Grimes ruined Jimmy's cover on his first day on the force, and Jimmy shot his leg in return. Jimmy taught everything about going undercover to Grimes. They were on a mission to catch the new leader of Hell who was revealed to be Aldermach Maggotbone. Grimes bungled the occasion and shot Jimmy who had taken the disguise as part of a wall. As a result Grimes repressed the memory that he ever was a cop.
35 years later, Aldermach is about to pass down his position to his daughter Callie. At the ceremony, he switches his choice to his assistant Cathy. When Cathy is about to receive the giant demonic snake Slitherax, Grimes arrives and shoots Cathy multiple times. As it turns out, Cathy is in fact Jimmy who has been undercover for 35 years, and Grimes screws him up once again.