Here’s the piece on Kristol by Judge. It’s interesting, although Judge doesn’t really come up with an answer to the question.
But I didn’t expect him to. I’ve long pondered what happened to Kristol, and haven’t really come up with an answer either. Yes, the facile answer is “Trump happened,” but to me that’s no answer at all. Why did Trump’s advent on the scene cause previously sane and thoughtful people to go over to the dark side – that is, supporting the left, which is what Kristol now does? It’s also easy to say that he was always shallow and only in it for notoriety or whatever downputting explanation you can devise, but as Judge writes:
I wrote for the Weekly Standard for the first couple years of its existence in the mid-1990s, and in those days Kristol was a serious yet kind man who saw that the threat of political correctness and academic Marxism was real. One of the first pieces I did for him was about the radicalism that had taken over Georgetown University. That radicalism has now metastasized into wokeness, which has destroyed lives and crushed free speech.
On his Twitter feed recently, Kristol posted a video of Ron DeSantis condemning this neo-Marxism. Kristol’s comment? “This is the way the American conservative movement ends—not with a bang but a whimper.”
I have my own experience with Kristol, too. I met him a couple of times, once at a medium-sized gathering where he gave a talk and then there was a dinner where I happened to sit at the same table of around eight people. We have a mutual friend who had known him for decades and thought highly of him, and this person now can’t explain his change either. I wrote a number of articles for the online Weekly Standard (you can find them here at the Washington Examiner, which seems to have taken over the Weekly Standard’s archives) and he was always kind and smart and seemed quite principled. So I am deeply puzzled by his behavior.
Why do I even care? I care because it is a case of political change, which is a special interest of mine, but also because it surprised me that it was such an extreme change after all those years, as well as change of the more rare right-to-left variety. You can say, “Oh, he never was really a conservative because he was a neocon,” but Kristol certainly appeared to hew to conservative principles in most things except foreign policy for most or perhaps all of his life. Was he also one of the world’s best actors? I don’t think so. And he had plenty of fame and I doubt he was ever hurting for money.
Others say that Kristol and others made their change in order to keep on going to the parties with the in-crowd. But that just seems like weak tea to me, if a person seems to be guided by principle in the first place. And his repudiation of the right was far more global than merely a rejection of Trump himself, which would be more understandable. For Kristol, it has involved a fairly full-fledged embrace of the left at a time when the left has become even more pernicious, dangerous, and powerful.
I think Judge comes closest to an answer when he writes this:
Lacking the experience of life change—Kristol inherited punditry from his dad…
I have long thought it’s incorrect to call Kristol a “neocon.” The claim is based on his truculent and interventionist foreign policy stances, but the reason it doesn’t seem quite right to me is that the original definition of the term (and the one I prefer) is someone who had a political change from left to right. Kristol never had that change; as Judge writes, he inherited his politics – and even his profession – from his father Irving Kristol. And his father was a bona fide neocon, a leftist turned conservative who was described by The Daily Telegraph after his death as “perhaps the most consequential public intellectual of the latter half of the [twentieth] century.” Those are big shoes to fill, to say the least. Irving Kristol died in 2009, before Trump became a large political figure, so we don’t know how he would have felt about him. But Bill always stood in his shadow and perhaps never quite freed himself from his influence. Perhaps this recent anti-Trump pro-left position is the son’s adolescent rebellion, long-delayed.
I admit I have no idea if that’s the case or not. But simple Trump-hatred really doesn’t explain how far Kristol has gone.

