The first guy gets the award for the worst spectator of all time. Perhaps the money on the table introduced unfortunate pressure.
When I did this "for the money," I always won and always got paid, but I took a different approach. I would say the whole thing was a scam and a trick, and the player was going to lose -- but if he paid attention he'd see what I did and make money for himself "tomorrow night."
Of course, this never happened.