Chapter 2

From Organizer to Politician

Barack Obama attended Harvard Law School from 1988 to 1991. On his entrance at age twenty-seven, he was several years older than most of the 548 students in his class, the majority of whom were recent graduates of Ivy League schools or other well-respected private and public colleges and universities.¹

What struck faculty and staff was how much more mature and self-confident he seemed than the rest of the students. Almost from his first days at Harvard, when classmates became both friends and rivals in the highly competitive atmosphere of the law school, his calmness and rationality set him apart from the largely high-strung, often ideologically driven, and ambitious class. Although he shared some of these qualities, he was able to balance ambition, commitment, and drive with confidence, modesty, and dispassion. His ability to reconcile these seemingly conflicting characteristics would define his entire political career, but not before resulting in his only electoral defeat. His years at Harvard through the beginning of his political career also revealed a natural conservativism in his political nature.²

Harvard Law School

Obama had several mentors while at Harvard. Among them was Laurence Tribe, who held the title of University Professor, awarded only to faculty who had done groundbreaking work across multiple disciplines. In the spring semester of his first year, Obama came by Tribe’s office to ask for a position as his research assistant. His request took Tribe by surprise because he was known for not hiring first year students. But he was so impressed by Obama’s intelligence, personality, and demeanor that he hired him as his primary research assistant.³

At the time, Tribe was preparing an essay arguing the need for judges to apply Albert Einstein’s theory of relativity to the law. Just as Einstein argued that the very act of observation altered phenomena, Tribe maintained that judicial decisions altered social relations. Contrary to claims by strict constructionists, he argued that the law was not passive in its relationship to society.⁴

Instead of giving his research assistant mechanical assignments like checking articles in law reviews, Tribe got together with him periodically, sometimes to walk along the Charles River in order to discuss the article he was writing and to exchange ideas on the relationship of the law to society. He also had him assist on a book, Abortion: The Clash of Absolutes (1990) in which Tribe argued that the judiciary’s proper role was “to preserve those human rights and other principles to which our legal and political system is committed.” He later said that he regarded his assistant “much more as a colleague than a student.”⁵

Obama had entered Harvard with the intent of learning about the nature of America’s power structure, which he planned to apply politically, probably by running for office, after he returned to Chicago. While at law school, new ideas also came to shape Obama’s thinking and personality. “Here was an opportunity for me to read and reflect and study as much as I wanted,” he later recounted. Having spent much of his time reading while a student at Occidental and Columbia, he was no stranger to the world of ideas. With the exceptions, however, of Black authors like Ralph Ellison and Malcolm X influencing his identity as an African American and some of Saul Alinsky’s ideas on community organization, they were not formative in the way they became while at Harvard. ⁶

During that time, the legal profession was going through a period of great division and intellectual ferment. Orthodoxies of the law, like original intent and strict construction, were being challenged by newer persuasions of legal realism, particularly critical legal studies, which rejected the very concept of a consistent jurisprudence. The debate over whether the Constitution had unaltered meaning or was a living document subject to changing interpretation was an old one. But critical legal studies, whose adherents shared the view of the Constitution as a living document, took increasing hold on law school campuses as faculty and students fell under the influence of new theories drawn from such academic disciplines as history, philosophy, psychology, and women’s studies. In history, for example, an earlier emphasis on the importance to the founding fathers of liberty, defined as protection of personal rights including property rights, was challenged by a new emphasis on the influence of equality and civic virtue on them. Similarly, philosophical pragmatists, Freudians, and feminist theoreticians pried the Constitution away from its foundation in natural rights and natural law.⁷

Although Obama never wrote an essay spelling out his legal views, he was clearly a proponent of critical legal theory, except that he was more optimistic than some critics of the legal establishment, who argued that since the law was written and interpreted to preserve existing power structures, it was impossible to change the status quo. His own experience as a community organizer and his belief that politicians like Harold Washington could make a difference, led him to believe otherwise. Knowledgeable in history and a student of the Constitution, he accepted the latest interpretation by historians that the founding fathers emphasized republican concepts of equality and civic virtue rather than liberty.⁸

Not only did he reject the notion of absolute truths in the law, he adopted the principles of philosophical pragmatism first propounded by Charles S. Peirce, William James, and John Dewey in the early years of the twentieth century. Like them, he rejected the view that pragmatism should be grounded on the idea that an action was justified solely by its success. Instead, he believed it should be based on weighing the consequences of that action on society. It should subordinate goals, policies, and objectives to the general welfare. It should incorporate an ongoing process of evaluation to determine whether they remained workable and achievable. It should emphasize the plasticity of society. It should be premised on the need for consistent adjustment to meet changing societal needs, and it should embrace democratic inclusion.⁹

In his second year at Harvard, Obama enrolled in Tribe’s courses in constitutional law. Tribe later referred to him as an “incandescent intellectual [who had a] deep appreciation for history and for the impossibility of fully appreciating its unfolding while in the process of being made,” an acknowledgment of Obama’s awareness of the ongoing dialogue among historians over the original intent of the founding fathers in formulating the Constitution. According to Tribe, his student focused especially on that part of the preamble that spoke of the nation’s commitment “to form a more perfect union,” which, he maintained, would always be, “an unfolding narrative—never completed, much less perfected.” Together, he became convinced that critical legal theory, philosophical pragmatism, and civic engagement pointed the way toward resolving societal differences.¹⁰

By the time Obama began the spring semester of his second year, he had achieved what few others in his class were able to accomplish. Because of his academic performance and the quality of the essay he had written as part of his application to be an editor of the Harvard Law Review, he was selected as one of eighty members of its board of editors.

As a member of the board, he won the respect of other board members who barely coexisted in what was one of the most fractious faculty and student bodies in the nation. In addition to advocates of critical legal studies, these included proponents of more centrist liberalism and more conservative free-marketers known as Federalists. Even these groups were splintered into subgroups like ones on the political left concerned with feminist jurisprudence or racial discrimination and others on the political right concerned with original intent or free market economics. Finally, there were divisions on issues of race. Some conservative editors questioned the selection process to be a board member, which they believed favored minority applicants by not basing selection solely on the basis of academic records as had been the case until the 1970s when an alternative essay was incorporated into the process.¹¹

Former students and faculty from all sides of the political spectrum later recalled Obama’s efforts to reconcile these warring factions and to lower the heat of argument by encouraging a fair hearing of all viewpoints. As an editor on the Law Review, he purposely avoided taking sides in these highly charged discussions. As a number of his instructors and classmates at Harvard later pointed out, he understood nuance and complexity and did not think he had a monopoly on truth. This was one reason why he later hated presidential debates in which he was expected to give brief answers to questions on complex issues. As a student, he preferred, instead, to play the role of mediator and conciliator, a characteristic he would continue to follow throughout his political career and for which he would later be criticized.¹²

Friends encouraged him to run for president of the Harvard Law Review, something he was already planning to do. Being president of the Review was normally a path to a clerkship with a high-ranking federal judge, followed by a clerkship with a justice of the Supreme Court, and then a position with a major law firm or law school. Even as he prepared to run, he knew that this was not the course he was going to follow. Because he had gone deeply into debt to pay for his $25,000-a-year Harvard education and wanted to pay off this debt and accumulate some savings, he planned after graduation to work for two or three years in a corporate law practice before returning to Chicago where he now had more clearly in mind running for political office, possibly with the goal of becoming the city’s mayor.¹³

He realized that being the first Black president of the Harvard Law Review would attract national attention and open avenues of opportunity for him to help the Black community in his adopted city. He was also aware that as president of the nation’s most influential law journal he could influence the course of legal debate in the country and break racial barriers. He would become a model for other aspiring minorities. He also thought he could bring practicality and good management skills to running the Law Review.¹⁴

Just before the deadline for applying to be president, Obama submitted his application after a conversation with one of his friends. Eighteen other Law Review editors, including three other African Americans, also applied. The election process was long and complicated. Involving frequent voting by all the editors not seeking the position or eliminated in earlier ballots, it lasted in Obama’s case for seventeen hours of fractious debate along ideological lines. By the end of the process all his conservative opponents had been eliminated and the choice came down to a contest among the liberal candidates.¹⁵

In the final ballot Obama was chosen because the conservative editors believed he would be the liberal candidate least tied to ideology and most open to listening to them. As described by Brad Berenson, a conservative member of the board, in the final round of balloting “en masse the conservative vote swung over to Barack. There was a general sense that he didn’t think we were evil people, only misguided people, and he would credit us for good faith and intelligence.”¹⁶

His election as the first Black president of the Harvard Law Review attracted national attention. To the many newspapers and magazines that interviewed him including the New York Times, the Associated Press, Daily Mirror, and Vanity Fair, he gave the same answer when asked about the significance of his election: he viewed it as more an accomplishment for American Blacks and minorities than as a personal success. He also left many in disbelief when he stated that after graduation he intended to forgo a clerkship with the US Supreme Court followed by a well-paying position with a major law firm. “One of the luxuries of going to Harvard Law School,” he said, “is it means you can take risks in your life. You can try to do things to improve society and still land on your feet.”¹⁷

By the time of his election as president of the Law Review, he had entered into a romantic relationship with his future wife, Michelle Robinson, whom he met while interning during the summer between his first and second years at Sidley & Austin (now Sidley Austin), one of Chicago’s leading corporate law firms. Tribe had not been the only faculty member impressed by Obama’s first year performance at Harvard. Another was Martha Minow, the daughter of Newton Minow, a partner at Sidley & Austin, who had served as chairman of the Federal Communications Commission (FCC) during the Kennedy administration. Minow recommended to her father that he hire Obama, referring to him “as the best student” she ever had. When offered the chance to intern in Chicago, he grabbed at the opportunity.¹⁸

Hired a year earlier by Sidley & Austin, Michelle was assigned to mentor Obama while he interned at the firm. A graduate of Princeton University (1985) and Harvard Law School (1988), she grew up in Chicago’s South Side. Her parents, Fraser Robinson III and Marian Robinson, made great sacrifices to educate her and her older brother, Craig. Even though Fraser Robinson suffered from a debilitating case of multiple sclerosis that would eventually kill him, he worked for thirty years for Chicago’s water department where he rarely took a sick day and eventually rose to the position of foreman.¹⁹

Marian, who had been a housewife while raising their children, returned to secretarial work when she felt the children were able to fend for themselves after school. Fraser and Marian were determined to give them the best education possible no matter the cost. They even turned the living room of their small one-bedroom apartment on the top floor of a two-story bungalow into two bedrooms and a communal study area so that both children could have their own room and a place to do their homework. They also paid their children’s tuition with borrowed money.²⁰

From the first day he arrived at Sidley & Austin, Obama was struck by Michelle’s commanding appearance. “She was tall, beautiful, funny, outgoing, generous, and wickedly smart—and I was smitten almost from the second I saw her,” he later wrote. Nearly six feet tall, always well-dressed, and attractive, she had the toned body of an athlete. Within a few days after beginning his internship, Barack asked Michelle out for a date. She declined. Career-oriented, she thought it would be inappropriate to date an intern under her supervision, who was still in law school even though he was three years older than her. For over a month she turned him down notwithstanding the fact that he sent her flowers and called her regularly. She was attracted, nevertheless, to Barack, whose life story she found fascinating and whose intelligence was obvious. After being impressed during a church meeting in the Altgeld Gardens by his ability to communicate with people from the South Side like herself, she agreed to go out with him for lunch and a movie. Soon thereafter, she was dating him on a regular basis.²¹

As much as Michelle was interested in Barack, he still had to pass the litmus test of playing basketball with her brother, Craig, also a graduate of Princeton who had twice been named Ivy League Player of the Year and was an investment banker with a Wall Street firm. As Craig explained, Michelle had had a number of suitors before Barack. Setting high standards for herself she had turned most of them down after only one or two dates. The few who gained her interest she invited to her home to meet her parents and to play basketball with her brother, who believed that a basketball game revealed a player’s true character. Craig later wrote that Obama passed the litmus test with flying colors. “He’s very confident without being cocky,” he reported to his sister. For the rest of the summer Michelle and Barack became inseparable.²²

The relationship continued after he returned to Cambridge. In November, he spent Thanksgiving with Michelle and her family. Around this time, he told her parents that he was planning to run for president of the Law Review, something he had discussed with Michelle before returning to Cambridge. They were impressed. He also told them that he was biracial, a fact they had trouble absorbing but which they eventually accepted.²³

During Christmas break Michelle and Barack went to Hawaii where Michelle met Barack’s family for the first time and was welcomed warmly. Barack’s grandmother, Toot, reportedly told Barack to aim after graduation at serving on the Supreme Court while his mother, Ann, said that he should target the White House. As a result of the visit, Michelle understood where Obama got his confidence.²⁴

Back at Harvard from his vacation in Hawaii, Obama kept in daily touch with Michelle. Once elected president of the Law Review, he made plans for the next summer, when he expected to return to Chicago as a second-year intern, but not with Sidley & Austin. Although the firm was anxious to have him back and was intending to offer him a lucrative position after graduation, he had his own plans. As much as he had enjoyed his summer with Sidley & Austin and appreciated the firm’s liberal leanings, he did not want to work for a mainly corporate law firm.²⁵

Instead, he was attracted to a much smaller firm, Davis, Miner, Barnhill & Garner, with about a dozen lawyers who dealt primarily with civil rights and employment discrimination cases. The senior partner at the firm, Justin Miner, had worked as Harold Washington’s corporate counsel. Hoping he could attract to his firm such a promising prospect as Obama, he met with him several times for lunch while conducting business in Boston. During one of these luncheons he convinced Barack to intern with Davis, Miner the following summer. Having to divide his time between his obligations as Law Review president and as a summer intern, all the while continuing his romance with Michelle, Obama’s summer of 1990 was complicated even more when he accepted an offer to write his memoirs for an immediate advance of $40,000 and another $85,000 to be paid to him as the book was completed. ²⁶

His first task as president of the Law Review was selecting the masthead editors who would work with him daily in making the many editorial and managerial decisions and assignments involved in putting together and publishing eight numbers of the Law Review. Almost immediately, he alienated a number of Black and liberal members of the editorial board, many of whom had been his strongest backers and expected him to name them to top positions on the Review. Despite his reputation for open-mindedness and inclusion when discussing cases in class and as a member of the board of editors, they felt betrayed when Obama passed them over in favor of more conservative board members.²⁷

Obama worked fifty to sixty hours on the Law Review, often having to miss class in order to do so. By most accounts, he did his job well, especially in balancing the articles accepted for publication and in managing personnel. Typically, he tried not to interfere with the work of the masthead editors and welcomed their different points of view. They were the people who would be running the country in some form, someday, he told a reporter. “If I’m talking to a white conservative who wants to dismantle the welfare state,” he added, “he has the respect to listen to me and I to him. That’s the biggest value of the Harvard Law Review. Ideas get fleshed out and there is no party line to follow.”²⁸

Poised and confident, he never got ruffled even when he had to reject articles by some of Harvard’s most prominent faculty members or on the occasions when he had to differ with one of his top editors or writers or do a final copyediting of their work, to which they often objected. They were always impressed by his coolness and thoughtfulness in trying to explain the reasons for his decisions.²⁹

He was not above criticism. The most serious one—one that would be made about his presidency—was that, as editor of the Law Review, he was not transformational. While several of the articles in the Review reflected his commitment to civic engagement and philosophical pragmatism, he so excelled in navigating the scorched waters of ideological battles that he avoided setting forth his own ideological point of view. Concerned with building consensus, he also never established any new direction for the Review. Although aware of the opportunity he had, for example, to affect legal debate on race by selecting articles or book reviews that dealt with issues of racial inequality, he chose not to go in that direction. Except for one article dealing with racial discrimination in retail car sales, there were no other articles or reviews of books on racial inequality. Instead, the articles he and the board accepted for publication and the books they chose for review ran the gamut from criminal justice and constitutional law to corporate and labor law. Other than the fact that he was the Law Review’s first Black president, which benefited him more than the Review, he failed to make his mark on the journal.³⁰

While Obama was occupied mainly with editing the Review and attending classes when he could, Michelle stayed busy in Chicago working for Sidley & Austin. She became increasingly unhappy, however, finding corporate law unfulfilling and wanting more challenging assignments. In contrast to Barack, she was impatient and made known her unhappiness to her superiors. Although they responded by trying to give her what she wanted, she remained distraught.³¹

Following the death of her roommate at Princeton, who had always told her that the most important thing in life was a sense of fulfillment, and then the unexpected and devastating death of her father from complications of his illness, she also decided to give up corporate law in favor of giving back to the community. Recalling that her father found happiness without the trappings of wealth, she was willing to trade her $120,000 salary as a corporate lawyer to accept a $60,000 position on the staff of Mayor Richard Daley. Before being offered the job, she was interviewed by Daley’s deputy chief of staff, Valerie Jarrett, who was destined to become one of Michelle’s and Barack’s closest friends and a senior adviser to President Obama.³²

By the time of her interview, Michelle had become engaged to Barack, who had been reluctant to get married. As Michelle later explained to the New Yorker magazine, “We would have this running debate throughout our relationship about whether marriage was necessary. It was sort of a bone of contention.” But at dinner one night at a restaurant, after an argument that Barack purposely initiated over ever getting married, he surprised a flustered Michelle with an engagement ring. They were married on October 3, 1992.³³

Early Political Career

Back in Chicago after graduating magna cum laude from Harvard Law School, Obama reached out to leaders of the African American community with whom he made contact as a community organizer. Among these people were the Reverends Jeremiah Wright and civil rights icon, Jesse Jackson, whose sister, Santita, had been Michelle’s closest friend as a teenager and was a bridesmaid at her wedding.³⁴

The new lawyer also became a founding board member of Public Allies, a recently established nonprofit organization whose purpose was to train young and talented minorities to work in the nonprofit sector in the hope that they would become future public leaders. He also put off his legal career for six months to head a registration drive, Project Vote, for Democratic candidates running for office in 1992, most notably Bill Clinton for president and Carol Moseley Braun for the US Senate. Established in 1982 for the purpose of mobilizing underrepresented minority communities throughout the country, Project Vote had begun to branch out from its headquarters in Washington, DC, into other major cities with large minority populations. In Chicago, where it had not yet established a local office, its efforts to register voters had been largely through donations to Harold Washington’s own organization, which helped get him elected mayor of the city. Following Washington’s death, its still limited efforts failed to bring minority voters to the polls. Relying on the traditional machine established by his father, Richard J. Daley, Richard M. Daley was elected mayor in 1989, and held the office for the next twenty-two years.³⁵

Officially nonpartisan, Project Vote aligned closely with the Democratic Party because of the party’s historical support of minorities, including minority candidates. In 1992, the Democrats had a good chance to wrest the White House from twelve years of Republican control and to elect an African American to the US Senate following Braun’s primary victory over the incumbent, Alan Dixon. Key to victory would be getting out the minority vote in Chicago (Cook County), which often made the difference in the battleground state of Illinois.³⁶

To accomplish this objective Project Vote hired Obama as director of its operation in Chicago. He was hired not only because he had flourished at Harvard and gained national attention as the first Black president of the Law Review, but because of the influential network he had already established within Chicago’s political circles. By the time he graduated Harvard, people like Newton Minow, Judson Miner, the Reverend Jeremiah Wright, and Valerie Jarrett, who had met and taken an immediate liking to him, had begun to spread the word about this promising young star with political aspirations. “I was asking around among community activists in Chicago and around the country, and they kept mentioning him,” the founder of Project Vote, Sandy Newman, commented after the election.³⁷

In the six months that Obama served as director of Project Vote more than 150,000 African Americans were added to the voting rolls. For the first time in Chicago’s history, voter registrations in the city’s nineteen predominantly Black wards outnumbered those in the city’s nineteen predominantly white wards. Almost every local pundit attributed that historic development to Obama’s organizational skills and political acumen. “He helped train 700 deputy registrars, out of a total of 11,000 citywide. And he began a saturation media campaign.” reported Gretchen Reynolds for Chicago Magazine. The organization’s slogan, “It’s a Power Thing,” filled the airways, and posters with the slogan were plastered throughout African American neighborhoods. Minority-owned businesses, including Black-owned McDonald’s franchises, became registration sites, and the owners donated radio time to Project Vote. Labor unions and the Clinton campaign provided funding for the drive.³⁸

Chicago Magazine called Project Vote the “most effective minority voter registration drive in memory.” As a result of it, Braun, who had been in trouble during the campaign, was elected the first US African American woman senator, and Clinton, who had watched his lead against his Republican opponent, President George H. W. Bush, fade, won Illinois on his way to being elected the country’s forty-second president.³⁹

Obama became an instant political star. Chicago Business named him to its annual “40 under 40” list and wrote that he had “galvanized Chicago’s political community, as no seasoned political had before.” Influential friends helped get Obama appointed to the Woods Charitable Fund and the Lugenia Burns Hope Center, both of which promoted organization among African Americans on the South Side through small grants to local activist entities. He also got appointed as chairman of the board of directors of the Chicago Annenberg Challenge, whose purpose was to raise funds to improve Chicago’s school system. By serving on these organizations, he was honoring his lifelong commitment to community service, while laying the basis for a political career.⁴⁰

Obama remained coy about his political ambitions. He maintained that it was too early for him to run for political office, but he had already mentioned to Michelle while courting her that he could see himself “running for office.” He warned that if politicians on the local and state levels were not responsive to the needs of the African American community, he would “work to replace them” and that he would run if he felt he could accomplish “more that way than agitating from the outside.” He also told Federal Judge Abner Mikva of the DC Circuit Court, a former liberal activist in Chicago politics and a friend, whose offer of a clerkship Obama had turned down, that he hoped soon to run for political office.⁴¹

Even though he retained a commitment to community organization, he had by now fashioned a political identity for himself that ran contrary to some of the basic rules for a community organizer as set forth by Alinsky in his seminal book, Rules for Radicals. In the book Alinsky rejected the concept of leadership and agendas from the top down in favor of local leadership with local agendas. The role of organizers, he maintained, was to identity local leadership and promote the self-interests of the communities in which they worked, not to create a movement based on their own personal leadership. To the contrary, organizers needed to draw a clear distinction between their work and that of the political world.⁴²

For Obama, however, the political world was where meaningful change took place. To be successful, politicians needed to “undergird their efforts [with] a systematic approach to community organization.” It was, however, charismatic leaders, like Harold Washington and Martin Luther King Jr., winning political office or leading mass movements with vision and clear political agendas who could achieve change. As much as community organization was important to success, moreover, even more crucial was the network of power brokers with the money, workers, and volunteers needed to win an election. Instead of the slow change that Alinsky and his disciple, Jerry Kellman, believed was the route to success, Obama was convinced that change, while still incremental, would happen quicker by a combination of charismatic leaders carrying with them a political agenda and a message of hope.⁴³

Michelle proved to be an indispensable partner to her husband. After only a few months on the job, Valerie Jarrett, whom Mayor Daley selected to head the city’s Department of Planning and Development, appointed her as the city’s economic development coordinator. In that capacity she worked daily with the leaders of Chicago’s business community. Among them was billionaire Penny Pritzker, who helped bankroll Obama’s quest into politics. They also included powerful voices within the African American business community such as John W. Rogers Jr., who founded Ariel Capital Management, the largest Black-owned firm of its kind, and Martin Nesbit, who played basketball with Craig Robinson and ran a highly profitable airport parking company that Pritzker helped finance. Rogers later served as chairman of Obama’s 2009 Inauguration Committee. Nesbit became one of his closest friends and an unofficial adviser throughout his political career.⁴⁴

Following the election, Obama began working for Davis Miner. In addition, he accepted a part-time position as visiting law and government fellow at the University of Chicago Law School. He was offered the position based on a recommendation from Michael W. McConnell, a conservative member of the mostly conservative law faculty, who had been impressed by the editorial suggestions Obama had made on one of McConnell’s articles when he was president of the Harvard Law Review.⁴⁵

Obama’s positions at Davis Miner and the University of Chicago gave him ample time to establish the groundwork for a political campaign. At his law firm, Miner, who was white, and another managing partner, Allison Davis, who was Black and had close ties to the African American business community, assigned Obama to a team of lawyers. At no time was he a court lawyer. Mostly he prepared briefs and depositions. At the University of Chicago, where he received a small stipend and office, he was given only light teaching assignments. As a result, he was able to use most of his time at the law school writing what became Dreams from My Father and getting ready to run for office.⁴⁶

He threw his hat into the political arena in 1994 after the popular and progressive African American state senator from his predominantly Black district, Alice Palmer, decided to run for Congress in a special election to fill a vacant seat and backed Obama for her seat. With her support and his well-funded political network, he seemed likely to win the election.⁴⁷

The situation changed dramatically when Palmer lost the 1995 primary for the Democratic nomination to Jesse Jackson Jr., the son of Jesse Jackson. Encouraged by her supporters and with the support of Jackson Jr., Palmer decided to run again for reelection. Her backers asked Obama to withdraw his name, arguing that he was young and had a promising political future, but that he had to wait his turn. He refused, maintaining that Palmer had promised him she would not run against him even if she lost the primary. He also said that he had spent too much time and effort gathering the needed signatures to appear on the ballot, raising funds, and building a ground organization to withdraw from the race.⁴⁸

Although there were three other persons besides Obama and Palmer trying to get on the Democrat ballot in 1996, he realized that Palmer was his strongest opponent and that he would have an uphill battle if he had to run against her. He also knew that in Chicago an office seeker often challenged the signatures of potential opponents on ballot petitions, frequently with success.⁴⁹

He decided to follow that course. Suspecting Palmer had not had sufficient time to get enough valid signatures to be on the ballot, he sent lawyers and volunteers to examine her petition lists. They found enough invalid signatures to disqualify Palmer and the others from running. Unopposed in the Democratic primary, Obama went on to a lopsided victory in the November general election in his heavily Democratic district. He was easily reelected to two four-year terms in 1998 and 2002.⁵⁰

As he was preparing to run for office, his mother, Ann, was diagnosed with ovarian cancer that had metastasized. When he first learned that his mother was ill, he flew to Honolulu where she was living with his grandmother Toot. Taking an apartment in the same building where they resided, he helped Ann while she underwent chemotherapy treatments. When her health seemed to improve, he returned to Chicago. Just as he was about to launch his campaign, however, his mother took a turn for the worse. In November 2005, she died at the age of 52.⁵¹

Obama relationship with his mother had always been complex. He always understood the love his mother had for her children, the importance she attached to education, and the values she worked so hard to instill in him. One of his biggest regrets, he would later admit, was that he did not acknowledge fully the crucial role she played in shaping his character and the support she gave him throughout his career. In 2006, after he had been elected to the US Senate and was contemplating running for president, he dedicated his second book, Audacity of Hope, to Toot and to his mother whose “spirit still sustain[ed] him.”⁵²

In Audacity, Obama also described his mother as “an unreconstructed liberal,” whose political and cultural views were defined by the 1960s. Reflecting his own conservative values, he said that he could never identify himself with the radicalism of the decade. But he also acknowledged his progressivism by noting his fascination with the period and making clear that his mother’s rebelliousness against the status quo rubbed off on him. “If I had no immediate reasons to pursue revolution,” he wrote, “I decided nevertheless that in style and attitude I, too, could be a rebel unconstrained by the received wisdom of the over-thirty crowd.”⁵³

In his postpresidential memoir, A Promised Land, the former president called his mother “forever the architect of her own destiny” and described the last months of her life in a way that once more made clear his deep love for her. Knowing that she had been diagnosed with uterine cancer and that her prognosis was not good, he remarked that “at least once a day, the thought of losing her made my heart constrict.” He also pointed to the strength of will she maintained even knowing that she was ill with terminal cancer. “I’m not going anywhere until you give me some grandchildren,” he quoted her as saying, and remarked that, given her state of health, he asked his mother’s approval before deciding to run for the state senate. He even suggested that Ann come to live with him in Chicago, an offer she declined, preferring to live out the rest of her life in the familiar and warm surroundings of Hawaii.⁵⁴

In portraying her in this way, however, Obama ignored the other side of the relationship. While Ann loved her son and Maya as most mothers loved their children and was ambitious for Barack, believing he had unlimited potential, motherhood was not her highest priority in the way that Michelle’s mother, Marian, made Michelle and Craig her primary concern. Rather, she was an itinerant, fascinated by other cultures, who gave her career and work most of her attention. Although she tried to reunite with Barack several times a year, she was willing to let her parents raise him during his formative years while she spent most of her time in Indonesia pursuing her career. In contrast to Michelle’s mother, Ann did not provide her children with structure and stability.⁵⁵

Obama never completely forgave his mother for the vacuum she created in his life. It may even have been one reason why he chose to focus his first memoir, Dreams from My Father, on his father. Not surprisingly, Ann, who had long felt that Barack’s move to Chicago and his assumption of a strong Black identity was his effort to distance himself from her, was crushed at how little attention she received in Dreams from My Father and by his unflattering remarks in it about her.⁵⁶

Nevertheless, the telephone call from his half sister, Maya, informing him of his mother’s death, affected him more deeply than one might have expected from a person known for being stoic and aware that his mother was dying from a painful disease. Hit hard by news of his mother’s death, which he later referred to as “the worst day” of his life, he flew with Michelle to Honolulu, where a private memorial was held for Ann. After spending a few days with Toot, they flew back to Chicago where Obama carried on the campaign that led to his victory the next year to the state senate.⁵⁷

All the while he was teaching at the University of Chicago Law School, where he taught mostly required courses in constitutional law and elective seminars on matters involving issues of race and civil rights. As an instructor, he employed the Socratic method common at Chicago, Harvard, and most other law schools in which the instructor engages students with an ongoing series of probing questions on an unending search for truth. But his style was open-minded rather than intimidating. For assignments he prepared packets of documents and opposing readings instead of assigning whole books.⁵⁸

Obama developed a reputation as being an excellent instructor with a cool and friendly demeanor and middle-of-the-road classroom approach, who made students understand the complexities of the law including its moral and political implications. He even developed his own following among students. Although starting as a lecturer, the academic equivalent of an adjunct faculty member, he was promoted in 1996 to senior lecturer, a title usually reserved for those not seeking a tenure track position and equivalent to that of a professor.⁵⁹

In 2008, when he was the leading candidate for the Democratic presidential nomination, his course materials and exam questions became public record. According to a number of legal experts from different sides of the political spectrum who examined them, they were well thought out and demonstrated a subtle and sophisticated command of the law. Unlike other faculty members teaching constitutional law, he also did not require students to agree with a position he espoused since he tried to avoid taking a particular point of view in the classroom.⁶⁰

Several of the legal experts criticized Obama’s syllabi and exam questions, however, because they thought they were too conventional and did not confront such contemporary issues as the war on terror, which he would also face as president. Nor did they reveal any insights into how he thought Supreme Court doctrine could be improved. Despite Obama’s lifelong interest in multiculturalism and interracial relations, one expert even pointed out that his course materials on racism and the law were limited almost exclusively to issues involving Blacks and whites. Only one session was devoted to the unique issues of Native Americans.⁶¹

As these experts pointed out, even as an instructor Obama remained reluctant to interject his views into the classroom. He wanted his students to be open-minded in approaching the law and to think and argue like a lawyer. His assigned readings for a course he taught on racism and the law included such diverse figures as Robert Bork, Martin Luther King Jr., and Malcolm X. He saw his role in the classroom to be one of getting his students to be probing, to consider even the moral and ethical dimensions of the cases he assigned, and to hone and refine their responses to judicial decisions. Similarly, his exam questions were designed to ferret out his students’ understanding of the law. As in the classroom, he remained ideologically neutral in evaluating their performances.⁶²

Contrary to those who criticized him for not dealing with controversial issues, he required students for his course on racism and the law to make an hour-long group presentation on such contentious matters as immigration policy, interethnic tensions, reparations, hate speech, and welfare and reproductive freedom. Although he did not impose his own views in the classroom or in evaluating exams, he continued to be guided by the principles of critical legal theory, philosophical pragmatism, and civic republicanism in the readings he assigned and the questions he asked.⁶³

An offshoot of critical legal theory becoming prominent in major law schools like Chicago was critical race theory (CRT), most closely associated with Derrick Bell, an African American law professor at Harvard when Obama was there. Bell maintained that racism was so engrained in the fabric and system of American society that it perpetuated the marginalization of people of color. As a student, Obama greatly admired Bell for his principled stand on the lack of minorities and women on the law school faculty. At a 1990 protest meeting in support of Bell, he even hugged him. For his course on racism and the law at Chicago, he assigned a seminal article by Bell outlining CRT. During Obama’s campaign for reelection as president, Bell’s influence on him was blown far out of proportion by the right-wing media, which showed a video of him embracing Bell in 1990 to illustrate how he was being manipulated by left-wing extremists in 2012 with their un-American agendas.⁶⁴

Just as Obama rejected the pessimism inherent in critical legal theory, however, he rejected the even more pessimistic assumptions of CRT. His assigned readings included many critics of CRT and reflected his more optimistic view that economic and social uplift were possible starting with organization at the community level and continuing through the election of dynamic leaders able to bring about social and economic change. His selection, for example, of Martin Luther King Jr.’s essay, “Where Do We Go from Here: Chaos or Community,” suggested his optimism about the nation’s future even on matters of race relations and the nation’s political process. Rather than advocating CRT, his syllabi encouraged students to pursue a pragmatic and political approach to the issues they would be confronting after they graduated.⁶⁵

Toward the end of the campaign, the candidate took time off to attend the “Million Man March” in Washington, DC, organized by followers of the Black nationalist and anti-Semite, Louis Farrakhan. Even though he would later be criticized by his right-wing opponents for participating in the gathering, he justified his participation by pointing out that many of the issues the march was intended to highlight, such as higher than average incarceration rates, levels of poverty, and rates of unemployment for African Americans, were ones on his mind. After returning to Chicago from the nation’s capital, he rejected both Farrakhan’s racist and anti-Semitic remarks and the march’s organizers’ lack of “a positive agenda, a coherent agenda for change.”⁶⁶

Political Victory

In less than five years Obama had gone from being a newly minted graduate of Harvard Law School to an Illinois state senator. Almost as soon as the election was over, political pundits began to speculate on whether he would remain content with this office or had higher political ambitions, perhaps as mayor of Chicago or even as a United States senator. Whatever his political aspirations, he had become an important political force in Chicago with a powerful political network that crossed racial lines and needed to be included in any calculus involving Chicago politics.⁶⁷

His election as a state legislator revealed a side of him that had not been apparent earlier; the extent of his ambition and his determination to win. He first showed his ambitious side when he decided to run for president of the Harvard Law Review in 1989. But he became president of the Review because his moderation, patience, and willingness to consider all sides on issues convinced conservatives to vote for him. What stood out in his first election to public office, however, was his impatience and commitment to winning regardless of the cost. As a result, his opponents accused him of being little more than a callow newcomer and ruthless opportunist bent on furthering his own political ambitions even if that meant steamrolling over his opponents.⁶⁸

Although they misunderstood Obama, there was more than a grain of truth in what they said. Like most politicians he always justified his actions by the larger goals he sought to achieve, in his case elimination of the decay and dolefulness he found throughout Chicago’s South Side. Unlike many of these same politicians, who wrapped their political ambitions in campaign platitudes and sloganeering, his commitment to bettering conditions in the South Side went back to his years as a community organizer in Chicago. His idealism was what continued to stand out in his district. He was a man on a mission. But that did not negate his personal ambition and determination to win.⁶⁹

There was also an arrogant side to his personality. Throughout his adulthood he had been singled out for his brilliance, confidence, and charm. So many important figures who came into his life had told him so often that he had the talent and the ability to effect change for the public good that he believed it. He was so certain about his abilities and the righteousness of his ambition that he sometimes became callous toward those who seemed to stand in his way.⁷⁰

In Springfield, the state’s capital, Obama paid a political price for ousting Palmer. A cadre of rivals and friends of Palmer harassed him on the senate floor, even mocking his name. While it was a common practice to make newly arrived legislators go through the ritual of being questioned brutally on the floor by more seasoned veterans, they maintained a visceral dislike for Obama throughout his eight years in the senate.⁷¹

At one point, he almost got into a physical brawl with Rickey Hendon, an African American senator representing Chicago’s West Side, who may have regarded Obama as a potential threat to his own ambitions. Repeatedly, Hendon ridiculed Obama’s surname calling him “Yo Mama.” He also ridiculed him on legislative matters he was pushing. Finally the usually placid Obama decided he had enough and confronted his antagonist just outside the senate floor, almost leading to a fist fight.⁷²

His election and subsequent legislative responsibilities also took a toll on his young marriage. Michelle had played an important role in connecting Obama with a number of Chicago’s power players, but she had always been skeptical about his ambition to run for political office. “I married you because you’re cute and you’re smart, but this is the dumbest thing you could have ever asked me to do,” she said to him after he decided to run for Palmer’s senate seat.⁷³

Growing up on the South Side, Michelle had witnessed the power of the Daley machine and the seamy side of Chicago politics. She understood that her father owed his job with Chicago’s Water Department to the fact that he was a volunteer precinct captain for the Democratic Party. As Chicago’s economic development coordinator, she saw firsthand how favors were dispensed and deals made between the mayor’s office and those with whom she worked every day. Having left the corporate world to serve the public interest, she found herself serving special interests. She was ready, therefore, for a change. After only two years at city hall, she resigned her position and took another one as chief executive of the Chicago operations of Public Allies.⁷⁴

Despite her dislike for politics, Michelle played a prominent role in Obama’s campaign. As in future elections, she felt that if her husband was going to run for office, she would be a partner in helping him win. Accordingly, she did everything in the campaign from going door-to-door collecting the signatures needed to put her husband on the ballot to keeping open her political connections with the power brokers she trusted. But she disliked the idea of being the wife of a career politician, who would often be away from home. What she wanted was a comfortable income, children, and a husband who would be an equal partner in raising them.⁷⁵

Michelle’s concerns about being a politician’s wife became real after her husband assumed office in January. When the legislature was in session, he was in Springfield, able to come home only for long weekends. Even then, his time was stretched between his teaching duties at the University of Chicago and his lawyerly responsibilities at Davis Miner. Even when the legislature was not in session, he had to tend to his constituency, often going to nighttime meetings and social events. Complicating matters was the birth in 1998 of the Obamas’ first child, Malia Ann. “How full of joy the months that followed were!” he later wrote. “I lived up to every cliché of the expectant father, attending Lamaze classes, trying to figure out how to assemble a crib, reading the book What to Expect When You’re Expecting with pen in hand to underline key passages.”⁷⁶

His frequent absences because of his responsibilities as a state senator, however, meant that Michelle was often alone with the baby. Increasingly, she felt neglected by her husband. “Shuttling between mothering and work, [she was] unconvinced that she was doing either job well.” The former president also commented about the strains in his early marriage. “We began arguing more, usually late at night when the two of us were thoroughly drained.”⁷⁷

Making the situation even worse was the financial stress Michelle felt. Both she and Barack had borrowed heavily to attend law school. Had they pursued careers in corporate law, their financial plight might have been different. But Michelle gave up a career in corporate law and Barack never pursued one. He also lost the remainder of the $125,000 advance he was to receive for his memoirs because of his failure to deliver a manuscript on time. He was able to secure another contract with a much smaller $40,000 advance and to complete the manuscript two years later, but he did so only by isolating himself from Michelle. Reviewers gave the final product, Dreams from My Father, excellent reviews, but it sold only about 9,000 of the 12,000 copies printed before he rocketed to national fame in 2004. Even though the Obamas were still able to put together a comfortable annual income of around $250,000, they found themselves in enough debt for Michelle to worry about their financial future.⁷⁸

As a state senator, Obama practiced what he preached. Through legislation he sought to build community. At first, he had only limited success. In a Republican-controlled body with a group of African American senators determined to get payback from him for taking Alice Palmer’s seat, he was unable even to get through the senate a minor bill that would have established a registry of local job openings for community college graduates. Even senators who bore no grudge against him found him to be too aloof, too policy driven, and too overly intellectual.⁷⁹

By the end of his second term in the senate, however, the networking Obama had already done before his election began to pay dividends and boosted his career in a major way when the Democrats, already in control of the house, took over all branches of the state government in 2002. The leader in the senate after 2003, Emil Jones Jr., was another African American from Chicago. In contrast to Obama, Jones already had a long political career in which he had worked himself up from a patronage job as sewer inspector for Chicago to senate majority leader. As a machine politician, he sought not only to pass progressive legislation but to steer state money to his constituency and provide well-paying jobs for his family.⁸⁰

Despite the help Jones gave Obama in the 1980s in securing a state grant, Obama thought Jones was the type of hack politician who did not belong in Springfield. In Dreams from My Father, he even referred to him as an “old ward heeler.” For his part, Jones, who had known Obama since he was a community organizer a decade earlier, was leery of him and other community activists who, he believed, liked to manipulate and criticize politicians to further their own ambitions.⁸¹

Once in the senate, however, Obama added Jones to his network of power brokers. In an early meeting with the minority leader, the newly elected senator told him that he was prepared to work hard and hoped he would hand him “tough assignments on legislation.” Jones was receptive. United States senator Paul Simon, widely regarded as one of the most progressive and principled members of the Senate, who had taken a liking to Obama for a brief he had drafted while working at Sidley Austin, recommended him to Jones. So did Newton Minow, the senior counsel in the firm’s Chicago office and Abner Mikva, a former congressman, federal judge, and White House counsel to President Bill Clinton, who had known Obama since he was a law student.⁸²

Jones agreed with their assessments. He saw in the young legislator what he had never been; a handsome, articulate, and dynamic political figure whose potential for higher office was unlimited. Like Minow, Mikva, and so many others in Obama’s career, Jones took him under his wing and became his unofficial mentor, teaching him the intricacies of the legislative process and assigning him to a bipartisan task force to draft an ethics reform bill. With Jones and one of his career staffers, Dan Shomon, who became his legislative aide, by his side, the state senator learned the ropes of Illinois politics.⁸³

He also softened his image, playing golf with his colleagues and displaying his skills in poker during a regular game when the senate was in session. He even began to make friends across the aisle. His ability to adjust to new circumstances bore results. In 1998, he was key in getting an ethics reform measure, which the house had already passed, through the senate. In subsequent years, he also worked successfully to establish a state version of the earned income tax credit, was instrumental in persuading Republicans to soften their positions on adding a new work requirement to the state welfare laws, and successfully championed a requirement that police videotape interrogations in capital cases.⁸⁴

Political Defeat

He remained frustrated, however, by the power of the special interests in Springfield. Even more important, he never intended to spend his career as a state legislator. His ambitions ran higher than that. Over the objections of most of those closest to him, including Michelle, who would have been happy if he gave up politics entirely, he decided sometime around the end of 1997 to run against the incumbent congressman for his district, Bobby Rush. He reasoned that Rush, a former member of the Black Panthers, whom Mayor Daley had badly defeated in the recent Democratic primary for mayor, was vulnerable, especially in white districts where he received only 13 percent of the vote. Because of the political network he had established, he also believed he could capture the white vote in the district while gaining enough of the majority Black vote to defeat Rush. Although he did not have Rush’s financial resources, he was able to raise enough money through his political network to run a respectable campaign even before he officially announced his candidacy in the spring of 1998.⁸⁵

Ambition—and hubris in believing that a first-term and relatively unknown senator could defeat a three-term, popular, and progressive US congressman supported by most of the Democratic political establishment in Washington, including President Bill Clinton and Illinois senator Dick Durbin—was the major reason why he decided to oppose Rush. But it was not the only one. He also believed that Rush served just the interests of the Black areas of his district and that he sent the wrong message to young people—that one could gain enough fame as a gun carrying revolutionary threatening to kill white people to later gain a seat in Congress. What kind of incentive did that give kids, he wondered, to behave and earn their way to public office through hard work and a sense of social obligation? His heroes, like King and Washington, offered hope rather than despair and reform rather than revolution. In taking this position, he overlooked the fact that Rush had renounced his past and became a strong advocate of gun control and an ordained Baptist minister with two master’s degrees.⁸⁶

During a primary debate, Rush attacked his opponent for being an outsider and a Harvard “educated fool” whose “eastern elite degrees,” he said, would not impress his constituency. His opponent fired back. “When Congressman Rush and his allies,” attack me for going to Harvard and teaching at the University of Chicago, they are telling Black kids that “if you’re well educated, somehow you’re not keeping it real.”⁸⁷

Rush’s attacks on Obama proved effective. His campaign was even able to mobilize on his behalf two of the most influential groups in Black districts, ministers and funeral directors. At a “Clergy for Rush” rally, one hundred Black ministers stood in front of a banner that declared “We are sticking with Rush.” In speeches at the rally, they pointed to the seniority that Rush would gain if he was returned to the nation’s capital. They also remarked on how much the congressman had already achieved for his district, including saving an Amtrak ticket center and helping write legislation creating a tax on long-distance carriers to be used to fund the wiring of Illinois schools and libraries. For the South Side alone, he had obtained funds to create a new post office building and to resurface an important thoroughfare.⁸⁸

Responding to attacks on him for once being a gun carrying member of the Black Panthers, Rush emphasized how the situation had changed since the 1960s and how he now championed gun control. Turning on its head the Obama campaign’s criticism of him for being a Black Panther, his campaign argued that instead of talking the talk in the 1960s, he was proud that he had walked the walk at a defining period in the nation’s history.⁸⁹

As for the Obama campaign, everything went wrong, including even a personal tragedy for Rush when in October 1999, his twenty-nine-year-old son was shot to death, forcing Obama to suspend his campaign and creating a wave of sympathy for Rush. In December, while he was vacationing with Michelle and Malia in Hawaii, he missed a vote in Springfield on gun control, a key issue in the campaign, and the measure went down to defeat by only five votes. Although he defended his failure to show up for the vote on the grounds that he was tending to his sick daughter, his missed vote became an important issue in the campaign. Even his strategy of getting the congressman to debate him backfired. Rush was able to keep Obama, who seemed pedantic and distant, on the defensive.⁹⁰

Underestimating Rush as a bland figure and an obscure congressman, and overestimating his own personal appeal and political skills, he was surprised by just how wily Rush was. Believing that the First District, which Rush represented, was ready for a generational change, he missed the point that in the district Rush remained a hero of the civil rights movement and proof that a Black man could succeed. Only toward the end of the campaign did Obama realize that he was going to lose the election. When the votes were counted, Rush had defeated him by a margin of 31 percent. Only in the white parts of the district did he do well against the congressman, but even there he won only one ward.⁹¹

His defeat was a low point in his life. His political career seemed over. After the election, a Chicago political reporter asked on the air, “Is Obama dead?” It seemed that way. The state senator did not want to remain a legislator in Springfield, but having been defeated so badly by Rush, there seemed nowhere to go in terms of elective office. If he had dreams of being mayor of Chicago, those were shattered by the overwhelming Black vote against him. He did not have the personal resources to seek statewide office, and he was uncertain whether his political network would back him if he decided to run again.⁹²

When he flew to Los Angeles to attend the Democratic convention and tried to rent a car, his American Express card was declined until he got the credit company to increase his credit limit. His embarrassment was compounded when he was denied a floor seat at the convention hall and had to settle for a seat in the stands even though he was a state senator. Returning to Chicago, he was in a “dark mood.” “I was almost forty, broke, coming off a humiliating defeat and with my marriage strained,” he later recounted.⁹³

As he stated, his marriage was going through a rocky time. Never having wanted him to run for office, Michelle had strongly opposed his decision to run against Rush, believing it would drain what resources they had and keep him away from home. Despite their income, bills continued to pile up. Malia was now a toddler. She needed a father, and Michelle, who had given birth on June 10, 2001, to a second daughter, Natasha Marian (“Sasha”), needed a full-time husband. She offered Barack a choice between becoming a full-time partner with her in raising their family or staying in politics without her being involved. Together they even sought marriage counseling.⁹⁴

After the election Obama had an opportunity to become head of the Joyce foundation, which funded community projects in Chicago and would have paid him a handsome six-figure salary plus two club memberships. It was a dream opportunity that would have assured the family life and security that Michelle so desperately wanted. He thought seriously of taking the position if he were offered it, but his political ambition prevailed. In 2002, he ran again, this time unopposed, for the state senate.⁹⁵

He found an alternative, however, to Michelle’s demands on him that satisfied her. He would not seek a fourth term as a state senator. He would continue his positions at Davis Miner and the University of Chicago Law School. He would become a better father and husband. But a seasoned and chastened politician now, he would make one more stab at elective office. If he won, he would remain in politics. If he lost, he would give up his political career and become a full-time attorney able to command a sizable income.⁹⁶

Perhaps because she did not think Barack could win a statewide contest and also understood how important political office was to her husband, Michelle agreed to his proposal. She was even prepared once more to become Barack’s political partner in what she considered the impossible goal on which Obama had set his political future—election in 2004 to the United States Senate. Her husband proved her wrong. Five years later, he was elected President of the United States.⁹⁷

The years 1988 to 2000 were as formative for Obama as had been his earlier years, from the time he grew up in Indonesia and Hawaii until he became a community organizer and then decided to go to law school. During these years, his views on how to bring about change in his adopted city of Chicago crystallized, and he launched his political career. What stands out in this period was that the future president was a pragmatist, who believed in the art of compromise, yet could be ruthless in pursuit of his goals and ambitions. He was also a middle-of-the-road progressive and conservative, who rejected extremist views, either from the left or the right of the nation’s political center. What was still to become clear was his belief that the road to a more perfect union was through the expansion of the middle class.