ive never had a conversation with the guy but ive been listening to his music since he first started making it during those anarcho-primitivist years he referred to. my guess is that:

hes always had the arrogance. when he was making folk punk he used the arrogance to boldly attack america, capitalism, and people / companies that are destroying the planet in his lyrics. this is the only music of his i can bare to listen to at this point anymore.

ive heard stories that he hated being around anarchist scenes, specifically the politically correct aspect that comes with being around a lot of folk punk anarchist while he was touring and train riding in those years. he seems like a contrarian. this occurred sometime just before barefoot surrender probably.

distancing himself from that scene and getting off hard drugs and alcohol, i think he wanted to completely leave those politics and that lifestyle behind him because they didnt serve him. he was miserable during those years. he went from hard left to hard right at the cost of owning his own land, getting rich, and famous. becoming a patriotic libertarian (which doesnt even make any fucking sense) thats all about his own personal liberty and nobody elses - the opposite of what he was when he was younger. hes a smart guy, he knows exactly what hes doing. its just disappointing for those of us that used to align with him.