Not really my point. This is a SUPER grey area, and the Feds are not down with grey. Your paying someone, who is not your employee for a service thats really what exactly, and then asking to deduct a loss for What? A service he didn't perform. "Well I paid the guy a million dollars, but he was a bust, and never played in a game, and now he went to another school, so I want my money back". Say what? I mean if you use the charade that he does a car commercial, and he does it, then you can't claim a loss. BUT, how do you write off on your taxes that the guy didn't work out, and left for another school, with your bag of cash?