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Speaking for myself and people I associate with, I think I can give a pretty good explanation. Obama had a background that we have not seen in politics for a long time. No, I don't mean that he's black - I'm talking about the fact that he was an academic intellectual - a group that had been permanently marginalized as elitist, out-of-touch, Ivory Tower socialists who speak in incomprehensible jargon.
The vast majority of professors in the humanities are far more radically 'progressive' than the general view prevalent on Salon. Right-wingers say that this is because academia is in the grip of a Marxist conspiracy; I think it is a natural consequence of being willing to hold up to scrutiny and discard any assumptions about human nature. In any case, they generally hold views that are not allowed in the mainstream media, whether on Israel, religion, gender, or socialism. To me, this indicates a huge and problematic divide. On the one hand, society accepts people as being smart experts and entrusts to them the teaching of our youth; on the other, it dismisses them as kooks and imprisons them in an ever-shrinking bubble.
So imagine my surprise when all of a sudden a guy who is not only black and a professor, but friends with a pro-Palestinian professor of Middle Eastern Studies and a professor of education who is a former Weather Underground member comes out of nowhere as not a fringe candidate but someone who actually has a chance. It was a bit ironic to see professors who had only recently held the view that American politics is a complete sham getting excited about him. And, to be honest, it was also kind of nice.
In the end, the reasons that people like this supported Obama were the same ones that the Right demonized him. You could also say it was the same reason that blue-collar types voted for Bush - because of the impression that he was 'like us'. Many remain firmly convinced that personally, he is a radical leftist. After all, how could he not be when he studied at Columbia (likely taking classes with Edward Said) and associated with Khalidi and Ayers? At the very least, he must have been open to considering their ideas.
I actually think this could still be the case, but I was never under any particular delusion as to what he would actually do. Most progressives I know would have ideally preferred Kucinich but knew he didn't have a chance. No matter how he felt personally, I did expect Obama to become integrated into the Democratic machine, though I didn't expect him to lurch quite so far to the center as he did.
I do not think, however, that all is lost. After seeing 8 years of Bush and the damage that could be done simply by dumbing down our discourse to bumper-sticker slogans, having a president who speaks with logic and nuance would be an important step in itself (though unfortunately he has gradually been toning down this quality as well). Furthermore, I have several friends who, previously expecting to work in academia, have gone into fields like green energy and public policy. If this is indicative of any sort of trend, it will bear good fruit. Right now, about all the experienced Democrats that Obama can tap are Clinton holdovers. But they won't live forever, and if we start preparing now, the Democratic Party door could be open to a new generation of progressives.