What a silly notion. You're not affiliated to a company merely because you are their customer.
I'm not involved in any of this except as a spectator. I don't even use Wordpress. Just saying, I could see why someone might not want to split legal hairs with their leadership right now, even where it's very likely you'd win such an argument in court.
I wouldn't be so sure. He seems to have gone off the deep end. I know folks, including some successful ones, who legitimately believe that anything that commercially hurts them is illegal, and when a judge sides against them, it's due to bias and not the law.
(I don't know if this type of auto-victimisation has a name. You see it parodied by South Park in "The Worldwide Privacy Tour." And, less hilariously, by public figures complaining about their free speech on talk shows and at press conferences they called.)
One time a friend of mine was showing me a bunch of fancy camera gear he'd bought for his wife's ghost hunting business. I pulled him aside and asked him if he really believe in the spirits and apparitions she talked about. He replied, "oh, for tax purposes I completely believe this bullshit."
By analogy, even if Matt's lawyers privately agreed that a lawsuit over the meaning of "affiliation" is silly and doomed to lose, I can imagine them replying "oh, for billable hours I completely believe it."
Most commonly this comes in the form of false victimhood, e.g. look at how hard they are trying to shut me down. Other times it manifests like this. The problem is it's a logical attractor; whatever belief it first attaches to, it monotonically increases faith in.
Sounds exactly like one of the candidates running for POTUS!