The first meaningful internet presence he had was the whole WP engine debacle, which seemed to be a pretty ill-advised thing to do from a legal standpoint and a

The first meaningful internet presence he had was the whole WP engine debacle, which seemed to be a pretty ill-advised thing to do from a legal standpoint and also upset the open source community, who are rightly concerned about that sort of thing. Some of the actions taken then broke a number of small sites, upsetting those users. Overall, you've got a baseline reasonable number of pissed off hobbyists with internet presences. Microsoft has had its controversies, but the reason the interest became personal here is it seems this was his own initiative (he kicked everything off with a public blog post). And once again in this case, it looks like a bunch of chaotic behaviour centred on the individual more-so than standard "unpopular corporate decision making". That sort of thing has a big PR blast radius and has exposed him to criticism more than necessary (or normal). Given how avoidable the above is (by simply operating through his lawyers / the organisation), it's feeding speculation on his mental state.