[riskable]

It's an interesting question because it hasn't been litigated before!

If you make/sell a Winnie the Pooh bear and Disney sues they can't make the claim that they own the copyright to it (anymore). What they could claim is that it's a trademark of theirs but that protection doesn't necessarily trump the fact that WtP is public domain now. So the courts will have to decide if trademarks can overrule works derived from the pubic domain.

Legally speaking I don't think that makes any sense. It feels like it's the equivalent of trying to get a trademark on a common word or phrase which you can do (in theory) but it has to be severely limited in scope and trying to litigate it is basically wishful thinking.

[extra88]

I expect Disney’s trademark on Winnie the Pooh’s likeness will remain intact and be effective at stopping the distribution of any Winnie the Pooh images other than maybe faithful reproductions of the specific images in the first book. Trademark is all about avoiding confusion and outright fraud in the marketplace.

If I’m wrong, it’ll be an interesting precedent for when the first Mickey Mouse cartoon, “Steamboat Willie,” enters the public domain in 2024.