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The Making of a First Lady

She’s confident and levelheaded, and she carries the nurturing legacy of a close-knit South Shore family, an experience she wanted to re-create in her own home. After years of resenting her husband’s political career, Michelle Obama found her voice and flashed her style on the road to the White House

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Michelle, his belle: The couple commune after she introduces him in Iowa in August 2007, months before the primaries
Michelle, his belle: The couple commune after she introduces him in Iowa in August 2007, months before the primaries.  more photos »



Michelle’s likes and dislikes, as drawn from interviews and published sources

Dressed up or down, Michelle stands tall as a natural fashion star

She has her priorities, but motherhood will be her only mission

From October 2004: Native Chicagoan Michelle Obama married a skinny kid with a funny name. She’s keeping it real.

Although Michelle was not finished with questions of race, at Harvard she found a way to contribute by devoting herself to the student-run Harvard Legal Aid Bureau, spending many hours in the Greek revival Gannett House. The building also held the offices of the Harvard Law Review, where a few years later, Barack Obama would launch his trajectory to the White House by becoming the first African American president of the prestigious journal.

Dave Jones, now a member of the California state assembly, worked in legal aid with Michelle, a job he recalls as intense and time consuming, as much as 20 hours a week. Although the students were supervised by a practicing attorney, the welfare of the clients rested on the students’ competence. Michelle handled landlord and tenant cases, among others. Many Harvard Law students start out professing a desire to practice public-interest law when they graduate, but only a small percent do, at least in part because the big money and the most sophisticated cases are at the large corporate law firms. Charles Ogletree, Michelle’s and later Barack’s adviser, encouraged students to do well and do good by working at a firm and taking on pro bono cases.

After her second year at Harvard Law, in 1987, Michelle became a summer associate at Sidley & Austin, one of the biggest and most prestigious corporate law firms in Chicago. A job offer followed, and after graduation, Michelle headed home. She lived with her parents to save money, but she worked in Chicago’s Loop, a distance much greater in status than in miles.

“The idea of making more money than both your parents combined ever made is one you don’t walk away from,” Michelle recently told Geraldine Brooks of More magazine, explaining why she took the job. Also, Sidley had a reputation for supporting lawyers who wanted to do pro bono work. Ogletree points out that Michelle could keep a promise to her parents: “that she would do good even if she did well.”   

She joined the firm’s marketing group, which dealt with intellectual property, trademark, and copyright law. “We were the fun group,” says a woman who worked at the firm at the time. “We had good parties, interesting work; we were all very collegial. There was not this blind ambition.” Michelle worked on issues related to Barney the Dinosaur and also on the Coors beer account. Still, vetting scripts for television commercials was a long way from standing up for an impoverished single mother involved in a dispute with her landlord.

Most of her colleagues say that had Michelle stayed at the firm, she would have become a partner. But she was not happy at Sidley, says her friend Hilary Beard. Michelle didn’t feel “like she was making a difference, like the work mattered in a larger sense.”

In the summer of 1989, Michelle was assigned to mentor Barack Obama, a 28-year-old who had just completed his first year at Harvard Law. If Michelle, with her two Ivy League degrees and her African American roots, was a big deal at Sidley, Barack was much bigger. He was working on the Harvard Law Review and was soon to be elected its president. Andrew Goldstein, a colleague from those years, recalls hearing in Sidley’s corridors that Barack could be the first African American president of the United States.

Barack was late on his first day, which didn’t impress his mentor.  When they had lunch, Michelle later told the Obama biographer David Mendell, “he had this bad sport jacket and a cigarette dangling from his mouth.” 

“Man, she is hot!” Barack later told Dan Shomon. “So I am going to work my magic on her.” Initially, Michelle acted less than interested. “He would try to charm her, flirt with her, and she would act very professional,” says Kelly Jo MacArthur, then an associate at the firm. “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.” 

“I’m his mentor,” Michelle told MacArthur. “It would not be appropriate for me to go out with him.” Michelle also pronounced it “tacky” for two of the handful of African Americans in the firm to date each other.

When Barack finally won her over, Shomon recalls, “he was very proud.” On their first conventional date that summer, they visited the Art Institute of Chicago, walked up Michigan Avenue, and saw Spike Lee’s Do the Right Thing, followed by ice cream at Baskin-Robbins and their first kiss. Michelle’s one big complaint about Barack, her Sidley colleagues say, was that he smoked. She also didn’t feel that she knew him well enough to make a commitment. She asked her brother for help. Craig, now the head coach of Oregon State, took his basketball seriously and thought that a man’s character could be deciphered by his behavior on the court. “He’s confident but not cocky,” Craig would later recall reporting to his sister. “He’ll take the shot if he’s open, he’s a team player who improves the people around him, and he won’t back down from any challenge.”

When Michelle announced that she was leaving Sidley and taking a pay cut to go to City Hall as an assistant to the new mayor, Richard M. Daley, Kelly Jo Mac- Arthur was not surprised. “You just knew that you weren’t going to contain her in that law firm. And people knew Barack wasn’t coming back, either. It was obvious that his destiny was one that would affect the rest of our destinies.”


In July 1991, Michelle sent her résumé to the mayor’s office, and it landed in the hands of Valerie Jarrett, then Daley’s deputy chief of staff. Jarrett, who herself had left a Loop law firm to work in City Hall, interviewed Michelle and was so impressed, she told a reporter for Vogue, that she immediately offered her a job as one of the three assistants to the mayor. The next day, Michelle called to say that before deciding, she wanted Jarrett to meet her fiancé, Barack Obama. “Barack just wanted to make sure that this was substantive, and it was something that would be good for Michelle,” says Cindy Moelis, who worked with Michelle at City Hall. Others say that Barack needed assurance that Jarrett would protect Michelle—that she would handle work that she (and he) would be proud of and that she could survive the internecine politics of the mayor’s office. After the three had dinner at a seafood restaurant in the Loop, they were all in agreement that City Hall was a good move for Michelle. 

Avis LaVelle, then the mayor’s press secretary, was also impressed by the way Michelle carried herself: “with dignity—a lot of tall women slump or act like they don’t want to fill their shoes or stand up and be counted. She filled her own shoes; she filled her own space.”

Michelle and Moelis worked to develop programs addressing infant mortality, afterschool activities, and immunizations via mobile health units, among other projects. Michelle did not need her legal training, but her personality was well suited to the work, says MacArthur, because Michelle is a careful listener. Within six months, Jarrett was named the city’s commissioner of planning and development, and she enticed her young protégée to join her. Michelle became the assistant commissioner of planning and Jarrett’s troubleshooter, making sure that projects moved forward. MacArthur recalls Michelle saying earlier of Jarrett, “There’s some incredible woman working at the mayor’s office, and I’m going to learn a lot from this woman.” 


When Cindy Moelis and her husband had a Bulls basketball party at their house in 1992, she and Yvonne Davila, then Daley’s speechwriter and assistant press secretary, met Barack. “I knew he was different,” says Davila, “and I can’t explain why.”

Michelle wanted to get married; Barack argued that marriage was a meaningless formality. One night he took her to dinner at Gordon, an elegant restaurant on North Clark Street, and expounded on the subject. Then Michelle’s dessert plate arrived with a box containing an engagement ring. “That kind of shuts you up, doesn’t it?” Barack said.

Santita Jackson sang at their wedding on October 18, 1992, and the Reverend Jeremiah Wright of Trinity United Church of Christ officiated. The reception was at the South Shore Cultural Center, formerly a country club that excluded blacks and Jews. It was “one of the happier weddings that I had been to,” says MacArthur, “because people understood that putting the two of them together was like putting hydrogen and oxygen together to create this unbelievable life force. Everybody knew it. We understood that together they were going to be so much more than they would have been individually.”


Photograph: M. Spencer Green/AP Photo


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