Does Thompson really cast himself as an outsider? Seems to me it’s more like he says the system is a boondoggle, and he knows it because he has been in it. That isn’t the same as posing as an outsider.
I think you’re right on the money. Fred himself has never said “I’m an outsider” rather he has indicated he’s been on both sides and has been in it enough to know just how much of a boondoggle it is. However, since he has worked in the private sector too (granted, as a lawyer), he’s got more credibility.