He also said several times in the conversation with her I don't dislike you so which one is it JJ??? I don't think he knows. He is just hating on her because he knows she got booed and knows there will be some big ugly butter face girls hating her out there so he thinks he will look good.
Josie is another pawn in his game. Josie is not a looker so Mr James plays her along and thinks the votes for him will come rolling in from the butterface girls. What a game he is playing. But constantly picking on someone when you can just leave them alone is going to be his downfall.