I know that it is common to turn a symbol initially built against you into one which now benefits you, but I don't think that's whats going to happen with Clippy primarily because of message here isn't "Clippy wants us to move into a future where we own our tech/social infrastructure" but instead "man, im really nostalgic for the way corporations used to treat us"
I have no problem using a symbol developed my Microsoft to spread anti-big tech messaging. The problem is that to a lot of people, the messaging doesn't feel ant-big tech or anti-capitalist so much as it is just nostalgic. Microsoft was never a nice company. Even in the 1990s they were exercising their E.E.E (Embrace, Extend, Extinguish) strategy to beat federated and decentralized platforms and technologies. The goal of these companies (and you can see it now in their attitudes towards AI) is to own as much social infrastructure as they can. From where you get your news to where you get your friends. The only way to work against this is to work against big tech. There is no other way.
Part of me wonders if the message behind the current Clippy symbol can be bent into something more forward facing, but I also feel that that would be hard/would feel artificial because of the fact that Clippy is just now so connected to nostalgia.
reading this at first i was thinking of things other then hasan