Exactly, it hearkens to the halcyon days when Microsoft was the biggest evil in tech.
Learned a bit more about this initiative since then. I guess this is a great example of why I heavily dislike creator initiatives like this. In their world getting more people to comment is a good thing, no matter what the comment says. In the real world this mostly benefits the creator and harms the initiative, since the first interaction people have with it is about the initiative being dishonest.
The point of choosing Clippy is to imply that much of what we have now is more anti-user than one of the most anti-user pieces of software of the 90's.