To have a history of trademark enforcement would be my guess, but I think we're all learning that Matt is way over his head, probably from before the whole WPE situation. There's no consistent strategy or narrative.

What I got from other sources is that Automattic's finances in general are not looking too good, and this is just one very public occurence of a flailing, under qualified CEO trying to be hands-on to solve the situation.

It would be hilarious if it’s to get a history of trademark enforcement, I don’t think you can do that after 10 years of no enforcement and after already being in litigation.

If that's what he's doing, I eagerly look forward to the judge's choice of language.

I’ve worked with Matt’s team while I was in the hosting industry- Matt has always cared very deeply about it being called WordPress. I’ve written recursive web crawlers to alert us on miscapitaizations for this specific issue, even 10 years ago.

The simplest non-conspiracy theory is that he didn't regularly visit that subreddit until recently.