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Born to a poor family in a nondescript village, Winthrop has only known struggle. Being very small for his age, a genetic fluke, he learned very quickly that he will never quite make it by through brute force. So, he learned how to trick and confuse very early on so he could get by on his brains alone. His mother left the village when he was very young, and his father died in a drunken brawl, so he has been on his own for as long as he could remember. And, as far as he is concerned, it's better that way. He now travels around, following the flow of coin from crowds of travelers to line his own pockets.

He is very short but has a cute, charming look to his eyes. He finds his youthful appearance garners more trust from passerby's and uses it to his full advantage. His hair is choppy and short, and he usually wears ragged, plain clothes to help him blend into a crowd. His left ear is pierced and he has a dusting of freckles all over his face and neck.

Mostly looking out for his own well-being, Winthrop is a silver tongued devil with an eye for reading people. He is as good humored as he is manipulative, and will say and do whatever to swindle a rich gentleman out of a few pieces of gold. He is a real stickler against authority but knows when to hold his tongue and follow orders to save his skin.