Jimmy is a pre-war ghoul from Pennsylvania, before the war he did a spectrum of odd jobs he was not particularly good at until he signed up for the army. There he was able to do one thing he was damn good at - standing and guarding a boarder. He left the military before the war, which left him stranded in the midwest. After wandering around for nearly 200 years, he attached himself to a couple of young bucks by the name of Adolin and Sketch. They have wandered around since then for a few years.

When the player finds Jimmy, he is currently awaiting a dispute against him for the damages to a bar caused by a bar fight at the Inn & Out that left a man dead at his hands. He was found to have acted in self defense for the killing, but the damages to the bar needs someone to pay, so the owner Scott Killian has made a dispute against him.

The player can later decide if Jimmy is responsible for the damages or not in a trial held in the center of town. Depending on how the trial is decided, Jimmy will save Buck (owner of Jerky in Sandlot) from certain death or bolt from the town to never be seen again.