We’re at a point where Howard is almost BFF material in comparison, and we all know Jimmy would probably love to string Howard up by his belt loops and permanently lock him inside the mail room.
At this point, Chuck and Jimmy’s relationship is as frayed as we’ve ever seen it, and it’s probably as bad as it’s ever been.
Plus, Jimmy knows people that can “take care” of Chuck, should he not want to get his own hands dirty.
(Although he’d have to get them dirty at some point for this theory to play out.)