Greg's Boss, Mr. Savitsky, volunteered to sponser a criminal in a work release program. He doesn't want to do the "dirty" work, so he passes it off on to Greg. Greg in turn passes the criminal off to Jimmy because he doesn't want any part of working side by side with a convicted felon. He feels bad when Jimmy seems to be making a real impact in the life of the inmate (Travis Tritt), so Greg decides to prove that he isn't s stuck up snob, and he finds a work-release prisoner of his own (Trace Adkins)to mentor.
Greg and Jimmy are in a competition to see who is the most generous and best mentor. They end up leaving the lot to take the criminals out for a big lunch of shrimp and beer. On the way back to the studio lot, they stop at a convenience store, where the work-release prisoners rob the store and everyone in it - Mr. Savitsky of course, being one of the customers robbed at gunpoint.