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Role: The Mad Hatter
Age: 21
Face Claim: Cameron Monaghan
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Then the Evil Enchantress turned Madsy into Damon Gilroy, a young man who causes chaos and pain wherever he goes, partly for the Enchantress' approval, but mostly for his own entertainment. That's how he is professionally, anyway - which is probably a good thing for an Evil Enchantress' executioner. In what spare time he has, though, Damon is... well, odd, to say the least. His behavior is so erratic, it's difficult for anyone who knows him in any sort of personal capacity to even describe his character.
One of the few things he's kept from his previous life is his love for puzzles, riddles, and the like. He's unpredictable and boisterous, flamboyant and mischievous.
If he wasn't so well-liked by the Enchantress, what with his willingness to torture and kill for her in cold blood, he'd probably have gotten himself into quite a bit of trouble a long time ago. He likes to explore, when he's allowed to; and when he's not, he spends a disturbing amount of time in the dungeons, taunting the prisoners.
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The only glimpse of his past that he ever has is when he's killing people, because it brings back memories of his own parents' murder. Now, you'd think that would make him not want to do it, but because that's the only memory he has of his parents at all (even though he really thinks it's some sort of hallucination, not a real memory of a real family), all of the pent up happy memories he doesn't believe he has left from his childhood somehow got stuffed into that moment. Somehow, things got twisted around; and now, he serves the Enchantress as her Head Executioner and Interrogator, and he relishes in every minute of it.
Sometimes he dreams about older versions of the family and friends he lost as a child, and even hallucinates about a grown up Alice advising him, but as far as he's concerned, they don't really exist outside of his head. He thinks they exist at all because his mind is the only friend he has, the only friend he ever had to begin with,
and the only friend he will ever have. While most of the princes share some kinship with each other even after losing their memories, the ever-loyal Madsy is long gone, and Damon's only interest in the other princes is to see how easily he can torment them without getting into trouble with the Enchantress.