In the fall of 1991, Barack was still weighing the many options that were available to him. As the first African American president of the Harvard Law Review, he was all but guaranteed a shot at clerking for a Supreme Court justice. One powerful judge on the U.S. Court of Appeals for the DC Circuit, Abner Mikva, had taken the initiative and approached Barack with an offer to clerk for him in Washington—which Barack promptly turned down. When Barack told Mikva he intended to return to Chicago to enter politics, Mikva thought, “Boy, this guy has got more chutzpah than Dick Tracy. Has he got something to learn. You don’t just come to Chicago and plant your flag.”
Back in Chicago, the brash newcomer sought the advice of the many powerful and politically savvy friends he had made during his years as a community organizer—people like the Reverend Jeremiah Wright, the Reverend Jesse Jackson, Mikva, and Minow. What they all told him was that, since his election as Chicago’s mayor in 1989, Richard J. Daley’s son Richard M. Daley held the key to political power in Illinois.
At Barack’s urging, in July of 1991 Michelle sent her résumé to Mayor Daley with a cover letter asking to join his staff. Across the letter someone had scrawled:
This woman is no longer interested in being at her law firm.
She wants to be in government and give back.
Daley aide Susan Sher walked the letter and résumé over to Daley’s Deputy Chief of Staff, Valerie Jarrett. “She is made for you,” Sher told Jarrett. “This is exactly what you did.”
A member of Chicago’s African American elite—her mother was a noted psychologist and her father an internationally recognized geneticist and pathologist—Jarrett was actually born in Iran, where her father was running a hospital for children in the mid-1950s. As a child, she spoke Persian and French as well as English. After a year in London, the Jarretts returned to the Windy City, where Valerie’s father became a professor at the University of Chicago. Yet he continued to do genetic research across the world. As a result, she recalled, “we would spend summers traipsing across Africa. One summer we went from Ghana to Nigeria to Ethiopia to Uganda to Egypt and then back to Iran.”
After graduating from Stanford and then Michigan Law School, Jarrett went to work for a big Chicago law firm with offices on the seventy-ninth floor of the Sears Tower. “I would sit in that office and just cry,” Jarrett said. “Cry my heart out. ‘I’ve got to get out of here. This is not what makes me tick.’”
Where the deaths of Michelle’s father and her best friend led her to reevaluate her life, Jarrett’s self-evaluation was triggered by the birth of her daughter. “I wanted to do something,” Jarrett said, “that she would be really proud of me for.”
No sooner had she been handed Michelle’s résumé than Jarrett picked up the phone and called her. “I was just unbelievably bowled over by how impressive she was,” Jarrett recalled of that first conversation. Drawing parallels between her own dissatisfaction with working for a big law firm and Michelle’s, Jarrett saw in Michelle a kindred spirit. “This is why Michelle and I connected,” Jarrett said. “She felt the same way.”
Later, when they met face-to-face in the office of Mayor Daley’s chief of staff, Michelle impressed her even more. “An introductory session turned into an hour and a half. Michelle was so mature beyond her years, so thoughtful and perceptive and confident and committed and extremely open.”
Michelle was so mature that, before Jarrett realized it, she had essentially turned the interview process on its head. “She really prodded me about what the job would be like, because she had lots of choices,” Jarrett said. “I offered it to her on the spot, which was totally inappropriate because I should have talked to the mayor first. But I just knew that she was really special.”
Before she could accept the sixty-thousand-dollar-a-year job as an assistant to Mayor Daley, Michelle had to talk it over with her future husband. Together, she and Barack still owed more than three hundred thousand dollars in student loans. “How are we ever going to pay back these loans if I take a fifty percent cut in salary?” she asked. But Barack was confident that, by combining their incomes, sharing rent, and cutting back on living expenses, they would have enough to survive and at least chip away at their debt. Besides, he still had nearly all the money—more than sixty thousand dollars—he had been advanced by Simon & Schuster.
Michelle’s reticence had less to do with finance and more to do with plunging into the cutthroat world of Chicago city politics. “She had some serious reservations,” Jarrett recalled, “about whether she was going to leave the practice of law and leap into the mayor’s office in a political environment.”
Remarkably, Michelle then asked Jarrett if she wouldn’t mind joining her and Barack for dinner. “My fiancé wants to know,” Michelle explained, “who is going to be looking out for me and making sure that I thrive.” So, she continued, “how about we have dinner and go out and talk this through?”
“Michelle told me Barack wanted to meet me,” Jarrett said, “so he could figure out if he was comfortable with her going to work for Mayor Daley…. I can’t think of many people you hire who say, “I’d like you to meet my fiancé.” But I would have done just about anything to get Michelle.”
So, just as he would engineer Michelle’s departure from Sidley Austin, Barack took charge of Michelle’s entry into public service. They met at a downtown restaurant for dinner, and from the very outset Jarrett felt as if she would have to prove herself worthy of their trust. “I knew,” she said, “that unless this conversation ended well, probably the two of them were going to go home and say, ‘Well, not so much. Maybe that’s not the right move.’”
Jarrett, Michelle, and Barack slid into a booth—Barack directly opposite Jarrett. Then, Jarrett recalled, “he interrogated me in the nicest possible way.” While Michelle listened quietly, Barack quizzed Jarrett on the details of the job, what was to be expected of his future wife, how much power the position actually entailed, how much autonomy she would have, what her access to Mayor Daley would be, and—most important—what her political exposure would be. Barack wanted Jarrett to promise that, whenever infighting arose, she would “have Michelle’s back.”
Anyone else might have thought Barack’s involvement to this degree was highly presumptuous, not to mention an unsettling indicator of the sway he held over his future bride. Not Jarrett. She even seemed to enjoy being grilled by Barack, although she hesitated to even call it that.
“Barack never grills,” Jarrett said. “That’s part of what is so effective about him: he puts you completely at ease, and the next thing you know he’s asking more and more probing questions and gets you to open up and reflect a little bit.”
In the same way that she instantly identified with Michelle, Jarrett quickly discovered that she and Barack had much in common. “That night we talked about his childhood compared to my childhood,” she said, “and we both realized we had rather…unusual childhoods.”
When they were finished and Jarrett paid the tab, she leaned back in her seat and asked, “Well, did I pass the test?”
Barack smiled broadly. “Yes,” he said, much to Jarrett’s visible relief. “Yes, you did.”
Michelle moved into a small office down the hall from Jarrett’s and quickly gained a can-do reputation. “You didn’t go to her with a 311 problem,” Jarrett said. “You went to her with a 911 problem, and she fixed it right away. She’s that good.” Avis LaVelle, Mayor Daley’s press officer at the time, concurred: “Michelle was formidable—successful, smart, well liked, someone you paid attention to.”
Barack was never far away. “She talked a lot about her fiancé, and he visited the office a few times,” said another operative at city hall. “Suddenly she’s giving him instant access to the powers that be in the Daley organization, and all that that entails.”
Of all the contacts Michelle made, none would prove more valuable than Valerie Jarrett. A fixture on Chicago’s social scene, Jarrett moved effortlessly among Hyde Park’s intellect
ual elite, the rank-and-file Daley Democrats who really ran the city and environs, and the “lakefront liberals” (aka “limousine liberals,” “Learjet liberals,” and “latte liberals”) who occupied the glittering high-rises that line the shore of Lake Michigan. “If you were raising money for a homeless shelter, a concert hall, or a campaign for the U.S. Senate,” said a city hall colleague, “there was nobody better to know than Valerie.”
Just as valuable were the contacts Michelle forged with leaders of the African American business community. Foremost among these was John W. Rogers Jr., son of Republican powerhouse (and Ambassador-at-Large in the George H. W. Bush administration) Jewel Lafontant and Circuit Court Judge John Rogers Sr. In addition to founding Ariel Capital Management, he established the first two mutual funds managed by African Americans.
Through Michelle, Barack also met Martin Nesbitt, one of Craig Robinson’s college basketball buddies. With the financial backing of billionaire Penny Pritzker, who would later play a huge role in Barack’s political career, Nesbitt had founded a hugely profitable airport parking company known simply as the Parking Spot and would go on to head the Chicago Housing Authority.
Michelle had been in the Mayor’s office for only a few months when Jarrett was picked to head Chicago’s Department of Planning and Development. Jarrett brought Michelle with her as the city’s new economic development coordinator, a job that put her in close personal contact with the top tier of Chicago’s business community.
In her new job, Michelle not only promoted projects that would stimulate economic growth, but she put her legal skills to use negotiating contracts between the city and a wide range of business entities. Real estate developers, bankers, retailers, venture capitalists, and union bosses—essentially anyone who sought to start or expand a business within the Chicago city limits—would find themselves sitting across the table from Michelle.
“She was very personable but also very tough,” said one developer who dealt with Michelle during this period. “She always came in totally prepared, very commanding, and she knew her stuff. She paid a lot of attention to the stuff on the ground—what the impact would be on neighborhoods, people’s lives.”
Michelle reveled in her newfound authority, and proved just as take-charge when it came to running her office. Where Jarrett and other managers were understandably reluctant to discipline or discharge a staffer, Michelle did not hesitate to lower the boom. “I don’t mind telling people what they need to know about their job performance,” she said. “If it’s great, I’ll let them know. If it’s lousy, I’ll let them know that, too.”
For the most part, Michelle was, in the words of one city hall colleague, “always kind” to the people who worked under her. A favorite ploy was to tell an employee he or she had “outgrown” the job and needed to “move on”—usually to graduate school for additional training. “You were halfway down the hall and feeling pretty good about yourself,” recalled one staff member who was given one of these talks by Michelle, “before you realized you’d just been fired.”
Barack, who had had to deny promotions to disgruntled minority editors at the Harvard Law Review, was proud of what staffers routinely referred to as Michelle’s “tough but fair” approach at work. He was also impressed that she was able to accomplish what she needed to as a manager without leaving a trail of bad feelings in her wake. “So you just told him he had to move on?” he asked. “And he was just perfectly fine with that?”
With Michelle entrenched at city hall and making valuable contacts among the heavy hitters doing business with the city, Barack was free to continue laying the groundwork for a grassroots power base outside Chicago’s political machine.
Toward that end, he became a founding board member of Public Allies, a nationwide nonprofit organization aimed at steering young people away from the private sector and toward public service. Public Allies signed up eighteen- to thirty-year-olds to work for a year with nonprofit or government agencies providing services to the poor. In exchange, these “allies” were paid a stipend of up to eighteen hundred dollars a month plus health and child care.
Central to the purpose of Public Allies was creating a small army of like-minded young activists on the ground in cities like Chicago, New York, Los Angeles, and Washington. By way of grooming this new generation of “social entrepreneurs,” Public Allies conducted a series of seminars and retreats during which Barack and other organizers exhorted recruits to shun “the money culture.”
Although it was ostensibly nonpartisan, Public Allies had a clear agenda from the outset. The young people who joined were urged to agitate for “social change” through picketing, sit-ins, and boycotts. “Our alumni,” the organization would soon boast, “are more than twice as likely…to engage in protest activities.”
There was a heavy psychological component to the Public Allies regimen as well. Every week there were “diversity workshops” during which recruits were required to take part in various exercises designed to break down racial, ethnic, religious, and gender barriers. “You’re not going to be able to work together to get anything done,” Barack told a group of new Public Allies recruits, “if you’re fighting among yourselves. You’ve got to think and act as one if you want to effect real change.”
Both happily consumed with work, neither Michelle nor Barack saw any reason to set a wedding date. They were content with the status quo: he maintaining his own apartment in Hyde Park, she staying with her recently widowed mother at her childhood home on South Euclid Avenue.
In early 1992, Toot phoned from Hawaii with the news that Gramps had taken a turn for the worse in his long battle with prostate cancer. When he died that February, Barack traveled to Hawaii to comfort Toot and attend the funeral. Gramps had served in France under “Old Blood and Guts” George Patton during World War II, and as a veteran was entitled to be buried at Punchbowl National Cemetery. His family and a few old friends from his bridge-playing days looked on while a bugler played taps and the American flag that had draped Gramps’s coffin was carefully folded into a triangle and presented to Toot.
Later, as the family gathered at Toot’s apartment, Barack’s mother announced that she had finally finished the PhD dissertation she had been working on for nearly twenty years. She dedicated the opus—a one-thousand-page analysis of peasant blacksmithing in Indonesia, to her mother, her doctoral adviser, and “to Barack and Maya, who seldom complained when their mother was in the field.”
Barack returned to Chicago with a renewed sense of urgency. He told Michelle that, having spent so much time at school, he now wanted to “get on with life”—and that meant starting to get serious about making wedding plans.
Since she had been prodding him to do precisely that ever since he proposed to her eight months earlier, Michelle’s reaction was predictable. “You’re kidding, right?” she asked sarcastically. With the help of Michelle’s mother, the couple began planning for their October nuptials. Barack’s main caveat: “Just as long as it’s not around election time, that’s all.”
He wanted to be unencumbered during the 1992 presidential elections—and with good reason. With Public Allies poised to deploy thousands of young activists into homeless shelters, AIDS clinics, abortion clinics, and welfare offices across the country, Barack turned his attention to politics on his home turf.
Arkansas Governor Bill Clinton had hoped to wrest Illinois, a swing state that had gone to George H. W. Bush in the previous election, from the Republicans. Moreover, Cook County Registrar of Deeds Carol Moseley Braun was seeking to become the nation’s first African American female Senator. Even though the black vote was going to be crucial to the outcome of these contests, the fact remained that the Daley machine had never pushed registration in the city’s predominantly black wards.
Barack was determined not to let this opportunity slip through the Democrats’ fingers. Starting in April of 1992, he would spend seven months running the local office of Project Vote, a DC-based national voter registrati
on drive aimed squarely at low-income inner-city residents.
Devising a comprehensive media campaign based on the slogan “It’s a Power Thing,” Barack enlisted the aid of local churches, college students, and some of the Alinsky-inspired activists he had worked with during his community-organizer days to knock on the doors of thousands of homes on the South Side. In addition to helping train some seven hundred deputy registrars, Barack often rolled up his sleeves and hit the streets himself, making his face familiar to thousands of potential voters in the process.
While Project Vote was ostensibly nonpartisan, there was little doubt in anyone’s mind that the overwhelming majority of these first-time voters—by most estimates more than 95 percent—would register as Democrats. “It was not very subtle,” said a former Democratic alderman. “There were these big black-and-yellow posters with “Power!” in bold letters and a big X. The message was definitely one of harnessing black power at the ballot box—it sure as hell wasn’t aimed at getting whites to sign up.” Confirmed one volunteer: “We targeted areas where there were blacks and Latinos. Period.”
Project Vote proved to be something of a baptism by fire for Barack, who promptly found himself having to cope with various turf wars between elected officials and grassroots activists. He was determined not to let any of these petty rivalries get in his way. “He was typical,” said ward chairman Ivory Mitchell, “of what most aspiring politicians are: self-centered—that ‘I can do anything and I’m willing to do it overnight.’”
Not quite. But in the span of just six months, Barack’s army of volunteers registered more than 150,000 black voters. This was enough, it would turn out, to secure the state for Clinton—the first time Illinois had gone Democratic since Lyndon Johnson was elected in 1964—and a Senate seat for Moseley Braun.
The payoff for Barack came in the form of valuable new connections made with grassroots leaders, officeholders, and liberal donors—all connections he actively sought out. Abner Mikva remembered a typical exchange:
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