Factual error: In the scene of Jimmy driving with his new Mercedes, we can see a Subaru forester that is definitely a model after 2010. Season 2 is set in 2002 so this couldn't be possible.
Continuity mistake: Once Jimmy realises Chuck is about to enter the room, he reaches for his glass and holds it up to his face for a drink. In this shot, Kim is looking down at the table. The camera changes angles as he's taking a sip, and suddenly Kim is looking to the side at him.
Answer: It might be the Panavision cap he wore when directing his terrible commercials.