Hot take: He's been getting dozens of upvotes immediately after he posts his comments, and is interpreting them as broad support, rather than people egging him on or giving the comments visibility due to their outrageous nature.

It's another case of tech CEO caught in a self-reinforcing social media feedback loop/echo chamber - a la Elon.

could even be a little from column A, a little from column B

I don't even know if it's a vendetta about WP specifically or just the result of his general disposition. About a year ago he had an embarrassing public meltdown after some random Tumblr users talked shit about him because they didn't like his moderation policies. Banning people, then publicly shaming them, then replying to their posts on other social media sites...

> some random Tumblr users talked shit about him because they didn't like his moderation policies

Was that the hammers thing, or something else?

That would be the infamous "car covered in hammers", yes. And it was from February this year - time flies (like a hammer).

My take is this is 100% someone sticking to a naive worldview because they are smart and logical (and I don't doubt that they are). But the world doesn't work like that. And as much as I hate to admit it, these WPE people are playing the game and just baiting and provoking a response from him. They're like schoolyard bullies that poke and wave hands inches from your face, then cry foul to principal Government when you rightfully retaliate. As much as a smart and "fair" person would think this is a reasonable and logical response, the principal does not think so. They will look at the rules, say "a ha, you broke rule 3(a) and hit someone", and then send you to detention. No amount of if, buts, and logical "reasons" will matter at that point.

There’s a whole-ass archetype among founder-owners of successful companies who stick with them long-term, that looks like this. It’s not all of them, by any means, but it’s definitely one sort. In ordinary circumstances it manifests as a preference for maintaining control over making moves that might, by some measures, be better (improving business success, or limiting liability, say) and a string of quiet and maybe fishy-seeming but not exactly red-flag dust-ups; when a big enough obstacle (especially to that whole “control” thing) shows up and throwing their weight around can’t make it go away, though, things can get real dicey.