Will Disney take legal action against someone using the Steamboat Willie character within a year of its copyright expiring?
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The original incarnation of Mickey Mouse, as portrayed in the 1928 short film Steamboat Willie, is set to lose its copyright and enter the public domain on January 1st 2024. This would in principle give anyone the right to portray this character in any way they like without Disney's permission.

However Disney has stated that they believe Mickey Mouse to be so tightly linked to their brand that its representation should be treated as a trademarked logo, and therefore should never enter public domain they should be allowed to continue exerting control over its use.

This market will resolve Yes if Disney takes legal action against someone for their portrayal of the Steamboat Willie character in the calendar year following the end of its copyright on January 1st 2024 (i.e. after 1/1/2024 but before 1/1/2025). This legal action does not need to be successful, the only requirement is that it be initiated. For example a lawsuit filed by Disney that later gets thrown out in court would be acceptable.

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Wikipedia has a list of works that could be challenged on this theory.
https://en.wikipedia.org/wiki/Works_based_on_a_copyright-free_Mickey_Mouse

It may also be relevant that there were no legal challenges to the recent Winnie-the-Pooh horror movie.

Disclaimer: I am not a lawyer and attempted to explain the situation to the best of my ability. If any inaccuracies are brought to my attention I will update the description to reflect them.