Matt’s position is (ostensibly) based on his hard line views about the moral obligation to contribute created through the use of open-source. The trademark sideshow is based on Matt’s understanding that a moral argument isn’t going to convince a private equity backed company to spend money they don’t need to spend. Matt believes WPEngine has a moral obligation to contribute and the trademark licensing fee is the easiest tool he has to force action.
Matt is making a moral argument. WPEngine don’t care because they’re driven by money not morals.