He got associated with the "intellectual dark web" for occasionally having opinions outside of the mainstream. The NYTimes was even planning on writing a hit piece on him back in the day that scared him so bad he shut down his original site. I think his writing today lacks the sort of honesty or novelty it once had because he's very sensitive to being called out.
I don't quite see it that way. Imo he's been to involved in anti-woke culture waring, but I still found him to be wonderfully interesting to read.