He grew up in Indonesia and Hawaii (a great place, but very untypical of the US), and later spent his life in academic or political cocoons or trying to organize people in the inner city. That is, he has spent most of his time around people who think pretty much like he does, and can't admit that other opinions are legitimate.
I thought that during the Skip Gates controversy, he read his lines like a college prof in the lounge, a clueless idiot of a protected class. Even our WASP Brahmins were more in touch with what constituted America’s inner core. And I thought the Joe the Plumber case was a bit of election year drama, not an indicator of what was to come.