I think he does know in some general way that he's playing Robin Hood in reverse; but I don't think he could describe or defend the process and I am certain that he doesn't care about those he would hurt.

<Like Romney, he thinks that by being given a fortune by his father, he hit a triple.>
Exactly; but I think Romney (like the Bushes) genuinely cares about people less fortunate than he, even if he has a hard time empathizing with them. I think it would be impossible for Donald Trump to care less than he does about the victims of his lies and broken promises.