Obama arrived late for his first day at Sidley’s offices at 10 South Dearborn. It was a rainy June morning. Some days earlier, he had spoken by phone with Michelle Robinson, whom Geraldine Alexis and senior associate Linzey Jones had assigned as Barack’s summer adviser because of their mutual Harvard ties. Obama remembered that “she was very corporate and very proper on the phone, trying to explain to me how the summer program at Sidley and Austin was going to go.”
Barack was shown to her office that first day, and Michelle recalled in 2004 that “he was actually cute and a lot more articulate and impressive than I expected. My first job was to take him to lunch, and we ended up talking for what seemed like hours.” She had expected a biracial, Hawaiian-raised Harvard Law student to be “nerdy, strange, off-putting” and even “weird,” but instead Barack was “confident, at ease with himself … easy to talk to and had a good sense of humor,” she recounted. “I was pleasantly surprised by who he turned out to be.” She did however recall that “he had this bad sport jacket and a cigarette dangling from his mouth.”
Rob Fisher was also working at Sidley’s Chicago office for the summer, and he remembered Barack coming by his office soon after they arrived. “He came in one day and said, ‘My mentor is really hot.’ ” As Michelle’s friend and Sidley colleague Kelly Jo MacArthur recalled, Barack wasted little time in making his interest clear. “He would try to charm her, flirt with her, and she would act very professional. He was undeniably charming and interesting and attractive,” but Michelle rebuffed Barack’s repeated suggestions that they do something together. “She was being so professional, so serious,” MacArthur remembered, and she also knew that Michelle was someone with “conservative morals.”
When Barack pressed, Michelle was characteristically direct and told him that as his adviser, it would look bad if they began going out together. Instead, she tried to set him up with several of her girlfriends, just as she did with Tom Reed, another African American 1L summer associate and Chicago native who had been one year behind her as an undergraduate at Princeton. But Barack persisted. Finally, toward the end of June, Michelle reluctantly agreed. “OK, we will go on this one date, but we won’t call it a date. I will spend the day with you.”
On Friday, June 30, they left Sidley’s offices at about noon and walked the few blocks to the Art Institute of Chicago on South Michigan Avenue to have lunch. “He was talking Picasso,” Michelle remembered. “He impressed me with his knowledge of art.” Then they “walked up Michigan Avenue. It was a really beautiful summer day, and we talked, and we talked.”
Barack had a plan. Opening that evening was a movie that already had been the subject of three different articles in the Chicago Tribune: young African American director Spike Lee’s Do the Right Thing. It was an ingenious idea, but Michelle’s concern about appearances turned all too real when they saw Sidley’s Newton Minow and his wife Jo at the theater. “I think they were a little embarrassed” at being seen together, Minow recalled. After the film, Michelle remembered, “we had a deep conversation about that” and then ended the day “having drinks at the top of the John Hancock Building,” which “gives you a beautiful view of the city.”
“I liked him a lot. He was cute, and he was funny, and he was charming,” Michelle remembered thinking, but after their encounter with the Minows she was all the more determined not to become a subject of office gossip. But when Barack invited her to accompany him to a training he had agreed to do for DCP at one of the Roseland churches, she agreed to go along.
The small group was “mostly single parent mothers,” but she recalled that Barack’s “eloquent” presentation “about the world as it is and the world as it should be” was one she would never forget. “To see him transform himself from the guy who was a summer associate in a law firm with a suit and then to come into this church basement with folks who were like me, who grew up like me,” Michelle recounted, “and to be able to take off that suit and tie and become a whole ’nother person … someone who can make that transition and do it comfortably and feel comfortable in his own skin and to touch people’s hearts in the way that he did, because people connected with his message,” was remarkably impressive. “I knew then and there there’s obviously something different about this guy,” something “special,” and “it touched me … he made me think in ways that I hadn’t before,” Michelle explained. “What I saw in him on that day was authenticity and truth and principle. That’s who I fell in love with” in that church, and “that’s why I fell in love with him.”
Every summer Linzey Jones hosted a picnic at his home in south suburban Park Forest for all of Sidley’s minority attorneys and summer associates. Events like this were standard fare because summer programs at big law firms were aimed at enticing the students into eventually accepting a permanent job offer. Evie Shockley, an African American 1L from the University of Michigan Law School who shared an office with Barack for part of that summer, recalled attending a Cubs game, seeing Phantom of the Opera, and other theater outings. “It was easy to feel like you weren’t working,” she explained.
That weekend day, Linzey Jones remembered Barack and Michelle being “very friendly with each other,” but Barack joined in when many of the men went to a nearby junior high school to play basketball for an hour. Michelle still lived with her parents in their South Shore home, a few miles below Hyde Park, and when she drove Barack back to his apartment, he offered to buy her an ice cream cone at the Baskin-Robbins on the north side of East 53rd Street. Michelle accepted, and ordered chocolate. Sitting outside, Barack told her about working at Baskin-Robbins in Honolulu “and how difficult it was to look cool when you had the apron and the little brown cap on.” Then, in a direct reprise of a question he had posed three summers earlier, also in Hyde Park, he asked Michelle “if I could kiss her. It tasted of chocolate.”
“We spent the rest of the summer together,” Barack later wrote, but a mid-July phone call informed him that a letter inviting him to join the Law Review was in the mail. That good news meant he had to be back in Cambridge by August 16 to work on the Review’s first issue. He took several days to ponder his choice. “We had a conversation about whether or not he was going to do Law Review,” fellow summer associate Tom Reed recalled. “ ‘I’m not sure if I’m going to do it,’ ” Tom remembered Barack saying. “He was clearly on the fence,” and “there was a moment where he was considering whether that was appropriate for his path.” But finally he told HLR as well as Sidley that he was accepting the offer.
Barack and Michelle kept a very low profile at the law firm, and neither Tom Reed nor Evie Shockley had any idea they were dating. Michelle told only Kelly Jo MacArthur. “When she met Barack, things happened pretty quickly,” Kelly Jo remembered. Michelle recalled years later during a joint interview her memories of “the apartment you were in when we first started dating,” the sublet near Baskin-Robbins. “That was a dump.” But bumping into people they knew seemed inevitable. Jean Rudd of the Woods Fund recounted, “I have a very vivid memory of having lunch on Dearborn Street at an outdoor café there, and Barack and this tall, beautiful woman walk by. And he stopped and introduced us and said that ‘This is my boss.’ … We chatted a little while,” and when they left “I remember saying, ‘What a couple.’ ”17
One late July evening, Michelle invited Barack home for dinner to meet her parents and brother. Craig Robinson, at twenty-seven years old, was two years older than his sister and also had attended Princeton University. As a senior he was Ivy League basketball’s 1983 Player of the Year, and after graduation he had played professional basketball in Europe for several years before returning home. Craig met Janis Hardiman, a 1982 Barnard College graduate, soon after she moved to Chicago in 1983, and by 1987 they were engaged and living together in Hyde Park while Craig took classes toward an M.B.A. degree at the University of Chicago. Janis and Craig married in August 1988, soon after Michelle’s graduation from Harvard Law School.