Poe's law here, I can't tell if you're being satirical or genuine. By one argument, he's a shill for trying to 'run the world' in the approved, nominal 'establishment' way. By another argument, he's a (I know we all hate this word) maverick who has become popular with extremists and republicans who are dissatisfied with their party and its leadership. Therefore, anti-establishment.
Because the President can't do most of the things these people are promising/threatening without at least their party backing them, they're either fooling themselves or cynically manipulating burned out votes trying to recreate Obama's trick of winning through the votes of people who don't vote. My money is on the latter for the most part; Trump is pretty open about it.