My impression is he's used to getting what he wants because most of the time he does. Whether it's daddy fixing it or whatever else is done so he gets his way. I forgot exactly what he said in the episode his character first appeared but it was something like, "C'mon Leslie! Why don't you quit already so I can win this thing?" as if it's a foregone conclusion. I think Paul Rudd does a nice job of playing him because he doesn't come off as a spoiled brat. More like someone who just thinks that's the way the world works.