Automattic has had the trademark for a little under a decade. WP Engine has existed since 2010. The argument for the trademark has been lost. If you don't actively crack down on usages of your trademark, you can't arbitrarily decide to enforce it in the future. Especially not against a company allegedly making hundreds of millions in revenue from your trademark: you've had to actively ignore its use for a decade.
That's even ignoring the question of whether you can really argue that they're violating your trademark for calling their service "WordPress hosting" as shown in the exhibits. They're not passing something off as WordPress, it's literally WordPress that's being hosted.
Highlighting Reddit and Twitter posts calling WPE "WordPress engine" is nonsense. Highlighting a page where a WPE partner uses the wrong company name ("WordPress Engine") is embarrassing for WPE but still something of a reach. Highlighting a content farm post saying "WP Engine" stands for "WordPress Engine" is absurd. Making the argument that "WP" is covered by the trademark is ridiculous, especially when the replies on Twitter screenshot the receipts of WayBackMachine snapshots showing Automattic telling folks it's totally fine to use "WP".
I own a trademark for my business, and my lawyers had a (very gentle and kindly written) letter sent to two teenagers who started a podcast whose name infringed on the mark. If my lawyers care about that, Automattic has exactly no business trying to turn around on WPE at this point. This is just petty drama.
Agreed the trademark case seems pretty thin and then when you see they changed the trademark page today it seems like a loser for Automattic
Related:
WP Engine sent “cease and desist” letter to Automattic (279 points, 1 day ago, 223 comments) https://news.ycombinator.com/item?id=41631912
Open Source, Trademarks, and WP Engine (30 points, 1 hours ago, 19 comments) https://news.ycombinator.com/item?id=41642597
Why do otherwise smart people start feuds like this?
I think that most people on HN would agree that 1) the most likely outcome of this feud is negative for Automattic and 2) Matt should have reasonably known that from the start.
Is it some consequence of a passionate founder having the influence to choose emotions over business sense?