Philadelphia -- Martin Scorsese
Ah, this one is bound to raise some hackles. "But he's from New York!" you carp. "He's too good for the Iggles!" Both are valid points. However, it all boils down to the fact that Scorsese, like Thrilly, can't win the big one even though it seems like both should have by now. The Departed looks promising and a lot of sportswriters are improbably picking the Eagles to go to the Super Bowl. And the Super Bowl goes to...Dances With Wolves.
Washington -- Michael Bay
Give them enough money and they'll give you a sad excuse to waste yours. Pearl Harbor and the Deion Sanders signing are similarly epic, costly blunders. Roland Emmerich or James Cameron could probably also fit here, but Cameron is too cool now that he's been on Entourage. I go with Bay because it has already come to pass - UM reported that crew from The Transformers Movie was on hand Sunday at FedEx for the Jags-Indigenous Peoples game to get film of Brunell morphing into a decent quarterback for a week.
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