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I'm with you on almost everything you said, *except* the idea that Obama's perspective on Palestine is going to be informed by the heated animosities between black and Jewish populations in Chicago. Yes, those animosities exist. But I don't see why we should assume that these conflicts have influenced Obama one way or another; that just seems like a leap without a foundation. I mean, just because he taught at the U of Chicago law school where there are many prominent Jewish scholars, that's not a reason to assume he's pro-Israel (or not pro-Israel).
I think I understand your basic point, which seems to be this: unlike people in other parts of the country, Obama has been exposed to people who are sympathetic to the Palestinian people, not JUST the pro-Israeli perspective. But it seems a little screwy to argue (if you were) that people like Farrakan or people who resent Jewish business owners are going to supply a helpful perspective on the Palestine-Israel conflict.
What seems most promising to me about Obama is his calm, reflective approach to tough international problems. I don't think local Chicago animosities (which, let's face it, have currents of anti-semitism in them) are going to direct him.