Jon is 9 years old, with and attitude of a teenager, I suppose. He has no respect for anyone or anything, except of course, the TV. He's the only character here that adds the kind of dry humor he does. Of course, he's hardly ever trying to be funny. Anyway, Jon first came into contact with Cas when he bought Cas at the pet store for a nickel. He's tied with Cas's number one human tormentor with The Kid Across The Street. Ever since he bought Cas, he's done various things to him, because he figured out that Cas is impossible to kill. We think that he's trying to prove that theory wrong, like he tries to prove every adult wrong.
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