I think there is a better way to make this bet.
Both of you put in $750 (total $1500) and enter the LVH Supercontest.
You guys alternate weeks where one of you guys pick 3 games and the other picks 2.
Whoever picks the most losers for your team pays the other $250.
BUT if you guys place in the money, the other has to donate 25% of their half if the winnings to a charity or political party.
This way you guys actually have a shot at something big!
With Willie's picks, I'd be down $500 afterward. Can't do it.