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I did once.

 

I bought Crimson Skies for the Xbox and had played it and beaten it to death. A few months later Halo 2 was about to be released, and I wanted Xbox live. So I went out and got a Xbox live 1 years subscription bundle and it had a copy of Crimson Skies.

I just traded in that second copy and I think I got a whopping $2 for it.