Jerome Valeska

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Jerome Valeska was a deranged mass murderer. He was the more vengeful and chaotic twin brother of the obsessive and methodical mastermind, Jeremiah Valeska. Born and raised in Haly's Circus, Jerome murdered his mother roughly at the age of eighteen, which led to his arrest and incarceration at Arkham Asylum. Following a breakout with other inmates orchestrated by Theo Galavan, he became the leader of The Maniax and wreaked chaos upon the city. This later led to his betrayal and murder at Galavan's hands, although his death brought about an underground movement devoted to him and his way of thinking.

David Nolan

33

 Prince Charming is the husband of Snow White, though neither of them remembers this in the cursed Storybrooke, where the character's name is David Nolan ("Charming" is the nickname given to him by Snow White). In his previous life, David is actually the brother of the real prince James who died and was replaced with his twin. Both brothers were born to a poor farm couple who made a deal with Rumpelstiltskin to save their farm; they gave up one son to King George, whose wife could not conceive. After James's death his brother found out the truth and took his place, becoming engaged to Abigail, daughter of King Midas (reluctantly, after his family is threatened by King George) in a deal that unites two kingdoms with Midas giving King George gold in exchange for the prince defeating a dragon. Later, the prince meets and marries Snow White with whom he has a daughter named Emma. In Storybrooke, David is a John Doe with amnesia who meets and falls for Mary Margaret, who is really Snow White, before recovering his memory and working at the Storybrooke Sheriff Department. He later has another child with Snow White named Neal.

Jonathan Crane

28

Jonathan Crane, also known as the Scarecrow, is a deranged, criminally insane teenage psychopath and anarchist. He is the son of the late Gerald Crane and the late Karen Crane. As a child, his mother died in a house fire, causing his father to try curing fear until his inevitable death. Not long before this, his father injected his son with the serum he had made which had overloaded Jonathan's fear response causing his mind to create a boogeyman of what he feared the most: a scarecrow, driving him insane.