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The Wit's End complex is broken up, roughly, into thirds when the Player Characters arrive: One portion has yet to be explored since the time of Wit, one portion is now occupied by dwarves come seeking Duncin Flathead's treasure and one third are sea caves occupied by a pirate from the Sea of Dread, left marooned for far too long now ...
Cobbler Owlhootby Beau Yarbrough
Lawful Evil male hin pirate and Rogue 1
Cobbler Owlhoot fell in with the wrong crowd in Shireton Port as a young hin and quickly drifted into the company of a particularly savage group of pirates aboard the Snapping Turtle roaming the Sea of Dread.
Cobbler has been left in the pirate caves - which, unknown to the crew, were part of the Wit's End complex - to guard a treasure chest full of booty from their last raid. The ship was sunk at sea by the Ierendian navy, and Cobbler has been left alone in the caves now for over two years. In that time, he's grown madder and more dangerous. He's discovered the shadow grue and mastered the outer third of the complex, dragging the pirate chest to the centre of a maze where he now makes his home. While he is desperately lonely, he's also grown increasingly paranoid, meaning he will shadow any visitors to Wit's End, soaking up their company from the shadows, but will turn violent if actually spoken to or approached. Never too stable to begin with, Cobbler is now fully insane, and becoming dangerously so.
He's a seedy looking hin, whose shipmates once described him as a "drowned ferret," with a long nose, still-chubby cheeks, crazed beady eyes and limp pale brown hair, wearing a much-the-worse-for-wear sailor's uniform, along with a filthy blue kerchief tied around his neck.
Cobbler is a stealthy sort, quick to understand gadgets and magical items (including his Wand of Unlight) but with a fairly repellent personality. At the moment, he cares about little other than guarding the treasure, finding company and getting something other than fish and sea gulls to eat, all of which add up to a growing tendency towards kidnap and, eventually, cannibalism.
So long as his treasure is endangered but not discovered - i.e., intruders are moving through Wit's End under their own power - Cobbler will conceal himself and track the intruders. Once they discover it, or he thinks they're likely to - heading the right way in the maze, or having passed the "dragon" successfully - he becomes violent, setting off traps (including using his wand to plunge intruders into complete darkness where the shadow grue is likely to find them) and eventually attacking with a dagger in each hand. If he should somehow interact with others in a situation where he is in power - after capturing a wounded intruder, for instance - he will alternately dote on and rage at intruders before eventually succumbing to hunger and madness, butchering and eating them.
He is vaguely aware that Gorwarf siblings have broken into Wit's End on the far side of the rusted door, but as they've made no serious attempts to enter the sea cave portions of the complex, he ignores them.
Out of boredom, Cobbler has tattooed the top of his right foot with the crude image of a crab, which now peeks out through sandy foot hair.