A trick similar to the recursive Barf compressor (add information to the filename). http://mattmahoney.net/dc/barf.html A longer running challenge is http://www.drdobbs.com/architecture-and-design/the-enduring-... No entry fee, $100 prize, and just as unfair. A completely serious compression challenge with serious consequences for AI and NLP: http://prize.hutter1.net/ up to 50.000$ prize money, but severe restriction…
At the 10-year scale, a whole new set of tricks opens up. Invent a sufficiently popular programming language, or contribute a lot to the linux kernel, and start surreptitiously hiding bits of the file on his OS (the easiest would be for you language to have a builtin function that spits out a small part of the file).