2004 Election: Obama's Ascent

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In 2002 the chosen one was Cory Booker, then a Newark, N.J., city councilman. He ultimately lost a close race against Mayor Sharpe James after Booker was accused of not being "black enough." At the Democratic Convention this summer, Booker walked into the hall and encountered a group of admirers. "One of them said I should be Vice President. I said I thought that might be going a little too far." One woman took out her camera and asked, "Could I take your picture, Mr. Obama?" Booker laughs as he tells the story. "I said, 'Ma'am, there's more than one sexy black man at this convention.'"

For Booker, who plans on challenging James again in 2006, his biggest obstacle has been the entrenched black leadership's resistance to new faces and different ideas. In the Senate, warns Walters, Obama will encounter similar challenges. "He could reach a point where he has some very serious conflict between the agenda of [a potential presidential] ticket and the agenda he's got to carry as the only African American in the Senate," says Walters. Says Rush, who has not fully forgiven Obama's audacious run against him: "In my community, the basic desire is to get a black into the Senate. Once he gets in, we can nudge him along on the path that might be less comfortable for him."

For now, Richard Durbin, the senior Senator from Illinois, counsels Obama to follow the model of Hillary Clinton. As a national figure entering the Senate with more buzz than clout, Clinton did her homework, kept her head down and stayed in tireless contact with her New York constituents. Gradually, her political capital rose. Obama says he plans to ask for her advice. Depending on how the conversation goes, maybe they could wager on the chances of them ever running together for the White House. --With reporting by David E. Thigpen/Chicago and Jeannie McCabe/Honolulu