by Peter Slevin
It was how he felt about his mother. The love that he felt for his mother. His relationship to women. His work ethic. We worked together in a firm. He did his work, and he was good, and he was smart, and I liked that. And he was low-key. He wasn’t impressed with himself, and he was funny. And we joked a lot. And he loved his little sister. And he was a community organizer—I really respected that. Here we are in a big law firm, right? And everybody was pushing to make money. He was one of the smartest students at Harvard Law School, one of the smartest associates in our firm. He had the chance to clerk for the Supreme Court and I thought, “Well, you’re definitely going to do that, right?” Only a few people even have the chance to do that. He was, like, “Not really. I think I can do more work working with folks in churches.” I was like, whoa, that’s different. And he meant it. It wasn’t a line. He wasn’t trying to impress me. It was those kinds of values that made me think, “you don’t meet people like that often.” And when you couple that with talent, and he’s cute. You know, I always thought he would be useful.”
“WE GAVE IT a month, tops,” Craig Robinson said after Michelle introduced Barack to the family. Not because there was anything wrong with him. He was quick, engaging, handsome, and six-foot-two, which mattered to Michelle, who stood nearly six feet tall. “But we knew he was going to do something wrong, and then it was going to be too bad for him. She held everybody to the same standard as my father, which was very high.” Craig usually found no reason to dislike Michelle’s boyfriends, but “you sort of felt sorry for them because you knew it was just a matter of time before they were getting fired.” He called her “one tough girl” and made clear that she could be demanding. “She’s very accomplished, so she needs someone as accomplished as her, and she also needs someone who can stand up to her. So, we in the family, we were just hoping she could hang onto this guy, because it was readily apparent he could stand up to her.”
Marian, no pushover, was favorably impressed with Barack. “She found that he never talked about himself. He was always focused on who was around him,” Michelle said. “He was somebody that shared the values of our family. He believed in honesty, treated people with respect and kindness, no matter who they were.” Marian had white cousins and aunts who had married into the family, and one of her brothers married a white woman. But she was wary of Barack’s biracial heritage. “A little bit,” she said. “That didn’t concern me as much as had he been completely white. And I guess that I worry about races mixing because of the difficulty, not so much for prejudice or anything. It’s just very hard.”
Barack’s odds remained unclear. Fraser always said that you could tell a lot about a man by the way he played basketball. So one day Michelle asked Craig to include Barack in a pickup basketball game and report back. “When she asked me, I thought, ‘Oh, no, she’s going to make me be the bad guy,’ ” Craig said. But Barack was neither selfish with the ball nor shy about taking an open shot. He got extra points for not being overly deferential to his girlfriend’s big brother during that first session, where they played for hours on a public court near Lake Michigan. “Confident without being cocky, selfless without being wimpy, and willing to sublimate his ego for the team. I gave her a good report.”
After the summer in Chicago, Barack returned to Harvard for his second year of law school while Michelle continued her work at Sidley. He pursued a job in a different Chicago firm, but his plans to spend a leisurely summer in the Windy City were interrupted by his groundbreaking February 1990 election to the presidency of the Harvard Law Review. Never in its 104-year history had a black person led the esteemed journal, and his election drew media attention. He told The New York Times that he expected to spend two or three years at a law firm, then return to community work or enter Chicago politics. “The fact that I’ve been elected shows a lot of progress. It’s encouraging,” Barack, then twenty-eight, told the reporter. “But it’s important that stories like mine aren’t used to say that everything is okay for blacks. You have to remember that for every one of me, there are hundreds or thousands of black students with at least equal talent who don’t get a chance.”
FOUR MONTHS LATER, Suzanne Alele died.
Michelle’s effervescent Princeton friend, the one she admired for making decisions based on fulfillment, not expectations, lost a fight with cancer on June 23, 1990. She was only twenty-six, barely five years out of college. Her devastated friends had pulled together during her illness, supporting her in Washington, D.C., where she had become a computer specialist at the Federal Reserve after earning an MBA. Angela Kennedy, who helped organize a memorial fund, said of Michelle, “If Suzanne or I picked up the phone and needed or wanted anything, she was here in a heartbeat. Suzanne’s death was the first time I really got to see the depth of her love for her friends, how loyal she is.” Alele’s passing had a profound effect on Michelle, putting into focus frustrations she was feeling at Sidley and reminding her, against the backdrop of Barack’s more purposeful inclinations, that the choice was hers to make. If she herself died young, she wondered, was being a corporate lawyer “how I would want to be remembered in life. Was I waking up every morning feeling excited about work and the work I was doing? The answer to the question was no.”
She soon suffered an even deeper blow. Her father, after many years of living with multiple sclerosis, had been growing weaker. He started having breathing problems, but delayed telling anyone. One late winter night, Marian awakened to find him struggling for air. He passed out. She called an ambulance. Doctors at the University of Chicago found a host of problems, including a large growth in his airway and bleeding ulcers. Surgeons operated, but unable to get enough oxygen to his brain, he slipped into a coma. The family gathered and Barack flew in from Boston to be with Michelle. On March 6, 1991, at age fifty-five, still employed at the water plant, Fraser died. He was buried a few days later at Lincoln Cemetery on the South Side. In their grief, Michelle and Craig argued over the wording of a remembrance. “Would you just stop it?” Marian demanded. “Do you know why you’re arguing? You’re arguing because you miss your father.” The three of them burst into tears.
At the gravesite, Michelle rested her head on Barack’s shoulder. “As the casket was lowered,” Barack wrote later, “I promised Fraser Robinson that I would take care of his girl. I realized that in some unspoken, still tentative way, she and I were already becoming a family.”
MICHELLE KNEW THAT she needed to find more meaning in her professional life. Exactly how, she had no clear idea, but she knew she had to leave Sidley. Among other factors, she was increasingly uncomfortable with the money she was making. She asked herself, figuratively, “Can I go to the family reunion in my Benz and be comfortable, while my cousins are struggling to keep a roof over their heads?” More than the matter of dollars and cents, she saw that making a difference in the city where her cousins, neighbors, and friends lived was important to her. “Just like that, I’d lost two of the people I loved most in the world,” she told North Carolina A&T students in 2012. “So there I was, not much older than all of you, and I felt like my whole world was caving in. And I began to do a little bit of soul searching. I began to ask myself some hard questions. Questions like, ‘If I die tomorrow, what did I really do with my life? What kind of a mark would I leave? How would I be remembered?’ And none of my answers satisfied me.”
SEVEN
Assets and Deficits
The file that landed on Valerie Jarrett’s desk in Chicago City Hall was relayed by a colleague who had just interviewed a startlingly impressive young woman dissatisfied with her job at Sidley & Austin. The colleague was Susan Sher, a senior attorney for Mayor Richard M. Daley, elected two years earlier to his father’s old job. Sher quickly realized that she could not tempt Michelle Robinson with a position in the legal department. “I don’t want to be a lawyer,” Michelle told her. “I want to do public service, but I think lawyers look at things from too narrow a perspective.” Not wanting to let her get away, Sher
alerted Jarrett, who was on the lookout for talented recruits, especially African Americans. Jarrett was so impressed after meeting Michelle that she offered her a job in the mayor’s office on the spot. On the receiving end, Michelle was gratified and intrigued, but wary. She had an unusual request: Would Jarrett be willing to meet with her boyfriend, Barack Obama, and talk things over?
“He wanted to kick my tires,” Jarrett recalled. The three of them—Jarrett the oldest at thirty-four, Barack turning thirty, and Michelle twenty-seven—met for dinner at a restaurant in the West Loop. Jarrett, who would become a friend, mentor, and one of the most powerful players in the Obama White House, recalled that Barack did much of the talking. He spoke little about himself. “I remember him, in a very nonthreatening way, tickling out what I was all about. He did it not in an intimidating way, but in a way that made me want to talk.” He wanted to know where she was born. Iran, she told him. “He wanted to know how I’d gone from being born in Iran to Mayor Daley’s office.” That was a longer story.
Born in November 1956, Valerie Bowman had grown up in a highly educated family with ambitions to match. “Valerie, put yourself in the path of lightning,” her grandmother used to tell her. For an African American family in the middle of the twentieth century, the educational lineage was exceedingly rare. “Everybody in my mother’s generation went to college,” said Jarrett’s mother, Barbara Taylor Bowman, who was born in Chicago in 1928. “And the generation before that went to college. My grandfather, his brothers, all of their kids and, of course, us. We all went to college.” One great-grandmother attended seminary at Oberlin before the Civil War. One grandfather was the first black graduate of the Massachusetts Institute of Technology and a deputy to Booker T. Washington at the Tuskegee Institute. Her father was the first black chairman of the Chicago Housing Authority, and she herself graduated from Sarah Lawrence College in 1950. Two weeks later, she married James Bowman, a dentist’s son born in 1923 in Washington, D.C. He and his siblings all attended college, with Jim earning two degrees from Howard University. Yet, for all of their drive and success, the Bowmans experienced prejudice firsthand. Barbara recalled that, as one of about thirty black students at an integrated South Side elementary school, no white child would hold her hand as they walked into the building after recess.
In the Bowman family, the messages about racial identity were as clear as the ones about the importance of education. “My grandmother always kept telling us that they cannot make you uncomfortable; only you can make yourself uncomfortable,” Barbara recalled. She said her grandmother could have passed as white, “but she took pride in being black and I also took pride in being black.… My great-grandmother, she took her stick and she would say, ‘You know, you are a Negro. You should always be proud of that.’ ”
Valerie spent much of the first six years of her life outside the United States because her father was fed up with racial inequality in Chicago, where he had embarked on a medical career. With two internships behind him, he became the first African American resident at St. Luke’s Hospital. Showing up for work in 1947, he was told that black employees were expected to use the back entrance. He defied the dictum and walked through the front door. The next day, he arrived to find other black employees waiting out front to walk through the door with him. He spent three years as chairman of pathology at Provident Hospital and three more as an army pathologist in Colorado, but when Provident executives invited him to return in 1955, they offered him less than half the salary white doctors were making. That was the breaking point. He said, “My wife and I decided that we were not going back to anything that smacked of segregation.”
“We said, ‘Let’s look for someplace to go, and we may or may not ever come back,’ ” Jim Bowman recalled. He accepted a job as pathologist at Nemazee Hospital in Shiraz, an ancient crossroads in southern Iran, not far from the Persian Gulf. When they finally did head back to Chicago, following a stint in London, it was largely for Valerie’s sake. “Because she didn’t know who she was, and we wanted her to know who she was. In those days, we were called Negroes, but when we would say to our daughter, ‘You are Negro,’ she would say, ‘Well, what does that mean?’ We tried to explain it to her, but she said, ‘Everywhere I look, I see lots of people with dark skin, but they are not called Negroes. Why aren’t they called Negroes?’ ”
As educators who prospered in Chicago after their return, the Bowmans passed their wisdom along to their students, as well as to their daughter. Barbara Bowman helped create the Erikson Institute, a graduate program in early childhood education. Born seven years before Michelle’s father, she told students that her generation took a certain satisfaction in confronting racism. “Because it was so hard, we thought about ourselves as being made stronger by the struggle.” Jim Bowman told his black medical students at the University of Chicago that feeling sorry for themselves would get them nowhere. “In order to compete, you have to be better than the rest,” he said. “You can’t be just as good. You have to be better. And once you realize that and stop feeling sorry for yourself, then and only then will you succeed.”
Like Michelle, Valerie became a lawyer at a blue-chip firm before reporting to City Hall, but she arrived by a different path. She attended the private University of Chicago Laboratory Schools and graduated from prep school in Massachusetts before attending Stanford and the University of Michigan. Well into adulthood, by her own account, she was “painfully shy.” In the Chicago legal community in the 1980s, she felt much the same lack of fulfillment that Michelle would experience a few years later. She worked in plush surroundings on the seventy-ninth floor of the Sears Tower, then the world’s tallest building. “I had a great office overlooking the sailboats on Lake Michigan, but I was miserable. A friend advised me to think about city government. I was hesitant. I was on my path and, miserable as I might be, it was my path. But Harold Washington had become the first black mayor of Chicago, and I made the move.”
GIVEN HER OWN INITIAL DOUBTS, Jarrett was not surprised by the questions posed by Michelle and Barack over dinner. Michelle had long been suspicious of politics and the practitioners of its more unsavory arts. She knew from growing up as the daughter of a Democratic precinct captain the many ways that City Hall could seem remote, at best, from the lives of average citizens. Abner J. Mikva, an independent Democrat first elected to Congress in 1968, put it more bluntly. Until Washington’s 1983 election, he said, “there was no reason to be happy with Chicago politics if you were black.” Washington’s tenure was messy and short. He died at his desk in November 1987 and was followed briefly in office by Eugene Sawyer, appointed by the city council. Now occupying the fifth-floor office was the unproven scion of Richard J. Daley, who had ruled City Hall for twenty-one years without paying more attention than absolutely necessary to his African American constituents.
Barack was a student of Chicago politics, and Jarrett recalled that he had “a certain trepidation” about Michelle working in the highly politicized office of the mayor, where she would not have a network to nourish and protect her. “She was a political novice,” Jarrett said. “Was Mayor Daley going to be committed to the kinds of ideas Michelle cared about? Was he going to do only what he wanted to do or was he open to ideas? I think I convinced her that, together, we could do some unique things for the city.” As they moved on to other subjects, Jarrett sensed that during the rest of the evening the younger couple was silently assessing whether they should trust her judgment. The experience told Jarrett that “before they were married, they were best friends. They had each other’s back.”
There was, of course, the matter of money. Although Michelle had concluded that finances would not be the deciding factor in her professional choices, the quest for fulfillment was going to cost her. Leaving Sidley for City Hall meant cutting her salary roughly in half, to $60,000 a year, when she still had significant student loan debt. “It just seemed incredible at the time that she’d leave,” Angela Kennedy, her Princeton friend, said. The elde
r Robinsons had always counseled Michelle and Craig that if they took a job for the money alone, “ultimately you’re not going to make enough money to put up with the mess.” But even her father, aware before his death of her restlessness, had been concerned about a move. He asked Michelle, “Don’t you want to pay your student loans?”
From the time she was young, Michelle had watched her pennies even as she made calculated indulgences. One was a Coach handbag she bought with her babysitting money. Marian gasped when Michelle informed her of the cost, telling her daughter that she would never spend such a crazy amount on a purse. Right, Michelle answered, but you’ll go through ten handbags in the time I have this one. In fact, without the debt from her years at Princeton and Harvard, Michelle said she might have gone straight from Sidley to a nonprofit or a grassroots organization, a move she would make less than two years after reporting to City Hall. “City government, in addition to being interesting, was less of a setback to me, and I could manage that,” she said. “My stint in city government was amazing. I was very young, but got a lot of responsibility.”
AS MICHELLE WAS SETTLING into a job in the Daley administration, Barack was choosing an unconventional path of his own, one substantially less lucrative than the ones open to him as president of the Harvard Law Review. He spurned coveted judicial clerkships and six-figure law firm positions even though he could have had his pick. Instead, he cobbled together an eclectic array of jobs and pursuits, to the frustration of his mother and grandmother, who had both known financial hardship. His mother, Ann, in fact, had once been on food stamps. They believed Barack should fill his own pockets before he tried to save the world. Madelyn Dunham, his grandmother, “despaired” about his early choices, said her brother, Charles Payne. “We all thought Barack was going to make a lot of money. Because he was so good, so well spoken and, even with his dark skin, so white. Barack could fit in anywhere and he did. And with a Harvard law degree.” He recalled his sister lamenting that she did not know what Barack was doing with his life. “Sometimes she was supporting six or seven people and her great hope was that Barack would make an awful lot of money and there wouldn’t be these money problems.”