Yes, the people who are somehow getting the message that Louis Rossmann was praising Microsoft either didn't watch the video or generally struggle with nuance, or both.
If you told Clippy that you were having a bad day, he wasn't going to use that information to try and figure out which advertiser to sell you to, nor was he trying to steal your personal data or get you to purchase other Microsoft products. He had no ulterior motives.
Talking about what Microsoft as a company might or might not have done or wanted to do in '97 is irrelevant.
The point is that Clippy was a better assistant product because it did not do the things that the current generation of assistant software products do.
Oh, you're right, I just scanned over it and didn't recognize that it was a reference to a political opponent.