When he decided to do deadly tricks he couldn't possibly survive, he survived, but with a price.
When he was young, Jay was a card cheat. Charlie took him under his wing and trained him to be a magician. Along with their friend Vernon Haskell, they used to be very successful but lost their touch after losing their youth.
Depressed at being unable to compete with the younger magicians, he decided to kill himself by undertaking an impossible (and deadly) trick, The Table of Death, with the intention of letting it kill him.
But he survived the trick, and it seemed that he had regained his old talent. When he tried another dangerous trick and another rival magician died, Sam and Dean confronted him and accused him of using real magic. Jay had them arrested, but when he performed The Table of Death again and Charlie died, he realized that Sam and Dean could have been right.
At the theater a young man appeared and revealed himself to be Charlie. He had an enchanted pack of Tarot cards that gave him immortality. He offered eternal life to Vernon and Jay although it meant Sam and Dean would have to die. Jay, however, pickpocketed Charlie's deck of cards, leaving one with Charlie, and then stabbed himself, killing Charlie. He later regretted this decision, saying it would haunt him for the rest of his life.
- ↑ Criss Angel Is A Douchebag