the one that first laid hands upon the saber of sorrow, a powerful cursed weapon long lost in Black Dog's Caves. Over the course of weeks, the saber warped Ianen's personality until he was among the vilest of the blackguards in Freeport. Eventually, during a long period of downtime, Ianen joined the crew of the White Shark, captained by Grinning Jand, the single most depraved, feared, and powerful of the city's many pirate captains. Ianen's twin sister, a noble paladin of Pelor, shudders still when she thinks of Ianen's behavior during that dark time.
Eventually, the White Shark and Ianen returned to port, and with good planning the rest of the group -- most of them siblings, of the merchant house Zarin -- took him down and (barely) alive. Michaela had the saber of sorrow melted down, shaped into a ball of metal, and dropped somewhere in the open ocean. Over several more weeks, Ianen recovered, though he was never quite the same devil-may-care scoundrel he'd been pre-saber. (He also never again strayed from Goodness.)
Two years later, game time and real time, on their way to stop cultists of Yarash from releasing YADG (yet another dark god) to plague Freeport, who should attempt to stop their small and ill-armed vessel but, yes, the White Shark. The battle was furious, the presence of the heroes prolonging the inevitable, but eventually the superior numbers of the Shark's crew and the vicious fighting skills of her captain meant the boarding of the weaker vessel.
That's when Grinning Jand came face to face with Ianen, or -- as he'd been called during that dark time -- "Mako." The Zarin family, Ianen's siblings, blanched as Jand threw his head back and laughed, recounting tales of murder and pillage, expressing his admiration for "ol' Mako here, th' only lad o' all me bloodthirsty crew t' ever give me cause t' heave me guts." And then Ianen lunged for Jand, their sabres crossed with a resounding crash, and the battle was rejoined.
Eventually, battered and bloody, Ianen prevailed over Grinning Jand, and the remainder of the heroes defeated his crew. Ianen's love, Duvray, long disguised as a male navigator, was revealed as a woman. (The group, out of character, never knew Duvray was a woman. They just assumed Ianen was British Royal Navy, I guess, shrugged, and went about their business. There were disapproving looks from Michaela, of course, but paladins are notoriously prudish.) Ianen and Duvray claimed the White Shark as their own, and as the remaining Zarins sailed toward Hell's Triangle, to be carried toward their destiny, the White Shark sailed into the setting sun, tacking her way back to Freeport.
(And, a day later, Ianen's player moved to Seattle, where he'd taken a kick-ass job as a game designer for Microsoft. He's missed. I have some great players, but Ianen's has been the only one so far to truly embrace the piratical cliches that make Freeport so much fun. Thinking about it, the synchronicity of being able to provide so much closure to Ianen's saga was pretty incredible. The timing just all seemed to work out perfectly.)