He's really the same as he's always been, just the more you watch and listen the more you find out about his questionable views.
I disagree with him on most things, but I respect him as a pundit because you can really tell that he's providing opinions that are truly his own. He's a conservative democrat that everybody hates, and he ignores the pressure to fall in line with either side. He's pro-military, pro-gun, pro-surveillance, but also all for drug legalization, medicare for all, and vehemently supports separation of church and state. It's a weird mix and even inconsistent at times (he loves individual freedom but hates women so abortion is tricky for him!) but you at least have to admit he's one of the last remaining pundits that isn't a mouthpiece for politicians.