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I took the 6 months comment as Hamlin being asked by Chuck to hire Jimmy, he gives then gives Jimmy the song and dance they are ok for now, see how things go, re-evaluate in 6 months, which was about as polite as he could be to Chuck's brother to tell him to GTFO, it will never happen.
Jimmy has burning hatred for him ever since then. I also think Chuck has a selfish streak and will take the case and toss Jimmy in a second. He jumped on that case with "we" pretty quick and caught Jimmy off guard.
I think we'll find out that Chuck didn't fight too hard for Jimmy. His initial response to Jimmy passing the bar was pretty underwhelming and objectively, Jimmy wasn't qualified for a job at HHM. I think he sent in Hamlin to do his dirty work and tell him no. Not giving him a job is perfectly reasonable, but I think Jimmy will take it personally, especially since Chuck didn't have the guts to do it himself.
I agree about Chuck's selfish streak.
One could interpret Chuck's narcissism as instead, a fear of embarrassment of Jimmy going back to being Slippin' Jimmy.
Chuck is clearly someone who places a great emphasis on doing things the right way. He is very obviously embarrassed by Jimmy's past antics (or occasional present-day schemes). He even gets nervous about Jimmy going dumpster diving for the shredded docs.
Chuck's initial reaction to Jimmy's good news seeming underwhelmed, could be not so much selfishness, but a reaction of a) disbelief that Jimmy could do something like this without it being a con and b) skepticism of the College of American-Samoa as a legit law school. I could easily see Chuck feeling that getting a law degree through correspondence courses, is not the "proper way" to do things.
I don't think Chuck is so much selfish as neurotic. He gets completely stressed out by appearances and propriety and the Slippin' Jimmy antics are a big stress on him.
Now the selfish-ness may show up in the future. If he wants to go back to Hamlin (as I predict he will) and take Jimmy's case with him, then that's pretty selfish and crummy.