>>212569179You've missed the subtext that Jimmy's gift is people, and it comes to him innately just as it did to their father and that's why he was always the favourite.
Chuck is a man of rules and rigor and simply isn't likeable, so even when he has Jimmy dead to rights with records of pilfered money they side with him.
Chuck ends up clinging to the fact that he's a lawyer with an illustrious career whilst Jimmy is a no good slippin' bum, but then Jimmy manages to get a law degree and Chuck knows the business well enough to understand that his people skills will take him far, perhaps as far as Chuck even.
So Chuck is simply left with nothing. He's not the intellectually superior and accomplished but coarse older brother, he's just the worse of the pair like how he always felt with their parents.