4

He must have driven past Michelle’s house a thousand times…

He must have driven past Michelle’s house a thousand times in his beat-up Honda, without ever knowing it. As soon as he landed there in the summer of 1985, Barack crisscrossed Chicago’s South Side in search of African American pastors willing to band together for the common good.

After all, it had been two years since black voters joined together with Latinos and white liberals to send Harold Washington to city hall as Chicago’s first black mayor. Now that Barack had been hired by veteran community organizer Jerry Kellman to bring black churches together as part of his Developing Communities Project (DCP), he had little doubt that he would succeed.

Barack had been in Chicago just once before, at the age of ten, when his grandmother had taken him and his half sister Maya on a monthlong whirlwind tour of the U.S. mainland. But he knew from carefully studying the works of Martin Luther King Jr. that the South Side of Chicago had been the epicenter of the civil rights movement in the North—the “capital of the African American community,” Obama proclaimed, as well as “the birthplace of community organizing.”

Chicago was also the home of Saul Alinsky, the leftist firebrand whose 1946 book Reveille for Radicals was widely regarded as the bible of the protest movement. Colorful, outspoken, and often outrageous, Alinsky believed that the only way to effect change was by confronting power—with boycotts, protest marches, sit-ins, and strikes. The agitator emeritus believed in a win-at-all-costs approach in the battle for power, and that required zeroing in with laserlike focus on one’s enemies. Advised Alinsky: “Pick the target, freeze it, personalize it, and polarize it.”

But there was also a more pragmatic side to Alinsky’s teachings—one that appealed to the twenty-three-year-old biracial Ivy Leaguer. Alinsky, rightly considered the founder of community organizing, advised activists to immerse themselves in the culture and language of the people they hoped to represent. Toward that end, he urged organizers to learn “the local legends, anecdotes, values, idioms” and to listen carefully to their community’s grievances. It was only by bonding with the poor and disenfranchised on a personal level, Alinsky argued, that community organizers could help them acquire the only thing that counted: power.

It was a message that had not been lost on a young Wellesley College student named Hillary Rodham back in the late 1960s. For her trenchant analysis of Alinsky and Chicago’s Community Action Program, part of the larger War on Poverty, the future Mrs. Bill Clinton received an A+.

Hillary so impressed Alinsky that he offered her a chance to work with him after she graduated from Wellesley, but she turned him down. Instead, choosing the same road Barack would choose years later, Hillary applied to several of the country’s top law schools. Accepted by both Harvard and Yale law schools, Hillary chose Yale. “The only way to make a real difference,” Hillary told Alinsky when he accused her of selling out, “is to acquire power.”

Jerry Kellman, the battle-scarred community organizer who had lured Barack to Chicago, was another of Alinsky’s loyal disciples. In bringing Chicago’s black churches under the banner of the Developing Communities Project, Barack would willingly employ Alinsky’s methods. “Once I found an issue people cared about,” he reasoned, “I could take them into action. With enough actions, I could start to build power.”

That Chicago’s black churches were a repository of political power was undeniable. But, as Barack soon discovered, the ministers who wielded that power were loath to share it with anyone. Those pastors who deigned to meet with him at all dismissed him as a naive young do-gooder. The response at the grassroots level was no less discouraging. As the old Chicago saying went, “We don’t want nobody that nobody sent.”

“Well,” Barack’s fellow organizer Mike Kruglik said, “Barack was somebody that nobody sent.”

Discouraged but not defeated, Barack persevered. Operating out of a cramped office at Holy Rosary Church at 113th Street and Calumet Avenue, he followed Jerry Kellman’s explicit instructions to contact thirty people every day. Older black women, understandably, were the first to warm to the skinny young man with the cherubic looks. They called him “Baby Face.”

“He was a skinny young man,” Jerry Kellman said. “And in some of the communities he worked, there were a lot of single moms, single grandmothers, and they wanted to take him in and feed him and fatten him up. He was an eligible young man. They wanted to introduce him to their daughters and to their granddaughters.” According to Kellman, Barack “found a home” in Chicago and was “very comfortable there.”

Three women in particular—Linda Randle, Yvonne Lloyd, and Loretta Augustin-Herron—became nothing less than surrogate mothers to Barack. “He was so young—most of us had children who were older than he was,” Augustin-Herron remembered. “It’s funny to look back now and realize that even then, when he was just twenty-three, nobody challenged him. We accepted him immediately because he had a way of making you know right off the bat that he really cared. He listened—really listened—which was something none of us were used to.”

Barack pushed his surrogate moms and other community activists to stand up for themselves against landlords and bureaucrats. Toward that end, he would put them through their paces with hours of role-playing so that they could state their case to the appropriate authorities. “We’d say, “Barack, why don’t you do this?’” Yvonne Lloyd recalled, “and he’d say, ‘No, this is your community, not mine. You all need to do this for yourselves, not for me.’” When tempers ran high, as they often did, it was Barack who “told everyone to calm down and stay focused,” Linda Randle said. “We were all strong women and pretty high-strung anyway. He’d say, ‘All you’re raising is your blood pressure. We’ll take the high road.’ He was always cool, nothing ever seemed to bother him.”

Yet Randle, Augustin-Herron, Lloyd, and the others worried about him. “He worked ten, twelve hours a day,” Augustin-Herron said. “He never ate anything except salads. We told him he was too skinny, and he’d just laugh.”

They were also concerned that he did not seem to have time for anything except work and his cat, Max. “He worked day and night,” Lloyd said. “I don’t know if he ever slept.” When he bought a used yellow Datsun 210 hatchback from a Glenview, Illinois, police officer for five hundred dollars, they had even more cause for concern. The Datsun (Barack said it reminded him of an “overripe banana”) was pitted with rust and had a hole in the door that allowed passengers to watch the pavement zipping by.

“All of us would cram into Barack’s little car,” Lloyd said, “and I’d ask, ‘Why are you drivin’ around in this raggedy thing? When are you going to get a real car?’”

“Hey,” Barack always answered with a laugh, “it gets me from point A to point B, right?”

As eager as they might have initially been to set him up with their daughters and the daughters of friends, the church ladies who were such a large part of Barack’s life during this period—he now referred to them as “my other family”—soon realized that he preferred to keep the details of his love life to himself.

“Barack definitely dated,” Jerry Kellman said. “But he was just too driven to get deeply involved with a woman.” With one exception: For several months, Barack lived with a dark-haired young white woman who would remain a mystery even to his church moms. “They were obviously both very private people when it came to that,” Augustin-Herron said. “They obviously wanted to keep the details of whatever it was they had to themselves.”

For the most part, over the two and a half years he spent as a community organizer, life for Barack was one mind-numbing meeting after another. Lloyd recalled that he was always jotting thoughts down in an ever-present notebook, ostensibly for the purpose of reporting back to his superiors. He also liked to doodle caricatures—usually of dour-looking officials he would draw laughing. A few of his doodles were less charitable—like the ones that depicted certain pastors or intransigent city officials with pointy heads.

To be sure, Barack could boast of a few concrete achievements at community organizing during his initial stint in Chicago. The most significant of these was his participation in a very public crusade—actually spearheaded by fellow activist Hazel Johnson—to remove asbestos from Altgeld Gardens, a decaying public housing project that was home to over two thousand people.

Barack’s main assignment—to bring together the black churches as a single, monolithic force for good—did not go quite so smoothly. “The pastors of these churches were used to running things. They weren’t interested in sharing the power and the glory with anybody else,” Randle said. “You’re talking about some pretty big egos.”

One of those who first pointed out to Barack the folly of this approach happened to be the South Side’s most flamboyant and influential black clergyman, the Reverend Jeremiah Alvesta Wright. The son of a Philadelphia preacher, Wright had been arrested for grand theft auto at the age of fifteen, enlisted in the marines, and then served as a navy corpsman specializing in cardiopulmonary care. In his office, Wright displayed a photo of himself in scrubs, tending to President Lyndon Johnson following LBJ’s throat surgery in 1966.

Wright went on to earn a master’s degree in sacred music from Howard University. Through a combination of bombast and showmanship, the dapper, goatee-sporting minister built Trinity United Church of Christ at Ninety-fifth and Parnell Streets into an ecclesiastical powerhouse with over eight thousand congregants.

Wright was one of the first church leaders Barack had approached in his efforts to build a coalition of black churches. The brawny minister, who had placed a Free Africa sign on the church lawn to protest apartheid, had listened patiently as Barack made his case.

“Oh, that sounds good, Barack, real good,” Wright said, his voice tinged with sarcasm. “But you don’t know Chicago, do you?”

Barack looked puzzled. “You are a minister,” he said. “Why are you sounding so skeptical?”

“Man, these preachers in Chicago,” Wright told him. “You are not going to organize us. That’s not going to happen.”

“But why—?”

“Barack,” Wright interrupted, “no, no, no. Not going to happen.”

They were not the words Barack had wanted to hear, but in time he came to appreciate Wright’s candor. So much so that, when it came time to determine which church would be appropriate for him to join—a process that involved Barack actually interviewing each pastor—he ultimately chose Trinity United. There was an added advantage to joining that particular church: it sat just outside the boundaries of Barack’s carefully circumscribed organizing district. “Trinity was as close as it could be to the area Barack was operating in without actually being in it,” said Alvin Love, pastor of Lilydale First Baptist Church and one of the local clergymen who worked closely with Barack. “If he joined my church or any of the others he was working with, it would look like he was playing favorites. He got around that problem by joining Trinity.”

Not that Barack had ever been much of a churchgoer. He had inherited a distinctly laid-back attitude toward religion from his parents and his grandparents, and although he had sampled both the Christian and Muslim faiths as a child, he considered himself something of an agnostic by the time he arrived in Chicago.

Now that he had bonded with his fellow African Americans in the City of Big Shoulders, he realized that something was missing. Those wonderful, warm grandmothers and mothers notwithstanding, he still felt emotionally isolated, a person apart. He could never fully share in the black experience, he realized, without belonging to a church.

“Early on,” a confidant later said, Barack “was in search of his identity as an African American and, more importantly, as an African American man.” Jeremiah Wright “was instrumental in helping him understand the black experience in America.”

But Trinity United wasn’t just any African American church. It was the church of Chicago’s black elite. When Oprah Winfrey arrived in Chicago from Baltimore in 1984, joining Trinity was a way for her to connect with the established movers and shakers in Chicago’s black community.

What they got was a heavy dose of Afrocentrist, black liberation theology. Often clad in a colorful dashiki, Wright devoted much of his time at the pulpit to railing against whites in general and the U.S. government in particular. With Ronald Reagan in the White House, Barack often heard Wright blame Reagan’s America for many, if not most, of the world’s ills. “A nation that will keep people in slavery for two hundred and forty-four years will exploit poor people generally,” Wright said, adding that “all of America’s wealth today could not adequately compensate us for centuries of exploitation and humiliation.”

Less than a year before Wright met Barack, the reverend had accompanied his friend Louis Farrakhan, controversial head of the Nation of Islam, to visit Libyan strong man Muammar Gadhafi. Trinity United gave Farrakhan, a virulent anti-Semite who called Judaism a “gutter religion,” praised Hitler as “a very great man,” and described white people as “potential humans,” a lifetime achievement “Empowerment Award” for his “commitment to truth, education, and leadership.”

In addition to praising Farrakhan in his sermons, Wright denounced his own countrymen as “war criminals,” described America’s military as “some demonic destructive suction tube,” and proclaimed that the United States had “committed more war crimes almost than any other nation in the world and we won’t stop because of our pride, our arrogance as a nation.” To Wright, America was simply “the greatest purveyor of violence in the world.”

Wright, said Chicago journalist Salim Muwakkil, “had the reputation of a militant guy who provided kind of a vicarious militance for Chicago’s black elites. So they could get a dose of militance on Sunday and go back home and feel pretty good about doing their part for the black movement.”

Barack was intrigued by Wright’s message of black empowerment; the pastor’s rantings against the “white power” structure in Washington and the state of Israel—not to mention his defense of Communists in Nicaragua and the Castro regime in Cuba—were met by a chorus of amens every week, and fellow churchgoers remember that Barack chimed in with the rest.

Wright’s politically charged sermons weren’t the only thing that distinguished him from his fellow black clergymen. While most African American pastors regarded homosexuality as a sin, Wright was an ardent supporter of gay rights.

Trinity United’s policy of inclusion undoubtedly appealed to Barack, as did Wright’s passionate take on the black experience in America. But just as important was the caliber of people who flocked to Trinity United each Sunday. The congregation included doctors, lawyers, entrepreneurs, sports figures, and recording stars. None shone brighter than Oprah. Although she would apparently not recall it, Oprah first met the fresh-faced community organizer when he walked up to her after services and introduced himself as a big fan. “Oprah was already a big, big deal,” one church member recalled. “Barack couldn’t take his eyes off her. I think that’s when it clicked, you know, like ‘this is the place where I gotta be!’”

Chicago City Alderman Toni Preckwinkle agreed. “Not only does it have one of the largest African American congregations in the city,” Preckwinkle said, “but there are a lot of influential people among the parishioners. It’s certainly a good place for a young politician looking to make social connections.” But Preckwinkle believed that Wright was the deciding factor in Barack’s decision to join Trinity United. “Jeremiah Wright is a powerful speaker and a very charismatic individual.” Barack, she believed, “could not have helped but be impressed by him.”

Jeremiah Wright was not the only black leader Barack idolized. Mayor Harold Washington had become a bona fide hero to the black citizens of Chicago, and when he died of a massive coronary in November of 1987, they were devastated. Barack was no exception. Depressed and discouraged by his limited success as a community organizer, Barack set his sights on a specific goal: to become the next black mayor of Chicago.

Barack surveyed the political scene and noticed that Washington—and for that matter most elected officials—had one thing he did not: a law degree. “I’m not going to accomplish anything significant,” he told Wright, “unless I get a law degree.”

Aiming for the top, Barack enlisted the help of several influential figures to get him into Harvard Law School. One of his more colorful Chicago associates was Khalid Abdullah Tariq al-Mansour, a radical Muslim who had been a mentor of Black Panther Party founders Bobby Seale and Huey Newton. At al-Mansour’s request, Percy Sutton, the respected New York political figure who had once been Malcolm X’s lawyer, wrote a letter of recommendation on behalf of Barack. So did Northwestern University professor John McKnight, another disciple of Saul Alinsky, who had been impressed by Barack’s work in the community.

In February of 1988, Barack received notice of his acceptance to Harvard Law. Before he left, he returned to Trinity United to hear Rev. Wright give yet another sermon—one that, he would later say, changed his life.

Wright spoke of a painting titled Hope, which depicts a harpist sitting on a mountaintop. On closer examination, Wright continued, you could “see that the woman is bruised and bloodied, dressed in tattered rags, the harp reduced to a single frayed string.” In the valley below, “everywhere are the ravages of famine, the drumbeat of war, a world groaning under strife and deprivation.”

Although years later Barack would claim not to have been aware of Wright’s more incendiary comments, the reverend used this sermon—Barack’s favorite—to denounce the bombing of Hiroshima as genocide, attack the callousness of U.S. government leaders, and proclaim that “white folks’ greed runs a world in need.” Still, the overriding message of the sermon was one of hope—or, to be precise, the “audacity” of hope.

“Hope! The harpist,” Wright continued, “is looking upwards, a few faint notes floating upwards towards the heavens. She dares to hope…. She has the audacity…to make music…and praise God…on the one string she has left!…The audacity of hope! The audacity of hope.”

The sermon, which also drew parallels between American blacks emerging from slavery and the Jews being led out of Egypt, reduced Barack to tears. “Those stories—of survival and freedom, and hope—became our story, my story,” he later recalled. “The blood that had spilled was our blood, the tears our tears; until this black church, on this bright day, seemed once more a vessel carrying the story of a people into future generations and into a larger world.”

At another Sunday-morning service, Wright would baptize Barack. As moving as Wright’s “Audacity of Hope” sermon had been, Barack would later concede that his baptism was a calculated decision—a matter “of choice and not an epiphany.” The doubts he had about religion “did not magically disappear.” By formally joining Trinity United and accepting Wright as his spiritual mentor, Barack embraced a tradition of faith that had sustained the black community through slavery and segregation. He was also signaling to Chicago’s African American community that he intended to return and be a part of it.

But first he would have to relocate to Boston and earn that all-important Ivy League law degree. In this new phase of his life, there was no place for the young woman he had been living with. “It was the one time when Barack seemed to be really stressed,” Loretta Augustin-Herron said. “He broke it off because he didn’t think the situation was fair to her—he didn’t want her to put her life on hold for him, which she had offered to do. But Barack was pretty upset about leaving—it seemed to me that he obviously cared for her—and he seemed to be asking if it was the right thing to do.”

Offering what she described as “words of motherly advice,” Augustin-Herron told him, “Look, if you need to go to Harvard, then go. If she puts her life on hold for you, then the day will come when she will resent you. And if you put your life on hold for her, then the day will come when you resent her. So you’re doing the right thing.”

Before starting classes at Harvard, Barack decided to see a bit of that larger world. The year before, Lolo Soetoro, the Indonesian stepfather he had once been so close to, had died of a liver ailment at the age of fifty-one. Like Barack’s biological father, Lolo had been disappointed by life and sought to mask that disappointment with alcohol. This latest death in Barack’s far-flung family prompted him to once again turn outward, away from America, in search of his identity.

First, he spent three weeks in Europe before deciding it wasn’t really where he wanted to be. The maternal side of his family might have been firmly rooted in the soil of England and Scotland, but that was of little consequence to someone the world saw as black. “It wasn’t that Europe wasn’t beautiful,” Barack said. “It just wasn’t mine.”

Kenya, however, was Barack’s. His subsequent five-weeklong pilgrimage to his father’s homeland would be a transforming experience for Barack. Not only would he meet many of his Kenyan relatives (including at least five brothers, two sisters, a step-grandmother, and assorted uncles, aunts, cousins, and stepmothers), but he would also finally confront the bitter truth about his father.

None of this came quickly. When he first set foot on African soil, Barack expected to experience a soul-jarring sense of “homecoming”—an instant and visceral connection with the land of his ancestors. Instead, the grinding poverty he witnessed as he made his way to his ancestral village of Nyang’oma Kogelo—first by all-night train and then via an overcrowded matatu ( jitney) with bald tires—left him feeling “exhausted and numb.”

Gradually, as family members welcomed the young American into their lives and answered many of the lingering questions about his father that had haunted him since childhood, Barack would begin to experience the same stirrings of self-realization that many of his friends had talked about after they visited Africa for the first time. It was a gradual process, one that by necessity would require a “span of weeks or months,” he would later write, during which time “you could experience…the freedom of believing your hair grows as it’s supposed to grow and that your rump sways the way a rump is supposed to sway…. Here the world was black, and so you were just you.” Coming on the heels of his Chicago interlude, this voyage of self-discovery to Africa would at long last enable Barack to reconcile the two halves of his divided inheritance.

Barack stood out from the crowd the moment he set foot in Harvard Square—and not just because he was the son of a midwestern white woman and an African man. Barack was, at twenty-seven, five years older than most of his fellow first-year law students. He had also been raised in Hawaii and Indonesia, attended college in California and New York, and worked as a community organizer in one of Chicago’s toughest neighborhoods. As had been the case at Occidental and Columbia, he seemed to possess a kind of quiet confidence and maturity—“suave and debonair” were the words one female classmate chose to describe him—that impressed students and faculty members alike.

Michelle Robinson had graduated just a few months before Barack arrived at Harvard, and the atmosphere was just as tense. “There was,” recalled Harvard law professor Laurence Tribe, “a very rich stew of issues there to greet him.” At the law school, black students continued to press for more minority representation on the faculty, and one professor, Derrick Bell, quit in protest.

Barack stood on the law school steps before a lunchtime crowd to publicly laud Bell for his courage—and kidded the professor about how much he was appreciated for his “good looks and easy charm.” He also joined the Black Law Students Association, where he called upon his own experiences as an activist in Chicago in urging his fellow African Americans on campus to commit to giving something back to the less fortunate in their communities after they graduated. “Everybody says they’re going to give back,” Barack observed, “but sometimes there’s a mighty chasm between the saying and the doing.”

For the most part, however, Harvard Law was a repeat of Barack’s near-monastic experience at Columbia years earlier. Between hastily consumed meals at the C’est Bon sandwich shop in Harvard Square, he hunkered down in the poorly lit law library, a serious, solitary figure poring over case law and statutes well into the night.

Larry Tribe, one of Harvard’s best-known constitutional scholars, was so impressed with Barack that he took him on as his research assistant. “He had a maturity, a sort of levelheadedness that was not common for people of his, or for that matter, any age,” Tribe recalled. “He actually thought carefully before he said anything, and when he spoke, he spoke in complete paragraphs. For the first time in all my forty years in this profession, I hired him on the spot.”

For a paper Tribe was writing titled “The Curvature of Constitutional Space,” Barack researched and then analyzed Einstein’s theory of relativity, the concept of curved space, and Heisenberg’s uncertainty principle. He also helped with the research on two of Tribe’s books—On Reading the Constitution and Abortion: The Clash of Absolutes.

“Barack didn’t come to an issue with a set of prepackaged ideas. He was entirely open to new approaches, fresh ways of looking at things. Back then, when he was just a first-year law student, I didn’t hesitate to tell people that he was amazing—the most all-around impressive student I’d seen in decades.”

Tribe wasn’t alone. Michelle’s former adviser, Professor Charles Ogletree, marveled at how the first-year student quickly emerged as “a moderating influence on the campus by being mature, very much open to a variety of perspectives, but trusted by everyone.” Martha Minow, whose father, Newton Minow, had famously described television as a “vast wasteland” while heading the Federal Communications Commission during the Kennedy era, was another of Barack’s professors. She considered him to be flat-out “brilliant—I don’t think I’ve ever had a student quite like him.”

But it was at the prestigious Harvard Law Review—which Michelle Robinson had eschewed in favor of joining Harvard’s legal aid office—that Barack would ultimately make his mark. In addition to the racial storms that rocked the university as a whole and the law school in particular, an ideological battle raged on the Law Review between liberals and conservatives. The political environment was “borderline toxic,” said Bradford Berenson, one of Obama’s seventy-nine fellow Law Review editors and a member of the conservative Federalist Society. “We stopped short of physical violence, but I remember plenty of raised voices.”

In fact, shouting matches were common at the Law Review offices, which were housed on the upper floors of Gannett House, a white-columned Greek Revival building that was the oldest structure on campus. (As if to underscore its less lofty status, the legal aid bureau where Michelle had toiled was located in the building’s basement.) Berenson, who would go on to work on the Supreme Court and at the Bush White House, described the politics on the Law Review as “the bitterest [he’d] ever seen in terms of it getting personal and nasty.” Christine Spurell, one of the black writers on the Law Review and an outspoken foe of the Federalists, agreed: “People did a lot of talking and a lot of fighting. By the end, it’s like one big, unhappy family.”

Yet somehow Barack remained above the fray, in part by making himself equally accessible to blacks and whites, liberals and conservatives alike. Although he never wavered in his liberal beliefs—the only article he actually wrote for the publication, for example, was a spirited defense of abortion—Barack carefully considered the views of the conservative minority, rather than dismissing them outright.

He was also able to bridge the racial divide on the Law Review. “The black kids were all sitting together,” Spurell said. “Barack was the one who was truly able to move between the different groups and have credibility with all of them.”

Having spent his entire life walking the fine lines between races, cultures, religions, and classes, it seemed only natural for Barack to assume the role of mediator and peacemaker. But when he actually made friends with several of the conservatives on the Law Review, his fellow blacks were less than amused.

“I don’t know why at the time he was able to communicate so well with them,” Spurell wondered, “even spend social time with them, which was not something I would ever have done…. I think he genuinely thought, ‘Some of these guys are nice, all of them are smart, some of them are funny. All of them have something to say.’ I don’t think he had an agenda.”

Whether or not he had an agenda at the Harvard Law Review remained to be seen. He was very clear, however, about his plans for Chicago. “From the moment I met him, there was never any doubt in my mind that he was interested in going into politics,” said Cassandra Butts, another classmate who became a close friend. “He only talked about running for one office. He wanted to be mayor of Chicago.”

None of which would have come as a surprise to Larry Tribe. “I saw Barack as an activist, not an academic, and was quite convinced that he would climb through the ranks of whatever political jungle he found himself in,” Tribe said. “He obviously has the steadiness of purpose and the affability that makes it possible for him to move through a crowd of very sharp elbows without getting jabbed.”

Wrapping up his first year of law school, Barack was eager to get back to Chicago. He needed to reconnect with his spiritual mentor, Jeremiah Wright, and to tend to the many friendships he had made on the South Side. He also needed the kind of summer job that would pay for his stay in Chicago, build his résumé, and help him forge the kinds of connections with Chicago’s moneyed elite that he would need to fuel his political ambitions. Along the way, he might even find a woman—a true Chicagoan—to help him build the future he sought to pursue.

“Barack Obama?” Michelle asked, one hand planted firmly on her hip. “What the hell kind of name is Barack Obama, anyway? Who names their kid Barack Obama?” It wasn’t the first time she had listened to a colleague at Sidley & Austin rave about the gifted, handsome, suavely urbane Harvard first-year law student who was coming to work there as a summer associate.

It had helped that Martha Minow’s father, Newton Minow, was now a senior partner at Sidley & Austin (soon to be renamed Sidley Austin). Newton had been instrumental in spreading word of Barack’s imminent arrival, going so far as to praise his letter of introduction to the firm as poetic. Soon the firm’s rank and file were buzzing about his towering intellect, his exotic background, and his equally exotic good looks.

In a less-than-subtle maneuver to bring together two of the relative handful of black lawyers in the five-hundred-lawyer Chicago office, Michelle was assigned to be the new arrival’s mentor. She was not amused. She had already pledged to her mother just a week earlier that she was “not worrying about dating. I’m focusing on me.”

Besides, Michelle insisted she really didn’t have time “to babysit some guy.” As for the breathless comments from her coworkers, Michelle reacted with characteristic skepticism. “I figured,” she later said, “they were just impressed with any black man who has a suit and a job.”

After all, it wasn’t as if Michelle hadn’t been down this road before. Barack, she said, “sounded too good to be true. I had dated a lot of brothers who had this kind of reputation coming in, so I figured he was one of those smooth brothers who could talk straight and impress people.”

Before he arrived, Michelle pulled out Barack’s bio. “I’ve got nothing in common with this guy,” she thought as she read it. “He grew up in Hawaii! Who grows up in Hawaii? I’ve never even met somebody who grew up in Hawaii. He’s biracial. Okay, so what’s that about? Hmmm. This guy’s going to be a little strange, a little weird, a little off-putting.” She had managed to create in her mind “an image of this very intellectual nerd.”

Despite her misgivings, Michelle was fully prepared to be polite, professional, and as helpful as she could to the hotshot law student everyone was talking about. After all, this was the task she had been given, and she took her responsibilities at the firm seriously.

For his part, Barack was attracted to Michelle the moment he stepped into her forty-seventh-floor office. He was immediately impressed by her laugh (“She knew how to laugh, brightly and easily”), her stature—“my height in heels”—and her beauty. Michelle’s first impression: “He was a lot cuter than I thought he’d be.” And it certainly helped that, at six feet two inches to her five feet eleven, he was taller than she was.

That first day, Michelle, who at twenty-five was three years younger than Barack, took him out to lunch to get better acquainted. Gazing at him from across the table, she soon realized how much she hated the loud, ill-fitting sport jacket he was wearing. Within a couple of minutes, he took out a pack of cigarettes, offered her one, and, when she declined, began smoking at the table. Watching the cigarette as it dangled from his mouth, Michelle thought, “Oh, here you go. Here’s this good-looking, smooth-talking guy. I’ve been down this road before.”

But as she listened to him talk about his Kenyan father, his white mother from Kansas, and his years in Indonesia, Michelle suddenly “found him intriguing in every way that you can imagine.” To her surprise, the nerd that she had created in her mind was “funny and self-deprecating. He could laugh at himself. He was down-to-earth despite his exotic background. We clicked right away.”

Barack was equally fascinated by Michelle’s life story, perhaps less exotic but certainly no less compelling than his own. He listened intently as she spoke of her father’s courageous struggle with MS, her all-American girlhood in South Shore, the parents who worked overtime to help pay for Michelle and her basketball-star brother to attend Princeton, her experiences doing legal aid work during her years at Harvard Law School.

He had known her for only a matter of hours, but already Barack saw in Michelle both the embodiment of the African American experience and a means to fully share in that experience. Those credentials were further enhanced when Michelle mentioned in passing that Jesse Jackson’s daughter Santita had been a friend since childhood.

“Her roots in Chicago went deeper than his roots in Chicago,” Jesse Jackson later said of Michelle and what she brought to the table. “She comes from a middle-class working family with working family values and strong church values. She went to public school. And she and my daughter were friends. And so she has roots in Chicago and so she would know people he did not know in the places he would not know.”

Barack’s friend Cassandra Butts agreed. The fact that Michelle was “so rooted in the community,” Butts observed, “had obvious value.” Jeremiah Wright put it succinctly: “Michelle is from the ’hood.”

None of which occurred to Michelle at the time. All she knew was that Sidley Austin’s newest summer associate was actually interested in what she had to say, and she was flattered. Having spent so much time at restaurant tables across from men who talked only about themselves, she seldom got the opportunity to discuss the things that really mattered to her—family, friends, community. She allowed herself to think that maybe, just maybe, “this guy was as special as everybody said he was.”

For his part, Barack was simply blown away. Years later, when recalling these early courtship days to his friend Dan Shomon, he remembered thinking to himself, “Man, she’s hot! So I am going to work my magic on her.”

Michelle’s mind, however, was on her responsibility as Barack’s adviser at the firm, and not on dating. “This guy is going to be a good friend of mine,” she told herself. “I like him. I like him a lot.”

But just to make it clear that she was not in the market for a boyfriend, she told Barack in no uncertain terms that she had big plans, was on the fast track, and had “no time for distractions—especially men.”

Barack found this particularly touching. There was, he later said, “a glimmer that danced across her round, dark eyes whenever I looked at her, the slightest hint of uncertainty, as if, deep inside, she knew how fragile things were, and that if she ever let go, even for a moment, all her plans might quickly unravel. That touched me somehow, that trace of vulnerability.”

Barack had only been at Sidley Austin a few days when he marched up to Michelle and declared, “I think we should go out on a date.”

“No, nope,” she told him bluntly. “Very nice of you, but I’m not really interested in dating anybody right now.” Besides, she told her brother, “Barack and I are the only two black people in my department, and if we start dating it’ll just look, well, tacky.”

Michelle found Barack’s interest in her “touching.” She also felt sympathy for the young man who, in spite of the friends he had made during his years as a community organizer on the South Side, seemed awkward and alone. Michelle brought him along to a couple of corporate parties—“tactfully,” he recalled, “overlooking my limited wardrobe.” She also tried to set him up with several of her friends. None of those efforts amounted to anything, and for one reason: Barack wanted Michelle.

For over a month, Michelle resisted Barack’s advances. He bombarded her with notes, flowers, and phone calls, and, on a daily basis, asked her to go out with him. “He would try to charm her, flirt with her, and she would act very professional,” said Kelly Jo MacArthur, another associate at Sidley Austin. “We would just laugh, because he was undeniably charming and interesting and attractive, and the harder he had to try, the harder he had to try, because the less interested she appeared to be.”

A turning point came when she agreed to tag along with him on a Sunday-morning visit to one of the churches in Altgeld Gardens where he had done some community organizing work. That meeting took place in the church basement and was, like so many of the meetings Barack attended, filled primarily with single African American mothers.

“When he took off his jacket and rolled up his sleeves,” Michelle later recalled, “it was like seeing him for the first time.” As he delivered an impassioned speech about “the world as it is and the world as it should be,” she thought to herself, “This guy is really different, in addition to being nice and funny and cute and all that…. To see him transform himself from the guy who was a summer associate in a law firm with a suit, and then come into this church basement with folks who were like me, who grew up like me, who were challenged and struggling in ways that I never would, and to be able to take off that suit and tie and become a whole ’nother person and connect with and feel comfortable in his own skin and to touch people’s hearts in the way that he did….”

Michelle wondered if she had underestimated Barack. Of course she had known all along that he was different, even exceptional. But to watch him in the church basement, connecting with the sort of people she had known all her life, made Michelle feel that he was speaking directly to something inside her. “Barack lived comfortably in those two worlds—his own and mine—and it was impressive,” she said. “I mean, it touched me.” She even allowed herself to think, “Well, you know, I’d like to be married to somebody who felt that deeply about things.”

It was about the only way Barack could impress Michelle. “He had no money,” she said, “he was really broke. He was never going to try to impress me with things.” Certainly not his wardrobe, which she described as “kind of cruddy.” Barack owned exactly seven blue suits, five shirts, and a half-dozen ties. “I had to really tell him to get rid of the white jacket.”

As for his car, Barack was still driving his battered, rusted yellow Datsun 210 hatchback with the hole in the passenger door. “You could see the ground when you were driving by,” Michelle recalled. “He loved that car. It would shake ferociously when it would start up.”

From the look in her eyes, Barack could tell that Michelle was gradually changing her mind about him. Emboldened, he asked her out again—and to his dismay, the answer was still no.

“Why not?” he demanded.

“Nothing has really changed, Barack,” she said, sounding more tentative than she had in the past. “We work together, and I just don’t think dating is the right thing to do. It just wouldn’t look right.”

“Who cares?” he shot back, more exasperated than ever. “I don’t think the partners will consider one date a serious breach of firm policy.” He asked her if he’d have to quit the firm before it was all right for them to go out on a date.

“Okay, okay, okay,” she said with a loud sigh. “You wore me down. You win. I’ll spend a day with you,” she added, “but we won’t call it a ‘date.’”

“Fair enough,” Barack replied, beaming. “You won’t be sorry.”

It was a sunny, warm Saturday in late July when Barack took Michelle on their “nondate.” Their first stop was the Art Institute of Chicago, where he impressed her with his “deep understanding” of impressionism, the Old Masters, and modern art. They stopped for lunch at one of the institute’s outdoor cafés, where a jazz group was playing (“That was really sweet,” she would recall), and then strolled up Michigan Avenue. “We talked and talked and talked.”

From there they went to see a movie at Water Tower Place, Spike Lee’s groundbreaking tale of simmering racial tensions in the Bedford-Stuyvesant neighborhood of Brooklyn, Do the Right Thing. The significance of Barack’s movie choice was not lost on Michelle. “So you see, there he was doing his cultural thing,” she said. “He was pulling out all the stops.”

As they stopped to get popcorn before the film, Michelle realized to her horror that one of her bosses, Newton Minow, was also waiting in line with his wife, Jo. “Darn it,” Michelle whispered to Barack after they settled into their seats. “Of all the theaters in Chicago, they had to pick this one…. It’ll be all over the office tomorrow.”

Minow remembered that Barack and Michelle “were like a couple of teenagers, both obviously a little flustered that they’d been spotted together. It struck us as kind of sweet,” he said. “When you saw them it was obvious they belonged together.”

Years later Barack would corner Spike Lee at a reception and tell him, “I owe you a lot.” It was while watching Do the Right Thing that Michelle allowed Barack to touch her knee for the first time.

When the movie let out, Barack had another surprise up his sleeve. He took Michelle’s hand and led her across the street to the John Hancock Building, where they were whisked by elevator to the ninety-ninth floor. There, with the lights of Chicago twinkling beneath them, they sipped cocktails—and talked some more. “By the end of that date,” Michelle said, “it was over. I was sold. He swept me off my feet.”

A few days later, since they lived not far from each other—Barack in Hyde Park, Michelle with her parents in South Shore—she offered to drive him home after a company picnic. As they pulled up to his apartment building, Barack offered to buy her an ice-cream cone at the Baskin-Robbins at the corner of Fifty-third and Dorchester.

Sitting on the curb, trying to eat their ice cream before it melted in the sweltering summer heat, he told her about his summer job as a teenager working at a Baskin-Robbins in Honolulu and, more specifically, “how hard it was to look cool in a brown apron and cap.” She talked about her high school field trip to France, and how thrilled she had been to actually try out her French on real Parisians. Rather than stealing a kiss, he asked for her permission—and got it. “Mmmm,” he said, “chocolate.”

It was not long before Michelle brought Barack home to meet her parents—a major achievement in itself, since, as Craig put it, “almost no one got to the meet-the-parents stage.” Michelle’s parents were impressed with how polite and soft-spoken her new young man was. He, in turn, marveled at what he called her idyllic, straight-out-of-the-1950s Leave It to Beaver family.

At this point, Fraser Robinson was using a walker to get to the family car and then, with considerable difficulty, driving himself to work each day. Soon he would have to use a motorized cart to get around. Whether he was struggling to button his shirt or brush his teeth—he would give himself two hours just to get ready for work each morning—Michelle’s father never succumbed to self-pity. Marian Robinson was equally upbeat, although Barack was sensitive to the emotional toll her husband’s illness had taken on everyone in the family.

In fact, Fraser Robinson’s MS had a lot to do with Michelle’s penchant for perfection—a desire for order that verged on the obsessive-compulsive.

Fraser’s disease meant that even the most quotidian tasks—dressing, eating, going on a family drive, shopping, dining in a restaurant—had to be mapped out in advance and executed with military precision. These tasks were rendered that much more difficult by the family’s desire to never put Fraser in a potentially embarrassing position.

“When you have a parent with a disability,” Michelle explained, “control and structure become critical habits, just to get through the day.”

Unfortunately, this need to remain in control at all times made Michelle less tolerant of potential suitors—and vice versa.

“He was very, very low-key,” Craig said of Barack’s behavior during that first meeting with the family. “I loved the way he talked about his family because it was the way we talked about our family. I was thinking, ‘Nice guy. Too bad he won’t last. ’” How long, Craig wondered, “is it going to be before this poor guy gets fired?”

This time, when she took her brother aside and asked him to put Barack to the test on the basketball court, Michelle made her feelings known. “I really like this guy,” she told him. “Now I want you to take him to play, to see what type of guy he is when he’s not around me.” It was, of course, one more rite of passage for anyone who wanted to be part of the Robinsons’ world—and a way for Craig to gauge Barack’s character.

But, for Craig, this vetting assignment was different from the others. First, he liked the fact that Barack was taller than most of the guys Michelle dated; he knew that his sister felt awkward dating men who were shorter than she was. Then there was the simple fact that Barack impressed Craig as a nice guy. “I was very nervous because I liked him a lot,” Robinson said. “This guy seems like a pretty good guy. I hope he makes it. I was rooting for him.” Of course, he added, “if he turns out to be a jerk, I’ve got to be the one to tell her.”

Barack thought he was a pretty decent basketball player, and didn’t hesitate to say so. But Michelle’s brother discovered when they played a five-on-five game that Barack wasn’t overconfident, either. “He wasn’t cocky or talking trash,” Craig said. “Barack was very team-oriented, very unselfish; he’s confident—not afraid to shoot the ball when he’s open—and he fit right in.”

However, what most impressed Craig about that first game was that, even though they were on the same team, Barack did not always pass him the ball. “He wasn’t trying to suck up to my sister through me,” Craig said. “I thought, ‘You know, I like that.’”

Right after the game, Craig called Michelle with his verdict. “Your boy is straight,” he told her, “and he can ball.” Still, he wondered if what he said really made any difference at all. “If the test had proven negative,” he said with a shrug, “who knows what would have happened.”

Marian and Fraser Robinson were equally delighted to hear that Barack had passed Craig’s basketball test. There were two facts about Barack, however, that might have dampened their initial enthusiasm. Michelle and Barack were careful not to tell her parents that he smoked—or that his mother was white. “Mr. and Mrs. Robinson were very solid, very proud, in some ways quite conservative black Americans,” said a longtime friend of Michelle’s. “Michelle and Barack didn’t want to spring his biracial, multicultural past on them until they came to know and love him as a black man, as one of them.” According to Marian, it would be months before she and her husband learned that Barack’s mother was Caucasian and that he had essentially been raised by his white grandparents.

Even Michelle had a hard time absorbing it all.

“Can you believe it?” she told her friends. “He’s got white grandparents from Kansas!”

She reasoned that they actually had more in common than they realized. “When there are people who are different from us,” she later mused, “we automatically think, well, that’s nothing like me and we have nothing in common. But we have more in common than not. His grandparents are very much midwestern, and in that respect, the midwestern value is: work hard, treat people with decency and respect, and do what you say you are going to do, your word is your bond. We’re both worried about doing our best,” she said of Barack and herself, “and doing the right thing.”

Notwithstanding his midwestern lineage, Barack’s family was, as he put it, “scattered to the four winds.” What he lacked—stability, roots, a sense of place and belonging—Michelle and her family had in abundance. Conversely, he was different, exotic, more open-minded and, in a sense, free-spirited than she had ever been. “Barack has opened my eyes to a lot of things about the world,” she said. “No doubt about it—he’s a fascinating guy.”

For the rest of the summer, Barack and Michelle were inseparable. They refrained from public displays of affection—“They were too cool and sophisticated to be hanging all over each other,” said a mutual friend—and tried to downplay their blossoming romance in the office. “It was cute,” said another lawyer in the intellectual property office. “Barack would be in her office and they’d be talking in these hushed tones. Then you’d knock, and they’d snap to, clearing their throats, pretending to be all business. It was silly, since everybody knew they were an item.”

Actually, Michelle had been far from reluctant to share the good news with her friends. Verna Williams, her pal from Harvard, had often commiserated with Michelle over the sorry state of their love lives. “Verna! Guess what?” Michelle now told Williams over the phone. “I’ve got this great guy in my life. His name is Barack.”

“I could tell this was something different,” Williams later said, “something special. We had known each other when we dated other guys. You go through this whole ‘he’s not ready for commitment’ thing…but Barack was none of these things. He was just a good, solid guy.”

He was also someone who was even more driven than Michelle to accomplish great things. “This brother is not interested in ever making a dime,” she thought to herself. “I would just have to love him for his values.”

Michelle knew Barack was joking when he teased her about some of the clients she handled, especially Barney and Coors beer. But at the same time, she also felt that her law degree was good for more than just making money.

Both Barrack and Michelle wanted to lift their fellow African Americans out of poverty, to give them better health care, housing, and educational opportunities. Barack had thought long and hard about how to acquire the kind of political power that could bring about those changes. He did not want to sound presumptuous or egotistical, he told her, but he had already mapped out his political future. He would share those plans with her, if she agreed not to discuss them with anyone else.

First, he planned to write a memoir. John F. Kennedy had launched his political career with Profiles in Courage, Barack pointed out. What he had to offer was the inspirational story of a biracial American whose journey of self-discovery bridged races, cultures, continents. Michelle was astonished to learn that for years Barack had been taking meticulous notes with the idea of just that kind of book in mind.

Barack had total confidence in his abilities as a writer—in fact, he had told several of his fellow students at Harvard that he might forgo legal practice altogether to pursue a career as a novelist. Finding a publisher would not be easy, but Barack had a plan for that, too.

“When I go back to Harvard,” he told Michelle, “I think I’m going to run for president of the Law Review.” Michelle was sufficiently impressed by the fact that Barack, who was only starting his second year at Harvard Law, already had a masthead position on the Review. That he might try to become its first African American president seemed as far-fetched as it was exciting.

Barack explained that the Review was in a state of turmoil, that it was sharply divided between liberals and conservatives, and that he was really the only editor who had taken pains not to offend anyone. By his calculations, the balance of power would rest in the hands of the conservatives and their more moderate allies. Barack had made an effort to get to know members of the Federalist Society, and discovered that he actually liked some of them—so much so that he was hanging out with them as much as he was with his liberal black friends. The conservatives, he explained to a skeptical Michelle, “are really very nice, and smart, maybe the smartest guys there. And some of them are just fun to be around.”

“Have you told anyone you want to run for president of the Law Review?” Michelle asked.

“No, I don’t want anyone to know that I’m even interested,” he said. “I don’t want to look too eager.” He stood his best chance to get elected, Barack said, if he appeared to be a last-minute compromise candidate. “So, please,” he said. “Don’t tell anybody right now—not at the office, not even your family. I don’t want it getting back to anyone at Harvard.”

In the middle of explaining his grand plan, Barack took a long drag on a cigarette—his twentieth that day. “You’re gonna have to stop that,” Michelle told him.

“Stop what?”

“The smoking—gotta quit,” she said. Growing up in a household where both parents smoked, as children Michelle and her brother used to pull the tobacco out of their parents’ cigarettes and douse it with Tabasco sauce so they would quit. The ploy didn’t work, of course, but Michelle was no more tolerant toward smokers than she had been as a little girl on the South Side. “It’s a nasty habit,” she told Barack, “and it’s going to kill you if you don’t stop. So I’d really like it if you quit smoking.”

Barack, who had no intention of quitting, rolled his eyes, snubbed out his cigarette, and continued: If he could manage to emerge as a peacemaker at the Law Review and get himself elected as its first black president, the publicity would be “enormous.” Although by no means a slam dunk, finding a publisher for his book under those circumstances would certainly be a lot easier.

Once his book had become a bestseller, Barack would return to Chicago, law degree in hand, to pick up where his idol Harold Washington had left off and run for mayor. And after that? Michelle asked, half in jest.

“I think maybe I’ll run for the Senate,” he answered without skipping a beat. “Then President—why not?”

Michelle threw back her head and let out a hearty laugh. “He’s pulling my leg now,” she thought to herself.

“Why are you laughing?” he asked, feigning a wounded look. He certainly appreciated how absurd it sounded. “Hey, come on, now. Don’t laugh. Stranger things have happened.”

That November, Barack returned to Chicago to spend Thanksgiving with Michelle. Since things were obviously getting serious between his sister and the Harvard Law hotshot, Craig, now working as an investment banker on Wall Street, thought it was time to turn up the heat. “You know,” Craig said, “I thought I’d do the obnoxious big brother thing and ask him about his future.”

“So, Barack,” Craig said, clearing his throat, “what do you want to do with your life?”

“Well,” Barack replied with an earnest smile, “I thought I might like to get into politics.”

“So you might run for alderman or something like that someday?” Craig asked.

“No,” Barack said, shaking his head. “I was really thinking more on a national scale. Maybe run for Congress or the Senate.”

Barack paused for a moment, obviously considering whether he should go on, and Craig was about to jump in when the brash young law student continued. “Who knows?” he said. “If I did a good job, I might even run for President someday.”

Craig’s eyes darted around the room, hoping that his Aunt Gracie, whose contempt for politicians was legendary, hadn’t heard Barack. “Don’t say that too loud,” Craig cautioned his sister’s boyfriend. “Someone might hear you and think you were nuts.”

In truth, Barack and Michelle had not even let on about his more immediate plans to seek a different presidency at Harvard. “He didn’t talk about himself,” Marian remembered. “He didn’t tell us that he was running for president of the Harvard Law Review. We never realized that he was as bright as he is.”

It was around this time that Michelle told her parents about Barack’s white mother and grandparents. Marian Robinson in particular was “very surprised”—and “a little bit worried” about his white relatives and how they would all get along if her only daughter wound up marrying him. At least he’s not white, she thought to herself. “I guess I worry about race mixing,” she explained, “because of the difficulties, not so much for prejudice or anything. It’s very hard.” (As it happened, Craig would marry a white woman.)

Now it was Michelle’s turn to meet Barack’s family, and to gain some insight into the people and places that had shaped the young man she had fallen in love with. Barack had always spent Christmas in Hawaii with Gramps, Toot, and—when they could make the journey from Indonesia—his mother and Maya.

Landing at Honolulu International Airport, Barack and Michelle stepped off the plane onto the tarmac and into the bright Hawaiian sunshine. When they had left Chicago nine hours earlier, the city was in the icy grip of a winter storm. “So you grew up here,” she said, nodding her head. “Poor guy.”

Hand in hand, they walked toward the terminal and the teenage greeters who would stand on tiptoe to wrap flower leis around both their necks. Once inside the terminal, Barack searched the crowd for familiar faces.

“Barry! Barry!” Gramps shouted. “Over here!” Barack looked over to see them all smiling and waving—his eighteen-year-old sister Maya, his grandmother, and his mother, clad in a muumuu-like Indonesian batik daster and—as was so often the case—crying with joy.

Michelle had been warned that Barry was the name Barack had grown up with, but she was surprised to hear it nonetheless. Gramps gave Michelle a welcoming hug, and Michelle bent down to embrace Ann, Maya, and Toot one by one. “Well, Barry,” Gramps said, nudging Barack, “she’s quite a looker.”

Toot rolled her eyes. She would be no less impressed by Michelle, but for very different reasons. From that first meeting, it was clear to Toot that Michelle was what she called a “no-nonsense” woman like herself—someone who would support Barry while at the same time grounding him in reality.

Michelle told Toot and the others about Barack’s plan to run for office, and shared her doubts about seeing such a “decent guy” in the rough-and-tumble world of Chicago politics.

“He’s a dreamer, like his mother,” Toot explained. “That’s why he needs someone like you around.” In the end, Toot would pay the young lawyer from Chicago what she considered to be the ultimate compliment. “Michelle,” Toot told her grandson, “is a very sensible girl.”

Ann Dunham Soetoro might indeed have been a dreamer, but Michelle connected with her as well. Barack’s mother and sister had just flown in from Indonesia, where she was helping to build a microfinance program that granted small loans to credit-poor entrepreneurs. It was Ann’s anthropological research into the ways people actually work that set the guidelines used by the Bank Rakyat Indonesia. Eventually, the microfinance program Ann helped set up would rank number one in the world, with more than thirty million members.

Now a heavyset woman with frizzy black hair, Ann was, in the words of her friend Mary Zurbuchen, “a big personality and a big presence.” As a grassroots activist, she had been thrilled when Barack became a community organizer in Chicago. As an academic who was still working on her PhD dissertation in anthropology, she was equally delighted when her son enrolled in Harvard Law School and when he made the Law Review. “All of us knew where Barack was going to school,” said another of Ann’s friends, Georgia McCauley. “All of us knew how brilliant he was.”

Ann, unlike her mother, saw no reason to doubt that her son would succeed if he decided to pursue a career in politics. Contrary to what Toot might have thought of her, Ann was not all dreamer. She spoke passionately about her desire to help the world’s poor, but her approach—as evidenced by her success with the microfinance program in Indonesia—was focused, pragmatic. “She wasn’t ideological,” Barack would later say. “I inherited that, I think, from her. She was suspicious of cant.”

While Toot urged her grandson to aim for a career in international law and ultimately a spot on the U.S. Supreme Court, Ann told her son to aim for the White House. If anyone had a shot at being the first black President, she said, it was him.

If Michelle had ever wondered where Barack got his confidence and his seemingly boundless ambition, here was the answer. Barack had been the focus of these people’s lives just as she and her brother had been the focus of their parents’ lives. “We’re all products of the Midwest, really,” she said. “There’s a lot of Kansas in his grandparents and his mother, and that means there’s a lot of Kansas in Barack.”

Perhaps. But Michelle would also learn that, in her words, “to understand Barack you must first understand Hawaii.” During that first eye-opening Christmas visit to the islands, the “very sensible” midwesterner immersed herself in the people, places, and things that had shaped the young Barack. He took her to the beaches where he liked to snorkle and bodysurf, to the parks and palis (cliffs) that were no less beautiful to the locals because they attracted thousands of tourists, to the campus of Punahou prep school, to the Baskin-Robbins store on South King Street where he had found it so hard to look cool scooping ice cream. There were also sunset luaus, torchlit hula demonstrations, romantic walks on the beach, and mai tais at the Royal Hawaiian Hotel on Waikiki.

This was a world as far away from the South Side of Chicago as it could possibly be, and yet what impressed Michelle most were the similarities in their backgrounds. Like Fraser and Marian Robinson, Toot and Gramps were hardworking people who had never gone to college but did not hesitate to make the sacrifices necessary to send their children—and in Barack’s case, their grandchild—to college. The Dunhams’ modest two-bedroom apartment in a white concrete building had a tiny balcony, but in most other respects it was comparable to the Robinsons’ cramped apartment on South Euclid.

Barack’s family also reveled in the kind of small, reassuringly familiar traditions shared by so many American families. “From the start,” Maya said, “Michelle was a ready convert to our lazy and fun Christmas rituals.” These included marathon games of Scrabble, watching TV Christmas specials, and the obligatory Christmas-morning package-opening frenzy followed by a brunch of pancakes, cheddar cheese eggs, papaya, and freshly squeezed orange juice.

For Michelle, the Christmas visit to Hawaii yielded other insights into Barack. During the long Thanksgiving weekend he had spent with the Robinsons in Chicago, he had handled an inebriated uncle of Michelle’s with compassion and respect. Now she could see from the way he interacted with his grandparents that he had a lifetime of practice dealing with drinkers. He had shared with Michelle the details of his father’s life—how disappointment over the course of his government career in Kenya had resulted in his becoming a hopeless, self-destructive alcoholic. Now she witnessed firsthand the drinking problem that also existed on the maternal side of Barack’s family. In addition to the smoking habit they shared with their grandson, Toot and Gramps were both two-fisted drinkers. “It’s one way of coping with life’s disappointments,” he explained. “They’ve done everything for me. I’m in no position to judge.”

In truth, Barack shared with Michelle the nagging concern that he might be genetically predisposed to substance abuse. It was one of the reasons why, after spending his high school and early college years drinking to excess, smoking pot, and occasionally snorting cocaine, he suddenly decided to quit—everything, that is, except smoking.

“You’re a runner,” Michelle pointed out. “You exercise regularly. Don’t you see how crazy it is to do all that and then light up a cigarette?”

“Hey,” Barack would answer with a wink, “you have to keep at least one vice. Besides, I’m not that strong.”

After they returned to the mainland—she to Sidley Austin in Chicago, he to resume his law studies at Harvard—Michelle and Barack were fully committed to their long-distance relationship. “We were both determined,” he recalled, “to do whatever it took to make it work.” As for the smoking: “I’m working on him,” she told one of her coworkers at Sidley Austin. “I’m working on him…”

For the next two years, they would burn up the phone lines between Cambridge and Chicago. Although he devoted as much as sixty hours a week to his studies and the Law Review, on the odd occasion Barack would hop a plane to Chicago for a quick weekend visit. “It’s not something I would have had the maturity to do before,” Barack later said. “Michelle centered me in a sense. She made it possible for me to really concentrate on what was important in life.”

Just one month after he returned from visiting Hawaii with Michelle, Barack launched his carefully thought-out plan to become the first black president of the Harvard Law Review. The mere fact that he was already serving as an editor of the highly regarded publication was impressive enough. The Law Review numbered among its esteemed alumni Supreme Court Justices Felix Frankfurter, Stephen Breyer, Antonin Scalia, and Ruth Bader Ginsburg, former Secretary of State Dean Acheson, Pulitzer Prize-winning poet Archibald MacLeish, Harvard University President Derek Bok, Yale University President Kingman Brewster, and Elliot Richardson, who at various times served as Secretary of Defense, Secretary of Commerce, Secretary of Health, Education, and Welfare, and Attorney General. The Law Review elections were quirkily arcane. In accordance with tradition, the process began Sunday morning with the nineteen candidates—including four African Americans—cooking meals for their fellow editors while they cast ballots. At first Barack was not among those running. Sticking to his plan not to appear eager for the job, he grudgingly agreed to run only after being urged by his friends to do so.

“He was clearly seen as a leader, but at the same time he never put himself out as a leader,” Cassandra Butts said of her friend and classmate. “He had a very quiet, very calm presence. And his leadership style was such that people were drawn to him and they embraced him as a leader.”

Brad Berenson agreed. “Barack was very laid-back, much less nakedly ambitious than some of the others on the Law Review,” he said. “He never struck me as one of the strivers. He didn’t come across to people as a political operator, which is testament to what a good political operator he really was.” At the same time, Berenson said, “I never thought that he was disingenuous or twofaced—saying one thing to me and another to somebody else. We were on opposite sides of the political spectrum, but there was no escaping that he was a very, very decent person—a classy guy.”

The balloting continued for the next sixteen hours, as one by one candidates were eliminated from the race. By midnight, no clear front-runner had emerged. “It’s late at night and we’re trying to figure out how to resolve this thing,” recalled Kenneth Mack, one of the other black candidates, who was out of the running early on. “Clearly Barack has a lot of support, but it’s not resolved yet.”

Then a conservative editor who disagreed with just about everything Barack stood for spoke up. “We are a divided institution,” he said, “and what we need is the best person to reach out to all constituencies and lead us forward. That person is Barack.” According to Mack, “Conservatives marveled at his use of language and metaphors that resonated with their core beliefs.”

When the votes were tallied and Barack had won, a tearful Mack leaped up and embraced the first black president of the Harvard Law Review. The first call Barack placed was to Michelle in Chicago.

“Say hello,” he told her the minute she answered the phone, “to the new president of the Harvard Law Review.”

“You’re kidding!” Michelle squealed. “Oh, baby, that’s wonderful.” When she told her parents, they were even more surprised. “But,” Marian Robinson said, “he never even told us he was running…”

Later that day at Sidley Austin, Michelle’s fellow attorneys dropped in to congratulate her and sing the praises of their recent summer associate. “She was glowing,” said one, “and obviously very proud of Barack. But she kept her cool about it, too. There’s a quiet dignity about Michelle—a sense of what’s appropriate behavior in the workplace, and she was still soft-pedaling their relationship to some extent.”

The African American editors on the Review were jubilant, and even the white conservatives were pleased with Barack as their new leader. “Conservatives were eager to have somebody who would treat them fairly,” Bradford Berenson said, “who would listen to what they had to say, who would not abuse the powers of the office to favor his ideological soul mates…. Somebody who would basically play it straight. Barack fit the bill better than anyone else.” Another conservative on the Review echoed that sentiment: “Whatever his politics we felt he would give us a fair shake.”

Barack was so evenhanded, in fact, that he risked alienating his liberal friends by appointing three members of the Federalist Society to top spots on the masthead, and only one African American. “Barack took ten times as much grief from those on the left on the Review as from those of us on the right,” Berenson said. “And the reason was, I think there was an expectation among those editors on the left that he would use his position to advance the cause.” Instead, Berenson added, his “foremost goal was to put out a first-rate publication, and he was not going to let politics or ideology get in the way of doing that.”

As he had predicted, Barack’s election as the first black president of the Harvard Law Review in February of 1990 made national news. He was profiled in the New York Times and the Los Angeles Times, and told the Associated Press, “From experience, I know that for every one of me there are a hundred, or thousand, black and minority students who are just as smart and just as talented and never get the opportunity.” In his first TV interview, he observed that his election “symbolizes some progress, at least within the small confines of the legal community. I think it’s real important to keep the focus on the broader world out there and see that for a lot of kids, the doors that have been opened to me aren’t open to them.”

Leaning against a pillar in jeans, black turtleneck, and Bass Weejuns, the collar of his windbreaker turned up to frame his boyish face, Barack cut a dashing figure on campus. He was, bar none, the best-known and most respected student at Harvard. Seasoned professors gossiped about which Supreme Court Justice he was likely to clerk for, and female classmates joked that Blair Underwood would probably be best suited to portray Barack in the movie version of his life.

For all his successes at Harvard, Barack did suffer one embarrassing defeat. When a panel of coeds charged with screening candidates for a pinup calendar of black men at Harvard rejected him, Barack was peeved. The reason he didn’t make the cut: “Barack,” one of the judges recalled matter-of-factly, “just wasn’t hot enough.”

Jane Dystel disagreed—at least in terms of the young man’s potential as an author. Spotting the glowing profile of Barack in the New York Times, the young literary agent asked him to write up a brief book proposal based on his life. Dystel then submitted the proposal to several editors and a deal was struck with Poseidon Press, a small imprint of Simon & Schuster. He pocketed the first half of the $150,000 advance—a hefty sum for a first-time author—and returned to his law studies with the intention of writing the book between classes.

Understandably, Michelle was thrilled that her boyfriend had landed a lucrative book deal, and shared the news with one of her dearest friends, her old Princeton roommate Suzanne Alele. The Nigerian-born daughter of two physicians, Alele was raised in Kingston, Jamaica, and moved to Washington, DC, as a teenager. At Princeton, the beautiful, bright Alele majored in biology, ran track, managed the lightweight football team, and, according to one classmate, “saved the rest of us from computer catastrophes.”

Alele earned her master’s at the University of Maryland and went to work for the Federal Reserve as a computer specialist, but she was always seen by those who knew her as laid-back, fun-loving, and not at all concerned about trying to please others. She traveled the world and made a point of urging her friends—especially Michelle—to lighten up.

In February, around the time Barack was elected president of the Harvard Law Review, Alele was diagnosed with advanced lymphoma. Four months later, Michelle got the call she had been dreading. Michelle rushed to the National Institutes of Health in Washington and was holding her friend’s hand when she passed away on June 23, 1990. Alele was just twenty-five.

“I was confronted for the first time in my life with the fact that nothing was really guaranteed,” Michelle recalled. Although Suzanne’s life was cut short, Michelle envied the way her friend had chosen to spend it. “One of the things I remembered about Suzanne is she always made decisions that would make her happy and create a level of fulfillment,” Michelle said. “She was less concerned with pleasing other people, and thank God.”

After Alele’s funeral, Michelle seriously began to question the path she had chosen. “If I died in four months,” she asked herself, “is this how I would have wanted to spend this time? Am I waking up every morning feeling excited about the work I’m doing? I need to figure out what I really love.”

She worried that she had “unthinkingly” taken the “automatic path” from Harvard to a corporate career. “I started thinking about the fact that I went to some of the best schools in the country and I have no idea what I want to do,” she said. “That kind of stuff got me worked up because I thought, ‘This isn’t education. You can make money and have a nice degree, but what are you learning about giving to the world, and finding your passion and letting that guide you?’”

Besides, she began to feel guilty about the material trappings of success. Known as something of a clotheshorse by her Sidley Austin colleagues, she was careful to dress down around less affluent relatives and South Shore neighbors. “Can I go to the family reunion in my Benz and be comfortable,” she wondered, “while my cousins are struggling to keep a roof over their heads?”

Despite these mounting doubts, Michelle continued to make her mark in the intellectual property department at Sidley Austin. It would take another, even more personal tragedy to force a change in the course of Michelle’s life.

In March of 1991, Fraser Robinson went through his time-consuming daily ritual of getting out of bed, dressing, and driving to his job at the water treatment plant. It had become all the more painful in the wake of a recent kidney operation, but he was determined to tough it out.

Fraser never made it to the plant. Unbeknownst to Michelle’s dad, he was suffering major complications from the kidney surgery. He died behind the wheel of his car at age fifty-five.

Michelle was devastated, but she was also able to draw inspiration from her father’s death. “He died on his way to work,” Michelle said. “He wasn’t feeling well, but he was going to get in that car and go. That’s how we grew up, living your life to be sure that you make the most of it. If what you’re doing doesn’t bring you joy every single day, what’s the point?”

Barack rushed to Michelle’s side, and she wept on his shoulder as her father’s casket was lowered into the ground. It was then, Barack later said, “that I promised Fraser Robinson I would take care of his girl.” (Strangely, although Barack would later write that this took place only six months after he met Michelle, he had actually known her for nearly two years by the time her father died.)

Graveside promise or no, Barack had been dancing around the subject of matrimony for well over a year. There was never any question about how he felt. “I’m hooked, I’m in love,” he told his Occidental roommate Vinai Thummalapally and anyone else who would listen. “She was highly intelligent, highly educated, and gorgeous,” Newton Minow said. “He was completely devoted to Michelle.” But Barack remained skittish when talk turned to marriage. The issue had become, Michelle conceded, “a bone of contention between us.”

“Come on,” she would say to him, only half kidding. “What’s your problem? Let’s get with the program here.”

“It’s just a piece of paper,” he said, rolling his eyes in exasperation. “I mean, what does it really mean?”

“Oh, brother…”

The debate continued as Barack approached graduation in June of 1991. When Chicago attorney Judson Miner called the Law Review offices to offer him a job, Barack’s assistant answered, “You can leave your name and take a number. You’re number six hundred and forty-seven.”

At first Barack passed on all the offers—including one from Michelle’s firm, Sidley Austin. Determined to do something in public service, he resolved to return to Illinois and take the bar exam. He passed on the first try. (Michelle had failed on her first attempt but passed on the second.)

That night, Barack took Michelle to celebrate at Gordon, the landmark Chicago restaurant famous for its contemporary American cuisine. Over artichoke fritter appetizers, they once again launched into their long-running debate over marriage.

The argument died down enough for them to enjoy their entree, but began to heat up again as dessert approached.

“Marriage, it doesn’t mean anything,” Barack insisted. “It’s really how you feel.”

“Yeah, right,” Michelle replied sarcastically.

“I mean, come on, Michelle,” he continued. “We know we love each other. What do we need to get married for?”

She shot him a withering glance. “Look, buddy,” she said, “I’m not one of these girls who’ll just hang out forever. That’s just not who I am.”

Barack just sat there smirking as Michelle smoldered. In the middle of her tirade, the waiter arrived with Gordon’s signature dessert—flourless chocolate cake. On the plate was a small velvet box. “So I’m sort of stopped in my tracks,” she later said of the moment. Michelle opened the box to reveal a one-carat diamond engagement ring.

She looked up at Barack in stunned silence. “That,” he said, “sort of shuts you up, doesn’t it?”

For once, Michelle was indeed speechless.

It is true my wife is smarter, better looking. She’s also a little meaner than I am.

—Barack

I cannot be crazy, because then I’m a crazy mother and I’m an angry wife.

—Michelle

Every high-flying kite needs somebody with their feet on the ground. And that’s Michelle.

—Avis LaVelle, friend

I trust her completely, but at the same time she’s also a mystery to me in some ways.

—Barack