Lifson is overthinking here. Romney’s actions are much easier to explain when you just realize he is like the smarmy little arse from high school who can’t get invited to join the “in crowd” no matter how much he tries to suck up to them, so he just keeps trying harder. Most all of us knew little worms like that back in high school, didn’t we?
So, I take it you were one of the “in” crowd, and viewed others who didn’t have your credentials, as inferior.
I don’t care one whit for Romney; I find him repulsive. To me, he seems more like one of those from the “in” crowd that you describe. He doesn’t like Trump because Trump isn’t an insider like him.