The Bridge: The Life and Rise of Barack Obama

by David Remnick

  It was time, Obama told Kellman, for him to get a legal education. He wanted to go to Harvard.

  "Harvard Law School was also a personal security decision," Kellman said. "He wanted to make a living, a decent living. He wasn't a materialist at all. He wanted security to support a family." Money certainly was a part of his decision. By then, Obama's salary had gone up to thirty-five thousand dollars. He was not uninterested in making more than that. He wanted a family, and a reliable income. But above all he wanted to move on, acquire the tools he needed for politics. More often than not, Obama said, organizing ended up in failure; the gains were too small, too rare. Kellman, who soon left organizing himself for a while, did not argue the point. If anything, his level of frustration ran deeper. The conversations at the divinity school intensified Kellman's conviction that one day Obama would return to Chicago and run for public office.

  On November 25, 1987, Harold Washington, who had been reelected the year before, died at his desk at City Hall--a death, Obama wrote, that was "sudden, simple, final, almost ridiculous in its ordinariness." Like most of the city, Obama spent much of that Thanksgiving weekend watching on television as the lines of mourners at City Hall stood in the cold rain; he listened to WVON, the main black talk-radio station in town, take calls from African-Americans who regarded Washington as a fallen king. In many ways, Obama revered Washington, but he also despaired that Washington had not left behind a strong political organization: "Black politics had centered on one man who radiated like a sun." After eight days of negotiations, the City Council installed Eugene Sawyer, a black member of the old machine, as mayor. Sawyer had shown support for Washington but now had to rely on the white conservative aldermen like the "Eddies," Edward Vrdolyak and Ed Burke, Washington's archenemies in what was known as the "Council Wars." (Vrdolyak, the epitome of a corrupt machine alderman, finally ended his long career in 2008 with a string of federal indictments and a conviction for mail and wire fraud.)

  Obama went to City Hall to witness what he called "the second death": Sawyer's official elevation. Outside, Obama watched as the crowd, mainly older black men and women, denounced the African-American aldermen who were doing business with Vrdolyak and waved dollar bills at Sawyer, calling him an Uncle Tom. In the weeks after Washington's death and the sorry spectacle of Sawyer's installation, some of Obama's friends, including Mike Kruglik, became even more convinced that he would one day return to Chicago and run for office.

  Toward the end of his time as an organizer, Obama met with Bruce Orenstein, an organizer for the United Neighborhood Organization, who had worked with him in an attempt to devise a way to profit off of the local landfills to fund community improvements on the far South Side. A proposal they had put together had won support from Harold Washington, but it collapsed after he died. Sawyer was not Harold Washington. Both Obama and Orenstein were frustrated and ready to move on--Obama to law school, Orenstein into video projects. When Orenstein asked him over a beer where he planned to be in ten years, Obama replied, "I'm going to write a book and I want to be mayor of Chicago."

  Obama asked John McKnight, a co-founder, with Greg Galluzzo, of the Gamaliel Foundation and a professor of communications at Northwestern, and Michael Baron, his politics professor at Columbia, to write letters of recommendation for him to Harvard Law. (He also applied to Yale and Stanford.) McKnight had met Obama when he arrived in Chicago as a trainee. Obama told him that now that he had seen what could be done on a "neighborhood level," he wanted to explore what could be done in public life. McKnight, who has been involved with organizing for decades, and who shared the organizer's traditional wariness of politicians, cautioned him: an organizer was an advocate for people and their interests; a politician, he said, is "the reverse," someone who synthesizes and compromises interests. Would he be satisfied with that? "That's why I want to go into public life," Obama replied. McKnight agreed to write the letter. He had the idea that Obama had not received exceptional grades as an undergraduate--"I don't think he did too well in college"--but he had been deeply impressed by his intelligence and his commitment as an organizer.

  Just after he left his job as an organizer, Obama published a short article in a local monthly, Illinois Issues, entitled "Why Organize? Problems and Promise in the Inner City." In the article, Obama makes clear that he came away from the experience in Chicago believing that neither electoral politics nor government development programs would help the inner cities unless they were "undergirded by a systemic approach to community organization." Despite the hope created by the election of black mayors like Washington, in Chicago, and in Gary, Indiana, the high-school dropout rates were still at nearly fifty per cent; the old forms of discrimination had been replaced by institutional racism; the flight of the middle class and a Reagan-era decline in public support had left inner cities in despair.

  Obama was not entirely frustrated with his experience in Chicago. He credited the Developing Communities Project and programs like it with gains in job training, school accountability, and better crime and drug programs. He and his colleagues had been able to set up a jobs-training center on Michigan Avenue in Roseland, on the site of a shut-down department store. (Harold Washington himself came to the ribbon-cutting.) And yet, like so many projects that Obama and his fellow organizers worked on, the jobs initiative floundered because there was so little work around. The center closed after three years. "I do know that we got some training done," Alvin Love said. "But I don't know how many people really got new jobs."

  By 1988, Obama's ideas about organizing no longer focused much on Saul Alinsky. For Obama, organizing was a way of thinking about fixing specific problems and also building a culture. "We tend to think of organizing as a mechanical, instrumental thing," Obama said in 1989 at a roundtable discussion organized by the Woods Charitable Fund, in Chicago. "I think Alinsky to some extent may not have emphasized this, but I think the unions that Alinsky saw--I think John L. Lewis understood that he was building a culture. When you look at what's happened to union organizing, one of the losses has been that sense of building a culture, of building up stories and getting people to reflect on what their lives mean and how people in the neighborhood can be heroes, and how they are part of a larger force. That got shoved to the side."

  Obama now saw Alinsky's theories and opinions as deeply flawed. Alinsky's critique of Martin Luther King, for example, showed a dismissal not only of charismatic leadership but also of long-term vision. Obama particularly disputed Alinsky's emphasis on confrontation. He thought the time had come to find new ways to reach young African-Americans. "They are not necessarily going to town hall meetings, and they are not going to pick up Reveille for Radicals," Obama said. "They are going to see the Spike Lee film, or they are going to listen to the rap group."

  Obama was clearly thinking about broader politics now and about how he, or anyone, could bring the experience of organizing to elected office. "How do you link up some of the most important lessons about organizing--accounting, training, leadership, and that stuff--with some powerful messages that came out of the civil-rights movement or what Jesse Jackson has done or what's been done by other charismatic leaders?" he asked the panel. "A whole sense of hope is generated out of what they do. Jesse Jackson can go into these communities and get these people excited and inspired. The organizational framework to consolidate that is missing. The best organizers in the black community right now are the crack dealers. They are fantastic. There's tremendous entrepreneurship and skill. So when I talk about vision or culture it has to do with how organizing in those communities can't just be instrumental. It can't just be civic. It can't just be, 'Let's get power, call in the alderman,' etc. It has to be recreating and recasting how these communities think about themselves."

  Obama could not have foreseen the full scope of his political future, but it's evident that he was thinking about the effect that someone like him could have both in imbuing a community with a sense of hope and in providing the organized framework for ma
king that hope an asset for reform. He rejected organizing's "suspicion of politics." To disdain politics, he told the panel, was to disdain "a major arena of power. That's where your major dialogue, discussion, is taking place. To marginalize yourself from that process is a damaging thing, and one that needs to be rethought."

  Obama, who had been attracted to community organizing by the example and the romance of the civil-rights movement, was, by the time his experience with it was over, thinking about how to combine elements of charismatic leadership, the principles of organizing, and a set of liberal political and policy principles. He was no longer interested in being an outsider; his thoughts were turning to elective politics. Going to law school--and, not incidentally, going to an institution like Harvard--was part of learning the fundamentals of a system he had seen mainly from the street.

  Obama never completely left the world of community organizing. On vacations from law school, he visited a new girlfriend in Chicago named Michelle Robinson, and also Kellman and Kruglik. He later served on the boards of the Woods Fund and the Lugenia Burns Hope Center, which helped fund organizing efforts in the city. He spoke at numerous retreats and training sessions. And while he learned a tremendous amount from his experience, he had also come to embrace the possibilities of charismatic leaders--whether an outsider like King or an insider like Washington--and what can be reaped in a political process of battle and compromise.

  In May, 1988, Obama made a clean break with the first chapter of his life in Chicago. He had split up with his old girlfriend. ("I ran into her a couple of weeks after he left and she seemed upset, brokenhearted," John Owens recalled. "Barack tends to make a strong impression on women.")

  As Obama handed over the leadership of the Developing Communities Project to Owens, he was determined to work on a broader level. "Barack's biggest success in Chicago had not been in bricks and mortar," his friend and comrade Reverend Alvin Love said. "He'd found out things about himself and his community. That was important. But what he really did was give people like me and Loretta, John Owens, and Yvonne Lloyd, and dozens and dozens of others, the tools to keep the work going, whether he was around or not."

  Before leaving, Obama gave his cat, Max, to Jerry Kellman. Then he said good-bye to his friends and drove out of town.

  Chapter Five

  Ambition

  In the early fall of 1988, Obama arrived in Cambridge sure that he would learn what he later called "a way of thinking." He was taking on thousands of dollars in debt for the privilege. Unlike many students who end up in law school without quite knowing why, apart from its value as another blue-chip credential, Obama approached Harvard purposefully, as a serious place that offered dimensions of knowledge that he could never acquire as an organizer on the South Side of Chicago. At Harvard, he would join the world of the super-meritocrats of his generation, shifting from outsider to insider. "I would learn about interest rates, corporate mergers, the legislative process, about the way businesses and banks were put together; how real-estate ventures succeeded or failed," he wrote. "I would learn power's currency in all its intricacy and detail, knowledge that would have compromised me before coming to Chicago but that I could now bring back to where it was needed, back to Roseland, back to Altgeld; bring it back like Promethean fire." Harvard also had a personal dimension: Barack, Sr., had left his wife and his two-year-old son to go there. If Obama had inherited anything from his father it was the notion that Harvard was the sine qua non, the place you went to go the farthest, achieve the most. At Harvard he would match his father, then surpass him; at Harvard he would acquire his serene self-confidence and a sense of his own destiny.

  A modern would-be politician, particularly a Democrat like Barack Obama, arrives at Harvard Law School keenly aware that the law school--its students and faculty--provided much of the brainpower for the New Deal, the New Frontier, and the Great Society. Before Obama, Rutherford B. Hayes was the only President to graduate from the law school, but Harvard alumni have always been well represented in Congress and, especially, on the Supreme Court. On the current Supreme Court, John Roberts, Antonin Scalia, Anthony Kennedy, and Stephen Breyer all graduated from the law school. (Ruth Bader Ginsburg attended for a year and made the Law Review, then moved with her husband to New York, and finished at Columbia.)

  The law school, which is just a short walk north of Harvard Yard, is a jumble of architectural styles, ranging from Austin Hall, the Romanesque creation, in 1883, of H. H. Richardson, to the Harkness Commons, a fairly brutal concoction from the Bauhaus catalogue of Walter Gropius. The land was the bequest of the Royall family, Southern plantation owners who brought their slaves North, to an estate in Medford, Massachusetts. In 1781, Isaac Royall, Jr., left Harvard an endowment that served to establish the college's first chair of law. The proceeds from the sale of the Medford estate, in 1806, became the seed money of the law school as a whole. The school, which was established in 1817, was small at first and fairly insignificant, until, in 1870, Christopher Columbus Langdell came to Harvard and instigated a new curriculum, based on the study of individual legal cases and a style of Socratic inquisition.

  By the time Obama arrived at Harvard, the law-school curriculum had grown much more flexible than in Langdell's day and the student body more diverse, but the school was still a fractious place, riven by political conflict and intramural resentments. As if to flaunt its own unhappiness, the law-school community commonly referred to itself as a bastion of Levantine infighting--alternately "Beirut on the Charles" and "the Beirut of legal education."

  Obama said that Harvard Law School was the "perfect place to examine how the power structure works." Indeed, the "power structure"--a phrase common in organizing circles--and how it is, or is not, examined by the likes of Harvard Law School was the focus of a battle that had already raged for a decade when Obama enrolled. In 1977, a group of legal academics--radicals, as most would readily have identified themselves--met at a conference in Madison, Wisconsin, to discuss a barely formed school of thought that was soon to be called Critical Legal Studies. Influenced by post-structuralism, the Frankfurt School of critical theory, and the Legal Realism of the nineteen-twenties, the scholars interested in Critical Legal Studies sought to demystify the law and the language of law and legal studies, to challenge its self-regard as a disinterested system of precedent. Critical Legal Studies posited that law is politics by other means, that the practice and discourse of law--and legal education--is merely another lever of entrenched power, a way of enforcing the primacy and perquisites of the wealthy, the powerful, the male, and the white. According to the adherents of Critical Legal Studies, many of the conditions of the legal status quo--the high incarceration rates among people of color, the higher penalties for drugs used mainly among the poor--are inscribed in a legal system that only pretends to be consistent and non-ideological.

  Many students at Harvard in the late seventies, the eighties, and the early nineties, who were not necessarily left-wing, were excited by this analysis. The leading Crits at Harvard were three vastly different scholars: Morton Horwitz, Duncan Kennedy, and Roberto Mangabeira Unger.

  "Barack didn't study directly with Horwitz or Kennedy, but they were very much in the air, and he absorbed what was going on," Obama's classmate Kenneth Mack, who is now himself a professor of law at Harvard, said. "The Crit who was most important to his studies--not that he was an acolyte--was Roberto Unger."

  Unger, a social theorist, born in Brazil, was one of those academics who combine a personal charisma and a mode of study that attract young students. The American legal system, Unger contends, pretends to neutrality and a reliance on precedent, but what it actually does is enforce the permanence and the property rights of elites; the law guards against radical challenges to the elites and engages only in narrow issues. Unger is less a legal scholar than a political philosopher, and the more conventional students at Harvard avoided his courses. "His course descriptions in the catalogue were impenetrable and you knew he was worse i
n class," a near-contemporary of Obama's said.

  Obama took two of his courses. The first was Jurisprudence. As Unger taught the course, Jurisprudence was a radical critique of contemporary Western political thought and legal theory and Obama's most prolonged academic exposure to the rudiments of Critical Legal Studies. A classmate who took the course with Obama described Jurisprudence as a "multi-step argument" that inspected, and then undermined, the presumptions of American legal thought. In his third year, Obama enrolled in Reinventing Democracy, a course in which Unger combined a critique of Western democracies--or neo-liberalism, as he referred to it--and the potential forms democracy could, or should, take. Unger argued against the "mandarins" who presided over contemporary democratic society and tried, in often highly experimental terms, to urge a rethinking of Western institutions. He urged the adoption of a "universal social inheritance" going well beyond the terms of the New Deal.

  "The Reinventing Democracy course was relatively small and very intense," Unger said. In class, Unger contrasted the "bold but shapeless" course of F.D.R.'s initiatives in the early days of the New Deal, his "institutional experimentalism," with the more "restrictive focus" of his later years in office. He also expounded on what he saw as the Democratic Party's failure in the second half of the twentieth century to follow up on the efforts of the early New Deal. The reforms of the Johnson Administration, for example, were deemed modest. The class debated the Republican ascendancy in post-war America--its concessions to moneyed interests and its cultural rhetoric, directed toward the white middle-class majority.