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Though the ballots had been counted and the downtown revelers had all gone home, Everett Whitfield was still politicking early Wednesday morning. “I happen to believe that there are two Americas. Mr. Obama can tell me to forget the past, but then he goes to Israel where the Jews’ mantra is ‘Never forget, always remember your past,’ and he’ll tell them they’re right.” A lifelong liberal, aging with aged teeth, Whitfield addressed a miscellaneous breakfast crowd at a McDonald’s on Stony Island Avenue, admittedly looking very much like a man “waiting for someone to put a microphone in front of my face.” Although he voted for Green Party candidate Cynthia McKinney—”the first time in a long time I’ve voted with my conscience”—Whitfield proved a fair barometer of the attitude among some African-American Obama supporters in this South Shore neighborhood.

The wary tone in this overwhelmingly Democratic neighborhood, just blocks from Obama’s home, is a telling indicator of the challenge that lies ahead. Isaiah, waiting at a bus stop wearing an Obama T-shirt, was blunt. “Do I expect a change? No, not too much. I don’t expect too much.” The president-elect knows very well that these men and women—desirous of change, but careful not to expect too much—represent his biggest challenge, as well as his greatest reward if he can manage to win them over. He knows as well as they do that much work remains to be done before “someday we might” becomes “Yes we can.”