So my point stands doesn't it? If Clippy was as hostile as it could be with the technology available then, and the trillion dollar companies hoarding our data are as hostile as they can be with the technology present now, is Clippy a good mascot for an initiative like this or is it a good mascot for the trillion dollar companies?

Clippy is a mascot for the trillion dollar companies. It's emblematic of the beginning of the end of user-centric computing. It marks the new era of intrusive business-centric computing.

It's not about data or technology at all. It's about property rights. User-centric computers (ideally) don't do anything their users don't want them to do. Business-centric computers don't care about what the user wants; they serve the interests of business (either the manufacturer or the user's employer).