We had the sense . . . that he genuinely cared what the conservatives had to say and what they thought and that he would listen to their ideas with an open mind. And so there was just a much greater comfort level with the notion of Barack . . . than some of the others.
—BRAD BERENSON, A HARVARD LAW SCHOOL CLASSMATE
Community organizing is high-burnout work. Battling a harsh world that often ignores the poor and dispossessed gave rise to perhaps the first extended period of disillusionment in the life of the young idealist from Hawaii. Before that point, Barack Obama had had little contact with failure. At a minimum, he had found modest success at whatever he tried, from pickup basketball to college studies to attracting young women.
Initially, one of his biggest organizing projects—the asbestos campaign in Altgeld Gardens and its nice run of media coverage in Chicago—seemed to be a small victory for Obama and other Altgeld activists. Ultimately, though, the victory proved ephemeral. Budget priorities in Washington soon sapped much of the activists’ sense of lasting accomplishment. Federal officials told the public-housing residents that they had a choice between repairing Altgeld’s antiquated plumbing and leaky roofing or cleaning up the poisonous asbestos—there was not enough funding for both. This left many residents wondering what all their hard work and activism had wrought. “Ain’t nothing gonna change, Mr. Obama,” one dispirited resident complained. Moreover, squabbling between members of Obama’s Developing Communities Project and another group did not help instill optimism about the long-term success of organizing efforts in Altgeld. Thus, a couple of residents told Obama they were so busy trying to make ends meet in their households that they no longer had time for public activism, especially since it appeared to be leading to scant advancement.
As these frustrations mounted for Obama, an abrupt external event radically altered the political and racial landscape in Chicago. In November 1987, the city’s first black mayor, Harold Washington, suffered a massive heart attack at his desk in city hall and died. Washington’s election in 1983, the year before Obama arrived, was a seminal moment for Chicago’s African-American community, even if it cracked wide open the city’s deep and lingering racial divide. It was also an object lesson for Obama in the real power that American democracy bestows on its duly elected political leaders.
Organizers had registered more than one hundred thousand new black voters, and Washington squeaked through a three-way Democratic primary in which the vote was largely divided along racial lines. The two white candidates, incumbent Jane Byrne and Richard M. Daley, son of the longtime mayor Richard J. Daley, had split the white vote. Washington, meanwhile, won nearly all the black vote and captured just enough support from liberal, reform-minded whites. Typically in Chicago, where the Cook County Democratic Party reigns supreme, the Democratic primary winner is a lock in the fall general election. But Washington was a different story. He barely eked out a November victory against Republican Bernie Epton, who suddenly found support among white Democrats and powerful ward organizations in white neighborhoods. Even after Washington took office, he encountered stubborn white resistance on the city council and could not win enough votes to enact his programs and appoint his chosen nominees. The city council descended into a bitter, racially polarized battle dubbed the “Council Wars,” after the then-popular science fiction film Star Wars. In 1986, two years after Washington took office, special elections were called and enough Washington-endorsed candidates were victorious to allow his agenda to go forward.
Obama wrote poignantly in Dreams of the significance of Washington’s ascendance in the lives of Chicago’s more than one million blacks. When Washington died, it was a devastating blow to that community. Thousands attended his two-day wake in the lobby of city hall. “Everywhere black people appeared dazed, stricken, uncertain of direction, frightened of the future,” Obama wrote.
With Washington’s abrupt death, and considering his own modest organizing successes, Obama grew dispirited. This Chicago adventure—to follow his sense of mission in assisting poor African Americans—was worthwhile in many ways. It opened his eyes to both the complexities and the shortcomings of a unique racial culture, as well as to the cruel reality of American priorities. But after three years of working close to the “streets” he had so longed for, Obama felt shackled by the limited power of a small nonprofit group to create expansive change.
Bobby Titcomb, his friend from the Punahou Academy, visited Obama around this time and found his teenage chum far less optimistic and readily enthusiastic than during their Hawaiian childhoods. One night, an extremely frustrated Obama arrived at his apartment near the University of Chicago from a meeting of unhappy residents at a church. “I just can’t get things done here without a law degree,” Obama told Titcomb. “I’ve got to get a law degree to do anything against these guys because they’ve got their little loopholes and this and that. A law degree—that’s the only way to work against these guys.” It had not gone unnoticed by Obama that Mayor Washington had a been a graduate of the Northwestern University School of Law, and he had parlayed that lofty degree and his own personal charisma into a highly successful political career. Indeed, Obama watched closely as Washington unabashedly wielded his power to pour resources into the city’s ailing minority communities. The mayor led the fight to redistrict council wards to give more representation to Latinos and blacks; he issued an executive order to increase city contracts with minority-owned businesses; he upgraded city services in poor black and Latino neighborhoods. Washington could do more for Chicago’s poor blacks with the wave of his veto pen than Obama could in countless days and nights of community meetings in Roseland and Altgeld.
Titcomb was not prone to Obama’s activism and was grappling with a set of family problems at the time, so he had only a partial understanding of Obama’s personal disheartenment. But he could see the resolve in his friend’s eyes. Obama would soon be accepted at the most prestigious law school in the country, lifting him even higher into a world of intellectual elites and setting him on a course to the kind of political power that even Harold Washington could only dream of possessing.
OBAMA ARRIVED AT HARVARD LAW SCHOOL WITH A UNIQUE pedigree. At twenty-seven, he was several years older than his typical classmate, who most likely had come straight from a highly regarded undergraduate school. Like many of the students, however, Obama had been privileged to receive an elite primary and secondary education. Punahou Academy, Occidental College and Columbia University—all were excellent private schools. Yet Obama’s life was already much different from that of the typical Harvard Law student. He was a black man from Hawaii who had been a community organizer in Chicago for three years; by now, he had also taken his first trip to Kenya to explore his father’s roots. After his several years of a minimalist life in New York, and several years of diligent work in Chicago’s neighborhoods, Obama had attained a maturity level and an extraordinary degree of self-discipline that would greatly abet his success at Harvard. He was now committed to his studies as never before, and his grades reflected this—he would graduate magna cum laude. A classmate, Michael Froman, who would later work in Bill Clinton’s Treasury Department, said it was readily evident that Obama was operating on a different plane from everyone else. “He was mature beyond his years in being able to approach issues in the way that he did. I saw people who were much older and more seasoned who have similar attributes as Barack. And he was doing this in his twenties. This is a temperament and a style that he clearly developed ahead of his peers.” (In 2004, Froman would reconnect with Obama and serve as a key adviser in organizing his Senate office.)
As in New York and, to some degree, Chicago, Obama spent a vast amount of time by himself while in Cambridge. In his initial year, his daily routine included carving out a spot for himself in one of the sections for first-year students at the library and burrowing in for several hours of intense study.
Obama again made friendships with the small number of black students on campus. But after largely coming to terms with his mixed racial ancestry, he also reached out and secured several close white friendships. He researched and wrote articles for the Harvard Civil Rights–Civil Liberties Law Review. He was active in the antiapartheid movement on campus, gave a speech at the annual dinner hosted by the Black Law Students Association and served on the association’s board of directors.
Harvard was the forum in which Obama’s long-term public message of unity and altruism would take its first oratorical shape. At the Black Law Students’ dinner, Obama asked his audience to remember that their privileged education meant that they now had the means, opportunity and, yes, the responsibility to use their prestigious law degrees to return something to the less privileged. Friends and professors recalled that Obama invoked similar rhetoric in his often fiery and inspirational speeches concerning the importance of cultures and ideas mixing on campus—his hope being that if students with differing philosophies interacted more often, they would be less wary of opinions the opposite of their own. This bridge-building approach to racial and partisan politics was the first indication of the tightrope he would walk throughout his career. He would give voice to minorities who felt slighted but in a conciliatory tone that did not threaten whites; in addition, he would give conservatives the impression that he was willing to listen to their arguments. In his political career, Obama would deliver numerous speeches along these lines—about the value of helping those less privileged and the ideal of multiculturalism. And, of course, Obama would center his presidential campaign on the message of uniting a bitterly divided country.
His message of racial and intellectual unity may not necessarily have been controversial, but it certainly flew in the face of events on the Harvard campus in the early 1990s. Black students, in particular, were agitating for more minority representation among the faculty ranks. Toward that end, a group of blacks sued the school for discrimination; and a black professor, Derrick Bell, resigned over the matter. Obama largely steered clear of the fray, but he did give a speech calling for greater faculty diversity and heaping praise on Bell for his defiant stand.
Besides these racial tensions, Harvard Law was in the midst of a bitter ideological war. Liberals and conservatives waged fierce intellectual battles in classrooms, lunchrooms, at parties and, of course, in the offices of the prestigious Law Review. Despite these differences, Harvard Law is considered by most to be a bastion of liberal thought. This left-leaning history is rooted in the Vietnam War era when progressive activists at Harvard Law railed against school policies and, most vociferously, the war. In recent years, liberal professors like Laurence Tribe and Alan Dershowitz have gained national reputations, pushing the school’s image even farther in that direction. The Economist magazine went so far as to dub the school “the command centre of American liberalism.”
Obama immediately made a mark at Harvard among his peers and professors. He went to work for Tribe as a research aide and so thoroughly impressed the renowned legal scholar that Tribe would later call Obama his “most amazing research assistant.” In a 2006 Harvard admissions blog written by an administrator, Tribe added this incredible statement: “He’s a guy I hope will be President someday.”
Obama made enduring friendships at Harvard, one of the most significant being with a black woman named Cassandra Butts, who would later become a senior adviser to Representative Richard Gephardt of Missouri. The two met in the financial aid office the first week of classes. Obama’s personal charm, interesting background and unique perspective intrigued her. “But you know, once you get past the charm, what keeps you, what engages you—or at least, what engaged me—was his decency and the intellectual curiosity. And you know, that combination, and the experience that he had from his work as an organizer, the international experience that he had—he just saw the world in a different way than anyone I had met, to that point, and definitely anyone who was in law school with us. And so that, you know, that just made him interesting. [He] was a wonderful filter through which to see what we were learning and how you apply what we were learning to the outside world. He came to discussions with much more life experience than most of the students. I mean, we all had big ideas, but Barack had the experience.” This experience often gave his opinions a greater weight, although she said Obama did not offer them as such.
THE MOST GLARING EXAMPLE OF OBAMA’S DIFFERENT PERSPECTIVE came during a large organized discussion among black students of Harvard’s law, medical and business schools. The meeting was convened to discuss a hot topic of the day among educated blacks: Should they refer to themselves as “blacks” or “African Americans”? This debate would not end in the 1980s. In an essay in the Chicago Tribune Magazine nearly a decade later, columnist Clarence Page explored the source of the issue. He asserted that the label debate was a way for black Americans to define their own identities rather than having the white majority define it for them. But he conceded that this led to great confusion among people of all races. “Diversity is enriching,” Page wrote, “but race intrudes rudely on the individual’s attempts to define his or her own identity. I used to be ‘colored.’ Then I was ‘Negro.’ Then I became ‘black.’ Then I became ‘African American.’ Today I am a ‘person of color.’ In three decades I have been transformed from a ‘colored person’ to a ‘person of color.’ . . . Changes in what we black people call ourselves are quite annoying to some white people, which is its own reward to some black people. But if white people are confused, so are quite a few black people.”
At Harvard, that identity confusion came forth passionately in the organized conversation among the black students, with participants arguing heatedly for each side. But when Obama stood up to speak, he didn’t take sides. Instead, he looked at the discussion from the pragmatic viewpoint of a former community organizer. He said the whole issue was immaterial to the real world. As Butts recalled it, Obama told the crowd: “You know, whether we’re called black or African Americans doesn’t make a whole heck of a lot of difference to the lives of people who are working hard, you know, living day to day, in Chicago, in New York. That’s not what’s going to make a difference in their lives. It’s how we use our education in these next three years to make their lives better. You know, that’s what’s going to have an impact on making the U.S. a more just place to live, and that’s what’s going to have an impact on their lives.”
OBAMA’S MOST IMPORTANT EXPERIENCE AND DEFINING ROLE AT Harvard would be his tenure as a writer, editor and, finally, president of the Harvard Law Review, the most influential legal publication in the country. It was hard for him to see the significance of this role at the time, but the Review presidency would provide him with his first lessons in managing both bitter electoral politics and the personal agendas of individual people.
The Review is edited by students, allowing them a high-profile public forum in which to display their research and writing skills. But it also permits scholars and others to voice their arguments in the most highly read publication in the legal community. A Law Review post, especially the presidency, is an immediate attention-grabber on any résumé. Even so, the top job held little appeal for Obama. As his first year of law school wound down, he garnered a position on the Review through high grades, a writing competition and endorsements from other students and professors. Almost immediately, friends urged him to run for the presidency, but Obama expressed no interest. He told them that overseeing the legal journal would do nothing to enhance his future as a lawyer. After all, he did not envision clerking for a federal judge or seeking a position at a prestigious law firm. Obama wanted to return to Chicago and use his degree to help the city’s disadvantaged, or perhaps follow Harold Washington’s model and take a stab at politics. Therefore, the credential of Law Review president seemed of little value.
In 1990 the Review’s staff of about seventy-five students was riven by intense partisan feuding. Large factions of liberals and small bands of conservatives were engaged in titanic ideological struggles, with each side trying to push the Review’s leading viewpoint in its own direction. Since the liberals outnumbered the conservatives, they mostly dominated the discussion. But a growing movement of conservatives on campus had gained a foothold and was pushing for a larger voice. The Federalist Society, a national group of attorneys and law students that describes itself as “conservatives and libertarians dedicated to reforming the current legal order,” was gaining more adherents among students of Harvard Law. (Over the next two decades, the Federalist Society would grow exponentially and become a force of conservatism at the school. And the group would gain national prominence for exerting great influence in the Republican administration of George W. Bush, with society members appointed to cabinet posts and throughout the Department of Justice.) Brad Berenson, a classmate of Obama who later served in Bush’s Justice Department, said he had never seen more vicious political infighting and backbiting than during his Harvard Law days. He said the law school campus “was populated by a bunch of would-be Daniel Websters harnessed to extreme political ideologies.” He added that “political rivalries and personal divisions inside the Review were just ridiculously bitter, given how little was at stake.”
This heated battle of ideology and personalities played out fiercely as the Review conducted elections for its 1990–91 president. The electoral process itself is like no other. Inside the Review’s cluttered, cramped offices in a three-story Greek Revival building that was formerly a single-family home, candidates spend election day preparing food for their roughly seventy-five colleagues as ballots for the presidency are cast. Over hours of spicy chili and less spicy spaghetti, candidates are eliminated and the field is winnowed down. At the last moment and at the urging of his friends, Obama cast his hat in the ring. He was one of nineteen editors who ran for the presidency—about one in four of the staff. As such, the balloting session was egregiously long that year, lasting from a Sunday morning into the wee hours of the following Monday morning. Candidates eliminated from the next round of balloting typically sit down for a meal and start casting ballots themselves.
Finally, after the last conservative was voted out of the competition, that faction threw its support behind Obama, tilting the election in his favor and bestowing on him the honor of being the first African American to hold the presidency in the more than a century of the Review’s existence. As the final outcome was announced, another black student with tears in his eyes, Kenneth Mack, threw his arms around Obama. The decision would provide Obama with his first bit of national media exposure, profiles quickly appearing in the New York Times and several other publications. That publicity, in turn, opened up the opportunity for Obama to publish Dreams.
Berenson, a member of the conservative group, said that Obama won over his peers for various reasons, but race was not among them: “He was picked completely on the merits.” Obama was a devoted liberal, but conservatives believed he would give their opinions a fair hearing. Obama seemed less ideologically rigid and more evenhanded than the other progressive candidates, Berenson recalled. “Barack always floated a little bit above those controversies and divisions. Barack made no bones about the fact that he was a liberal, but you didn’t get the sense that he was a partisan—that he allied himself with some ideological faction on the Review and had it in for the other ideological factions on the Review. He was a more mature and more reasonable and more open-minded person. We had the sense, and I think it was borne out by the experience of his presidency, that he genuinely cared what the conservatives had to say and what they thought and that he would listen to their ideas with an open mind. And so there was just a much greater comfort level with the notion of Barack as president than some of the others.”
The conservatives were indeed correct in their assessment. Obama was an avowed social and economic liberal, but his reasonable tone and attentive listening skills gave him a nonthreatening appeal to partisans on the right. Obama, in fact, used some of his appointment power to place conservatives in key editorial positions on the Review. He asserted that each viewpoint deserved a fair hearing—a magnanimous sentiment that would produce some criticism from people in his own progressive crowd, as well as from minorities who wanted him to put their advancement at the top of his Law Review agenda. But Obama was more interested in making his publication run smoothly and convey diverse opinions than in pleasing everyone in the liberal and black contingents. His tenure as Review president, in fact, would foreshadow his future political style: a belief in giving attention to people with views other than his own; a desire to reach across the aisle to form consensus; a tendency to disappoint people in his own crowd—blacks and progressives—by not being more strident in his demeanor or behavior.
Despite this grumbling, however, the Review ran rather peacefully under Obama, especially considering how bitter the partisan feuding had been. “He did show great political deftness as president of the Review in maintaining good relations with most, if not all, of the editors of the Review,” said Berenson, the devout conservative. “He made people feel generally included and valued and he got everybody in harness, working toward a common goal, notwithstanding a lot of the other problems and fissures that existed. I remember marveling at the amazing set of interpersonal and political skills that he had. It was a fractious, headstrong bunch. And he led the group with considerable skill and finesse.”
One group disenchanted with Obama’s Law Review performance was some campus blacks who criticized him for not filling more management posts with African Americans. This is a criticism that Obama concedes has dogged him, and would continue to beset him throughout his public career. Obama has consistently advocated racial diversity and affirmative action, but he has also advocated promotion based on merit. So when he appointed some conservatives to the Review’s upper editing ranks and bypassed some minorities and women, the criticism rang forth. Butts defended Obama’s choices, even though she wasn’t as close to the Review’s internal workings as he was. She said he was fixed on making the best personnel choices based on talent, dedication and temperament.
Obama, for his part, would not talk in specifics about his personnel choices. But in the weeks leading up to his inauguration as a U.S. senator, he told me that the Law Review experience was a precursor to what he expected to confront in Washington—that he would anger some minorities and liberals by concentrating on serving a constituency of all races, ethnicities and political affiliations. “On the Law Review, that was the first time I had to deal with something that I suspect I’ll have to deal with in the future, which is balancing a broader constituency with the specific expectations of being an African American in a position of influence,” he said. “I had to manage a Law Review with seventy students who all want their own positions and who all want their advancement. And I had to make decisions about promoting diversity but also ensuring that people feel that I am being fair. So as for the criticism, I’m not sure there was anything all that surprising about that.”
As his Harvard schooling wound down, Obama began setting his sights on the mission that he had been training for—politics back in Chicago. All through his time in Cambridge, he had never mentioned running for any office but mayor of Chicago. Harold Washington’s tenure in that position had so impressed Obama that, in his mind, overseeing Chicago City Hall was the top political job in the country. “He wanted to be mayor of Chicago, and that was all he talked about as far as holding office,” Butts said. “He never talked about the U.S. Senate; he never talked about being governor. He only talked about being mayor, because he felt that is really where you have an impact. That’s where you could really make a difference in the lives of those people he had spent those years organizing. He could have gone on to great acclaim, but those people still were his mission.”