by Peter Slevin
Not that she intended to date him. That would be going too far. Besides, as she told her mother while feeling luckless at love, she had sworn off romance that summer, declaring, “I’m going to focus on me.” Michelle had dated an array of young men all the way back to high school, when she went to the Whitney Young prom with David Upchurch. She had posed for a photo that night in a silken evening gown with a V neck and a thigh-high slit, a pattern she chose and modified, insisting on the slit. Her mother did the sewing. At Harvard, one beau was law student Stanley Stocker-Edwards, the adopted son of singer Patti LaBelle. Nothing lasted. She said later, “My family swore I would never find a man that would put up with me.”
WHEN BARACK ARRIVED at Sidley, it was the second time he had lit out for Chicago. His background was, indeed, exotic, and he had made many ports of call in his search for purpose and identity. His parents met in the autumn of 1960 at the University of Hawaii, where his mother, Stanley Ann Dunham, born in Kansas, had just enrolled as a seventeen-year-old freshman. Barack Hussein Obama Sr. was six years older, married, with one child in Kenya and another on the way. Within a few weeks of the start of classes, Ann was pregnant. She left school after the first semester and the couple quietly married in a county courthouse in Wailuku. At the time, laws prohibiting interracial marriage were on the books in twenty-one states. Barack Hussein Obama II was born in Honolulu on August 4, 1961, at Kapiolani Maternity and Gynecological Hospital. In Arabic, Barack means “blessed by God,” while Hussein means “good” or “handsome.” Within months, his parents had split up and young Barack would see his father only once more, when he was ten years old. For four years in his childhood, he lived with his mother and her Indonesian husband, Lolo Soetero, in Jakarta. His younger sister was born there. Dissatisfied with the Indonesian elementary schools, his mother often awakened him at 4 a.m. and tutored him, sometimes for as long as three hours. When Barack complained, her refrain was always the same: “This is no picnic for me either, buster.”
By the time Barack was ten, Ann had decided he should be schooled in the United States. While she stayed in Indonesia to continue her research, he moved to Honolulu, where he lived in a small apartment with his middle-class midwestern grandparents, Stanley and Madelyn Dunham. They, too, had married young, eloping before her eighteenth birthday, on the night of her high school prom. During World War II, Stanley served in the Third Armored Division while Madelyn, known to the family as Toot, worked in a B-29 bomber factory. After Ann was born, their peripatetic existence took them to California, Oklahoma, Texas, Washington State, and, eventually, Hawaii, where Stanley found work in a furniture store and Madelyn worked as a bank secretary. Stanley was a bluff man, a dreamer and a drinker considerably less industrious than his wife. Basically a good man but “too old and too troubled to provide me with much direction,” Barack said. They “stayed married through thick and thin,” said Charles Payne, Madelyn’s younger brother, who retired in 1995 as assistant director of the University of Chicago library. “They were both strong-willed persons and Stanley believed that he was the master of the household in all things. Madelyn made the money that paid the rent. In fact, Madelyn was the one, year after year, who got up and went to work and earned some money. Stanley could never do that consistently.” In Payne’s view, it was the women in Barack’s life—his mother and his grandmother—who set the terms and the tone: “They were both very strong and tended toward the domineering.” Musing about their impact on the future president, he said, “Well, he ended up pretty strong himself.” Barack, in fact, once told Michelle, “You know, I got my toughness from Toot.”
When Barack—then known as Barry—returned to Honolulu from Jakarta, his family enrolled him in the elite, private Punahou Academy. In Dreams from My Father: A Story of Race and Inheritance, the memoir he published at age thirty-three, Barack described a directionless adolescence. “Indifferent” was how he recalled himself. He played basketball, studied only as much as necessary, and smoked so much pot that he and his friends called themselves the Choom Gang. “I rebelled,” he once said, “angry in the way that many young men in general, and young black men in particular, are angry, thinking that responsibility and hard work were old-fashioned conventions that didn’t apply to me.” By senior year, he had doubts about going to college. His mother asked him one day whether he was being a little casual about his future. He mused that he might stay in Hawaii, take a few classes, maybe get a part-time job. “She cut me off before I could finish,” he said. “I could get into any school in the country, she said, if I just put in the effort. ‘Remember what that’s like? Effort? Damn it, Bar, you can’t just sit around like some good-time Charlie, waiting for luck to see you through.’ ”
Barack roused himself. He made his way to Occidental College in Southern California. “A few miles from Pasadena,” he wrote, “tree-lined and Spanish-tiled. The students were friendly, the teachers encouraging.” In Hawaii, he had spent time with Frank Marshall Davis, a dashiki-wearing black nationalist poet and former Chicago newspaperman. Before Barack set out for the mainland, Davis warned him that the price of admission to college was “leaving your race at the door, leaving your people behind,” a bluntly phrased version of the dilemma that absorbed Michelle at Princeton and Harvard. Davis said the experience would give the young man “an advanced degree in compromise.” Indeed, when he arrived at Occidental—a first-rate school, but no one’s idea of the Ivy League—Barack found that most of the concerns of black students “seemed indistinguishable from those of the white kids around us. Surviving classes. Finding a well-paying gig after graduation. Trying to get laid. I had stumbled upon one of the well-kept secrets about black people: that most of us weren’t interested in revolt; that most of us were tired of thinking about race all the time; that if we preferred to keep to ourselves, it was mainly because that was the easiest way to stop thinking about it.”
His own internal conversation about race and identity, however, was deep and unremitting, a product of his biracial heritage and an upbringing unconventional in white and black terms alike. Hawaii, Indonesia, the absent Kenyan father. Even the Dunhams. “We always just thought of Barack as just being Barack. Not black or white. Another family member who was just like us, only not quite,” Charles Payne said. Barack said his grandmother more than once “uttered racial or ethnic stereotypes that made me cringe” and “once confessed her fear of black men who passed her by on the street.” He came to envy, perhaps idealize, traits he saw in black students from working-class urban neighborhoods, young people who came from Watts or Compton or, as it happened, Chicago. In Dreams from My Father, which relied on composites of characters from his life, he assigned the role of alter ego to a black woman from the South Side.
He called her Regina, Latin for “queen,” and identified her as an Occidental student, “a big, dark woman who wore stockings and dresses that looked homemade.” She was studious—she spent a lot of time in the library—and she helped organize black student events. She had an evenness about her, an honesty and authenticity that “made me feel like I didn’t have to lie.” Her father was absent, her mother was struggling to pay the bills in a Chicago apartment cold in winter and so hot in summer that people sometimes slept outdoors to keep cool. Regina, he wrote, spent many “evenings in the kitchen with uncles and cousins and grandparents, the stew of voices bubbling up in laughter. Her voice evoked a vision of black life in all its possibility, a vision that filled me with longing—a longing for place, and a fixed and definite history.”
When Barack told Regina that he envied her memories, she started to laugh. Confused, he asked why. “Oh Barack,” she said, “isn’t life something? And here I was all this time wishing I’d grown up in Hawaii.” Barack published Dreams six years after meeting Michelle. They were married by then and he had been steeped in her South Side life, even living with her for a time in the house on Euclid. In his second book, The Audacity of Hope, he would use similar language to describe the real-life Michelle and h
er family.
ONE THING THAT STRUCK Michelle that first summer in Chicago was the way Barack seemed to move so easily among many different worlds. She also saw a sense of purpose not tied to wealth or corporate success. The Sidley brass took a keen interest, hoping to lure him back to the firm for good. He went to one cloth-napkin lunch after another. A member of Sidley’s executive committee took him to a board meeting, while Newt Minow urged him to enhance his credentials by becoming a federal law clerk. The estimable attorneys saw what the Harvard professors saw. “Barack Obama, One L!” wrote constitutional scholar Laurence Tribe on his desk calendar on March 29, 1989, commemorating an encounter with the first-year student. “I was impressed by his maturity and his sense of purpose, his fluency. Barack wasn’t just a wonk of some kind. He cared about how people ticked.”
The man was undeniably smart and smooth and it did not take long before Michelle found him intriguing “in every way you can imagine. He was funny. He was self-deprecating. He didn’t take himself too seriously. He could laugh at himself. I mean, we clicked right away.” But she hesitated to date him. She thought it might be inappropriate, given the responsibility conferred by Sidley in assigning her to be his mentor. And quite possibly tacky, should two of the firm’s relatively few black professionals find themselves in a romantic relationship. “When I first met him, I fell in deep like,” Michelle explained. “Right off the bat, I said, ‘This guy can be my friend. We’re going to be friends.’ And it was later on, when he pressed for a little more than friendship, that’s what I pushed away from. Because I thought, you know, we’re working together.” She even tried to set him up with her friends. Over the course of several weeks, with no small amount of verbal jousting, Barack wore her down, challenging her professed reasons one by one. Along the way, she learned something more about him: “He is very persistent.”
“So,” she recalled, “I said, okay, we’ll go on this one date, but we won’t call it a date. I’ll spend the day with you.” The day arrived sunny and warm. Michelle was living in South Shore. Barack had an apartment in nearby Hyde Park, not far from the University of Chicago. They started at the Art Institute, where Michelle’s father had studied forty years earlier. They ate lunch in the museum’s leafy stone courtyard to the sounds of a jazz combo and then took a long walk to see the new Spike Lee movie, Do the Right Thing. Afterward, they had a drink on the ninety-sixth floor of the John Hancock building, as the city and the lake stretched into the distance. “I was sold,” she said.
Barack saw many things to like in Michelle, including her beauty: “I thought she looked real good.” He admired her “strong sense of herself and who she is and where she comes from.” But he also spotted a trait that was not part of her public persona. “In her eyes,” he said later, when Michelle was in her early thirties, “you can see a trace of vulnerability, or at least I do, that most people don’t know, because when she’s walking through the world, she is this tall, beautiful, confident woman and extremely capable. But there is a part of her that is vulnerable and young and sometimes frightened and I think seeing both of those things is what attracted me to her.” Michelle’s vulnerability flowed from a sense that life was “terrifyingly random,” Barack wrote in The Audacity of Hope. He said he spotted “the slightest hint of uncertainty, as if, deep inside, she knew how fragile things really were, and that if she ever let go, even for a moment, all her plans might quickly unravel.”
One afternoon after a Sidley picnic, they went for ice cream in Hyde Park. As they sat on a curb outside Baskin-Robbins, they shot the breeze. Barack told Michelle how he had once scooped ice cream at a Baskin-Robbins in Hawaii. He said he would like to meet her family. He asked if he could kiss her.
“WE SPENT THE REST of the summer together,” trading stories and getting to know one another, Barack wrote in The Audacity of Hope. To impress him, she borrowed her mother’s seafood gumbo recipe, persuading him that she was a more versatile cook than she actually was. She was saving money by living with her parents in the Euclid house, which Fraser and Marian had bought from Aunt Robbie for $10 in April 1980. Later, when he was president and Michelle told acquaintances the story of their courtship and what attracted her to him, Barack chirped merrily, “Black man with a job! Black man with a job!”
Barack said it was not until he met Michelle’s family that he “began to understand her.” In the Robinson household in those early days, he saw what he described as joy. He said visiting the bungalow on Euclid was like “dropping in on the set of Leave It to Beaver.” Beyond Fraser, Marian, and Craig, who graduated from business school and became a Chicago investment banker, “there were uncles and aunts and cousins everywhere, stopping by to sit around the kitchen table and eat until they burst and tell wild stories and listen to Grandpa’s old jazz collection and laugh deep into the night.” It was language that echoed his descriptions in Dreams of Regina’s extended family and its effect on him. The contrast could hardly have been greater between his untethered life and the world of the Robinson and Shields clans, so numerous and so firmly anchored in Chicago. He felt embraced and it surprised him. “For someone like me, who had barely known his father, who had spent much of his life traveling from place to place, his bloodlines scattered to the four winds, the home that Fraser and Marian Robinson had built for themselves and their children stirred a longing for stability and a sense of place that I had not realized was there.”
MICHELLE WAS STRUCK by Barack’s community organizing work and the way he still talked about making a difference. He seemed to care little about the legal profession’s traditional ladders of success, and even less about money. He reported to Sidley in serviceable clothes—“cruddy” was Michelle’s word. His only pair of shoes was a half size too small and he drove a car so rusty that she could sit in the passenger seat and see the road through a hole in the door. “He loved that car. It would shake ferociously when it would start up. I thought, ‘This brother is not interested in ever making a dime.’ ” He had graduated from Columbia University in 1983 after becoming more serious about his studies and transferring from Occidental. He worked in New York City for Business International, a publishing operation that produced newsletters and research reports, and he considered working in Harold Washington’s administration. But when he wrote to the mayor’s office, he received no reply. If he had cared more about money, he would not have answered a newspaper ad and spent three years before law school in Chicago, working for the Developing Communities Project, where the starting pay was $12,000 a year, plus $1,000 to buy a rattletrap.
The project descended from the work of Saul Alinsky, a Chicago organizer best known for his cagey opposition to Daley and his authorship of a book that was part manual, part manifesto, called Rules for Radicals. Still in New York, Barack aced the interview, took the job, and set off for Chicago. His mission was to mobilize the largely apolitical residents of Altgeld Gardens and Roseland to demand a fairer shake from the government—more attention, better services, a stronger chance of pulling their neighborhoods together. Fellow organizer Mike Kruglik said Barack possessed “a basic belief in the humanity of the folks on the South Side and their right to a decent life” and was “emotionally committed to African Americans getting ahead.” Political critics who disapproved of Alinsky’s philosophy, real or imagined, later accused Barack of being an acolyte. In fact, athough his supervisor, Gregory Galluzzo, liked to describe himself as Alinsky’s St. Paul, Barack borrowed some bits and discarded others, crafting his own strategies as he went.
Looking back, Barack said the work gave him “the best education I ever had.” In those deathly poor neighborhoods where he worked with African American ministers, he found persistent racial inequality that defied the progress that had erased the worst of segregation. He interviewed black Chicagoans, heirs to the Great Migration, whose family history mirrored Michelle’s, with grandparents barred from labor unions and parents kept out of good schools and jobs because of their skin color. Some had succeeded, whil
e many others had stalled out, perhaps permanently. It was the paradox of the talented tenth all over again. He was troubled by “this dual sense, of individual advancement and collective decline.” The need was clear enough, but what to do? Feeling his way, Barack saw limits to what he could accomplish as a local organizer and set out for Harvard, thinking maybe he could do more as a lawyer or a politician.
Back in Chicago that summer after his first year of law school, he invited Michelle to join him as he met South Side residents he had known as an organizer. It was there, in a church basement, watching Barack talk with African Americans living from paycheck to paycheck, that she fell in love. His theme that day was the world as it is and the world as it should be. “He said that all too often we accept the distance between the two and we settle for the world as it is, even when it doesn’t reflect our values and aspirations,” Michelle said in a campaign speech. “But he reminded us that we also know what the world should look like. He said we know what fairness and justice and opportunity look like, and he urged us to believe in ourselves, to find the strength within ourselves to strive for the world as it should be.” Barack’s talk that day, in a year that would see peaceful revolutions across Central Europe and an unarmed man defying a column of tanks in China’s Tiananmen Square, stayed with Michelle long after they were married. It would take two years and two jarring emotional blows before she quit Sidley, but what she saw in Barack strengthened her view that there was more to life than billable hours.
In Barack, Michelle felt she had found a man whose values meshed with her own, someone with whom she could share a purposeful life. “There are a lot of women who have the boxes—did he go to the right school, what is his income? It was none of that,” Michelle told British high school girls in 2011.