Since reading this book: en.wikipedia.org/wiki/On_Bull... -- I'm convinced Trump doesn't really care either way. He just wants to be in the headlines. It's his sycophants that are more worrying, because they're the ones who might actually act on his BS.

It's all speculation, but he might simply be under huge pressure from the investors in Automattic. Left or right, he's definitely handling it terribly and it's hurting the WP ecosystem.