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Yeah, it's not a benefit, except if the challenge-giver makes a mistake and offers a file that happens to have nicely-compressible characteristics. Basically you're spending $100 on the hopes that the file you're tasked with compressing just happens to have low enough entropy that it can be successfully compressed by more than the decompressor's size.

Not a good bet to take.

> my point is that this is not information-theoretically relevant.

Exactly. This whole post is about the challenger trying to be clever with the rules and trying to sidestep the core information theory.




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