So, total rumor, but I've heard from a few sources on the grapevine that one of the reasons for their antitrust spat with the DoJ was actually as a proxy battle, and the main thing the DoJ cared about was Microsoft's unwillingness to play ball wrt data collection and "lawful intercept".

The sense I've gotten is that Microsoft of the time really did have a very libertarian core thought process that wasn't really into spying on it's users.