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It is strange to me that a man who is obviously black as far as any white is concerned (and who certainly would have been treated as badly as any other "negro" under the one-drop rule of Jim Crow) would be condemned, even sotto vocce, by other black people simply because he refuses to... what, exactly? Talk using inner city slang? Play up to stereotypes of black victimhood? If that is what was expected of him by the black political community, then Obama was right to refuse. They were, in effect, asking him to predicate his first campaign upon committing long-term political suicide.
As for Obama's sense of entitlement, I'm not sure that this is the right word to use in characterizing a man who consistently earned the high honors which he has achieved. Yes, Obama went to Harvard. But where was the multi-millionaire father holding the door open for him? Could it be that he actually earned his way into one of the most prestigious universities in the country, then did really, really well there because he was simply a great student?
If Obama has loosened up, perhaps he has merely decided he has nothing left to prove to people who should have already figured it out.