He most probably says it because he knows it's going to get a reaction - I doubt he doesn't know how it makes you feel, that's the point, he knows it makes you feel crappy. My DD has tried it on both DH and I, but we found it quickly stopped when we both blandly said, "Okay, doesn't change anything - you still have to do it (or can't have it)" or "that's too bad" and left it at that. It had no collateral then. Kids love to push buttons, that's how they refine us as parents, how they test and understand boundaries, and the go to buttons are always the emotional ones. I think he is simply trying to manipulate the situation to get what he wants. It's a control issue, and kids normally try take on these control issues at home (where it is safe) because they feel out of control else where (i.e. school, where what he does is dictated by the teacher). Perhaps he needs a hobby or outlet where he can feel empowered so he doesn't keep lashing out in the wrong areas. Could he start his own business? My daughter runs her "Henny Pennies". We bought an extra chicken so that we would always have too many eggs so she could sell the surplus to the neighbours or mum's at school.