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As a senior partner at Sidley Austin, Newton Minow used…

As a senior partner at Sidley Austin, Newton Minow used his considerable clout to promote Michelle’s career at the firm. He had grown equally fond of her boyfriend and wasted no time trying to entice him into the Sidley Austin fold as well.

Yet Minow was not really surprised that Barack was now standing across from him, listing all the reasons why he was going to have to turn down Minow’s generous offer of a job in favor of a life in politics. After all, Minow was no stranger to public service himself; he had been Chairman of the Federal Communications Commission in the Kennedy administration and active in the Democratic Party all his life.

“You don’t have to explain anything to me,” Minow told Barack after listening to him outline his interest in grassroots activism followed by a run for state, and then national, office. “You can accomplish a great deal of good in the public sector. I’ll do whatever I can to help.”

Barack cleared his throat. “You may not feel that way,” he said tentatively, “after you hear the rest of what I’ve got to say. I suggest,” he added, “you sit down.”

Minow, nonplussed, eased into the chair behind his desk. “What the hell is this?” he thought. Barack sat down opposite him.

“I’m taking Michelle with me.”

Minow bounded to his feet and pointed a finger in Barack’s face. “Why, you no-good son of a—”

“Hold it,” Barack said, raising his hand. “Now just hold it! You don’t understand—”

“Oh, I understand, all right,” Minow shouted. “I understand perfectly—”

“We’re getting married,” Barack said, cutting Minow short.

“Oh,” Minow said, “that’s different.” He reached across his desk, pumped Barack’s hand, and congratulated him enthusiastically. He also reiterated his offer to help in any way he could to advance Barack’s—and Michelle’s—new career in the public sector.

It was only after Barack left that it occurred to Minow that Barack, who did not even work for the firm, had essentially resigned for Michelle. During a legal career that spanned a half century, Minow had never heard of a man acting so explicitly on behalf of his wife, much less his fiancée. This resignation by proxy seemed especially odd given the fact that Michelle had never exactly been hesitant to speak up for herself at the firm.

Although Michelle had not voiced her dissatisfaction to her superiors at Sidley Austin, the sudden deaths of her friend Suzanne Alele and her father had left her more confused than ever about the future. She was well aware that many of her fellow lawyers were happy with the work they were doing. But, she asked, “were they bounding out of bed to get to work in the morning? No.”

“You just knew that they weren’t going to contain her in that law firm,” Michelle’s Sidley Austin colleague Kelly Jo MacArthur recalled. Michelle wanted to make a real impact on public policy, but in this she was already deferring to Barack. “She was talking about him constantly,” another Sidley Austin lawyer said. “A lot of people brag about their husbands or boyfriends, but this was different. Her tone was almost worshipful. He was going to do great things, she kept saying.”

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 intellectual 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 registration 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:

“Abner, do you know so-and-so?” Barack would ask.

“Yes.”

“How well do you know him? I’d really like to meet him.”

“He wasn’t obnoxious about it—not at all,” Mikva recalled. “But he certainly wasn’t shy when it came to asking for help, either.”

Mikva, like so many others Barack approached for help, obliged by setting up a series of lunches. It was also during Project Vote that Barack met Bettylu Saltzman, daughter of Chicago shopping mall magnate and former Commerce Secretary Philip M. Klutznick. Saltzman not only touted the nervy political neophyte to her rich and powerful friends as a future President, but she introduced him to a man who had been chief political consultant to both Harold Washington and the incumbent Mayor Daley: David Axelrod.

Again, it was Barack who sought out the meeting with Axelrod. “I think he was strategic in his choice of friends and mentors,” Chicago Alderman Toni Preckwinkle said. “I think he saw the positions he held as stepping-stones to other things.”

At the same time, Barack had his mind on another important project that was in the works: his upcoming wedding. Michelle had seen the white half of his family during their Christmas trip to Hawaii, and he was grateful that she had gotten the chance to know Gramps before he passed away. But for Michelle to really understand the man she was going to marry, Barack felt it was important that she meet the people who had shaped his father’s life.

In late spring of 1992, Barack took Michelle to meet the other half of his far-flung family—the half brothers, half sisters, cousins, aunts, uncles, stepmothers, and step-grandmother who lived in Kenya. As they strolled the dirt roads of Alego, the small village on the shores of Lake Victoria where Barack’s father grew up, Michelle recalled, she was “deeply moved. Not just to be in Africa, but to be where Barack’s family lived for generations…it was overwhelming, really.”

In Alego, Michelle proved an instant hit with Barack’s relatives. With her statuesque bearing, athletic gait, ebony skin, and ready smile, she fit in easily. It also helped that she made a serious effort to learn Luo, the local dialect. Barack’s step-grandmother Sarah, who spoke only a few words of English and communicated with him through an interpreter, was especially impressed with his choice of fiancée. “She is very beautiful,” Granny said, “and obviously she has very good taste in men.”

When Michelle asked to see what life was like for urban Kenyans, Barack and his half sister Auma took Michelle to Nairobi’s Kibera district, the largest slum in Africa. This firsthand look at the desperate conditions Africa’s poor city dwellers live in left Michelle shaken. “I cried,” the usually hard-nosed Michelle confessed. “You couldn’t look at those children and not cry.”

Before they left, Michelle and Barack invited all of the Obamas to their wedding in early October. A few would actually make it, including Auma, who boasted a PhD in German literature from the University of Heidelberg, and Auma’s brother Malik. Also known as Abongo or Roy, Malik had a special assignment—to serve as best man.

On October 3, 1992—a Saturday—some 130 invited guests filled the pews of Trinity United Church of Christ to see Michelle LaVaughn Robinson wed Barack Hussein Obama. The best man wore a traditional black African gown trimmed in white and a matching cap. The ring bearers, Michelle’s five- and six-year-old cousins, wore little tuxedos with African cloth caps that matched their cummerbunds.

The rest of the men, including the groom, Michelle’s uncles, Barack’s old friends from Punahou Academy in Hawaii, and his roommates at Occidental, wore white tie.

In keeping with Barack’s Kenyan roots and the Afrocentric bent of Trinity United, several in attendance—including the Reverend Jeremiah Wright—joined Malik Abongo in wearing traditional African dress. But most, including Valerie Jarrett, Jesse Jackson, and the scores of public officials, corporate lawyers, business leaders, activists, academics, and community organizers who made up their rapidly expanding world, opted for the usual business suits and dressy outfits. Barack’s mother, Ann, who had flown in from Hawaii with his sister Maya, wore a knee-length black skirt and an orange silk blouse; Marian Robinson, a floor-length black skirt and a sequined black-and-white top.

Michelle’s maid of honor, Santita Jackson, sang as the bride walked down the aisle in a classic off-the-shoulder white silk sleeveless gown worn with long white gloves. As the afternoon light streamed through the cavernous sanctuary’s stained glass windows, Wright pronounced Michelle and Barack man and wife. Barack would later observe that, despite the emotion of the moment, only his half sister Auma cried. Still, Valerie Jarrett recalled, “it was magical. They were clearly madly in love with each other.”

The reception was held at the South Shore Cultural Center, a majestic pink-walled, tile-roofed Mediterranean-style villa that had once been an exclusive whites-only country club. For their first official dance as man and wife, they chose Nat King Cole’s “Unforgettable.” Santita Jackson also sang one of Michelle’s favorite Stevie Wonder ballads, “You and I.”

The Obama nuptials stood out from other weddings, Michelle’s friend and law firm colleague Kelly Jo MacArthur observed, “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.”

Barack’s church mothers—Loretta Augustin-Herron, Yvonne Lloyd, and Linda Randle—were also among the guests. “We were overjoyed with the choice he made,” said Augustin-Herron, who admitted that Barack’s “other family” had been wondering aloud if anyone would be good enough for their surrogate son. “Michelle was smart, attractive, fun—right up there on the same level with Barack. And she was so genuinely nice—none of that phony stuff. When she talked to you, she made you feel like she really cared—just like Barack. She had class.”

“It was obvious to all of us that Michelle was the right woman for our Barack,” Augustin-Herron said. “She is obviously his equal, and he needs to have an equal as his partner in life—someone he can talk to on the same level.” It was also obvious, Randle added, that “Michelle can stand on her own two feet. The last thing Barack needed was a woman who was high maintenance.”

As they met the wedding party on the receiving line, all three women were impressed by Ann Soetoro. “Barack’s mother was so warm and kind,” Lloyd recalled. “You could really see there was a lot of her in him. I told her she did a good job of raising her son, and she just nodded and smiled. Of course, later I discovered that Barack’s grandmother was probably an even bigger influence on his life.”

The couple honeymooned in California, driving up the narrow Pacific Coast Highway that winds along the coastline from Santa Barbara past Big Sur and Carmel on the way to San Francisco. They made the trip with the windows rolled down—despite Michelle’s objections, he was smoking more than ever—and whenever he flicked his ashes out the window, Michelle was quick to admonish him. “Hey,” she said, anxiously looking at the next blind bend in the road, “both hands on the wheel, buddy.”

When she wasn’t gasping at the oncoming trucks that seemed to come perilously close to running them off the road and into the sea, Michelle marveled at the endless vistas of blue-green water and waves crashing on the rocks below. “They reveled,” Maya said, waxing poetic, “in the majesty of the cliffs and the water.”

Back home in Chicago, Mr. and Mrs. Barack Obama moved in with Michelle’s mom while they looked for a place of their own. Six months later, they paid $277,500 for a two-bedroom apartment on the ground floor of a three-story condominium complex on South Eastview Park, near the lakefront and not far from the University of Chicago campus in Hyde Park.

The newlyweds gave several small dinner parties at their spacious new condo, which was decorated with paintings, photographs, and artifacts from their travels to Kenya and Hawaii. Over simple but elegant dishes like shrimp over pasta, the Obamas would entertain no more than two or three couples. “Michelle was charming, gracious, very professional,” Mikva recalled of these evenings. “It was obvious she was not the kind of woman who would be happy just baking cookies. And of course she was beautiful—strikingly so.”

At the time, there were those among Barack’s ever-widening circle of wealthy and influential friends who regarded him as something of a bore. “Because Barack was so smart,” said their friend Cindy Moelis, a Stanford Law School graduate whose father was president of New York’s Equity Leasing Corporation and a breeder of Thoroughbred racehorses. Moelis, who met Michelle when both women were working at city hall, was married to fellow Stanford Law School alum Robert Rivkin, the Harvard-educated son of John F. Kennedy’s Ambassador to Luxembourg.

“Barack was pretty serious when we were in our thirties,” Moelis said. So somber, in fact, that she used to poke him and say, “Come on, let’s talk about the last movie you saw.”

According to those closest to him at the time, Barack was preoccupied with one thing: following in Harold Washington’s footsteps. Once the November 1992 election was over and both the Clinton and Moseley Braun campaigns thanked Obama’s Project Vote campaign for making the difference in Illinois, Barack decided to join a law firm. He was thinking of taking up the offer of Judson Miner, the lawyer who had earlier been told that he was 647th in line. But first he wanted Michelle’s opinion. She told him that, if he wanted to join a legal outfit that was the diametric opposite of Sidley Austin, he could not do better than the small civil rights firm of Davis, Miner, Barnhill & Galland.

Unlike Michelle, who had appeared in court during her legal aid days at Harvard and occasionally written briefs in the civil cases handled by Sidley Austin, Barack would never be involved in a trial or write a brief on his own. Over the nine years he was associated with the firm—which primarily handled discrimination cases and worked with developers of affordable housing projects—Barack worked exclusively as part of a team of lawyers, apparently never taking the lead.

For Barack, who had also signed on as a visiting lecturer at the University of Chicago School of Law, there was far more to Davis, Miner, Barnhill & Galland than the practice of law. His name was Judson Miner. One of the chief legal minds behind the rise of Harold Washington, Miner served as corporation counsel—the city’s chief lawyer—during Washington’s tenure in city hall.

Whatever contacts Barack hadn’t already made through Michelle, Valerie Jarrett, and the Sidley Austin partners, he now secured through Miner. “If Judson doesn’t know somebody,” Barack cracked, “then I guess I don’t have to know them, either.”

It was just as well. Michelle was again beginning to feel restless in her job as Chicago’s economic development coordinator—a position that, since it catered directly to the business community, was beginning to resemble her old job at Sidley Austin.

Barack had his own reasons for wanting Michelle out of city hall. With his sights still set on becoming Mayor—or perhaps a U.S. Senator—both he and Michelle worried that her continuing association with the Daley regime might tarnish the reputation he sought to build as a young reformer. “You don’t have to think evil of Obama or city hall,” said veteran Chicago activist Quentin Young, “to realize that it could be a liability to a person who is politically on the rise.”

As it happened, Public Allies was looking for a new executive director, and Barack, who still sat on the board, proposed Michelle for the job. Before she took it, he resigned from the board to avoid any appearance of impropriety.

“It sounded risky and just out there,” she said. “But for some reason it just spoke to me. This was the first time I said, ‘This is what I say I care about. Right here. And I will have to run it.’”

As head of the nonprofit foundation that was eventually wrapped into the federal AmeriCorps program, Michelle proved to be even more aggressive—and effective—than her husband had been. Going after millions in contributions from Chicago’s long-established philanthropies, she now found herself introduced to a whole new set of movers and shakers—the old money crowd that wielded tremendous power and influence while managing to stay discreetly below the radar.

Once again, Michelle asserted herself as a tough taskmaster, upbraiding staff members who were not performing to her standards and, in some cases, telling them it was time to “move on.” Even those who were higher up in the chain of command were intimidated by Michelle. “Even though she worked for me,” said Vanessa Kirsch, who actually picked Michelle for the job, “I definitely felt like I worked for her.”

Through Public Allies, Michelle took scores of young activists under her wing. “Each ally was placed with a not-for-profit, about twenty to thirty a year,” said one of those protégés, Craig Huffman. “When you think of the number of people who got to know who Michelle was, and by extension Barack, that’s a whole generation from all over Chicago.”

Not all of the Obamas’ time was spent tending to their widening network of sociopolitical contacts. In fact, Barack was faced with another, more pressing deadline. The autobiography he was supposed to turn in to Simon & Schuster in 1991 was now two years overdue, and Barack remained hopelessly blocked.

When the publisher finally canceled the project in 1993, Barack worried that they would come after him for the $75,000 he had already been paid—half the agreed-to $150,000 advance. But when Barack informed them that he had spent the money—and that both he and his wife were still chipping away at their massive student loan debt—the publisher agreed not to press the issue.

With only a partial manuscript in hand, Barack turned again to his gravel-voiced agent, Jane Dystel, who promptly landed him yet another deal—this time for $40,000—with the Times Books division of Random House. For months Barack worked until the early-morning hours in what Michelle dubbed “the Hole,” his tiny, cluttered office tucked discreetly behind their kitchen.

“The Book,” as he now referred to it, was more than just a vanity project. Drowning in debt, the Obamas needed a massive infusion of capital if they were to stay afloat financially. “Let’s face it,” she told him point-blank, “one of us is going to have to get a job with a big corporate firm and make some real money or we’re going to have to move back in with Mom.”

But Barack had a plan. He was convinced that the book he was working on would become a bestseller, and he was already thinking of a sequel.

“It was like Jack and his magic beans,” she later recalled of those conversations. “He’s like, ‘Look, honey, I’m going to write these books and we’ll be fine,’ and I’m like, ‘Yeah, sure, right.’”

She had good reason to be skeptical. When he sat down to write what would become Dreams from My Father, Barack had filled up scores of legal pads with notes, all in his overarching left-handed scrawl. Beyond jotting down his thoughts and observations over the years, however, he had not really done much writing. At the Harvard Law Review, while he was responsible for selecting which articles were sufficiently scholarly to make the cut, his only Review article was an unsigned defense of legalized abortion.

Lamentably, Barack had tried his hand at verse. Back during his undergraduate years at Occidental, he published two poems in Feast, a student literary journal. Later, in a masterpiece of understatement, he would call these literary efforts “very bad.” From Barack’s poem titled “Underground”:

Under water grottos, caverns

Filled with apes

That eat figs.

Stepping on the figs

That the apes

Eat, they crunch.

In another poem, titled “Pop”—the only other known, signed example of his writing up until this point—Barack seemed to be writing about drinking and getting high with an older friend:

Under my seat, I pull out the

Mirror I’ve been saving; I’m laughing,

Laughing loud, the blood rushing from his face

To mine, as he grows small,

A spot in my brain, something

That may be squeezed out, like a

Watermelon seed between

Two fingers.

Desperate to finish the book, Barack and Michelle took a leave of absence from their jobs and decamped to the Indonesian island of Bali so that, as his sister Maya put it, he could “find a peaceful sanctuary, where there were no phones, to work on the book.” When he returned in early 1994, Barack burrowed even deeper into the Hole in a last-gasp effort to finish it.

Two months later, with a September 1994 deadline looming, Barack was still stymied. It was around this time that, at Michelle’s urging, he sought advice from his friend and Hyde Park neighbor Bill Ayers. Michelle had known Ayers’s wife, Bernadine Dohrn, at Sidley Austin, where Dohrn worked as a paralegal between 1984 and 1988. Dohrn’s father-in-law, former Commonwealth Edison CEO Thomas Ayers, just happened to be one of the firm’s most important clients.

Barack got to know Bill Ayers’s father and his brother, John, when all three served on the Leadership Council of the Chicago Public Education Fund. Another mutual friend of Ayers and Barack was Jean Rudd, whose nonprofit Woods Fund had provided Jerry Kellman with the money he needed to hire Barack as an organizer back in 1985.

Neither Michelle nor Barack seemed particularly troubled to discover that William Ayers and Bernadine Dorhn had been two of the 1960s’ most infamous radicals—leaders of the Weather Underground terrorist group that set off thirty bombs in the 1960s and 1970s.

After an explosion in the Weathermen’s Greenwich Village bomb-making laboratory killed three of their fellow Weathermen (including Ayers’s girlfriend at the time, Diana Oughton) and virtually destroyed the neighboring town house owned by Dustin Hoffman, Ayers and Dohrn went underground. In 1973 charges against them were dismissed due to prosecutorial misconduct, but Dohrn remained a fugitive until she finally turned herself in to police in 1980.

Ayers made no apologies for his terrorist past, and in the 1990s still described himself as “a radical, Leftist, small ‘c’ communist…. The ethics of communism still appeal to me. I don’t like Lenin as much as the early Marx.”

Ayers’s radical past didn’t seem to bother Chicago’s civic leaders, many of whom worked with him on education reform. He worked particularly closely with Mayor Richard M. Daley on reshaping the city’s school programs—an effort that also brought him into contact with one of Daley’s assistants at the time, Michelle Obama.

What did interest Barack were Ayers’s proven abilities as a writer. Unlike Barack, Ayers had written and cowritten scores of articles and treatises, as well as several nonfiction books beginning with Education: An American Problem in 1968. But it was the tone Ayers had set in his latest book—To Teach (1993)—that Barack hoped to emulate.

The tale of a maverick teacher who takes her students onto the streets of New York to teach them firsthand about history, culture, and survival, To Teach was written in a fluid, novelistic style. Barack asked for Ayers’s input, and Ayers, who like so many in his circle was greatly impressed by the charismatic young activist, obliged.

To flesh out his family history, Barack had also taped interviews with Toot, Gramps, Ann, Maya, and his Kenyan relatives. These oral histories, along with his partial manuscript and a trunkload of notes, were given to Ayers. “Everyone knew they were friends and that they worked on various projects together,” another Hyde Park neighbor pointed out. “It was no secret. Why would it be? People liked them both.”

In the end, Ayers’s contribution to Barack’s Dreams from My Father would be significant—so much so that the book’s language, oddly specific references, literary devices, and themes would bear a jarring similarity to Ayers’s own writings. Even the caveat at the beginning of Dreams, in which Barack points out that he uses invented dialogue, embellished facts, composite characters, inaccurate chronology, and pseudonyms to create an “approximation” of reality, resembles Ayers’s defense of the inaccuracies in his memoir Fugitive Days. In the foreword to his book, Ayers states that the book is merely a collection of his personal memories and “impressions.”

“There was a good deal of literary back-scratching going on in Hyde Park,” said writer Jack Cashill, who noted that a mutual friend of Barack and Ayers, Rashid Khalidi, thanked Ayers for helping him with his book Resurrecting Empire. Ayers, explained Cashill, “provided an informal editing service for like-minded friends in the neighborhood.”

Certainly none of these authors hesitated to acknowledge their admiration for one another at the time. In his 1997 book, A Kind and Just Parent, Ayers would cite the “writer” Barack Obama (along with Muhammad Ali and Louis Farrakhan) as one of the celebrities living in his neighborhood. In turn, Barack would write a glowing review of that same book for the Chicago Tribune, and Michelle would host a panel discussion on the book at the University of Chicago, with Ayers and her husband as the principal speakers.

Thanks to help from the veteran writer Ayers, Barack would be able to submit a manuscript to his editors at Times Books. With some minor cuts and polishing, the book would be on track for publication in the early summer of 1995. In the meantime, he began showing the rough draft to a chosen few relatives.

Toot, for one, was miffed at his portrayal of Gramps as a bitter man, and of the tensions that arose in the house when she became the principal breadwinner. And she didn’t like the profanity used in the book, particularly one word that described a part of the female anatomy. “It probably made her a little nervous, having the family written about,” Maya said of their grandmother, “just because you don’t do that in Kansas.”

Toot was also worried about passages where Barry admitted to being a regular user of pot and an occasional user of cocaine in his youth. It was a concern shared by Michelle. “That stuff isn’t going to sit well with the ladies at church,” she warned him—the very women, she pointed out, that he would need once he decided to run for Governor or the U.S. Senate.

Barack disagreed, and so did Jeremiah Wright. In recent years, Wright had become increasingly strident in his rhetoric—among other things, praising the likes of Louis Farrakhan, Fidel Castro, and Muammar Gadhafi, and attacking Washington for allegedly starting the AIDS epidemic as part of a vast conspiracy to annihilate the world’s black population. A number of church members—most notably Oprah Winfrey—left the church. Winfrey would later explain that there were a number of reasons for this, including a dissatisfaction with organized religion in general. Still, Wright’s increasingly militant statements were a factor. “Oprah is a businesswoman, first and foremost,” one longtime friend told Newsweek. “She’s always been aware that her audience is very mainstream, and doing anything to offend them just wouldn’t be smart.”

Barack, who heard such messages delivered from Wright’s pulpit scores of times over the years, apparently did not share Oprah’s misgivings. The reverend remained the Obamas’ closest and most trusted spiritual adviser. Wright, who had always been candid about his own teenage arrest record, urged Barack to share the details of his marijuana and cocaine use in the book. Not only was it an evocative illustration of Barack’s own “redemption,” Wright told him, but it would speak directly to young men in the black community who had struggled or were struggling with drugs.

Moreover, Barack, who now described Wright as “a father figure” to him, had shared his political aspirations with the reverend in detail. Wright reminded him that, despite Barack’s contributions to the black community, there were those who remained wary of him. While Trinity United’s congregation was more affluent and sophisticated than most, many people Barack encountered on the South Side still found the eager young activist too exotic (raised in Hawaii and Indonesia), too well educated (Columbia, Harvard), and too white (raised by his Kansan grandparents, his speech had neither the cadence nor the rich flavor of Chicago’s African American community).

Barack had long been concerned that he lacked “street cred,” and had already explained to Michelle that his book offered the fastest and most effective way to remedy the situation. Now that Wright agreed, Michelle dropped her opposition. “Barack loved and respected Reverend Wright,” said a fellow church member, “but not as much as Michelle. She had grown up going to church, and made that kind of attachment to her pastor. Michelle was in total awe of Reverend Wright.”

Barack also sent the manuscript to his mother in Hawaii. The book’s focus on Barack’s father, who had abandoned Barack and Ann to return to Africa, surprised her. It was Ann, after all, who—along with Toot and Gramps—had raised Barack and shaped his values. But Ann shrugged it off. “She never complained about it,” her friend Nancy Peluso said. “She just said it was something he had to work out.”

Around this time, Ann returned to Indonesia to do more fieldwork and to reconnect with several old friends. She was dining in the Jakarta home of one of them, economist Richard Patten, when she doubled over with a sharp stabbing pain in her stomach. The next day she went to a local doctor, who diagnosed her with indigestion, gave her an over-the-counter remedy, and sent her on her way.

The pains in Ann’s abdomen persisted, however, and when she returned to Hawaii three months later she visited a doctor again. This time, she was told she had advanced uterine and ovarian cancer.

Understandably, Barack was devastated by the news. That Christmas, he and Michelle flew out to Hawaii as they always did to spend the holiday with Barack’s family. Chemotherapy had caused Ann’s hair to begin falling out, but the prognosis was hopeful. What really concerned Ann at the time was the possibility that her insurance might run out, leaving her unable to pay for her cancer treatments. “At a time when she should have been focused on getting well,” he later said, “my mother was in a hospital bed arguing with her insurance company because they refused to cover her treatment on the grounds that she had a ‘preexisting condition.’”

Barack returned to Chicago more determined than ever to run for office. He went to his friend Abner Mikva and asked him to put out feelers to see if any office might be opening up. “He couldn’t wait,” Mikva said, “to get into the ring.”

He wouldn’t have to wait long. In early 1995, Illinois Congressman Mel Reynolds was facing charges of having sex with an underage campaign worker. In August, Reynolds would be convicted and sentenced to two years in prison (later he would be sentenced to an additional six and a half years for wire and bank fraud). Reynolds finally resigned his seat on October 1. But in the meantime, there was a frantic scramble to replace him. One of those most interested in Reynolds’s job was fifty-five-year-old African American State Senator Alice Palmer.

This was precisely the opening Barack had been searching for. He had actually paid a visit to his alderman, Toni Preckwinkle, to broach the subject in January of 1995. “If Alice decides she wants to run for Mel Reynolds’s seat,” Barack told Preckwinkle, “I want to run for her State Senate seat.”

His first run for office aside, 1995 would turn out to be an eventful year for the Obamas. On June 22, Barack was officially named chairman of the Chicago Annenberg Challenge—an Annenberg Foundation—funded grant that was the brainchild of Barack’s friend and neighbor Bill Ayers. The Challenge, aimed at promoting reforms in the public school system, would dole out $49.2 million to various experimental projects—including a “Peace School” where the curriculum centered on a United Nations theme—before shutting down in 2003 because, said the foundation’s final report, it had “little impact on school improvement and student outcomes.”

Five days after Barack’s appointment to head the Annenberg Challenge, Alice Palmer announced she was running for Congress and soon made it clear that she backed Barack to succeed her in Springfield. Not long after, Bill Ayers and Bernadette Dohrn hosted a small gathering for Palmer in the living room of their Hyde Park home. Barack was there as well, and while Ayers did not technically launch his political career as would later be widely suggested, he was most likely the first to introduce Barack as a candidate.

Then, on July 18, 1995, Dreams from My Father was published to generally positive reviews. Barack embarked on a ten-day national book tour, and although in this first incarnation Dreams would sell only ten thousand copies, it added considerably to the author’s cachet among Chicagoans.

One of several book parties honoring the novice author was thrown by Valerie Jarrett, who packed her elegant art deco-designed co-op in the Kenwood district of Hyde Park with some of Chicago’s wealthiest and most influential citizens. Coincidentally, it was the same week Mel Reynolds was convicted in his sexual assault case. Alice Palmer had already announced her intention to run for Reynolds’s soon-to-be-vacated seat, and Jarrett’s book party was abuzz with gossip about Barack’s impending run to fill her seat.

“Michelle was there,” remembered one guest, “working the room like a pro while he sat there autographing books.” Her mood changed noticeably, however, when talk of a possible State Senate run came up. “Everyone was buzzing about it, but,” said the guest, “Michelle was clearly not enthusiastic.”

Indeed, Michelle confided to one longtime friend that the subject had been the source of heated arguments between them. “It’s beneath you, Barack,” she told him. “It’s too small-time. What can you possibly accomplish in Springfield?”

But Barack persisted, and Michelle acquiesced. “I married you because you’re cute and you’re smart,” she said. “But this is the dumbest thing you could have ever asked me to do.”

On September 19, more than two hundred supporters showed up at the Ramada Inn Lakeshore in Hyde Park-Kenwood to hear Barack announce his candidacy in the same room where Harold Washington had announced his candidacy for mayor thirteen years earlier. “Barack Obama carries on the tradition of independence in this district,” Palmer said when she introduced him to the standing-room-only crowd. “His candidacy is a passing of the torch.”

In addition to setting him up with several of her key precinct operatives, Palmer went to her longtime supporters and asked if they would host a series of coffees to introduce Barack to voters. Over the course of the next six months, there would be as many as four per week.

One of the first of these meet-and-greet events was hosted by Rabbi Arnold Jacob Wolf. “Someday you are going to be Vice President of the United States,” Wolf told him.

Barack laughed. “Why not President?” he asked.

Another couple who hosted one of these coffees had no such reservations about Barack’s prospects. “This guy,” Martha Ackerman said to her husband, Sam, “could be the first African American President of the United States.”

It was during this period that, according to Barack, his relationship with controversial Syrian-born developer Tony Rezko “deepened.” Rezko had pushed for legislation to give hefty tax credits to real estate developers like himself who were willing to build low-income housing in Chicago’s run-down neighborhoods. Rezko hired Davis, Miner to represent his interests, and in the process became friendly with Barack.

While he had turned down Rezko’s frequent entreaties to go to work for him as far back as his days on the Harvard Law Review, Barack did consult him on his political future. He also relied on Rezko for financial support; the developer would become his largest single contributor, paying for a considerable chunk of Barack’s State Senate campaign.

One of Tony Rezko’s biggest boosters was Michelle, who had met him during her stint as Mayor Richard M. Daley’s economic development coordinator. The Obamas soon began socializing with Rezko, dining at his Wilmette, Illinois, mansion, and even visiting his sprawling vacation home in Lake Geneva, Wisconsin. “Michelle was impressed with the Rezkos and their devotion to her husband, and she clearly enjoyed their company,” said a Rezko business associate who dined with both couples on several occasions. “Michelle encouraged Barack to cultivate the Rezkos. I think she liked them even more than he did.”

With his March 1996 primary still five months away, Michelle pressed Barack to take time out to visit his desperately ill mother in Hawaii. Toot and Maya had been keeping Barack apprised of her worsening condition, but Ann kept insisting she was doing fine and responding to treatment. There was no reason, she said, for her son to interrupt his campaign to visit her.

Michelle wasn’t buying it. “Dad always said he was feeling great no matter how bad he really felt,” Michelle reminded Barack. That was precisely what he said when he went out the door to work that final morning. Michelle still regretted the fact that no family member was with her father when he passed away, and she did not want Barack saddled with the same feelings of remorse.

“I think you ought to take the time to go out and see your mother,” Michelle told her husband, trying to downplay the fact that it might well be the last time. “You can surprise her. She’ll be thrilled.”

Whether or not he was in denial about the gravity of his mother’s condition—she had been told at the time of her diagnosis that she had only a slim chance of survival—or actually believed Ann’s fervent claims that she was responding to treatment, Barack put off visiting his mother.

Instead, Jeremiah Wright had persuaded Michelle to let Barack accompany him to Nation of Islam leader Louis Farrakhan’s Million Man March in Washington on October 16, 1995. As soon as he returned, Barack approached the alternative newsweekly the Chicago Reader and offered to share his impressions of the event.

“Historically,” he told the Reader, African Americans have turned “towards Black Nationalism whenever they have a sense, as we do now, that the mainstream has rebuffed us, and that white Americans couldn’t care less about the profound problems African Americans are facing. What I saw,” he continued, “was a powerful demonstration of an impulse and need for African American men to come together to recognize each other and affirm our rightful place in society.”

Less than three weeks later, on November 7, 1995, Barack was back in Chicago working on his campaign when news came that Ann had died. She was fifty-two. As Michelle had predicted, he was overcome with guilt. “I should have been there,” he told her. “I should have been there…” Maya and Toot tried to reassure him that the end had come suddenly, unexpectedly—that they had all believed there would be time for him to say good-bye. But Barack would never forgive himself. “The single greatest regret of my life,” he would later say, “was not being there when my mother died.”

Barack and Michelle flew to Hawaii and, along with Toot and Maya, scattered Ann’s ashes over the Pacific. “My mother was the sweetest woman I’ve ever known,” he would say. “Everything I am, I am because of her.”

When Michelle and Barack returned to Chicago, they brought with them some of the treasures his adventurous mother had collected over the years—including her childhood arrowhead collection from Kansas and two trunks crammed with Indonesian batiks. Ann’s friends would also say that something of her lived on in her son. “When Barack smiles,” said Nancy Peluso, a pal from her days in Indonesia, “there’s just a certain Ann look. He lights up in a particular way that she did. There is this thing in his eyes.”

Barack would need all the optimism he could muster. As the primary election for Mel Reynolds’s Second Congressional District seat approached, it was clear to everyone that Alice Palmer was going to go down to defeat. Still upset by the loss of his mother, Barack met with a group of veteran black leaders who asked him to release Palmer from her promise not to run for reelection to the State Senate.

“We want you to step aside,” one of the men said, “like other African Americans have done—for the sake of unity.”

At first Barack did not reject their request. He told the older gentlemen—many of whom had resisted his efforts at community organizing in earlier years—that he would think about it. He hadn’t decided what he was going to do.

After Alice Palmer went down to crushing defeat at the hands of Jesse Jackson Jr. in the November 28, 1995, congressional primary, her backers again demanded that Barack withdraw from the State Senate race so that she could reclaim her old seat. “We don’t think Obama can win,” said Northeastern Illinois University political science professor Robert Starks. “He hasn’t been in town long enough. Nobody knows who he is.”

This time Barack refused. “I’ve gone out and raised money, opened an office, recruited people, put my name out there,” he said. “And I’m supposed to take that back because you now want to change the agreement we already had? That just doesn’t make a lot of sense.”

Alice was furious that the young upstart she had backed now refused to step aside for her. Armed with an endorsement from the very man who had just beaten her in the congressional race, Jesse Jackson Jr., Palmer dispatched volunteers to collect the signatures from registered voters necessary to get her on the ballot for the March 1996 State Senate election. On the December 18 deadline, she filed nominating petitions containing 1,580 signatures—twice the number required.

Based on his own experience signing people up for Project Vote, Barack knew that in Chicago (“where three out of two registered voters is a Democrat”), politicians took a less than punctilious approach to signing up prospective voters. It also struck Barack that Palmer’s volunteers had gathered the necessary signatures in an extraordinarily short period of time.

Barack ordered his campaign operatives—actually called “operators” in Chicago—to check out Palmer’s petitions filed at the Chicago Board of Elections. Comparing the names on the petitions with those on the actual voter registry, they uncovered scores of irregularities—enough to disqualify two-thirds of the signatures.

Palmer argued that in most cases the disqualifications hinged on such technicalities as the misspelling of a street name or whether or not an individual printed, rather than signed, his or her name on the petition.

No matter. Palmer was denied a spot on the ballot. Seeing how easy it was to knock one opponent off by challenging her petitions, Barack had his operators check his other opponents as well. By the time they were finished, all of his opponents had been knocked off the ballot. In his first bid for office, Barack ran unopposed.

“To my mind, we were just abiding by the rules that had been set up,” Barack said in defense of what some viewed as an underhanded tactic. Was it fair to deny the voters a choice of more than one candidate? he was asked by the Chicago Tribune. “I think they ended up,” he replied, “with a very good State Senator.”

Michelle could not have agreed more. She was immensely proud of her husband’s election victory and stood beaming by his side at all his public events. But as thrilled as she was that Barack now held elective office, she worried that the manner in which he had won might come back to haunt him. Michelle had, in fact, begged her husband not to challenge Alice Palmer’s petitions. “It will just leave a bitter taste in everybody’s mouth,” she told him. “The big Harvard lawyer comes here and uses his legal tricks to knock poor old Alice and everybody else off the ballot. Who the hell does he think he is?”

Moreover, even though she campaigned at his side—showing up in the living rooms of strangers for neighborhood coffee klatches and charming potential donors like the Rezkos over dinner—Michelle still believed that the State Senate would only sidetrack her husband. “She felt it was just too small-time,” one friend said. “They both already know so many important people, she just wanted him to go straight to the national stage. Either that, or make tons of money.”

As it sank from sight, it soon became apparent that Barack’s book Dreams from My Father was not going to provide the windfall they had hoped for. Between his salary at Davis, Miner, Barnhill & Galland and hers at Public Allies, they were grossing about $250,000 a year—still not enough to pay off their student loans. “I worried a lot,” she said of this period, “about where the money was coming from. Somebody had to.”

Barack floated above such petty concerns. “There will be plenty of time to make money—lots of it,” he assured his wife. “Right now is the time to make a difference.” Besides, he liked to say with a sly wink as he held up one of his credit cards, “have plastic, will travel.”

As was the case in many families, the Obamas’ household finances were handled by Michelle. While he was three and a half hours away in Springfield, she did the bookkeeping, wrote out the checks, filled out the insurance forms, even assembled records for tax purposes. Barack was asked only to submit his receipts so he could be reimbursed for legitimate business expenses, and that he did only sporadically. “It made her a little crazy that he had such a cavalier attitude toward money,” an aide said. “She was very grateful when we’d remind him every once in a while about keeping track of his expenses. But it was something that he had no interest in doing.”

According to his banker grandmother Toot, Barack, like his mother and grandfather, was “clueless” when it came to handling his personal finances. “Barry has no head for money,” said Toot, who sympathized with her daughter-in-law’s mounting sense of frustration in that department. She even apologized to Michelle for “not emphasizing that more” when Barack was growing up.

Michelle was also fretting about her husband’s personal habits. Barack did not pick up his socks and underwear, and was less than religious about hanging up his clothes at all. He left wet towels on the bathroom floor, cups and glasses scattered about the house, and the toilet seat up. Dirty dishes were left in the sink until Michelle placed them in the dishwasher, and all the laundry, ironing, vacuuming, and dusting was left to her. “And,” she told her mother and anyone else who cared to hear, “Barack never, ever replaces the paper towels—or the toilet paper.”

Early-bird Michelle, who was usually in bed by ten, also resented the fact that he stayed up alone until two in the morning, then slept in. And he snored.

For Michelle, Barack’s chain-smoking was particularly annoying. Aside from the obvious health concerns—“Buddy, did you ever hear of secondhand smoke?” she would tease—Michelle was fed up with the sheer messiness inherent in Barack’s nasty habit. Ashtrays brimmed with cigarette butts—which could also be found stubbed out in coffee cups and saucers—and there were cigarette burns in the carpet. The acrid smell of smoke lingered on their clothes, in the drapes, in the upholstery, in her hair. She moved a framed picture on the wall to reveal that the walls of their condo were turning a sickly yellow, along with his teeth and fingertips.

“Michelle is a very meticulous person,” Valerie Jarrett said. “Whether it’s the clothes she wears or her home, she maintains a very high standard.” A standard that her husband, much to Michelle’s near-constant frustration, was either unable or simply unwilling to live up to.

Absorbed in his nascent political career, Barack was oblivious to the trouble brewing at home. When Michelle did erupt, it often triggered arguments that seemed to last for days. “Like a lot of husbands,” said one of her friends, “Barack couldn’t figure out what her problem was. All her complaints about him being a slob—which I heard her call him many times, sometimes joking, sometimes not—well, he thought they were petty. You know, it was ‘Why are you bothering me with this crap while I’m busy changing the world?” That attitude “only made Michelle crazier. She was just as accomplished as he was, and she was out there changing the world, too. So why, she wanted to know, was she cleaning up after him?”

Underlying Michelle’s dissatisfaction was a deeper, more pressing concern. Not long after their marriage in 1992, Michelle and Barack began trying to start a family. “When it didn’t happen right away,” said Marian Robinson, “she got a little worried.”

By the time Barack went to Springfield to be sworn in as a State Senator in the spring of 1996, Michelle was frantic. When a physician friend pointed out that the stress of working sixty hours a week running Public Allies might be a factor in her inability to conceive, Michelle quit.

Instead, she took a job as associate dean of student services and the first Director of Community Relations and Community Service at the University of Chicago. When she arrived to interview for the job, she startled the dean of student services by announcing that, although she grew up just blocks from the university, she had never set foot on the campus. “All the buildings have their backs to the community,” she explained later. “The university didn’t think kids like me existed, and I certainly didn’t want anything to do with that place.”

Unfortunately for her husband, who lectured at “that place,” most blacks shared Michelle’s hostile attitude toward the University of Chicago. Viewed as a bastion of white intellectual elitism smack-dab in the middle of one of Chicago’s grittiest minority communities, the university had made little effort to connect with the working-class people who encircled it. “The University of Chicago is not a brand that helps you,” said Obama’s friend and onetime aide Will Burns, “if you’re trying to get votes on the South Side of Chicago”—votes he would need if, say, he wanted to run for Congress.

But for the time being, the votes from Hyde Park would be enough to keep him ensconced in the State Senate. When Barack arrived in Springfield, it was with a built-in reputation as, in Burns’s words, “a threat.” Precinct worker Ron Davis agreed: “He knocked off the incumbents, so that right there gave him some notoriety. And he ran unopposed—which for a rookie is unheard-of.”

When he landed at the state capitol in January of 1997, the high-minded, Ivy League-educated freshman Senator seemed like something of a hothouse flower to his backroom-dealing, often literally cigar-chomping colleagues. “What the hell are you doing here? You don’t belong here,” fellow Democrat Denny Jacobs said bluntly. Barack, he said, just “looked at me sort of strange.”

Corruption was as rampant as ever in the Illinois legislature, and to make matters worse, Republicans controlled the Senate when Barack arrived—and they would continue to control it for the next six years. Since state government was firmly controlled by the “Four Tops”—the Senate President, the House Speaker, and the two minority leaders—run-of-the-mill lawmakers like Barack were held in especially low regard. They were called “mushrooms” because, as Barack would explain with a laugh, “We are kept in the dark and fed shit.”

From the moment he set foot in Springfield, Barack was determined not to fall into that category. Right after being sworn into office, he approached the powerful Democratic leader Emil Jones, a friend from his organizing days.

“You know me,” Barack told Jones. “You know me quite well.”

“Yes? And?” Jones asked tentatively, squinting through a cloud of cigarette smoke.

“You know I like to work hard,” Barack continued. “So feel free in giving me any tough assignments.”

“Good,” said Jones, who promptly saddled him with legislation on campaign finance reform. In his caucus, Barack, who assiduously courted his Republican counterparts in search of a viable compromise, was the object of boos and catcalls.

“He caught pure hell,” Jones remembers of his protégé’s performance. “I actually felt sorry for him at times.”

Barack’s toughest critics were fellow African American Senators who viewed him as a know-it-all snob. “Just because you’re from Harvard,” Senator Donne Trotter would snipe, “you think you know everything.” Rickey Hendon, whose district was on Chicago’s West Side, frequently squabbled with Barack on and off the Senate floor. “What do you know, Barack?” he asked during one debate. “You grew up in Hawaii and you live in Hyde Park. What do you know about the street?”

One verbal sparring match on the Senate floor nearly escalated to the real thing. At one point, after yelling at each other for fifteen minutes, the normally unflappable Barack strode over to Hendon’s desk with fists clenched. “I’m gonna kick your ass!” he told Hendon before someone stepped in to break them up.

For the most part, Barack avoided his fellow African American Senators from Chicago, and instead befriended his fellow legislators—mostly white—from the suburban and rural southern part of the state. In addition to taking up golf (“An awful lot happens on the golf course,” he told his friend Jean Rudd), Barack joined fellow Senators and a few lobbyists for their weekly poker game. He quickly proved himself to be a methodical, if cautious, cardplayer. “I’m putting his kids through college,” complained Republican Terry Link.

One of Obama’s earliest allies in Springfield was Denny Jacobs, a self-described “old-school, backroom politician” and a member of Barack’s tight-knit circle of poker players. At first, Jacobs recalled, Barack was “always asking questions for the sake of asking questions. So I got up and said, ‘Listen, go learn on your own goddamned time. We’re doing business here.’ And he didn’t get ticked. He just listened, and took in the advice, and from then on when he asked a question it was right to the point. That’s the thing about Barack: he has a tremendous capacity to grow—to learn and to retain.”

At the urging of his new political adviser Dan Shomon, Barack also decided to test the waters outside Chicago—to see if he would stand a chance with white middle-class voters in the event he tried for statewide office. In order to make him seem like less of an elitist, Shomon played Pygmalion to Barack’s Galatea. Gone was Barack’s casual uniform—worn with obsessive-compulsive consistency—of a wide-collared black silk shirt, jeans, and Bass Weejuns with no socks. Now, when he played golf with the local Kiwanis and Rotary Club members, he donned polo shirt, khakis, golf shoes, and cap.

He made similar adjustments in his food preference when he was courting “downstaters”: now he drank beer instead of Chablis, used French’s yellow mustard squeezed out of a plastic bottle instead of Dijon, and was careful to order doughnuts, not croissants, when he dropped in to chat with town burghers at the local coffee shop.

More important than these cosmetic changes was the fact that, in the faces of these mostly white middle-class midwesterners, Barack saw Toot, Gramps, and his mother. He understood them just as easily as he understood the inner-city black population he represented, and they responded in kind. “I learned if you’re willing to listen to people,” he reflected, “it’s possible to bridge a lot of the differences that dominate the national political debate. I pretty quickly got to form relationships with Republicans, with individuals from rural parts of the state, and we had a lot in common.”

Back in Springfield, Barack labored in relative obscurity to get a handful of bills through. Between these efforts and his relentless network building, there was little time left for Michelle.

With Barack away from home in Springfield as many as four days a week during the legislative session and lecturing once a week at the University of Chicago Law School, Michelle would see him only on weekends. She did what she could to keep busy—up at four thirty to work out at the gym, then off to work at the university, lunch with friends, back to work, sometimes dinner with her mother, then home to television, some reading, and bed by nine thirty.

When Barack was in Springfield, he and Michelle shared the details of their days apart over the phone. While he said he would “fall asleep content in the knowledge of our love,” Michelle hung up feeling, she told one friend, “frustrated and sad.”

Unlike Barack, who lived in abject fear of ever leading a humdrum nine-to-five existence, Michelle cherished order and routine. These were the things that had sustained the Robinsons through her father’s long illness. But they could not disguise the fact that she missed her husband. “Michelle was feeling lonely,” Valerie Jarrett told a mutual friend. “Desperately so.”

The fact that they had been trying to have a baby for over four years now was also weighing heavily on Michelle’s mind. She was talking to friends about fertility clinics and adoption when, in November of 1997, a visit to her doctor confirmed the results of a home pregnancy test.

“Hey! You’re kidding!” Barack shouted when she broke the news to him over the phone. “Wow! Wonderful, wonderful.” Barack’s first impulse was to share the good news with the one person who, next to Michelle, meant the most to him. “Got to call Mom,” he said, reaching for the phone before reality struck. “Oh…”