Rewatching the 1st two episodes of season 1. For starters, I can see why he doesn't want Kim to be just a public defender because he was just that and he was at his most depressed state struggling as a public defender.
Also, it's crazy how ALL of this started over a skateboard con that went wrong. The thing, the Jimmy back then, still had the ability to bullshyt his way out of the situation. Jimmy right now was so out of his game, dealing with PTSD and dehydration that it's a good thing Kim was there.