There are, to me, abundant signs that he is severely burned out, dysregulated and irrational.

(In this statement, in other statements, in his actions that wilfully worsened his own case against WP Engine, in his blog posts etc.)

These are mental health issues. I have experienced many of them myself (I am indeed recovering from them now) and do not know what else you could possibly call them.

He is very evidently experiencing continuing poor mental health. I don't know why the board would say "leave of absence" if they were not themselves alluding to his health. He clearly needs a break from the thing he does for his own benefit.

I absolutely wish him well and hope he steps back and takes care of himself for a while; none of this is worth worse health.

The speed with which Matt hijacked that plugin was one of the funniest parts of this saga. All while complaining they don’t contribute!

Many an old open-source project ran into this trap. Elasticsearch is one good example. Back when the old GPL era open-source projects were invented, the idea of third parties taking open-source software and just making a shitload of money with it was unthought of - and certainly not at the scale of Amazon AWS.

The only counterexample was Wikipedia's MediaWiki, it similarly is GPL but from the start it was clear that there would be at least one commercial side actor - Wikia, nowadays called Fandom.

But moreover: I guess there's a presumption, whether fair or not, that well-paid executives overseen by wealthy boards of directors are pre-vetted and act in good faith, whether or not those actions pan out and make money; versus robbery or violent crime that people recoil from, that assumption of good faith isn't there, because it's self-evident to ordinary people that there is no justification for such actions.

I think if we are just looking at the media:

Most journalists wouldn't consider some nobody stealing $20 to be newsworthy in itself.

Most corporate scandals receive extensive media coverage. Even a CEO who was merely incompetent instead of corrupt, is still likely to get some bad press.

Now, you are completely right that the non-media consequences are very different – significant chance of criminal record (although in many jurisdictions, there are mechanisms which first-time offenders on minor charges can use to escape getting one) vs a multi-million dollar severance payment.

The issue with "golden parachutes" – if someone's employment contract creates an entitlement to a severance payment (and in some jurisdictions employment law creates one even if the contract itself doesn't) – then you generally have to pay them unless you terminate for "misconduct" (often even "serious misconduct"). The problem with terminating for "misconduct", is it creates a big incentive for the terminated employee to sue to try to get the severance payment they'd otherwise receive, and the larger the payment, the bigger the motivation – which creates an expensive legal and PR headache. The PR issue is especially acute for senior executives–a junior employee suing over a severance dispute will get a lot less media coverage than a former CEO doing it. So, unless the conduct was extremely egregious, there is a strong incentive for the employer/board to just pay the severance out and make the legal and PR headache go away.

Getting pushed out of a position is very career damaging at the executive level. Those golden parachutes are pretty rare, too. Most of the executives I know from companies you haven't heard of (and some that you maybe have) who were pushed out took a huge hit to their careers after that. The best play is to start calling up executive recruiters and try to get any job as soon as possible once the writing is on the wall that you're being fired.

And come on, stealing $20 doesn't register these days.