Sounds like a smart pick. If I were him I'd bet everything I have (up to like $100,000) on Dallas. Then either way you win money. And if Pitt wins and doesn't cover you're golden. Potential drawback to hedging is, what if the payout is 25,000 a year over 40 years?, you win the streak bet, but loose your hedge.... Also, if someone else gets to 25 and you lose the coin toss (or whatever)... well, sucks to be you.