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Having thought about it, I think that Chuck is the main driver here. When Jimmy thought that Chuck believed in him and could make something of himself, Jimmy busted his ass, got through law school at night, kept his nose clean, and built a law practice from nothing.
When Jimmy realized that Chuck thought Jimmy will always be a screw-up and a con-man, he turned down a good job and became a con-man.
Basically, Jimmy will become whatever he thinks that Chuck thinks he is.
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