In "Training Day," Jim and Pam try to make a good first impression on their new boss Deangelo Vickers. They believe they have started off well by showing him pictures of their baby, but Deangelo soon gets annoyed with them. In "The Inner Circle," Jim is shown to be one of Deangelo's favorites among the staff. He is temporarily banned from Deangelo's inner circle when he speaks up for the women after they object to Deangelo's sexist attitude. Jim later calls Deangelo out after the boss brags about a Michael Jordan dunk he can perform, which causes a traumatic brain injury and leaves Deangelo in a coma.