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  After college, Obama found a home, as well as a sense of himself, working on the South Side of Chicago as a community organizer. “When I started doing that work, my story merges with a larger story. That happens naturally for a John Lewis,” he told me, referring to the civil-rights hero and Democratic congressman. “That happens more naturally for you. It was less obvious to me. How do I pull all these different strains together: Kenya and Hawaii and Kansas, and white and black and Asian—how does that fit? And through action, through work, I suddenly see myself as part of the bigger process for, yes, delivering justice for the [African American community] and specifically the South Side community, the low-income people—justice on behalf of the African American community. But also thereby promoting my ideas of justice and equality and empathy that my mother taught me were universal. So I’m in a position to understand those essential parts of me not as separate and apart from any particular community but connected to every community. And I can fit the African American struggle for freedom and justice in the context of the universal aspiration for freedom and justice.”

  Throughout Obama’s 2008 campaign and into his presidency, this attitude proved key to his deep support in the black community. African Americans, weary of high achievers who distanced themselves from their black roots, understood that Obama had paid a price for checking “black” on his census form, and for living black, for hosting Common, for brushing dirt off his shoulder during the primaries, for marrying a woman who looked like Michelle Obama. If women, as a gender, must suffer the constant evaluations and denigrations of men, black women must suffer that, plus a broad dismissal from the realm of what American society deems to be beautiful. But Michelle Obama is beautiful in the way that black people know themselves to be. Her prominence as first lady directly attacks a poison that diminishes black girls from the moment they are capable of opening a magazine or turning on a television.

  The South Side of Chicago, where Obama began his political career, is home to arguably the most prominent and storied black political establishment in the country. In addition to Oscar Stanton De Priest, the first African American elected to Congress in the twentieth century, the South Side produced the city’s first black mayor, Harold Washington; Jesse Jackson, who twice ran for president; and Carol Moseley Braun, the first African American woman to win a Senate race. These victories helped give rise to Obama’s own. Harold Washington served as an inspiration to Obama and looms heavily over the Chicago section of Dreams From My Father.

  Washington forged the kind of broad coalition that Obama would later assemble nationally. But Washington did this in the mid-1980s in segregated Chicago, and he had not had the luxury, as Obama did, of becoming black with minimal trauma. “There was an edge to Harold that frightened some white voters,” David Axelrod, who worked for both Washington and Obama, told me recently. Axelrod recalled sitting around a conference table with Washington after he had won the Democratic primary for his reelection in 1987, just as the mayor was about to hold a press conference. Washington asked what percentage of Chicago’s white vote he’d received. “And someone said, ‘Well, you got 21 percent. And that’s really good because last time’”—in his successful 1983 mayoral campaign—“‘you only got 8,’” Axelrod recalled. “And he kind of smiled, sadly, and said, ‘You know, I probably spent 70 percent of my time in those white neighborhoods, and I think I’ve been a good mayor for everybody, and I got 21 percent of the white vote and we think it’s good.’ And he just kind of shook his head and said, ‘Ain’t it a bitch to be a black man in the land of the free and the home of the brave?’

  “That was Harold. He felt those things. He had fought in an all-black unit in World War II. He had come up in times—and that and the sort of indignities of what you had to do to come up through the machine really seared him.” During his 1983 mayoral campaign, Washington was loudly booed outside a church in northwest Chicago by middle-class Poles, Italians, and Irish, who feared blacks would uproot them. “It was as vicious and ugly as anything you would have seen in the old South,” Axelrod said.

  Obama’s ties to the South Side tradition that Washington represented were complicated. Like Washington, Obama attempted to forge a coalition between black South Siders and the broader community. But Obama, despite his adherence to black cultural mores, was, with his roots in Kansas and Hawaii, his Ivy League pedigree, and his ties to the University of Chicago, still an exotic out-of-towner. “They were a bit skeptical of him,” says Salim Muwakkil, a journalist who has covered Obama since before his days in the Illinois State Senate. “Chicago is a very insular community, and he came from nowhere, seemingly.”

  Obama compounded people’s suspicions by refusing to humble himself and go along with the political currents of the South Side. “A lot of the politicians, especially the black ones, were just leery of him,” Kaye Wilson, the godmother to Obama’s children and one of the president’s earliest political supporters, told me recently.

  But even as many in the black political community were skeptical of Obama, others encouraged him—sometimes when they voted against him. When Obama lost the 2000 Democratic-primary race against Bobby Rush, the African American incumbent congressman representing Illinois’ First Congressional District, the then-still-obscure future president experienced the defeat as having to do more with his age than his exoticism. “I’d go meet people and I’d knock on doors and stuff, and some of the grandmothers who were the folks I’d been organizing and working with doing community stuff, they weren’t parroting back some notion of ‘You’re too Harvard,’ or ‘You’re too Hyde Park,’ or what have you,” Obama told me. “They’d say, ‘You’re a wonderful young man, you’re going to do great things. You just have to be patient.’ So I didn’t feel the loss as a rejection by black people. I felt the loss as ‘politics anywhere is tough.’ Politics in Chicago is especially tough. And being able to break through in the African American community is difficult because of the enormous loyalty that people feel towards anybody who has been around awhile.”

  There was no one around to compete for loyalty when Obama ran for Senate in 2004, or for president in 2008. He was no longer competing against other African Americans; he was representing them. “He had that hybridity which told the ‘do-gooders’—in Chicago they call the reformers the do-gooders—that he was acceptable,” Muwakkil told me.

  Obama ran for the Senate two decades after the death of Harold Washington. Axelrod checked in on the precinct where Washington had been so loudly booed by white Chicagoans. “Obama carried, against seven candidates for the Senate, almost the entire northwest side and that precinct,” he said. “And I told him, ‘Harold’s smiling down on us tonight.’”

  Obama believes that his statewide victory for the Illinois Senate seat held particular portent for the events of 2008. “Illinois is the most demographically representative state in the country,” he told me. “If you took all the percentages of black, white, Latino; rural, urban; agricultural, manufacturing—[if] you took that cross section across the country and you shrank it, it would be Illinois.”

  Illinois effectively allowed Obama to play a scrimmage before the big national game in 2008. “When I ran for the Senate I had to go into southern Illinois, downstate Illinois, farming communities—some with very tough racial histories, some areas where there just were no African Americans of any number,” Obama told me. “And when we won that race, not just an African American from Chicago, but an African American with an exotic history and [the] name Barack Hussein Obama, [it showed that I] could connect with and appeal to a much broader audience.”

  The mix of Obama’s “hybridity” and the changing times allowed him to extend his appeal beyond the white ethnic corners of Chicago, past the downstate portions of Illinois, and out into the country at large. “Ben Nelson, one of the most conservative Democrats in the Senate, from Nebraska, would only bring in one national Democrat to campaign for him,” Obama recalls. “And it was me. And so part of the reason I was willin
g to run [for president in 2008] was that I had had two years in which we were generating enormous crowds all across the country—and the majority of those crowds were not African American; and they were in pretty remote places, or unlikely places. They weren’t just big cities or they weren’t just liberal enclaves. So what that told me was, it was possible.”

  What those crowds saw was a black candidate unlike any other before him. To simply point to Obama’s white mother, or to his African father, or even to his rearing in Hawaii, is to miss the point. For most African Americans, white people exist either as a direct or an indirect force for bad in their lives. Biraciality is no shield against this; often it just intensifies the problem. What proved key for Barack Obama was not that he was born to a black man and a white woman, but that his white family approved of the union, and approved of the child who came from it. They did this in 1961—a time when sex between black men and white women, in large swaths of the country, was not just illegal but fraught with mortal danger. But that danger is not part of Obama’s story. The first white people he ever knew, the ones who raised him, were decent in a way that very few black people of that era experienced.

  I asked Obama what he made of his grandparents’ impressively civilized reception of his father. “It wasn’t Harry Belafonte,” Obama said laughingly of his father. “This was like an African African. And he was like a blue-black brother. Nilotic. And so, yeah, I will always give my grandparents credit for that. I’m not saying they were happy about it. I’m not saying that they were not, after the guy leaves, looking at each other like, ‘What the heck?’ But whatever misgivings they had, they never expressed to me, never spilled over into how they interacted with me.

  “Now, part of it, as I say in my book, was we were in this unique environment in Hawaii where I think it was much easier. I don’t know if it would have been as easy for them if they were living in Chicago at the time, because the lines just weren’t as sharply drawn in Hawaii as they were on the mainland.”

  Obama’s early positive interactions with his white family members gave him a fundamentally different outlook toward the wider world than most blacks of the 1960s had. Obama told me he rarely had “the working assumption of discrimination, the working assumption that white people would not treat me right or give me an opportunity or judge me [other than] on the basis of merit.” He continued, “The kind of working assumption” that white people would discriminate against him or treat him poorly “is less embedded in my psyche than it is, say, with Michelle.”

  In this, the first lady is more representative of black America than her husband is. African Americans typically raise their children to protect themselves against a presumed hostility from white teachers, white police officers, white supervisors, and white coworkers. The need for that defense is, more often than not, reinforced either directly by actual encounters or indirectly by observing the vast differences between one’s own experience and those across the color line. Marty Nesbitt, the president’s longtime best friend, who, like Obama, had positive interactions with whites at a relatively early age, told me that when he and his wife went to buy their first car, she was insistent on buying from a black salesperson. “I’m like, ‘We’ve got to find a salesman,’” Nesbitt said. “She’s like, ‘No, no, no. We’re waiting for the brother.’ And I’m like, ‘He’s with a customer.’ They were filling out documents and she was like, ‘We’re going to stay around.’ And a white guy came up to us. ‘Can I help you?’ ‘Nope.’” Nesbitt was not out to condemn anyone with this story. He was asserting that “the willingness of African Americans [in Chicago] to help lift each other up is powerful.”

  But that willingness to help is also a defense, produced by decades of discrimination. Obama sees race through a different lens, Kaye Wilson told me. “It’s just very different from ours,” she explained. “He’s got buddies that are white, and they’re his buddies, and they love him. And I don’t think they love him just because he’s the president. They love him because they’re his friends from Hawaii, some from college and all.

  “So I think he’s got that, whereas I think growing up in the racist United States, we enter this thing with, you know, ‘I’m looking at you. I’m not trusting you to be one hundred with me.’ And I think he grew up in a way that he had to trust [white people]—how can you live under the roof with people and think that they don’t love you? He needs that frame of reference. He needs that lens. If he didn’t have it, it would be . . . a Jesse Jackson, you know? Or Al Sharpton. Different lens.”

  That lens, born of literally relating to whites, allowed Obama to imagine that he could be the country’s first black president. “If I walked into a room and it’s a bunch of white farmers, trade unionists, middle age—I’m not walking in thinking, Man, I’ve got to show them that I’m normal,” Obama explained. “I walk in there, I think, with a set of assumptions: like, these people look just like my grandparents. And I see the same Jell-O mold that my grandmother served, and they’ve got the same, you know, little stuff on their mantelpieces. And so I am maybe disarming them by just assuming that we’re okay.”

  What Obama was able to offer white America is something very few African Americans could—trust. The vast majority of us are, necessarily, too crippled by our defenses to ever consider such a proposition. But Obama, through a mixture of ancestral connections and distance from the poisons of Jim Crow, can credibly and sincerely trust the majority population of this country. That trust is reinforced, not contradicted, by his blackness. Obama isn’t shuffling before white power (Herman Cain’s “shucky ducky” act) or flattering white ego (O. J. Simpson’s listing not being seen as black as a great accomplishment). That, too, is defensive, and deep down, I suspect, white people know it. He stands firm in his own cultural traditions and says to the country something virtually no black person can, but every president must: “I believe you.”

  IV. “You Still Gotta Go Back to the Hood”

  Just after Columbus Day, I accompanied the president and his formidable entourage on a visit to North Carolina A&T State University, in Greensboro. Four days earlier, the Washington Post had published an old audio clip that featured Donald Trump lamenting a failed sexual conquest and exhorting the virtues of sexual assault. The next day, Trump claimed that this was “locker room” talk. As we flew to North Carolina, the president was in a state of bemused disbelief. He plopped down in a chair in the staff cabin of Air Force One and said, “I’ve been in a lot of locker rooms. I don’t think I’ve ever heard that one before.” He was casual and relaxed. A feeling of cautious inevitability emanated from his staff, and why not? Every day seemed to bring a new, more shocking revelation or piece of evidence showing Trump to be unfit for the presidency: He had lost nearly $1 billion in a single year. He had likely not paid taxes in eighteen years. He was running a “university,” for which he was under formal legal investigation. He had trampled on his own campaign’s messaging by engaging in a Twitter crusade against a former beauty-pageant contestant. He had been denounced by leadership in his own party, and the trickle of prominent Republicans—both in and out of office—who had publicly repudiated him threatened to become a geyser. At this moment, the idea that a campaign so saturated in open bigotry, misogyny, chaos, and possible corruption could win a national election was ludicrous. This was America.

  The president was going to North Carolina to keynote a campaign rally for Clinton, but first he was scheduled for a conversation about My Brother’s Keeper, his initiative on behalf of disadvantaged youth. Announcing My Brother’s Keeper—or MBK, as it’s come to be called—in 2014, the president had sought to avoid giving the program a partisan valence, noting that it was “not some big new government program.” Instead, it would involve the government in concert with the nonprofit and business sectors to intervene in the lives of young men of color who were “at risk.” MBK serves as a kind of network for those elements of federal, state, and local government that might already have a presence in the lives of these
young men. It is a quintessentially Obama program—conservative in scope, with impacts that are measurable.

  “It comes right out of his own life,” Broderick Johnson, the cabinet secretary and an assistant to the president, who heads MBK, told me recently. “I have heard him say, ‘I don’t want us to have a bunch of forums on race.’ He reminds people, ‘Yeah, we can talk about this. But what are we going to do?’” On this afternoon in North Carolina, what Obama did was sit with a group of young men who’d turned their lives around in part because of MBK. They told stories of being in the street, of choosing quick money over school, of their homes being shot up, and—through the help of mentoring or job programs brokered by MBK—transitioning into college or a job. Obama listened solemnly and empathetically to each of them. “It doesn’t take that much,” he told them. “It just takes someone laying hands on you and saying, ‘Hey, man, you count.’”

  When he asked the young men whether they had a message he should take back to policy makers in Washington, DC, one observed that despite their best individual efforts, they still had to go back to the very same deprived neighborhoods that had been the sources of trouble for them. “It’s your environment,” the young man said. “You can do what you want, but you still gotta go back to the hood.”