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I have no idea how much the NYT pays Silver, but they could create some sort of pay scheme such that on any given day, his pay is is a bet on the eventual outcome as a function of the odds he gives one candidate and the time until the election. Something such that as he gets closer, he should be more accurate, so a higher percent of his pay is tied to the outcome.
I'd be a lot more impressed if he bet something that had a bite if he lost. He's not going to miss $2000 given to charity.

He should bet that for 1 week after the election, the loser says nothing in public about the result.

That would be a loss with bite.

Wouldn't that bite be horribly uneven? Talking about the results of the election for a week after the election is (for better or for worse) essentially Joe Scarborough's job, but it isn't Nate Silver's (though it is tangentially related).

Having said that, I agree, $1000 is basically meaningless to either of these guys.

If Obama lost and Silver couldn't talk about the result for a week after? That'd hit him pretty hard.
Morning Joke still didn't take the bet.

Nate probably didn't care about whether he won or lost - it's just these right-wing media windbags say whatever they want, seemingly without consequence.

Good that he deflated that clown.

Scarborough didn't claim that Romney would win, so I don't see why he would ever take this bet.