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Authors: Jeffrey Toobin

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Obama excelled in the classroom—he too would graduate magna cum laude—and he succeeded in the writing competition to join the staff of the
Harvard Law Review
. Students on law reviews edit articles that are submitted by law professors around the country; about forty out of five hundred students in a class make law review at Harvard. Every February, the staff of the law review holds an election to select the president, or editor in chief, of the magazine for the following year. Obama won with broad support. Conservative students, who were a growing presence at Harvard, turned out to be the key to Obama’s victory. The Federalist Society—the national conservative legal organization—had been founded at Yale in 1982, but Harvard soon opened a chapter, and its members asserted themselves as a vocal minority on the staff of the
Review
. The conservatives recognized that Obama was not one of their own, but they felt he would give them a fair shake, especially about which articles to publish. In winning the confidence of conservatives, Obama’s maturity proved a tremendous asset. In that tumultuous time on campus, Obama always seemed slightly removed from the battle lines, in his customary posture of both observer and participant. He had an innate grasp of the politician’s gift for persuading others that you agree with them without ever making an explicit commitment. Obama’s earnest style earned him some mockery from his friends. One of them told David Remnick that a group would go to the movies and tease Obama by imitating his solicitude: “Do you want salt on your popcorn?
Do you even
want
popcorn?”

Suddenly, then, with his election as president of the
Review
, Barack Obama was a celebrity of sorts. The
New York Times
did a story about him. Turner Broadcasting asked Obama to record a “Black History Minute,” and the young man, struggling with the teleprompter, gave a brief tribute to Charles Hamilton Houston, one of Thurgood Marshall’s legal mentors.
Vanity Fair
, which does not generally track the leadership of scholarly publications, devoted a full page to Obama’s election. “
The
New York Times
ran a ‘First Black’ headline, which probably won’t be the last time that label is affixed to Barack Obama,” Elise O’Shaughnessy wrote, before concluding that Obama “responds warily to the assumption that he himself will run for office. ‘If I go into politics it should grow out of work I’ve done on the local level, not because I’m some media creation.’ Though, as media creations go, he’d be a pretty good one.” In addition, around this time, Jane Dystel, a literary agent in New York, approached Obama with the idea of his writing a book. Obama agreed, and signed a contract with a division of Simon & Schuster. (At that point, people embraced Obama without knowing much about him. One publisher thought he was raised in the Chicago ghetto;
Vanity Fair
said he grew up in Singapore, not Indonesia. No one seemed to know that his real home was Honolulu.)

It was all a rather extraordinary amount of attention to a mere law student, but during his debut as a public figure, Obama demonstrated precocious political skills. “The fact that I’ve been elected shows a lot of progress,” he told Fox Butterfield, of the
Times
. “But it’s important that stories like mine aren’t used to say that everything is O.K. for blacks.” Likewise, Obama was always careful to show respect for his forebearers in the civil rights movement, whose sacrifices, he said, made his own success possible. He told the
Boston Globe
, “To some extent, I’m a symbolic stand-in
for a lot of the changes that have been made.”

But for all that Obama showed respect for Marshall, Houston, and their peers, he also made clear in his own way what he expected of the contemporary legal system: not much. Those pioneers had used the courts to break down the legal barriers that oppressed African Americans. But by the time Obama was at Harvard, that work was mostly done. The task of legal progressives of Obama’s vintage was to try to hang on to the gains that had been made in the courts—and that wasn’t easy, or of particular interest to him. In 1991, Obama graduated from Harvard Law School into the world of the Rehnquist Court, where the social change on the agenda was (almost always) in the conservative direction. If the right was ascendant, the left was distracted—with the baroque inventions of Critical Legal Studies. For someone like Obama, who had spent years working on the real-world problems of poor people in Chicago, theories untethered to reality had no appeal.

Later, when Obama was a senator, he explained the nature of his disillusionment with the use of the courts for social change. It wasn’t just that things looked bleak at the Rehnquist Court. “I wondered if, in
our reliance on the courts to vindicate not only our rights but also our values, progressives had lost too much faith in democracy,” he wrote in
The Audacity of Hope
. Yes, he pointed out that he believed in the right to privacy and celebrated the legacy of
Brown
in civil rights, but it wasn’t up to lawyers to preserve those rights. “There was one way to ensure that judges on the bench reflected our values, and that was to win at the polls.” Unlike his honored forebearers, Obama would devote his life to elections, not lawsuits.

Almost as soon as the president and the other new executives were elected to their positions on the masthead of the
Review
, most of them turned their attention to obtaining judicial clerkships. Many sought opportunities with judges on the circuit courts of appeals who were known as “feeders” to Supreme Court clerkships. After Obama won the presidency, Abner Mikva, a former congressman from Chicago, who then served as a judge on the D.C. Circuit, sought him out as a clerk. Mikva was a feeder, and virtually all presidents of the
Harvard Law Review
went on to clerk on the Supreme Court. But Obama turned Mikva down. It was further proof that his interests lay outside the legal system.

Obama’s election as president of the
Review
drew particular attention in his adopted hometown of Chicago, and an article in the
Sun-Times
piqued the interest of a local lawyer named Judson Miner. Miner belonged to the small cadre of left-leaning Chicago lawyers who had devoted their careers to fighting the Daley machine as well as race discrimination in its many permutations in the city. At the time, Miner, who is white, had returned to his small law firm after a stint as the top lawyer on the staff of Harold Washington, who was the city’s first black mayor before his sudden death in 1987. On a whim, Miner called the
Review
, to try to speak with Obama. The receptionist corrected Miner’s pronunciation of the name and told him, “You’re 643rd on the list.” But Obama called Miner back that day. (Miner’s daughter garbled the message. “Some guy with a funny name called,” she told him.)

Obama had lived in the Chicago political world long enough to know of Miner, even if he did not yet know him personally. Obama told Miner he was coming to town shortly and he would be delighted to take up Miner’s invitation to meet. Obama was returning on a recruiting
trip paid for by Sidley & Austin, one of the pillars of the legal establishment in the city. (Obama had worked there the previous summer and hadn’t cared for the big-firm environment. Still, the summer was not a total loss, because he met an associate at the firm named Michelle Robinson, and in time they started a romance.) At this point, Obama was looking for a job after graduation, and he wanted to talk to Miner about joining his firm, then known as Davis, Miner, Barnhill & Galland. Miner’s firm did the kind of civil rights and political work that interested Obama, and it offered a sufficiently flexible and informal structure that might allow him to do other things as well. Obama approached the subject in his usual methodical fashion—there were about six or seven lunches with Miner, with each man interviewing the other, in a way—but Obama finally agreed to sign on following his graduation. He was one of about a dozen lawyers.

Obama was never a conventional associate. Almost immediately, he took a leave from the firm work to run Project Vote, a voter registration drive designed to build turnout for the 1992 elections. A little while later, Obama took time off to finish the book that became
Dreams from My Father
. (It was long overdue to the publisher.) Miner brought Obama along in some civil rights cases, like a suit against Illinois to compel the state to comply with the motor voter law. There were also routine commercial disputes and a few criminal matters. Soon enough, Obama had another claim on his time. At the law review, Obama had edited an article by Michael McConnell, a conservative professor at the University of Chicago Law School. (George W. Bush later appointed McConnell to the Tenth Circuit.) McConnell was so impressed with Obama’s work on the piece, which concerned freedom of religion, that he suggested that the head of the appointments committee at the law school should take a look at Obama.

Obama told Douglas Baird, the chair of the committee, that he wasn’t interested in a tenure-track job. But the University of Chicago was so eager to have Obama on campus that the law school offered him an office and a fellowship to work on his book. Two years later, in 1993, Obama started teaching law students. Because he was effectively an adjunct professor, he was given the title of lecturer, and he continued teaching a class every semester for about a decade. Obama was an elusive presence on the Hyde Park campus; he tended to teach his classes and leave. He was not expected to do scholarly work—writing law review articles and the like—and he didn’t attend faculty meetings.
The University of Chicago long enjoyed a reputation for conservatism, especially in economics, and that was somewhat true at the law school as well. Richard Posner and Frank Easterbrook were two celebrated conservatives who were appointed to the federal bench by President Reagan and kept their ties to the law school. During Obama’s time, there was a substantial core of liberals on the faculty too, notably Diane Wood and Elena Kagan. Obama’s relations with all factions were the same: friendly but distant.

To the extent Obama had an academic specialty, it was voting rights—not surprising, given his interest in politics and his experience in the voter registration field. In the midnineties, Obama heard that a group of professors including Richard Pildes, then of the University of Michigan Law School, were preparing a casebook on what they called the law of democracy. Obama sought out Pildes, obtained a draft of the book, and used it to teach his class. The two men struck up a friendship based on their shared interest in what was then a fairly obscure field. (After
Bush v. Gore
in 2000, the law of elections drew more public and scholarly attention.)

The hot subject in voting rights at the Supreme Court, and in the academy, was racial gerrymandering. The Voting Rights Act of 1965, and its subsequent reauthorizations, forced states to draw their district lines so that African Americans would be positioned to win certain seats, both in Congress and in state legislatures. Most traditional civil rights groups, and black politicians, made a sacred cause of the creation of these so-called majority-minority districts. To them, this was the core purpose of the Voting Rights Act: to get more blacks elected to public office.

Obama was skeptical. After the census of 1990, Republicans, especially in the South, recognized that they could make the Voting Rights Act work for them, too. So GOP strategists joined with some black Democrats in creating overwhelmingly minority districts. As a result, black politicians won seats in several states where they had not won races since Reconstruction. At the same time these new districts drained Democratic votes from other districts—making them ripe targets for Republicans. A few black politicians gained sinecures, but the Democratic Party suffered. Indeed, the Republican takeover of the House of Representatives in 1994 came about in part because of losses by moderate Democrats in the South whose districts had been denuded of African American voters.

To Obama, the civil rights groups had it wrong on voting rights. Of course, Obama had no objections to blacks winning elections, but such victories alone were just symbols. He thought the point of politics was actually to accomplish something—to vindicate democratic (and Democratic) values by passing laws. If black politicians just hoarded Democratic voters to stay in office, they’d never get anything done once they were there. Without coalition building, Obama told Pildes, the progressive cause was doomed.

Five years after graduating from law school, in 1996, Obama began his political career by winning a seat in the state senate. Like most other Illinois legislators, Obama worked part-time for the state, and he kept up his association with Miner’s firm and still taught a class every semester at the law school. At least initially, the Springfield post proved to be a disappointment to Obama. As a junior Democrat in a body run by Republicans, he had almost no power. He quickly started looking for an exit strategy. In 1999, Obama decided to challenge Bobby Rush, an incumbent congressman, in a Democratic primary. The Chicago district was exactly the kind of racial gerrymander that Obama abhorred—and Rush was the kind of candidate who tended to do well in that kind of district. A former Black Panther, Rush had authenticity in abundance but little in the way of accomplishments. Still, the Democratic establishment (including President Bill Clinton) backed the incumbent, and Obama was humiliated in the 2000 primary, losing 61 percent to 30 percent.

The defeat took Obama to a personal and professional crossroads. He thought seriously (with encouragement from his wife) about dropping out of politics altogether. A job as president of a local foundation beckoned. Instead, Obama decided to dedicate himself, for the first time, to his work as a legislator. Court-ordered social change still held little allure for him, as he made clear in a 2001 interview on local Chicago public radio. Many liberals tried for years to persuade the Supreme Court to step beyond desegregation orders and direct that public schools be funded equally. Obama explained why he believed that approach had failed, citing the 1973 case of
San Antonio Independent School District v. Rodriguez
. In
Rodriguez
, the Court found, by a 5–4 vote, that unequal funding of school districts in the same state did not amount to
a violation of the equal protection clause of the Fourteenth Amendment. As Obama described the decision, the Court “basically slaps those kinds of claims down and says, ‘You know what—we as a court have no power to examine issues of redistribution and wealth inequalities with respect to schools. That’s not a race issue, that’s a wealth issue, and something we can’t get into.’ ” The Court said that it was up to legislatures, not courts, to make judgments about redistribution of wealth—which was fine with Obama. “Maybe I am showing my bias here as a legislator as well as a law professor,” he went on, but “the institution just isn’t structured that way.”

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