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I've only traded crappy Mega Drive games, because at the time it was hard to know which games were good. It was a direct trade at the store though. I never lost a penny for it.

I remember trading Pinocchio for Virtua Fighter 2 and the Power Rangers fighting game for Separation Anxiety.

I also traded Toy Story, because it never worked well. I tried two copies but they always glitched at some point.

From there on, I never once lost or traded a game. I always keep them. Even if they suck.