Matt has claimed[1] before to be "post-economic", i.e. has enough money that it doesn't matter to him anymore. It's hard not to see this as personal, not financial.
WPEngine (and a horde of Emanuel Urquhart lawyers led by Rachel Kassabian) are taking him to the cleaners. This won't be pretty. A preliminary injunction is not easy to get, it's really likely WPEngine will win at least something.
Despite not needing the money, Matt seemed to be very upset that WPEngine was making money.