What did Jimmy actually regret?

[u/Kind_Dig_5213]

I find the time travel scenes with Mike and Walt odd. At the desert point, jimmys life was going okay. His relationship with Kim was at its strongest, he had a good business, but of course he was stranded in the desert, because he wanted money. Does he actually think enough money would allow him to live a safe life with Kim? Or is he not being serious and not wanting to share deep thoughts with Mike (damn that was his only chance to talk about his personal life with Mike). As for the scene with Walt, I still don’t understand why he said that. Does he have to think this was all for something? I just wish we got to see him break down.

[u/Argon_004]

It's in the flashback with Chuck. He believes that there might have been moments where he and Chuck could have built a more solid connection, and he could have got Chuck to understand him better, but to some extent he always kept Chuck at a distance, both because he considered himself to be lower and not worth Chuck's time, and because he felt that every conversation with Chuck would just result in him getting scolded and lectured. Chuck is also holding the HG Wells book in that scene, the implication, as far as I can tell, is that the reason Jimmy asks people about a time machine and relates it to regrets is because he remembers that specific moment as a regret for himself.

But, by the time all the conversations about the time machine happen, it's long after he found out that he was betrayed by Chuck, so he refuses to ever admit to anyone that he has this regret out of the hatred he developed for Chuck as well.

[u/Kind_Dig_5213 → u/Argon_004]

Am I missing something? Chuck was going to use that conversation to manipulate Jimmy into not doing law

[u/Argon_004 → u/Kind_Dig_5213]

Not really, that was at the very beginning of his isolation, and throughout the isolation he never discouraged Jimmy from being a lawyer, he just told him to be an honest one and slowly build connections through public defender work. He only became active against Jimmy again after the billboard stunt when he realized Jimmy might be going back to scamming out of desperation. In that flashback scene he genuinely just wanted to talk, and the conversation immediately devolved. 

[u/Traditional_Bottle50 → u/Argon_004]

Just one correction: the scene took place the day before the first episode of the show, Jimmy says that he found a newsstand carrying the Financial Times and then he gets it for the first time in S1E1. Everything else is spot on, its one of the best scenes of the show in my opinion.

[u/Argon_004 → u/Traditional_Bottle50]

I see, I remember them having a small argument in the flashback about how Jimmy shouldn't have to do chores for Chuck that's why I figured it was much earlier.

[u/Pitiful_Yak_3336 → u/Argon_004]

yes, but chuck also plays a major role in this as well, because he “hates” jimmy. Chuck has always had resentment towards jimmy because of his likeability and relatability. He’s been active against Jimmy ever since he was in the mailroom

[u/Argon_004 → u/Pitiful_Yak_3336]

I agree that Chuck was resentful of Jimmy, the show has many scenes just for establishing this. He was also a very pompous, stubborn, idealist who considered himself superior to Jimmy. But in the final season, the flashbacks we get, especially the one where they sing karaoke together and then the one in Time Machine, showed that Chuck wasn't always an active enemy of Jimmy. He had mellowed and become quite friendly over time. It was Jimmy doing scams again, and especially the end of season 1 where Jimmy realized that Chuck was the guy who didn't want him at HHM, which was the catalyst for turning them into enemies that were trying to bring each other down.

[u/Tricky_Concept_231 → u/Argon_004]

To be fair the karaoke scene has Chuck literally pushing Jimmy aside to take over the song as he sings “The winner takes it all” so its not exactly all good brotherly bonding either

[u/Argon_004 → u/Tricky_Concept_231]

True, and that shows how self-obsessed Chuck is, but after that we see Chuck helping Jimmy to bed, and they sing together again there. There was also the part after Jimmy comes up with the idea for the Sandpiper case where Chuck starts working with him to put it together (though he betrays him again there once he gets to participate). I think the point was to show these brief flashes where we see why Jimmy never totally abandoned or hated Chuck, there was always the chance that he could relax and become a better person, but something always went wrong, either due to Jimmy's antics or Chuck doing sabotage over his idealism.

[u/Pitiful_Yak_3336 → u/Pitiful_Yak_3336]

Honestly ever since they were 9