Like @Cane23 I often find it difficult to comment immediately after reading @CasualWanderer82's chapters because they are so full of emotion and thought provoking. Being so late to comment on this chapter there is little to add to the thoughtful comments already above.
Bishop is certainly flawed and has made flawed choices. I see him as content on his manicured lawn with his wife and daughter but not truly happy in himself. He craves the adrenaline that missing behind those Florida gates. Even when seriously injured because of the robbery and could be dying his response is "Can't believe...we pulled that off…"
So where is he now? His response to Pawn, "Yes," he whispered, his voice breaking. "Yes, you did." isn't just about the horse.
Once again @CasualWanderer82 phenomenal writing.