“They’re a rotten crowd,” I shouted across the lawn. “You’re worth the whole damn bunch put together.”
— F. Scott Fitzgerald, The Great Gatsby
I.
“Love Will Make You Do Wrong”
In the waning days of President Barack Obama’s administration, he and his wife, Michelle, hosted a farewell party, the full import of which no one could then grasp. It was late October, Friday the 21st, and the president had spent many of the previous weeks, as he would spend the two subsequent weeks, campaigning for the Democratic presidential nominee, Hillary Clinton. Things were looking up. Polls in the crucial states of Virginia and Pennsylvania showed Clinton with solid advantages. The formidable GOP strongholds of Georgia and Texas were said to be under threat. The moment seemed to buoy Obama. He had been light on his feet in these last few weeks, cracking jokes at the expense of Republican opponents and laughing off hecklers. At a rally in Orlando on October 28, he greeted a student who would be introducing him by dancing toward her and then noting that the song playing over the loudspeakers—the Gap Band’s “Outstanding”—was older than she was. “This is classic!” he said. Then he flashed the smile that had launched America’s first black presidency, and started dancing again. Three months still remained before Inauguration Day, but staffers had already begun to count down the days. They did this with a mix of pride and longing—like college seniors in early May. They had no sense of the world they were graduating into. None of us did.
Chapters
“Love Will Make You Do Wrong”
He Walked on Ice but Never Fell
“I Decided to Become Part of That World”
“You Still Gotta Go Back to the Hood”
"They Rode the Tiger”
“When You Left, You Took All of Me With You”
The farewell party, presented by BET (Black Entertainment Television), was the last in a series of concerts the first couple had hosted at the White House. Guests were asked to arrive at 5:30 p.m. By 6, two long lines stretched behind the Treasury Building, where the Secret Service was checking names. The people in these lines were, in the main, black, and their humor reflected it. The brisker queue was dubbed the “good-hair line” by one guest, and there was laughter at the prospect of the Secret Service subjecting us all to a “brown-paper-bag test.” This did not come to pass, but security was tight. Several guests were told to stand in a makeshift pen and wait to have their backgrounds checked a second time.
Dave Chappelle was there. He coolly explained the peril and promise of comedy in what was then still only a remotely potential Donald Trump presidency: “I mean, we never had a guy have his own pussygate scandal.” Everyone laughed. A few weeks later, he would be roundly criticized for telling a crowd at the Cutting Room, in New York, that he had voted for Clinton but did not feel good about it. “She’s going to be on a coin someday,” Chappelle said. “And her behavior has not been coinworthy.” But on this crisp October night, everything felt inevitable and grand. There was a slight wind. It had been in the 80s for much of that week. Now, as the sun set, the season remembered its name. Women shivered in their cocktail dresses. Gentlemen chivalrously handed over their suit coats. But when Naomi Campbell strolled past the security pen in a sleeveless number, she seemed as invulnerable as ever.
Cellphones were confiscated to prevent surreptitious recordings from leaking out. (This effort was unsuccessful. The next day, a partygoer would tweet a video of the leader of the free world dancing to Drake’s “Hotline Bling.”) After withstanding the barrage of security, guests were welcomed into the East Wing of the White House, and then ushered back out into the night, where they boarded a succession of orange-and-green trolleys. The singer and actress Janelle Monáe, her famous and fantastic pompadour preceding her, stepped on board and joked with a companion about the historical import of “sitting in the back of the bus.” She took a seat three rows from the front and hummed into the night. The trolley dropped the guests on the South Lawn, in front of a giant tent. The South Lawn’s fountain was lit up with blue lights. The White House proper loomed like a ghost in the distance. I heard the band, inside, beginning to play Al Green’s “Let’s Stay Together.”
“Well, you can tell what type of night this is,” Obama said from the stage, opening the event. “Not the usual ruffles and flourishes!”
The crowd roared.
“This must be a BET event!”
The crowd roared louder still.
Obama placed the concert in the White House’s musical tradition, noting that guests of the Kennedys had once done the twist at the residence—“the twerking of their time,” he said, before adding, “There will be no twerking tonight. At least not by me.”
The Obamas are fervent and eclectic music fans. In the past eight years, they have hosted performances at the White House by everyone from Mavis Staples to Bob Dylan to Tony Bennett to the Blind Boys of Alabama. After the rapper Common was invited to perform in 2011, a small fracas ensued in the right-wing media. He performed anyway—and was invited back again this glorious fall evening and almost stole the show. The crowd sang along to the hook for his hit ballad “The Light.” And when he brought on the gospel singer Yolanda Adams to fill in for John Legend on the Oscar-winning song “Glory,” glee turned to rapture.
De La Soul was there. The hip-hop trio had come of age as boyish B-boys with Gumby-style high-top fades. Now they moved across the stage with a lovely mix of lethargy and grace, like your favorite uncle making his way down the Soul Train line, wary of throwing out a hip. I felt a sense of victory watching them rock the crowd, all while keeping it in the pocket. The victory belonged to hip-hop—an art form birthed in the burning Bronx and now standing full grown, at the White House, unbroken and unedited. Usher led the crowd in a call-and-response: “Say it loud, I’m black and I’m proud.” Jill Scott showed off her operatic chops. Bell Biv DeVoe, contemporaries of De La, made history with their performance by surely becoming the first group to suggest to a presidential audience that one should “never trust a big butt and a smile.”
The ties between the Obama White House and the hip-hop community are genuine. The Obamas are social with Beyoncé and Jay-Z. They hosted Chance the Rapper and Frank Ocean at a state dinner, and last year invited Swizz Beatz, Busta Rhymes, and Ludacris, among others, to discuss criminal-justice reform and other initiatives. Obama once stood in the Rose Garden passing large flash cards to the Hamilton creator and rapper Lin-Manuel Miranda, who then freestyled using each word on the cards. “Drop the beat,” Obama said, inaugurating the session. At 55, Obama is younger than pioneering hip-hop artists like Afrika Bambaataa, DJ Kool Herc, and Kurtis Blow. If Obama’s enormous symbolic power draws primarily from being the country’s first black president, it also draws from his membership in hip-hop’s foundational generation.
That night, the men were sharp in their gray or black suits and optional ties. Those who were not in suits had chosen to make a statement, like the dark-skinned young man who strolled in, sockless, with blue jeans cuffed so as to accentuate his gorgeous black-suede loafers. Everything in his ensemble seemed to say, “My fellow Americans, do not try this at home.” There were women in fur jackets and high heels; others with sculpted naturals, the sides shaved close, the tops blooming into curls; others still in gold bamboo earrings and long blond dreads. When the actor Jesse Williams took the stage, seemingly awed before such black excellence, before such black opulence, assembled just feet from where slaves had once toiled, he simply said, “Look where we are. Look where we are right now.”
This would not happen again, and everyone knew it. It was not just that there might never be another African American president of the United States. It was the feeling that this particular black family, the Obamas, represented the best of black people, the ultimate credit to the race, incomparable in elegance and bearing. “There are no more,” the comedian Sinbad joked back in 2010. “There are no black men raised in Kansas and Hawaii. That’s the last one. Y’all better treat this one right. The next one gonna be from Cleveland. He gonna wear a perm. Then you gonna see what it’s really like.” Throughout their residency, the Obamas had refrained from showing America “what it’s really like,” and had instead followed the first lady’s motto, “When they go low, we go high.” This was the ideal—black and graceful under fire—saluted that evening. The president was lionized as “our crown jewel.” The first lady was praised as the woman “who put the O in Obama.”
Barack Obama’s victories in 2008 and 2012 were dismissed by some of his critics as merely symbolic for African Americans. But there is nothing “mere” about symbols. The power embedded in the word nigger is also symbolic. Burning crosses do not literally raise the black poverty rate, and the Confederate flag does not directly expand the wealth gap.
Much as the unbroken ranks of 43 white male presidents communicated that the highest office of government in the country—indeed, the most powerful political offices in the world—was off-limits to black individuals, the election of Barack Obama communicated that the prohibition had been lifted. It communicated much more. Before Obama triumphed in 2008, the most-famous depictions of black success tended to be entertainers or athletes. But Obama had shown that it was “possible to be smart and cool at the same damn time,” as Jesse Williams put it at the BET party. Moreover, he had not embarrassed his people with a string of scandals. Against the specter of black pathology, against the narrow images of welfare moms and deadbeat dads, his time in the White House had been an eight-year showcase of a healthy and successful black family spanning three generations, with two dogs to boot. In short, he became a symbol of black people’s everyday, extraordinary Americanness.
Whiteness in America is a different symbol—a badge of advantage. In a country of professed meritocratic competition, this badge has long ensured an unerring privilege, represented in a 220-year monopoly on the highest office in the land. For some not-insubstantial sector of the country, the elevation of Barack Obama communicated that the power of the badge had diminished. For eight long years, the badge-holders watched him. They saw footage of the president throwing bounce passes and shooting jumpers. They saw him enter a locker room, give a businesslike handshake to a white staffer, and then greet Kevin Durant with something more soulful. They saw his wife dancing with Jimmy Fallon and posing, resplendent, on the covers of magazines that had, only a decade earlier, been almost exclusively, if unofficially, reserved for ladies imbued with the great power of the badge.
For the preservation of the badge, insidious rumors were concocted to denigrate the first black White House. Obama gave free cellphones to disheveled welfare recipients. Obama went to Europe and complained that “ordinary men and women are too small-minded to govern their own affairs.” Obama had inscribed an Arabic saying on his wedding ring, then stopped wearing the ring, in observance of Ramadan. He canceled the National Day of Prayer; refused to sign certificates for Eagle Scouts; faked his attendance at Columbia University; and used a teleprompter to address a group of elementary-school students. The badge-holders fumed. They wanted their country back. And, though no one at the farewell party knew it, in a couple of weeks they would have it.
On this October night, though, the stage belonged to another America. At the end of the party, Obama looked out into the crowd, searching for Dave Chappelle. “Where’s Dave?” he cried. And then, finding him, the president referenced Chappelle’s legendary Brooklyn concert. “You got your block party. I got my block party.” Then the band struck up Al Green’s “Love and Happiness”—the evening’s theme. The president danced in a line next to Ronnie DeVoe. Together they mouthed the lyrics: “Make you do right. Love will make you do wrong.”
Video: The Making of a Black President
I had met the president a few times before. In his second term, I’d written articles criticizing him for his overriding trust in color-blind policy and his embrace of “personal responsibility” rhetoric when speaking to African Americans. I saw him as playing both sides. He would invoke his identity as a president of all people to decline to advocate for black policy—and then invoke his black identity to lecture black people for continuing to “make bad choices.” In response, Obama had invited me, along with other journalists, to the White House for off-the-record conversations. I attempted to press my points in these sessions. My efforts were laughable and ineffective. I was always inappropriately dressed, and inappropriately calibrated in tone: In one instance, I was too deferential; in another, too bellicose. I was discombobulated by fear—not by fear of the power of his office (though that is a fearsome and impressive thing) but by fear of his obvious brilliance. It is said that Obama speaks “professorially,” a fact that understates the quickness and agility of his mind. These were not like press conferences—the president would speak in depth and with great familiarity about a range of subjects. Once, I watched him effortlessly reply to queries covering everything from electoral politics to the American economy to environmental policy. And then he turned to me. I thought of George Foreman, who once booked an exhibition with multiple opponents in which he pounded five straight journeymen—and I suddenly had some idea of how it felt to be the last of them.
Last spring, we had a light lunch. We talked casually and candidly. He talked about the brilliance of LeBron James and Stephen Curry—not as basketball talents but as grounded individuals. I asked him whether he was angry at his father, who had abandoned him at a young age to move back to Kenya, and whether that motivated any of his rhetoric. He said it did not, and he credited the attitude of his mother and grandparents for this. Then it was my turn to be autobiographical. I told him that I had heard the kind of “straighten up” talk he had been giving to black youth, for instance in his 2013 Morehouse commencement address, all my life. I told him that I thought it was not sensitive to the inner turmoil that can be obscured by the hardness kids often evince. I told him I thought this because I had once been one of those kids. He seemed to concede this point, but I couldn’t tell whether it mattered to him. Nonetheless, he agreed to a series of more formal conversations on this and other topics.
The improbability of a black president had once been so strong that its most vivid representations were comedic. Witness Dave Chappelle’s profane Black Bush from the early 2000s (“This nigger very possibly has weapons of mass destruction! I can’t sleep on that!”) or Richard Pryor’s black president in the 1970s promising black astronauts and black quarterbacks (“Ever since the Rams got rid of James Harris, my jaw’s been uptight!”). In this model, so potent is the force of blackness that the presidency is forced to conform to it. But once the notion advanced out of comedy and into reality, the opposite proved to be true.
Obama’s DNC speech is the key. It does not belong to the literature of “the struggle”; it belongs to the literature of prospective presidents—men (as it turns out) who speak not to gravity and reality, but to aspirations and dreams. When Lincoln invoked the dream of a nation “conceived in liberty” and pledged to the ideal that “all men are created equal,” he erased the near-extermination of one people and the enslavement of another. When Roosevelt told the country that “the only thing we have to fear is fear itself,” he invoked the dream of American omnipotence and boundless capability. But black people, then living under a campaign of terror for more than half a century, had quite a bit to fear, and Roosevelt could not save them. The dream Ronald Reagan invoked in 1984—that “it’s morning again in America”—meant nothing to the inner cities, besieged as they were by decades of redlining policies, not to mention crack and Saturday-night specials. Likewise, Obama’s keynote address conflated the slave and the nation of immigrants who profited from him. To reinforce the majoritarian dream, the nightmare endured by the minority is erased. That is the tradition to which the “skinny kid with a funny name” who would be president belonged. It is also the only tradition in existence that could have possibly put a black person in the White House.
Obama’s embrace of white innocence was demonstrably necessary as a matter of political survival. Whenever he attempted to buck this directive, he was disciplined. His mild objection to the arrest of Henry Louis Gates Jr. in 2009 contributed to his declining favorability numbers among whites—still a majority of voters. His comments after the killing of Trayvon Martin—“If I had a son, he’d look like Trayvon”—helped make that tragedy a rallying point for people who did not care about Martin’s killer as much as they cared about finding ways to oppose the president. Michael Tesler, a political-science professor at UC Irvine, has studied the effect of Obama’s race on the American electorate. “No other factor, in fact, came close to dividing the Democratic primary electorate as powerfully as their feelings about African Americans,” he and his co-author, David O. Sears, concluded in their book, Obama’s Race: The 2008 Election and the Dream of a Post-Racial America. “The impact of racial attitudes on individual vote decisions … was so strong that it appears to have even outstripped the substantive impact of racial attitudes on Jesse Jackson’s more racially charged campaign for the nomination in 1988.” When Tesler looked at the 2012 campaign in his second book, Post-Racial or Most-Racial? Race and Politics in the Obama Era, very little had improved. Analyzing the extent to which racial attitudes affected people associated with Obama during the 2012 election, Tesler concluded that “racial attitudes spilled over from Barack Obama into mass assessments of Mitt Romney, Joe Biden, Hillary Clinton, Charlie Crist, and even the Obama family’s dog Bo.”
Yet despite this entrenched racial resentment, and in the face of complete resistance by congressional Republicans, overtly launched from the moment Obama arrived in the White House, the president accomplished major feats. He remade the nation’s health-care system. He revitalized a Justice Department that vigorously investigated police brutality and discrimination, and he began dismantling the private-prison system for federal inmates. Obama nominated the first Latina justice to the Supreme Court, gave presidential support to marriage equality, and ended the U.S. military’s Don’t Ask, Don’t Tell policy, thus honoring the civil-rights tradition that had inspired him. And if his very existence inflamed America’s racist conscience, it also expanded the country’s anti-racist imagination. Millions of young people now know their only president to have been an African American.
Writing for The New Yorker, Jelani Cobb once noted that “until there was a black Presidency it was impossible to conceive of the limitations of one.” This is just as true of the possibilities. In 2014, the Obama administration committed itself to reversing the War on Drugs through the power of presidential commutation. The administration said that it could commute the sentences of as many as 10,000 prisoners. As of November, the president had commuted only 944 sentences. By any measure, Obama’s effort fell woefully short, except for this small one: the measure of almost every other modern president who preceded him. Obama’s 944 commutations are the most in nearly a century—and more than the past 11 presidents’ combined.
Obama was born into a country where laws barring his very conception—let alone his ascendancy to the presidency—had long stood in force. A black president would always be a contradiction for a government that, throughout most of its history, had oppressed black people. The attempt to resolve this contradiction through Obama—a black man with deep roots in the white world—was remarkable. The price it exacted, incredible. The world it gave way to, unthinkable.
III.
“I Decided to Become Part of That World”
When Barack Obama was 10, his father gave him a basketball, a gift that connected the two directly. Obama was born in 1961 in Hawaii and raised by his mother, Ann Dunham, who was white, and her parents, Stanley and Madelyn. They loved him ferociously, supported him emotionally, and encouraged him intellectually. They also told him he was black. Ann gave him books to read about famous black people. When Obama’s mother had begun dating his father, the news had not been greeted with the threat of lynching (as it might have been in various parts of the continental United States), and Obama’s grandparents always spoke positively of his father. This biography makes Obama nearly unique among black people of his era.
In the president’s memoir, Dreams From My Father, he says he was not an especially talented basketball player, but he played with a consuming passion. That passion was directed at something more than just the mastering of the pick-and-roll or the perfecting of his jump shot. Obama came of age during the time of the University of Hawaii basketball team’s “Fabulous Five”—a name given to its all-black starting five, two decades before it would be resurrected at the University of Michigan by the likes of Chris Webber and Jalen Rose. In his memoir, Obama writes that he would watch the University of Hawaii players laughing at “some inside joke,” winking “at the girls on the sidelines,” or “casually flipping lay-ups.” What Obama saw in the Fabulous Five was not just game, but a culture he found attractive:
By the time I reached high school, I was playing on Punahou’s teams, and could take my game to the university courts, where a handful of black men, mostly gym rats and has-beens, would teach me an attitude that didn’t just have to do with the sport. That respect came from what you did and not who your daddy was. That you could talk stuff to rattle an opponent, but that you should shut the hell up if you couldn’t back it up. That you didn’t let anyone sneak up behind you to see emotions—like hurt or fear—you didn’t want them to see.
These are lessons, particularly the last one, that for black people apply as much on the street as they do on the court. Basketball was a link for Obama, a medium for downloading black culture from the mainland that birthed the Fabulous Five. Assessing his own thought process at the time, Obama writes, “I decided to become part of that world.” This is one of the most incredible sentences ever written in the long, decorated history of black memoir, if only because very few black people have ever enjoyed enough power to write it.
Historically, in black autobiography, to be remanded into the black race has meant exposure to a myriad of traumas, often commencing in childhood. Frederick Douglass is separated from his grandmother. The enslaved Harriet Ann Jacobs must constantly cope with the threat of rape before she escapes. After telling his teacher he wants to be a lawyer, Malcolm X is told that the job isn’t for “niggers.” Black culture often serves as the balm for such traumas, or even the means to resist them. Douglass finds the courage to face the “slave-breaker” Edward Covey after being given an allegedly enchanted root by “a genuine African” possessing powers from “the eastern nations.” Malcolm X’s dancing connects him to his “long-suppressed African instincts.” If black racial identity speaks to all the things done to people of recent African ancestry, black cultural identity was created in response to them. The division is not neat; the two are linked, and it is incredibly hard to be a full participant in the world of cultural identity without experiencing the trauma of racial identity.
Obama is somewhat different. He writes of bloodying the nose of a white kid who called him a “coon,” and of chafing at racist remarks from a tennis coach, and of feeling offended after a white woman in his apartment building told the manager that he was following her. But the kinds of traumas that marked African Americans of his generation—beatings at the hands of racist police, being herded into poor schools, grinding out a life in a tenement building—were mostly abstract for him. Moreover, the kind of spatial restriction that most black people feel at an early age—having rocks thrown at you for being on the wrong side of the tracks, for instance—was largely absent from his life. In its place, Obama was gifted with a well-stamped passport and admittance to elite private schools—all of which spoke of other identities, other lives and other worlds where the color line was neither determinative nor especially relevant. Obama could have grown into a raceless cosmopolitan. Surely he would have lived in a world of problems, but problems not embodied by him.
Instead, he decided to enter this world.
“I always felt as if being black was cool,” Obama told me while traveling to a campaign event. He was sitting on Air Force One, his tie loosened, his shirtsleeves rolled up. “[Being black] was not something to run away from but something to embrace. Why that is, I think, is complicated. Part of it is I think that my mother thought black folks were cool, and if your mother loves you and is praising you—and says you look good, are smart—as you are, then you don’t kind of think in terms of How can I avoid this? You feel pretty good about it.”
As a child, Obama’s embrace of blackness was facilitated, not impeded, by white people. Obama’s mother pointed him toward the history and culture of African Americans. Stanley, his grandfather, who came originally from Kansas, took him to basketball games at the University of Hawaii, as well as to black bars. Stanley introduced him to the black writer Frank Marshall Davis. The facilitation was as much indirect as direct. Obama recalls watching his grandfather at those black bars and understanding that “most of the people in the bar weren’t there out of choice,” and that “our presence there felt forced.” From his mother’s life of extensive travel, he learned to value the significance of having a home.
That suspicion of rootlessness extends throughout Dreams From My Father. He describes integration as a “one-way street” on which black people are asked to abandon themselves to fully experience America’s benefits. Confronted with a woman named Joyce, a mixed-race, green-eyed college classmate who insists that she is not “black” but “multiracial,” Obama is scornful. “That was the problem with people like Joyce,” he writes. “They talked about the richness of their multicultural heritage and it sounded real good, until you noticed that they avoided black people.” Later in the memoir, Obama tells the story of falling in love with a white woman. During a visit to her family’s country house, he found himself in the library, which was filled with pictures of the woman’s illustrious relations. But instead of being in awe, Obama realized that he and the woman lived in different worlds. “And I knew that if we stayed together, I’d eventually live in hers,” he writes. “Between the two of us, I was the one who knew how to live as an outsider.”
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 20th 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 Kansan and Hawaiian roots, 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 willing 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 co-workers. 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 18 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, D.C., 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.”
He was correct. The ghettos of America are the direct result of decades of public-policy decisions: the redlining of real-estate zoning maps, the expanded authority given to prosecutors, the increased funding given to prisons. And all of this was done on the backs of people still reeling from the 250-year legacy of slavery. The results of this negative investment are clear—African Americans rank at the bottom of nearly every major socioeconomic measure in the country.
Obama’s formula for closing this chasm between black and white America, like that of many progressive politicians today, proceeded from policy designed for all of America. Blacks disproportionately benefit from this effort, since they are disproportionately in need. The Affordable Care Act, which cut the uninsured rate in the black community by at least a third, was Obama’s most prominent example. Its full benefit has yet to be felt by African Americans, because several states in the South have declined to expand Medicaid. But when the president and I were meeting, the ACA’s advocates believed that pressure on state budgets would force expansion, and there was evidence to support this: Louisiana had expanded Medicaid earlier in 2016, and advocates were gearing up for wars to be waged in Georgia and Virginia.
Obama also emphasized the need for a strong Justice Department with a deep commitment to nondiscrimination. When Obama moved into the White House in 2009, the Justice Department’s Civil Rights Division “was in shambles,” former Attorney General Eric Holder told me recently. “I mean, I had been there for 12 years as a line guy. I started out in ’76, so I served under Republicans and Democrats. And what the [George W.] Bush administration, what the Bush DOJ did, was unlike anything that had ever happened before in terms of politicized hiring.” The career civil servants below the political appointees, Holder said, were not even invited to the meetings in which the key hiring and policy decisions were made. After Obama’s inauguration, Holder told me, “I remember going to tell all the folks at the Civil Rights Division, ‘The Civil Rights Division is open for business again.’ The president gave me additional funds to hire people.”
The political press developed a narrative that because Obama felt he had to modulate his rhetoric on race, Holder was the administration’s true, and thus blacker, conscience. Holder is certainly blunter, and this worried some of the White House staff. Early in Obama’s first term, Holder gave a speech on race in which he said the United States had been a “nation of cowards” on the subject. But positioning the two men as opposites elides an important fact: Holder was appointed by the president, and went only as far as the president allowed. I asked Holder whether he had toned down his rhetoric after that controversial speech. “Nope,” he said. Reflecting on his relationship with the president, Holder said, “We were also kind of different people, you know? He is the Zen guy. And I’m kind of the hot-blooded West Indian. And I thought we made a good team, but there’s nothing that I ever did or said that I don’t think he would have said, ‘I support him 100 percent.’
“Now, the ‘nation of cowards’ speech, the president might have used a different phrase—maybe, probably. But he and I share a worldview, you know? And when I hear people say, ‘Well, you are blacker than him’ or something like that, I think, What are you all talking about?”
For much of his presidency, a standard portion of Obama’s speeches about race riffed on black people’s need to turn off the television, stop eating junk food, and stop blaming white people for their problems. Obama would deliver this lecture to any black audience, regardless of context. It was bizarre, for instance, to see the president warning young men who’d just graduated from Morehouse College, one of the most storied black colleges in the country, about making “excuses” and blaming whites.
This part of the Obama formula is the most troubling, and least thought-out. This judgment emerges from my own biography. I am the product of black parents who encouraged me to read, of black teachers who felt my work ethic did not match my potential, of black college professors who taught me intellectual rigor. And they did this in a world that every day insulted their humanity. It was not so much that the black layabouts and deadbeats Obama invoked in his speeches were unrecognizable. I had seen those people too. But I’d also seen the same among white people. If black men were overrepresented among drug dealers and absentee dads of the world, it was directly related to their being underrepresented among the Bernie Madoffs and Kenneth Lays of the world. Power was what mattered, and what characterized the differences between black and white America was not a difference in work ethic, but a system engineered to place one on top of the other.
The mark of that system is visible at every level of American society, regardless of the quality of one’s choices. For instance, the unemployment rate among black college graduates (4.1 percent) is almost the same as the unemployment rate among white high-school graduates (4.6 percent). But that college degree is generally purchased at a higher price by blacks than by whites. According to research by the Brookings Institution, African Americans tend to carry more student debt four years after graduation ($53,000 versus $28,000) and suffer from a higher default rate on their loans (7.6 percent versus 2.4 percent) than white Americans. This is both the result and the perpetuator of a sprawling wealth gap between the races. White households, on average, hold seven times as much wealth as black households—a difference so large as to make comparing the “black middle class” and “white middle class” meaningless; they’re simply not comparable. According to Patrick Sharkey, a sociologist at New York University who studies economic mobility, black families making $100,000 a year or more live in more-disadvantaged neighborhoods than white families making less than $30,000. This gap didn’t just appear by magic; it’s the result of the government’s effort over many decades to create a pigmentocracy—one that will continue without explicit intervention.
Obama had been on the record as opposing reparations. But now, late in his presidency, he seemed more open to the idea—in theory, at least, if not in practice.
“Theoretically, you can make obviously a powerful argument that centuries of slavery, Jim Crow, discrimination are the primary cause for all those gaps,” Obama said, referencing the gulf in education, wealth, and employment that separates black and white America. “That those were wrongs to the black community as a whole, and black families specifically, and that in order to close that gap, a society has a moral obligation to make a large, aggressive investment, even if it’s not in the form of individual reparations checks but in the form of a Marshall Plan.”
The political problems with turning the argument for reparations into reality are manifold, Obama said. “If you look at countries like South Africa, where you had a black majority, there have been efforts to tax and help that black majority, but it hasn’t come in the form of a formal reparations program. You have countries like India that have tried to help untouchables, with essentially affirmative-action programs, but it hasn’t fundamentally changed the structure of their societies. So the bottom line is that it’s hard to find a model in which you can practically administer and sustain political support for those kinds of efforts.”
Obama went on to say that it would be better, and more realistic, to get the country to rally behind a robust liberal agenda and build on the enormous progress that’s been made toward getting white Americans to accept nondiscrimination as a basic operating premise. But the progress toward nondiscrimination did not appear overnight. It was achieved by people willing to make an unpopular argumen