Roscoe's Links
John's a good man. Really. Most lawmen would've probably shot him after all the chances they got. He wants to believe John could keep him safe if he abandoned Roxie, but... he's just one man. Not even he could stand up to all of her Boys.
How does a meek little fella like Roscoe end up in Roxie's Boys? For that matter, why? He doesn't even seem to enjoy the crimes he does. Is Roxie holding something over his head? Whatever it is, John'll figure it out.
Miss Roxie found him after he calmed down a raging bull. She must have thought he was useful, because she threatened him with all sorts of horrible things to get him to join her group. He's trying to play along until he finds a good opportunity to run, but there's nowhere in West Ridge he can run that will make him safe from her... and he doesn't have the money to flee any further than that.
Roscoe's a weak link. She knows it. But his ability to talk with animals makes him useful enough to keep him around. If he gets it in his head to leave, she'll just send someone to drag him back, and he won't get to stay in the nice bunks like he does now.