Just a crazy thought but might have some validity. What if Richard is really working for the man in black. When they go to where Jacob lives he doesn't go in, just says "Tell Jacob I said hello", is this because he isn't allowed to see Jacob but then how did he get orders from Jacob to give to Ben or does he hate Jacob. He says Jacob made him the way he is, maybe he is pissed that he lives forever on the island outliving everyone else, nothing is constant in his life, loses anyone he cares for always serving the new "leader" of the Others. Maybe he will age and die if Jacob is really dead. Just because he knew the answer to "what lies in the shadow of the statue" doesn't mean he isn't playing against Jacob with the man in black. Maybe when "John" comes back he understands who it is and so he follows his orders, questioning in front of Ben and the others to make himself not look complicit in their plans. Feel! free to rip apart the theory.
