Last season Chuck's history with Jimmy clouded him from seeing Jimmy's earnest attempts at going straight.

This season Jimmy's attempts at going straight will cloud Chuck from seeing that Jimmy still hasn't changed.

It is curious why Jimmy didn't immediately go to Cliff with the commercial for approval, but like someone mentioned above it'll surely come out at the meeting. Before the call from Cliff, I was thinking his misgivings with the tape was some sort of hollowness (or lack of a rush) from doing something without a con. I'm pretty sure I'm wrong in the case of the commercial, but that will probably end up being true down the line (in whatever ends up being the final straw between Jimmy and Kim).