Why is it sad? If he is self-dealing between wordpress.org and Automattic, that's a big no-no. It sure looks from his comments here like he sees the two as one entity.

Also, the man outright said "use 'WP' since we think 'WP' is generic" and then cried "brand confusion" years later. If you want to avoid brand confusion, maybe don't tell people they can use your trademark?