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In the first season of the show, Jimmy wasn't nearly so bad. He was trying to be someone his brother Chuck could respect. But the show does seem to be suggesting that was the deviation, an unstable state that he got knocked loose from to reach his lowest-energy state.

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Trying to be somebody Chuck would respect by doing that billboard stunt, lying to HHM about how he was recruiting clients, etc? He wanted Chuck to respect him but he wanted that respect on his own terms doing the things he wanted to do anyway. Chuck at one point said he was the same Slipping Jimmy, and he was right.

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