I've loved so much of what he's had to say over the years... However, I always differed slightly in his ultimate stance: that we can't really do anything about it and we need to keep supporting the state until something better (magically?) happens.

I haven't watched him for awhile - but his Trump stance doesn't surprise me too much... It's within the limits of the system, and (perhaps, admittedly, my inaccurate view of) his stance would be in alignment with it.