Dire Crowley is the masked Headmaster of the prestigious magical training school, Night Raven College. His catchphrase is, "Because I'm so kind." After Yuu ends up lost and is summoned to Twisted Wonderland, he is the one who takes them in and appoints them as Prefect and leader of the Ramshackle Dorm. Supposedly, Crowley is researching ways for Yuu to return to their original world.

Dire's face is concealed by a half-mask resembling a raven's beak. Through this mask, his eyes are occasionally seen glowing gold. He has pointed ears and short, wavy black hair. Dire sports a greatcoat over his suit. Thick blackbird feathers curl out from its blue-collar, while the tips of the coat are cut to resemble two bird wings. He wears black gloves on either hand, with golden claw rings over each of his fingers. Three mirror-like accessories are attached to his hip, with four golden keys dangling from them. He wears another mirror-like charm on his hat, which has three more keys - making a total of seven. Dire's staff is also shaped like a key, with a golden raven as its handle.