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For Barack to actually win he needs to get past Hilary Clinton, who has more fucking money than you can shake a stick at and who already has a pretty solid lead in Democratic polls from what I remember. Plus, more people know about her (for better or for worse) than Obama, who has been in the senate for a little over two years now.
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The Clintons don't make that much money. I remember reading (from somewhere reliable, I think) that most of the money they make comes from Bill's lecture tours, which was some figure in the low millions, and maybe more in the future from some business deals I forget what.
Oh, and yeah, Obama ain't gonna win. Much as I'd love to see that happen, it isn't going to. America just isn't ready for a black muslim president with only two years experience as a junior senator, any more than it is for a foul-mouthed atheist stand up comic. (s'up Stanhope)
Jam it back in, in the dark.