When Michelle reached ninth grade and was admitted to Whitney Young High School, west of downtown, she spent hours a day riding city buses to and from school. Craig won admission to Princeton in 1979, and his father insisted the family would make the necessary financial sacrifices for Craig to go there rather than accept a full scholarship from some less prestigious institution. Michelle grew up thinking she was smarter than her brother, and although Craig had a difficult freshman year, Michelle resolved that if he could attend Princeton, so could she. Her mother knew that test taking was not her forte, and a high school counselor discouraged her interest in Princeton, but Michelle applied anyway and was admitted. The difference between the South Shore world from which Michelle came and the privileged backgrounds of Princeton’s overwhelmingly white and often wealthy student body was profoundly stark.
“The first time when I set foot in Princeton, when I first got in, I thought ‘There’s no way I can compete with these kids … I got in but I’m not supposed to be here,’ ” Michelle recalled. “I remember being shocked by college students who drove BMWs. I didn’t even know parents who drove BMWs.” In addition, black undergraduates realized that Princeton’s racial climate, even in 1981, left much to be desired. Angela Kennedy, one of Michelle’s closest friends, with whom she spent one summer working as counselors at a girls’ camp in New York’s Catskill Mountains, recalled that “It was a very sexist, segregated place. Things reminded you every single second that you’re black, you’re black, you’re black.”
Michelle thrived in Princeton’s classrooms, and by the beginning of her senior year, she was applying to Harvard Law School. Yet in a reprise of high school, her faculty adviser on her senior thesis downplayed her chances. After initially being wait-listed, in late spring of 1985 she was accepted to Harvard.
Michelle’s college thesis, “Princeton-Educated Blacks and the Black Community,” was a powerfully self-revealing document. “My experiences at Princeton have made me far more aware of my ‘Blackness’ than ever before,” Michelle wrote. “I have found that at Princeton … I sometimes feel like a visitor on campus; as if I really don’t belong.” Growing up in South Shore, neither of her parents had been especially outspoken about race, but Marian Robinson’s father Purnell “Southside” Shields, who died in 1983, “was a very angry man,” Michelle’s mother explained. “I had a father who could be very angry about race,” and Marian had given Craig the middle name Malcolm after the early 1960s’ angriest racial firebrand. Marian was likewise wary of interracial relationships. “I worry about races mixing because of the difficulty,” she confessed years later. “It’s just very hard.”
But Princeton made Michelle understand that “I’m as black as it gets.” In her thesis, she observed that “with Whites at Princeton, it often seems as if, to them, I will always be Black first and a student second.” Looking ahead, that left her fearful. “The path I have chosen to follow by attending Princeton will likely lead to my further integration and/or assimilation in a White cultural and social structure that will only allow me to remain on the periphery of society; never becoming a full participant.” She confessed that “my goals after Princeton are not as clear as before” and she rued how “the University does not often meet the social and academic needs of its Black population.” In addition, “unfortunately there are very few adequate support groups which provide some form of guidance and counsel for Black students having difficulty making the transition from their home environments to Princeton’s environment,” as both Michelle and her brother had. She now knew that Princeton was “infamous for being racially the most conservative of the Ivy League Universities.” And her exposure to some fellow students had taught her something else, something prescient indeed: “a Black individual may be unable to understand or appreciate the Black culture because that individual was not raised in that culture, yet still be able to identify as being a Black person.”
Harvard Law School did not offer a much different experience. Czerny Brasuell, Michelle’s one black female Princeton mentor, recounted Michelle telling her by telephone from Cambridge that “If I could do this over, I’m not sure that I would.” A female classmate told Michelle’s biographer Liza Mundy that Harvard “was not a friendly, happy atmosphere.” But once again Michelle persevered. After her 1L year, she returned to Chicago as a summer associate at the law firm of Chadwell & Kayser, working for female partner Jan Anne Dubin and staying with her parents in the home that her great-aunt had deeded to the Robinsons several years earlier, prior to her own death.
Back at Harvard for her 2L year, Michelle volunteered significant time at the Legal Aid Bureau, located one floor—and many status rungs—below the Harvard Law Review on Gannett House’s ground level. After her 2L year, she was a summer associate at Sidley & Austin’s Chicago office. When Sidley offered her a position once she graduated, Michelle readily accepted. At Harvard, “the plan was you go into a corporate firm. So that’s what I did. And there I was. All of a sudden, I was on this path.”
At graduation, her parents paid for a teasingly congratulatory message in the 1988 Harvard Law School Yearbook: “We knew you would do this fifteen years ago when we could never make you shut up.” That summer, Sidley paid for the bar review class she took alongside a friend of her brother’s, Alan King, but only on May 12, 1989—after taking the Illinois exam a second time—did Michelle become a member of the Illinois Bar. Working in Sidley’s intellectual property group, Michelle yearned for meaningful assignments. Given her Harvard loans, her Sidley salary was attractive, but she had not really intended to be a corporate lawyer. “I hadn’t really thought about how I got there,” she recalled. “It was just sort of what you did.”
Craig Robinson recalled the late July evening when Michelle introduced Barack to her family. “My sister brought him over to my mom and dad’s house. We all met him, had dinner. They left to go to the movie, and my mom and dad and I were talking: ‘Oh, what a nice guy. This is going to be great. Wonder how long he will last?’ ” Craig thought Barack was “smart, easygoing, good sense of humor,” but given Michelle’s proclivity for discarding boyfriends, Craig remembered thinking, “Too bad he won’t be around for long.” Marian Robinson was also impressed because “He didn’t talk about himself,” but instead drew out the Robinsons about their own lives and interests. “I didn’t know his mother was white for a long time,” Marian recalled. “It didn’t come up.”
Barack’s taste in movies ran to the realistic, and opening that weekend was Leola, the story of a bright seventeen-year-old African American Chicago girl whose desire to attend college was endangered when she became pregnant. Filmmaker Ruby Oliver was a fifty-year-old former day care operator, and seven weeks after they saw it, Barack talked about the ninety-five-minute movie—later retitled Love Your Mama—while addressing the real-life challenges confronted by black youths. Michelle and Barack continued to see each other almost every day, and when they went out, Michelle usually paid. “He had no money; he was really broke,” she remembered, plus “his wardrobe was kind of cruddy.” Barack’s Occidental roommate Paul Carpenter was visiting Chicago that August,