Gwen Ifill’s ‘The Breakthrough’

A look at the much-anticipated book on black political leaders in the Obama generation.

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So it was that much more remarkable when Obama strode onto the dais at the annual dinner in March 2006. It could have been an intimidating evening. The room was filled with movers and shakers of the first order. But Obama, who had spent a lifetime challenging preconceptions about race, politics, and political timing, seemed en­tirely at home. He made fun of himself, poked light fun at President Bush and Vice President Cheney, and even sang a little. He was a hit. 

Roger Wilkins found Obama’s racial straddle to be shrewd poli­tics “that effectively calls on Americans to get serious about their nation’s founding ideals, including we don’t torture people, we don’t get involved in wars of choice, we don’t get wildly into debt as if the future doesn’t count, and we don’t ignore global warming because we think scientists are stupid. The racial issue gets subsumed in what he’s doing—and that’s a good thing. It’s very sophisticated and it’s very complex and sensitive; but right now he is pulling it off.”22 

But Obama was not naive. He was well aware there were voters who would never support him—the ones who bought the waffles and laughed. “I don’t believe it is possible to transcend race in this country,” Obama told me one day while he was on the campaign trail in New Hampshire. “The notion that if we just ignore race, somehow our racial problems are solved, is the kind of unfortunate thinking the Supreme Court recently engaged in on the Seattle schools case.” Obama was referring to a Supreme Court decision that limited the Seattle school district’s ability to use race as a factor in promoting integration.  

“Race is a factor in this society,” he said. “The legacy of Jim Crow and slavery has not gone away. It is not an accident that African Americans experience high crime rates, are poor, and have less wealth. It is a direct result of our racial history. We have never fully come to grips with that history.”  

“You just don’t walk away from the past,” Michelle Obama told me separately. “You bring it along with you. It is always a part of the tradi­tion. You don’t move to the next phase without understanding what happened in the civil rights movement.” 

Like many people of their generation, the Obamas operate at some­thing of a remove from that movement—speaking of it with respect but not with the passion expressed by their elders. Michelle did more of this than her husband did, and even then much was under the con­ventional political radar. While campaigning in South Carolina, where the black vote was crucial, she would invoke the names of Coretta Scott King, Harriet Tubman, and Rosa Parks. “These were all women who cast aside the voices of doubt and fear that said, ‘Wait, you can’t do that. It’s not your turn. The timing’s not right. The country’s not ready,’” she told an Orangeburg audience in a speech the campaign circulated to black voters online and on DVDs. “That gnawing sense of self-doubt that is so common in all of us, is a lie—it’s a lie,” she said, breaking into a preacher’s cadence that belied her Princeton and Harvard education. “It’s just in our heads. See, nine times out of ten, we are more ready. We are more prepared than we could ever know.”  

Obama saw himself as the bridge between those fears and the possi­bilities his candidacy represented. “Part of what happened in the sixties after the initial civil rights era was we lost some balance and we started thinking in terms of either-or,” Obama told me during the campaign. “Either you were picking yourself up by your own bootstraps, you were an integrationist, you were Sidney Poitier, or you were burning down the house.”  

Obama’s fiercest critics often came from the left. Princeton’s Glaude, who early on was one of Obama’s most prominent black skeptics, said he was frustrated with the way the nation’s first black presidential nominee was handling race.