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I wonder if Leslie’s lack of ambition comes from his mother? Or more specifically, a fear of BECOMING his mother.
While she makes it work, Ann Eiffel has always been driven by greed and deception above all else, and while we don’t know how Al made his living, and while he seems to be a lot more honest than Ann, he’s still shrouded in a bit of mystery. He doesn’t seem to be a bad guy now, but that’s no telling what his past was like.
Maybe Les thinks “being rotten is in my genes, so if I don’t excel, I’m protecting people from the me that I would become.”
At the very least, Leslie’s trying to be better than when he was in high school.