Bobby started doing numerous robberies around Old Town to make enough money for when his girlfriend, Mary, was released from prison. He used Tommy as his patsy when he tried to rob a bank (claiming it was merely a game of Cops and Robbers). However, Tommy's playful attitude ruined their first attempt at it. In their second try, Bobby had Tommy carry him while wearing a long coat to make him look like a tall person. The robbery was a success, until an old woman recognized him as "that midget". Bobby shot her in response, which propelled him backwards off Tommy's shoulders. Bobby tried to run away with the loot, but Tommy pursued him (still believing it was a game). The Sheriff joined the chase mid-way, but Bobby managed to escape. Bobby then went to the tavern to meet up with Mary, only to find Tommy and Sheriff disguised as her. Bobby tried to escape out of the window, but it turned out of be a fake window and he was arrested. Since Mary stood him up, Bobby concluded that he was the patsy all along.
Bobby has a very short temper. He takes great offense to the term "midget" and "retard" and calling him the former could make him furious. He's known to make squirrel noises (something Mary finds sexually exciting).