Barack was like, “Well, I wanna be a politician. You know, maybe I can be president of the United States.” And I said, “Yeah, yeah, okay, come over and meet my Aunt Gracie—and don’t tell anybody that!”
—CRAIG ROBINSON, BARACK OBAMA’S BROTHER-IN-LAW
Barack Obama seemed to know almost immediately upon meeting a round-eyed, statuesque African-American lawyer named Michelle Robinson that she was his choice for a spouse; the young Miss Robinson was far less sure about her future husband. And that in itself says much about the two people: Barack is the romantic dreamer; Michelle is the balanced realist. Upon meeting her, he was swept off his feet; she took some convincing.
Obama and Robinson met after Obama’s first year at Harvard Law, in 1988, when he was a summer intern in the Chicago office of the high-brow law firm now called Sidley Austin. Robinson, a young lawyer at the firm, was assigned to be his mentor. Initially, Robinson was skeptical about Obama because, even before he arrived for the summer, he had been talked up by so many others at the firm—too many others, she thought. Secretaries gossiped about how handsome he was. Associates marveled at his magnificent first-year performance at Harvard. Senior partners hailed an introductory memo by Obama as nothing short of brilliant. “He sounded too good to be true,” Michelle recalled. “I had dated a lot of brothers who had this kind of reputation coming in, so I figured he was one of these smooth brothers who could talk straight and impress people. So we had lunch, and he had this bad sport jacket and a cigarette dangling from his mouth and I thought, ‘Oh, here you go. Here’s this good-looking, smooth-talking guy. I’ve been down this road before.’ Later I was just shocked to find out that he really could communicate with people and he had some depth to him. He turned out to be an elite individual with strong moral values.”
Obama suffered no false preconceptions about Michelle and was immediately taken with her. Nevertheless, at first she resisted his amorous advances. She thought it would be improper to date an employee she was assigned to train. In addition, they were the only two African Americans at the law firm. “I thought, ‘Now how would that look?’” Michelle said. “Here we are, the only two black people here, and we are dating. I’m thinking that looks pretty tacky.” Michelle tried to set up Obama with a friend, but he showed no interest in anyone but her. Eventually, she relented and agreed to a date, and, over chocolate ice cream at a Baskin-Robbins shop near the University of Chicago, he won her affection. When Obama returned to Harvard in the fall, the two carried on a long-distance relationship that Obama conceded would have been impossible just a few years before. “Before I met Michelle, I was too immature to hold something like that together,” Obama told me, acknowledging that as he approached thirty he gained a different perspective on a secure romantic relationship. As a community organizer, Obama had had a serious girlfriend (and a pet cat), but all three parted amicably when he went to Harvard.
During his late twenties, Obama shifted his thinking toward the value of marriage and family. Even though his restless mind and ambitious energy made him fear a static life, he was beginning to desire a stable relationship and family. He considered the upheaval of his father’s family life and longed for a different outcome for himself. On trips back to Chicago from Harvard, Obama often visited Jerry Kellman and his wife at their house in the Beverly neighborhood, one of Chicago’s few racially mixed communities; he looked out at Kellman’s backyard and confided that he wanted “this kind of stability.”
Michelle Obama grew up in a tightly knit, working-class family in the South Shore neighborhood of Chicago’s sprawling South Side African-American community. Obama, who sometimes described his own childhood as that of “an orphan,” is fond of chiding his wife for “being raised by Ozzie and Harriet,” a reference to the idyllic American family from the 1950s sitcom.
The Robinsons lived in a small apartment on the top floor of a classic low-slung Chicago bungalow. Michelle’s father, Frasier Robinson, worked odd-hour shifts overseeing the inner workings of boilers at the city’s water filtration plant. Her mother, Marian, did not work outside the home until Michelle reached high school, when she took a position as an administrative assistant in the trust division of a bank, a job she still held in 2007. Michelle has one sibling, a brother, Craig, sixteen months older than she. A talented basketball player, he ultimately left a lucrative job in high finance to coach in the college ranks. (In 2006 he became head coach at Brown University.) Their father suffered from a debilitating illness that family members believe was multiple sclerosis, although he never received an official diagnosis. Both children were indelibly shaped by their father’s unstable physical condition—and the strong will he showed in coping with it. He was devoted to setting a sturdy paternal example and sufficiently providing for his family. He rarely missed work or time with his children, even as his physical state deteriorated. “We always felt like we couldn’t let Dad down because he worked so hard for us,” Craig Robinson said. “My sister and I, if one of us ever got in trouble with my father, we’d both be crying. We’d both be like, ‘Oh, my god, Dad’s upset. How could we do this to him?’”
Much of Michelle’s childhood was spent scurrying on the heels of her older brother and, to some degree, living in the tall shadow he cast. Craig was a good student and popular athlete, and Michelle had a deeply competitive spirit. Long limbed and extremely tall at five feet eleven inches, Michelle showed great athletic prowess in the neighborhood, often holding her own on the basketball court with her brother and his friends. But to fight comparisons with her high-achieving brother, she decided against playing organized sports. Instead, she immersed herself in pursuits of her own—learning the piano, writing short stories in her spiral notebook, serving as student council treasurer and excelling in school. She skipped the second grade and consistently made the honor roll at Whitney Young High School, one of the premier public institutions in the Chicago system. Her academic excellence secured her acceptance at Princeton University. She graduated cum laude from Princeton and then, like her husband, went to Harvard Law. Her brother also attended Princeton, at the urging of their father. Craig was gifted enough on the basketball court to attend a school with a strong Division I program, and he was offered full-ride scholarships at several colleges with top basketball programs. But his father said education was more valuable and sent him to Princeton, even though he had won only a partial scholarship. “Dad said it didn’t matter about the cost—it was the education that was important,” said Craig, who went on to be one of the top players in the history of the Ivy League.
At Princeton, Michelle underwent a racial identity crisis similar to what Obama experienced in his formative college years. For the first time in her life, she had stepped into a nearly all-white cultural and academic setting. And even though she was popular and quickly acquired a handful of good friends, she admitted in a thesis, titled “Princeton-Educated Blacks and the Black Community,” that she felt racially isolated as one of the few black women on the campus. “I have found that at Princeton, no matter how liberal and open-minded some of my White professors and classmates try to be toward me, I sometimes feel like a visitor on campus, as if I really don’t belong. Regardless of the circumstances under which I interact with Whites at Princeton, it often seems as if, to them, I will always be Black first and a student second.” Yet as she progressed through Princeton, Michelle said she realized that as an alumna of an elite college, she probably would move in predominantly white circles later in her professional life. She had wanted to use her education to serve the black community in some way, but she wrote that “as I enter my final year at Princeton, I find myself striving for many of the same goals as my White classmates—acceptance to a prestigious graduate or professional school or a high-paying position in a successful corporation. Thus, my goals are not as clear as before.”
The position at the firm now known as Sidley Austin certainly fit the description of a high-paying position in the upper echelons of the legal community. Yet a few years later, after marrying Obama, Michelle found herself moving out of that predominantly white world of high-powered law and into the public service sector that she had always envisioned for herself. First she left Sidley Austin to work for a deputy chief of staff to Mayor Richard M. Daley. Then, in 1993, she was hired to launch the Chicago office of Public Allies, a program established under Bill Clinton’s AmeriCorps to help young people find employment in public service. Michelle, exceedingly efficient and excessively organized, built the program from the ground up. Over her three-year tenure as executive director, she assembled a solid board of directors and raised enough cash to establish the program for the long haul.
I first met Michelle Obama during her husband’s U.S. Senate campaign, in January 2004, as I researched my first profile of her husband for the Chicago Tribune. At the time, she was directing community affairs for the University of Chicago Hospitals, just blocks from their town house and children’s school in Chicago’s Hyde Park neighborhood. Her credentials made her seem considerably overqualified for the position of community liaison for a hospital, and as I walked to her office on a blisteringly cold morning, I noted mentally that she had made a career sacrifice for the sake of the family. Her small office was situated in a difficult-to-find back corner section of a sprawling medical building. The structure was designed with a mind-bending maze of hallways that, each time I would visit, gave me the feeling of the proverbial rat in a science experiment. Her office was much as I would find her to be—highly functional with few frills. It was simply decorated with the same mass-produced wooden furniture found in her secretary’s waiting room. Attractive family photos of her children and her husband were atop seemingly every square inch of desk or cabinet space, and no visitor needed to guess about her top priority in life.
Having previously interviewed wives (and husbands) of political candidates, I was uncertain what to expect. Some spouses, fearful of a verbal gaffe, are heavily scripted by campaign aides, equally fearful of a blunder. Others are more at ease with their own words but are still generally cautious in their approach. Michelle Obama exuded neither quality. She was not the least bit scripted. She was open and relaxed and greeted me as if we had met many times before. As with her husband, one of her strengths is the ability to put others at ease in her presence. She answered my questions in such an unhurried and relaxed fashion that she seemed only mildly calculating, if at all. I found her to be comfortable with herself, personable, intellectually engaging and deeply committed to her husband. She knew that he badly wanted to win this election. Toward that end, she was adept at pointing out his positive traits; and yet she seemed to have little interest in putting an artificial gloss on her husband’s foibles and faults. “I call him ‘The Fact Guy,’” she told me. “He seems to have a fact about everything. He can argue and debate about anything. It doesn’t matter if he agrees with you, he can still argue with you. Sometimes, he’s even right.” She broke into a playful grin at this last remark.
She told me how Obama’s competitive streak sometimes led him to be overly boastful at winning family games, such as Scrabble or Monopoly. She stressed that her husband had made many sacrifices in his career, particularly financial sacrifices, in order to serve the public. The emphasis on this part of her husband’s character certainly would have been considered helpful to his campaign, but she spoke so openly about his faults that neither observation came across as overtly scripted.
Our interview ran almost two hours, at which time I ended the session. I stepped back into a maze of hallways with the impression of a woman who was confident in her own skills, confident in her marriage and her own career and also highly respectful of her husband’s abilities.
Obama has publicly portrayed Michelle as a reluctant political wife, and that has unmistakably been true. His immense personal ambition and good political fortune have pushed his career into overdrive, sometimes leaving his family breathing exhaust fumes. And this has caused friction in the marriage. But initially, her attraction to Obama was wedded, at least in part, to his mission to serve the public. When Obama first mentioned his desire to enter politics, she was encouraging. “I told him, ‘If that’s what you really want to do, I think you’d be great at it,’” she said. “‘You are everything people say they want in their public officials.’”
Their four-year courtship seemed rather effortless to outsiders. Both clearly were devoted to each other, although Michelle’s family expressed some initial hesitancy. Michelle’s mother, Marion Robinson, was fond of Obama but was concerned that his biracial ancestry might evoke a clash of cultures, or that their union might not be readily accepted by others. Michelle’s brother, meanwhile, wondered if Obama could live up to the rigorous standards that his exacting younger sister had placed on previous boyfriends. “My mom and I and my dad, before he died, we were all worried about, ‘Oh, my god, my sister’s never getting married because each guy she’d meet, she’s gonna chew him up, spit him out.’ So I was thinking, Barack says one wrong thing and she is going to jettison him. She’ll fire a guy in a minute, just fire him. . . . Unfortunately for these guys, and I don’t want this to sound conceited, but my dad was my dad. And so she had a definite frame of reference for a guy. She had an imprint in her mind of the kind of guy she wanted. And my mom used to tell her—and I used to tell her after she got older—I was like, ‘Look, you’re not gonna find guys that are gonna be perfect, because they didn’t have Dad as a father. So you’ve gotta sort of come up with your framework.’ But she was hardheaded and refused to let that go.”
Craig’s first impression of Obama was positive: “He was tall,” Craig said with a chuckle. Michelle had dated men shorter than she, and one surmises that her confident demeanor and extreme tallness for a woman could be intimidating to any suitor, especially one deprived of height. Craig’s most indelible impression of his sister’s new boyfriend came on the basketball court. Obama was not nearly as talented as Craig, who had played professionally in Europe after being drafted and cut by the NBA’s Philadelphia 76ers. But Obama had never been reticent about his own basketball skills and he was eager to step on the court with the former college star. That moxie impressed Craig. “Barack’s game is just like his personality—he’s confident, not afraid to shoot the ball when he’s open. See, that says a lot about a guy,” Craig said. “A lot of guys wanna just be out there to say they were out there. But he wants to be out there and be a part of the game. He wants to try and win and he wants to try and contribute.”
This extreme level of confidence is something that was ingrained in Obama’s psyche early in life. His maternal grandfather would tell Obama that this was the greatest lesson he could learn from his absent father: “confidence—the secret to a man’s success.” That is how Obama’s father led his life; and even in times of self-doubt, Obama has hearkened back to that wisdom.
Though Obama and Craig bonded on the basketball court, Craig was taken aback at one of their first holiday gatherings when Obama confided what profession he might pursue after Harvard Law—politics. And not only that, but Obama seemed to hint that he was destined for great things in this often poisonous field of endeavor. Obama speculated to his future brother-in-law that he just might be president one day. “Barack was like, ‘Well, I wanna be a politician. You know, maybe I can be president of the United States.’ And I said, ‘Yeah, yeah, okay, come over and meet my Aunt Gracie—and don’t tell anybody that!’”
Michelle, in contrast to her husband, was more circumspect about Obama’s lofty ambitions. She thought he had great talent, but looked at him as something of a dreamer as far as national politics was concerned. He might be a star in that realm one day, but that was of little interest to her. Beyond Obama’s keen intellect and personal charm, what sealed Michelle’s love for him was his civility and human compassion. She said she was intimately affected by his treatment of one of her uncles who had a drinking problem. Obama was studying at Harvard Law at the time and clearly had a bright future ahead of him. So he could easily have dismissed her uncle. Instead, “Barack treated him with respect and dignity, like an equal,” Michelle said. (Perhaps Obama had compassion for her uncle because Obama’s own family was not immune to alcohol issues. His maternal grandfather, who helped raise Obama, drank to excess, as did Obama’s Kenyan father.)
LOVE AND ATTRACTION ARE SUCH INTANGIBLE NOTIONS THAT IT IS impossible to definitively analyze what drew Obama to Michelle Robinson so intensely. But people close to him believe that race probably played a factor. After coming to the mainland from Hawaii, he sought to find not only his own cultural identity, but a comfortable human community in which to live. One can surmise that in choosing an African-American woman as his wife, he consciously (or subconsciously) decided to root himself in the black community. Kellman, for one, believes it was no fluke that Obama married a black woman. He said Obama was attracted to the black experience in America. “If you are biracial, I think as a kid, you begin to identify with the underdog, the people who have injustice thrust upon them,” Kellman said. “I think that has great appeal to you, and that is what Barack began to care about, intellectually. You can see that in college and in other places. I mean, blacks in America, this is the great injustice of our history. So why not opt for that and choose that path? I think it is very natural, in that sense, for him to do that and to be inspired by that. . . . In writing more about his dad than his mother, the person he knew and [who] reared him, it makes the case that this is what he chose for his future—the fact he chose to marry Michelle, the ideal person who could help him develop those kinds of roots, and the person to share this career with. And personally, it just seems to have worked out wonderfully for him.”
The Obamas settled in Chicago’s Hyde Park neighborhood along the lakefront on the city’s South Side. With the University of Chicago as its epicenter, Hyde Park is one of just two or three communities in racially segregated Chicago that is populated by significant numbers of both blacks and whites, many with college educations. A particularly trendy place for upwardly mobile blacks, Hyde Park is also in vogue for mixed-race couples. So when Obama married Michelle in 1990, he also married into her budding network among Chicago’s community of successful, white-collar African Americans. Indeed, as two attractive Harvard Law graduates, the Obamas made for a striking black professional couple. But despite this status, neither pursued financially rewarding careers. Michelle left Sidley Austin in the wake of losing two people close to her—her father (shortly before she and Obama married) and a college roommate who died suddenly at twenty-five—which prompted her to take a close look at how she conducted her own life. She interviewed for a Chicago City Hall post under Valerie Jarrett, then chief of staff to Mayor Richard J. Daley. When Jarrett offered her the job, Michelle had one rather odd request: She asked that Jarrett first meet with Obama, then her fiancé. It turns out that Obama had concerns about his impending bride going to work in Daley’s city hall. He worried that Michelle might be too straightforward and outspoken to survive in such an overtly political environment; and suspicions about Daley’s administration, which had been criticized as an updated version of Chicago’s machine politics and a vehicle designed primarily to serve Daley’s political interests over community interests. Jarrett promised Obama that he would protect Michelle from political backstabbing, and Obama eventually agreed to the job.
When Obama returned to Chicago from Harvard, he put off his legal career for six months to take a position directing a voter registration and education campaign targeting Chicago’s low-income blacks. Illinois Project Vote registered nearly one hundred and fifty thousand new voters for the 1992 presidential election. “It’s a power thing,” declared the project’s radio commercials and brochures. The effort was critical in electing two Democrats. It helped Bill Clinton win Illinois, and it greatly assisted an African-American state lawmaker, Carol Moseley Braun, in becoming the first black woman to serve in the U.S. Senate. But Obama was also working on another project at the time, and this dual workload caused strains in his marriage. Running Project Vote by day, Obama was writing his first memoir at night, leaving Michelle feeling rather lonely. Michelle is religious in her routine of going to bed early and rising at 4:30 A.M. to hit the treadmill, but her husband’s disappearance into his writing hole until the wee hours took some adjustment on her part. This was a pattern that the ambitious Obama would fall into throughout his political career: heavily burdening himself with work duties, much to the chagrin of his wife. Obama admits that this trait is a personal shortcoming. “There are times when I want to do everything and be everything,” he told me. “I want to have time to read and swim with the kids and not disappoint my voters and do a really careful job on each and every thing that I do. And that can sometimes get me into trouble. That’s historically been one of my bigger faults. I mean, I was trying to organize Project Vote at the same time as I was writing a book, and there are only so many hours in a day.”
Michelle has not been shy about grumbling in public regarding her husband’s busy career. Much like Obama’s no-nonsense grandmother, Michelle has consistently played the role of stabilizing influence in the Obama home, particularly after their two daughters were born. “I cannot be crazy, because then I’m a crazy mother and I’m an angry wife,” she said. “What I notice about men, all men, is that their order is me, my family, God is in there somewhere, but ‘me’ is first. And for women, ‘me’ is fourth, and that’s not healthy.” Michelle qualified the statement to say “all men,” which left her husband off the hook. But I think it would be fair to say that “all men” do not put themselves ahead of their family. More often than not in American households, it is indeed the mother who makes the career sacrifice for the sake of children, but not always. The man Michelle married, however, is prone to placing his professional ambitions at the top of his priority list. Indeed, someone who writes a nearly four-hundred-page memoir—at the age of just thirty-three—might be accused of self-indulgence. And Michelle was not the first woman in his life to accuse Obama of a certain level of self-absorption. A female friend at Occidental College told Obama spitefully, “You always think it’s about you.”
AFTER THE NOVEMBER 1992 ELECTION AND PROJECT VOTE’S CONCLUSION, Obama set out to practice law in Chicago. As a magna cum laude graduate of Harvard Law and the first black president of the Harvard Law Review, he had his choice of top law firms. He picked Miner, Barnhill & Galland, which specialized in civil rights and discrimination cases. The firm was in many ways the antithesis of the corporate Sidley Austin. Miner, Barnhill was an activist firm that strove to rectify social and economic injustice through the courts. In this sense, it fit Obama’s mission agenda perfectly. Miner, Barnhill had picked up Ivy League graduates before, but when senior partner Judson Miner had called the Law Review the year before to inquire about Obama, the response gave him little cause for optimism. “Leave your name and take a number,” Miner was told. “You are caller number six hundred and forty-seven.” Obama’s Law Review presidency had garnered him national media attention and put him at the top of the list of Harvard graduates.
Over the nine years that Obama’s law license was active in Illinois, he never handled a trial and mostly worked in teams of lawyers who drew up briefs and contracts in a variety of cases. He was one of the lawyers representing an activist group in a successful lawsuit that accused the state of Illinois of failing to apply a federal law designed to help the poor register to vote. In another case, Obama wrote a large portion of an appeals brief for a whistle-blower who exposed misconduct by Cook County and a private research institute in the handling of a five-million-dollar federal research grant. The grant money was used to study the treatment of pregnant substance abusers, and the whistle-blower was a doctor fired from the program after raising questions about expenditures. Obama was also among a group of attorneys who sued on behalf of black voters and Chicago aldermen who alleged that new ward boundaries drawn up after the 1990 census were discriminatory. An appeals court ruled that the new ward map violated the Voting Rights Act, and another set of boundaries was drawn.
But beyond the firm’s legal work, it was Judson Miner himself who appealed to Obama, for another reason. Miner had been corporation counsel in Harold Washington’s administration. Miner, in fact, was one of the lawyers who helped Washington lead the fight against the white political machine on the city council. From those days, Miner had a bevy of contacts in Chicago’s political circles. And as Obama had mentioned to friends and family, politics greatly interested him. He had seen how effective Washington had been in quickly altering the racial and social dynamics of the city. The speed of this change impressed Obama. “The courts are generally very slow and they are generally pretty conservative, not ideologically conservative necessarily, but conservative as institutions,” he said. “Law school and practicing law put the framework around how this country works, but it also drove home that social change through the court system is a very difficult thing. There are very few moments in our history, Brown v. Board of Education being a singular exception, where substantial change was initiated through the court system. . . . So it was at this point that I started thinking more seriously about political office.”