by Peter Slevin
THIS TERRITORY WAS NOT unfamiliar to Michelle. She knew something about upper-crust universities from her time at Princeton and Harvard. She also had a snapshot of life on the Hyde Park campus from her mother, who worked as a secretary in the university’s legal office in the 1970s, when Michelle was in high school. From the start in September 1996, it was clear to her thirty-two-year-old self that she had work to do. “I know the community does not trust and understand the university, and the university does not trust and understand the community,” Michelle said. “Until you can bridge those gaps and hear out both sides and understand why they are afraid, you can’t really have a conversation.” Her job, director of the University Community Service Center, was a new one that owed its creation to a faculty-student committee that found the university wanting on volunteerism. She aimed to have an impact on nearby neighborhoods, as well as on University of Chicago students. To succeed, she needed to design programs and sell them to her superiors, including Boyer. She also had to find agencies and organizations where students would be welcomed and put to good use.
Michelle built a small staff and set out to increase student awareness of the city’s geography, arranging bus tours beyond the Hyde Park campus. She developed a summer internship program infused with lessons from Public Allies and the Asset-Based Community Development approach. Called Summer Links, the project provided ten-week internships that included half-day training sessions on such themes as race relations, welfare reform, affordable health care, and homelessness. Separately, she developed a series of monthly conversations on urban issues, including one timed to coincide with the hundredth anniversary of the U.S. juvenile justice system. The panel included a former juvenile offender, a priest, and a teacher who had worked in a Cook County youth detention center. Barack was on the panel, as was William Ayers, the former Weather Underground leader and federal fugitive, who had recently published a book on juvenile justice. “Students and faculty explore these issues in the classroom, but it is an internal conversation,” Michelle said. “We know that issues like juvenile justice impact the city of Chicago, this nation and—directly or indirectly—this campus. This panel gives students a chance to hear about the juvenile justice system not only on a theoretical level, but from the people who have experienced it.”
Her interest in reaching out to African American residents beyond the campus, however, was largely incidental to the university’s focus on its own students. Boyer was looking for ways to attract and satisfy students at a time when the university was struggling. Improvements in the surrounding communities and the residents’ attitudes toward the university were welcome, but secondary. When Boyer became dean of the college in 1992, the University of Chicago was accepting nearly 75 percent of applicants. In his first year, 15 percent of the freshman class flunked out or dropped out, a statistic that would have gotten him fired at Harvard or Yale, “like, within two minutes.” Soon after university president Hugo Sonnenschein announced plans to increase student enrollment by one thousand, Boyer was glad to see Michelle walk through the door. He reasoned that her concentration on community service would give the college “a broader and more diverse profile, in the sense that our students came here not just to read Shakespeare and take calculus and debate the meaning of life well into the night.” Michelle was “convinced that the university was too inward-looking,” he said. He called their efforts “a convergence of what she wanted to do and what I was interested in doing.”
In Michelle, Boyer saw someone as pragmatic as he was, and as oriented toward results. Smart and tough, he said, persistent without being abrasive, “quite strategic in getting the resources she needed to accomplish her goals.” Given the university’s racial history, he was pleased to find that she seemed more interested in plotting the future than rehashing the past. He would not have been sympathetic to the argument that the university owed something to black South Side residents because of its history of bigotry, what he called a “reparations mentality.” She recognized that the community service program needed to benefit the students and “not just make us into some kind of NGO that would go out and do good in the neighborhood. I wasn’t interested in investing money in things that did not have some payoff for the education of our students. My job is dean of the college. I’m not here to save the world, even though I hope the world could be saved.”
Michelle expanded the scope of her office during her five years on the job. Many African American students, seeking a campus haven, considered the community service center a gathering spot, said Melissa Harris-Perry, who taught a course on black women’s social activism and relied on Michelle and her colleagues to find internships for her students. “They really saw her as an ally and a voice for their interests,” she said. Until Michelle arrived, Samuel Speers, associate dean of the university chapel, had served as the primary adviser to the community service center. He recalled her as savvy about navigating the university hierarchy and the politics of the surrounding neighborhoods. “She would wade right in. She’s not afraid of conflict, but she also doesn’t seek it. You had the sense she had the ear of the university president and the ear of the wider community.” Race was never far from the discussion. “You cannot do community-based work in Hyde Park and not engage questions of race,” Speers said.
Michelle did not win all of her battles. She argued unsuccessfully that students should get course credit for their volunteer work, a position that Arthur Sussman, who had hired her, considered “toxic” among university faculty. “It was possible that other elite schools were doing it,” he said, “but that was not going to be the Chicago way.” Overall, Michelle sought to expand the service program while ensuring that neighborhood organizations gained from the collaboration. That lesson stuck with Leif Elsmo, who followed Michelle to the university from Public Allies and worked with her for nearly fourteen years. She taught him to be “sensitive about the promises we made to communities,” he said. “We had to fulfill what we said we were going to do, because communities have been failed so many times.”
IN 1995, as Michelle was about to welcome her third class of Public Allies and start the job search that would take her to the university, Barack was still doing several things part-time. He enjoyed decent success, but was hardly a player. He taught law at the University of Chicago. He handled public interest cases at Davis, Miner, Barnhill & Galland. He conducted community organizing training sessions, and he served on boards of directors, including the Woods Fund, the Joyce Foundation, and The Chicago Annenberg Challenge. When he published Dreams from My Father that year and did a reading at 57th Street Books in Hyde Park, he was the amiable guy from the neighborhood, not a literary star. A grand total of nine people showed up for a reading at Eso Won Books, the leading African American bookstore in Los Angeles. Many years later, the reissued Dreams would make Barack and Michelle rich, with several million copies in circulation, but the first printing did not sell enough copies to earn back its $30,000 advance. For all of the buzz about his talents, it was safe to say that Barack’s great promise remained unfulfilled. No one felt it more than he did.
Alice Palmer, in 1995, was the state senator from the Illinois 13th Senate District, a swath of South Side turf that included the Obamas’ Hyde Park apartment and stretched south and west into tougher working-class neighborhoods. Progressive and well connected, she tended her political garden and faced no foreseeable electoral threat. She spotted a chance to move up the ladder when Representative Mel Reynolds, a black former Rhodes Scholar, became the latest in a string of Chicago politicians to be indicted, in his case for having sex with a sixteen-year-old campaign volunteer and obstructing justice. His conviction and forced exit meant a special election. When Palmer entered the congressional race, Barack declared himself a candidate for her state senate seat, but not before exacting a promise that if she lost, she would not jump back into the senate contest. He also lent his name to her congressional candidacy, an awkward proposition. Her principal opponent was Jesse Jackson Jr., so
n of a certain other Jesse Jackson, the Operation PUSH leader and two-time presidential candidate, and brother of Michelle’s friend Santita Jackson, who had sung at the Obamas’ wedding just three years earlier.
Palmer lost the Democratic primary to Jackson, placing third with just 10 percent of the vote. She reiterated that she would not try to keep her senate seat, but her reluctance soon disappeared. With the backing of South Side stalwarts including the elder Jackson and Emil Jones Jr., the Democratic leader of the state senate, she declared that she would run for her old job, after all. “Michael Jordan can come back and so have I,” she asserted. A number of her loyalists leaned on Barack to drop out. He refused. The way he saw it, a deal was a deal. After Palmer’s team cut corners in collecting signatures to qualify for the ballot, Barack challenged the validity of her petitions and those of the three other Democratic candidates. The board of elections disqualified all four. He was in. The November election against a pair of minor candidates would be just a formality.
Michelle had doubts about the wisdom of a political career. Indeed, she had no truck with politicians or their ways, but she worked hard for Barack’s election. “Michelle was determined to run a top-notch campaign, no cheesiness,” said Barack’s campaign manager, Carol Anne Harwell. “She brought elegance and class to the campaign. She was the taskmaster and she was very organized, even if she didn’t know a lot about politics then. When we started collecting petitions, we would set a goal for, say, two hundred signatures that day. There would be a blizzard and we would come back with only a hundred and fifty. Michelle would be furious and we’d have to go out and get the rest.” Asked why she went along with Barack’s plans despite her misgivings about the profession, she answered, “Because I believe in him.”
“How can you impact the greatest number of people? We always debated this,” Michelle said, “because my view was, well, you can also impact a lot of people if you’re the principal of a high school or a great teacher or a great dad. I wasn’t a proponent of politics as a way you can make change.” Her mistrust of politics was deeply rooted and would linger long into Barack’s political career. “We as a family were extremely cynical about politics and politicians,” her brother Craig said. That view was all but inescapable on the South Side in the second half of the twentieth century, a period scarred by schoolhouse inequity, economic neglect, and political corruption that no single politician could fix. Abner Mikva, former Democratic congressman and federal judge, traced Michelle’s dissatisfaction to race. “Michelle had a black life in black Chicago,” he said. “You can’t have any brains and not be influenced in a big way, and pretty negatively.”
Beyond her doubts that meaningful change could be produced in the well of the Illinois senate, Michelle worried that Barack would be eaten alive. “I don’t trust the people in there,” she told interviewer Mariana Cook in May 1996, two months after the primary. “I think he’s too much of a good guy for the kind of brutality, the skepticism.” Michelle also saw Barack’s political aspirations as a threat to the life she wanted for herself—a life fundamentally comfortable, controlled, and private. “When you are involved in politics, your life is an open book and people can come in who don’t necessarily have good intent,” she said. “I’m pretty private and like to surround myself with people that I trust and love.” She wanted to make a difference, sure, but she also wanted a full partner. She saw children in her future, as well as travel and quality time with friends and family. These happened to be among the things Barack had said he wanted when they married, but his entry into politics threatened to create a much different reality. He would be even less available. Gone, in fact. It was one thing for him to surprise her by saying he wanted to go to Bali for a month to work on Dreams soon after their California honeymoon. It would be quite another for him to drive three hours to Springfield most Mondays for who knew how many years. And that was if he did not make the jump to Congress or the Senate in far-off Washington. In 1996, Michelle rated the chances as “strong” that Barack would make politics his career. “There is a little tension with that,” she acknowledged, but she was trying to keep an open mind. “In many ways, we are here for the ride, just sort of seeing what opportunities open themselves up.”
FOR SOMEONE WHO HAD imagined himself running Chicago one day, and maybe the country, the life of a small-time pol in Springfield, Illinois, would seem to hold all the allure of a ten-cent prize at a boardwalk arcade. Yet, his first election behind him, Barack tore into his new work, determined to learn the riddles of power even as he discovered that being a junior member of the minority party gave him virtually no influence. Entrenched senators rolled their eyes at his transparent ambition and his floor speeches, which tended to be lofty and overlong. Some of the fiercest jabs came from black colleagues who mocked his biracial ancestry, his Harvard education, and his home turf in the bourgeois precincts of Hyde Park. To them, he seemed all too eager to accept half a loaf. “He was not any kind of mystery to me,” declared Rickey Hendon, a senator from Chicago’s suffering West Side. “My friends with all those degrees like to compromise and live in nice rich neighborhoods. They don’t see things as they really are. You’re not as willing to compromise if you see the poverty all the time.” It was a riff that played in different ways depending on the audience. Barack, after all, did tend to see the middle ground as the most likely path to progress, not to mention the functioning of the republic. He was pragmatic. In statewide and national campaigns, that would be seen as a net positive. But in large segments of the black community in the years ahead, the criticism would be rendered in shorthand: Was he black enough?
For all of his pleasure in the power of words, Barack took little satisfaction in scoring rhetorical points if he lost on substance. Sound bites, he said in a 1996 interview, were “dishonest.” They masked complexity and disguised “the very real conflicts between groups that are going to have to be resolved through compromise.” He had considered the possibilities and limitations of politics for many years before he entered the arena, and he had received no shortage of warnings. Back in Hawaii, former Chicago newsman Frank Marshall Davis advised him that black students emerge from college with an “advanced degree in compromise.” A decade later, when Barack gave up community organizing, John McKnight agreed to write a law school recommendation letter, but not before he tacked on a lecture about the price Barack would pay. The cost of surrendering his grassroots role, McKnight predicted, would be the loss of his intellectual integrity. “What you have been doing every day is creating polarities, conflict, and confrontation in order to get to the table. You are a person taking a position that you believe in and that feels a certain way,” McKnight told him. “I can tell you that if you get into the heart of politics, the important thing you will be doing is compromise. You will be an architect of compromise.”
The discussion had deep roots in African American political history. Modern variants of black political style and substance stretched from the calculations of the Chicago aldermen known as the Silent Six through Whitney Young, the Reverend Martin Luther King Jr. and the Black Panthers, to the post–civil rights era maneuverings of the Congressional Black Caucus and a raft of big-city mayors. Barack and Michelle shared a conviction that racial grievance, however righteous, was not a winning strategy. Results were what mattered most. “We have no shortage of moral fervor,” Barack told Hank De Zutter of the Chicago Reader in 1995. “The biggest failure of the civil rights movement was in failing to translate this energy, this moral fervor, into creating lasting institutions and organizational structures.”
Policymakers could find common ground, Barack argued, if only they could dispense with their partisanship and their invective long enough to discover it. “What if a politician,” he told De Zutter as he began his state senate run, “were to see his job as that of an organizer, as part teacher and part advocate, one who does not sell voters short but who educates them about the real choices before them? As an elected public official, for insta
nce, I could bring church and community leaders together easier than I could as a community organizer or lawyer. We would come together to form concrete economic development strategies, take advantage of existing laws and structures, and create bridges and bonds within all sectors of the community.”
Barack knew he was making a choice and he could guess how various constituencies might react. He had been leading training sessions and doing some lawyering for the Association of Community Organizations for Reform Now, the grassroots anti-poverty group better known as ACORN. As he entered politics, he alerted ACORN organizer Madeline Talbott that he would have to move toward the political center to be effective. “I may not be as liberal as ACORN members want me to be,” he told her. “I may believe some things and do some things that ACORN members believe are too middle of the road.” Talbott, inclined to cut him some slack, took his remarks as evidence that he wanted to make a difference and was realistic about what it would take. “He felt the need to give me fair warning, which was unusual. People just thought Barack was so talented even then,” she said. Friends sometimes nudged him and said he would be president some day. “He would pooh-pooh it always and say, ‘Don’t be ridiculous. I’m just trying to pay off some bills. Leave me alone.’ ”