"Unfortunately", because Matt did a lot of good for the internet over the past two decades. WordCamp is (or was) really amazing, the community he built is really great, the Automattic Lounge was cool, he's donated millions of dollars to good causes, and WordPress powers a large portion of the Internet.
The purchase of Tumblr was basically Elon purchasing Twitter without the political gain. I'm amazed the purchase decision was ever made, and more amazed that it still exists after the hit to the user base.
He read the commit logs and understood much of what he read. That's deep understanding of the product. That alone puts him in the top few percent of CEOs.