Jimmy saw their father's complete lack of a spine as a child.
We saw how Jimmy tried to let his pops know he was being scammed and pops would hear nothing of it.


Jimmy, as a young boy, was told that the world essentially consisted of predators and prey. Jimmy told pops what was going down and pops, a lot like Chuck, in fact, simply brushed him off. His dad gave him an example of prey and that’s where the seed was planted. Do you want to get got or be a taker?
So Jimmy took. If there’s a chicken or the egg argument, there’s still a case to be made that Jimmy’s father assisted greatly in the creation of Slippin Jimmy .

And when Jimmy made clear and honest efforts to get it together, Chuck despised him for it.

Here’s the thing: If Jimmy was still such a scumbag and Chuck couldn’t trust him, how was it that Chuck trusted him with his finances, his food, supplies, and pretty much everything else outside of wiping Chuck’s ass.

The firm would have gladly assigned someone to Chuck’s care, so it wasn’t as though Chuck was some old man with nobody to help him. Perhaps there was some embarrassment involved, given Chuck’s pride, but that ultimately illustrates the depth of trust he had for Jimmy.

In fact, Chuck trusted Jimmy implicitly. He put his life into the hands of the one person he knew would unfailingly take care of him in the way he needed. The one person with enough blind, unyielding loyalty to Chuck to be at his beck and call at all hours, without question.

His brother.

For a scumbag he didn’t trust, he certainly put a lot of trust in a man who could have poisoned him, signed a will leaving every penny of his share of his firm and ultimately taken everything from him.
Jimmy never asked for the keys. He just wanted a little respect and support from his brother for all the hard work he’d done. In fact, Chuck gave Jimmy the keys to pretty much everything and that just doesn’t jive with a guy who mistrusts Jimmy the way you say Chuck did.

The context and reasoning of every move Chuck has made has been nearly exclusively to Chuck’s benefit and Jimmy’s detriment. As I wrote earlier, Chuck hides his malice behind altruism. It’s crystal clear that while Chuck sincerely believes the law to be a sacred responsibility and Jimmy to be unworthy of such responsibility, that’s not his actual motive. It’s merely his justification and legal standing. He is a lawyer, after all, and a great one at that, and he’s hiding his true, emotional motivations behind the law.

Were Jimmy such an untrustworthy scumbag, Chuck would never have allowed him in the mailroom of his law firm. Think about that:

Slippin Jimmy in the mailroom of a high powered law firm? That’s a big deal. Like, a really big deal. A guy like SJ would see and find a goldmine through such a seemingly innocuous positon. One or two sensitive documents, one or two leaks, maybe some blackmail, something. Who knows. What we can deduce is that nobody with any sense puts a guy like Slippin Jimmy in the mailroom and you don’t have a mailroom if all you’re getting is the electric bill.

No way in hell Chuck allows Slippin Jimmy to take that job in the firm he built. Unless, of course, he believes Jimmy to be sincere.

Nope, Chuck’s distrust is only stirred when Jimmy shows his independence and true competence. Jimmy showed the sort of work ethic Chuck claimed he lacked when he literally pieced together the case in the old folks home. If Jimmy stayed in the mailroom and remained Chuck’s loyal manservant to Chuck’s kingdom, Chuck would trust lil Jimmy just fine.