I wonder if it would have been possible to win the challenge legitimately?
If a randomly-generated file happened to contain some redundancy through sheer chance, you could hand-craft a compressor to take advantage of it. This compressor would not work in general for random data, but it could work for this one particular case.
It's a bet worth taking, because the payoff, 50:1 ($5,000 to $100), is pretty good. Play the game 50 times and you might get a file you could compress.
The challenge, then, would be for the person offering the bet to generate a really random file that contained no such redundancy. That might not be easy.
If a randomly-generated file happened to contain some redundancy through sheer chance, you could hand-craft a compressor to take advantage of it. This compressor would not work in general for random data, but it could work for this one particular case.
It's a bet worth taking, because the payoff, 50:1 ($5,000 to $100), is pretty good. Play the game 50 times and you might get a file you could compress.
The challenge, then, would be for the person offering the bet to generate a really random file that contained no such redundancy. That might not be easy.