I’d go with the most obvious explanation: Matt found out their biggest competitor makes more money than WP.com and does’t give back (money or development time), got rughtfully pissed, but started doing ridiculous things instead of just calling them out.
Most of my other comments I was speaking in first person, in others I did not initially realize it wasn't as clear in some of them.
I also updated my bio here to reflect the product I am working for belongs to Automattic. Previously, it only mentioned the product which not everyone has to know belongs to Automattic.
Your employer has been served a cease and desist. Does your legal counsel know you are commenting on the legal matters on social media as an employee? This doesn’t seem like a wise position to put yourself or your employer in.