James and Brad Rutter know a lot more than I do, and James is a professional gambler, but it's still over thinking the game. How many times did James miss a Final Jeopardy in 32 games? Not once. If he doubled his wager and she missed hers with the wager she bet, then he wins by a wide margin, not the $1 he played out in his mind. Plenty of players have miscalculated and lost by a dollar. Even geniuses have lapses under pressure.