Barack and Michelle

by Christopher Andersen

  “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 a
t 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.”