At this point, he basically started leaning into controversy for pageviews. He'd start linking to the controversial section of each post right at the top of the post. After a few months or so I had to unsubscribe, after years of reading his blog and Dilbert cartoons/books.
He's become such a gremlin that I won't be 100% sure he's serious about this until he actually dies.
Well, that was already the first sign of senility. Trump, at that point, was already a know quantity for decades: a crook and a con man.