When Barack knuckled under to pressure from Michelle and refused to return from his annual family vacation in Hawaii to vote for gun control legislation, Rush held a press conference to excoriate him. Then, in the final week of the campaign, President Bill Clinton did a series of spots on black radio endorsing Rush. “I’m President Clinton,” he announced, “urging you to send Bobby Rush back to Congress where he can continue his fight to prepare our children for the twenty-first century. Illinois and America need Bobby Rush in Congress.” At that point, said Obama supporter Toni Preckwinkle, “it was hopeless.”
Barack lost by a staggering two-to-one margin. Back at the Ramada Inn Lakeshore, where Barack had launched his political career just five years earlier, Michelle stood by her husband’s side while he made his concession speech. “I’ve got to make assessments,” he told the crowd, “about where we go from here. We need a new style of politics to deal with the issues that are important to the people. What’s not clear to me is whether I should do that as an elected official, or by influencing government in ways that actually improve people’s lives.”
For the first time in his life, Barack tasted defeat. He took it hard. So did Michelle. “Michelle is great,” said a Springfield colleague, “at ‘I-told-you-so’s.’”
Ebullient in victory, Barack was incapable of disguising his disappointment in the face of his first loss. “I am very competitive, but nothing like Barack,” Michelle said. “He is a terrible loser. It really gnaws away at him.” Barack spent the next few weeks, he later said, “licking [his] wounds, and trying hard to figure out what went wrong—and what [he] could have done differently.”
Barack had been warned by Jesse Jackson that the shooting death of Rush’s son was a “game changer,” but Jeremiah Wright told Barack that it was only part of the reason he went down to crushing defeat. The reverend told him that he had jumped the gun, that he hadn’t taken the time to line up enough party leaders to support him. “You were,” he said, “kind of out there on your own.”
That fall, Michelle learned that she was pregnant for a second time. As happy as they undoubtedly were, the news merely reinforced Michelle’s concern about the family’s finances. Even though they were taking home combined salaries of $250,000, for some reason it was not enough for them to pay their bills and keep up with payments on their student loans. Occasionally they were, Barack conceded, “short at the end of the month”—falling behind on various payments and using credit cards to stay afloat.
Michelle worried that, if Barack continued to chase his political dreams at the expense of his family’s finances, they were headed for bankruptcy. “Calm down,” he would tell her. “Things are going to be fine. You worry too much.” Barack believed that differences in both their upbringing and their “wiring” accounted for the fact that she was rife with worry while he remained unfazed. “I don’t get as tensed or stressed,” he pointed out. “I’m more comfortable with uncertainty and risk.”
Michelle needed more than just soothing words from her husband. She pleaded with Barack to think more seriously about making what she called “serious money.”
Instead, he returned to Springfield determined to win over those Democrats who had been reluctant to support him in the past. Chastened, Barack appeared at his first poker game after being trounced by Bobby Rush and, before anyone else could speak, looked around the table, shook his head, and confessed, “I know, I know.” Disarmed by this mea culpa, Barack’s colleagues roared with laughter.
In the coming months, Barack turned down a chance to run for Illinois State Attorney General because he did not want to subject Michelle to another grueling campaign schedule so soon after his ill-fated congressional run. But he spent more time than ever in Springfield, shoring up alliances that would prove valuable in the future.
Of these, none was more important than Barack’s budding personal relationship with the party’s crusty, gravel-voiced Senate leader, Emil Jones. A contemporary of Michelle’s father, Jones had also grown up in the Robinsons’ old neighborhood and worked in Chicago’s sanitation department. His father, like Fraser Robinson, had been a Democratic precinct captain, and Jones had cut his teeth on South Side politics. Building his own organization from the bottom up, Jones was a force to be reckoned with—and after twenty-seven years in Springfield, was poised to take over the Senate once control of the legislature returned to the Democrats.
Even though Jones had supported Bobby Rush, he and Barack remained more than just close allies and friends. Although for years Barack often spoke of Jeremiah Wright as a father figure, he praised Jones as his “political godfather.” After he heard that, Jones began using the theme from the film The Godfather as his cell phone ring tone. “I am blessed to be his godfather,” Jones told a reporter at one point during this period, “and he feels like a son to me.”
With himself strategically positioned in Springfield as Emil Jones’s protégé, Barack also carefully tended to his Chicago connections. Already serving on both the Woods Fund board and the board of the billion-dollar Chicago-based Joyce Foundation, Barack now added the prestigious Saguaro Seminar to his list of obligations. Tackling the amorphous question of how to build “social capital” by getting people more involved in their communities, Barack was joined at the weekend seminars by the diverse likes of Christian conservative Ralph Reed and George Stephanopoulos.
During these meetings—carved from what little time he had to spend with his family—Barack could not conceal his naked political ambition from the other, better-known participants. According to Saguaro founder Robert Putnam, the Harvard professor who wrote Bowling Alone, Obama spoke so openly about his plans for higher office that they began teasing him. “So we were in the midst of one of our intensive discussions about civic engagement,” Barack’s former Harvard Law professor Martha Minow recalled, “and after one of these discussions, ranging across the political sectors, he did this tour de force summary. We just said, ‘When are you running for President?’ It became a joke. We started to nickname him ‘governor.’”
It was no joke for Michelle. The Obamas’ second child was born on June 10, 2001, and once again family friend Anita Blanchard was the attending obstetrician. This time, Barack carried Malia into the room and introduced her to her gurgling baby sister, Natasha. From this day forward, they would call her, simply, Sasha.
Even though the Senate had once again recessed for the summer and Barack was able to spend more time with his family, Michelle was becoming increasingly agitated. “It was hard,” she said. “I was struggling with figuring out how I was going to make it work for me.”
Sasha’s terrifying meningitis scare in September of 2001 brought them closer together emotionally than they had been in years. The horrors of 9/11 continued to make it easier to keep things in perspective. “In the grand scheme of things,” Michelle admitted, “our problems didn’t seem to amount to much.”
Incredibly, September 12, 2001, was business as usual in Springfield, where victorious Democrats gathered in the Stratton Office Building to redraw their legislative districts. Their goal was to give themselves a demographic advantage over their Republican opponents. “It was like nothing had happened,” said John Corrigan, an Obama strategist and the man responsible for redrawing the districts of all incumbent Democrats. “Everybody came in and all they cared about was their districts.”
Barack was not among them; he had attended to this task months earlier, sitting with Corrigan at a computer screen and carefully redrawing his district to include as many influential constituents as possible. “The exposure he would have to some of the folks on the boards of the museums and CEOs of some of the companies that he would now represent,” Corrigan said, “would certainly help him in the long run.”
Barack, already mindful of a larger responsibility to history, was hard at work at home in the Hole, writing his own position paper on the 9/11 attacks. “We will have to make sure, despite our rage,” he wrote in the September 19 issue of the Hy
de Park Herald, “that any U.S. military action takes into account the lives of innocent civilians abroad. We will have to be unwavering in opposing bigotry or discrimination directed against neighbors and friends of Middle Eastern descent. Finally, we will have to devote far more attention to the monumental task of raising the hopes and prospects of embittered children across the globe.”
For a time, it looked as if the 9/11 attacks might also carry with them the seeds of Barack’s political ruin. “My God, Michelle,” he told his wife. “They’re saying Osama Bin Laden planned the attacks. Osama. Jesus…”
Barack valued Michelle’s opinion above all others, in part because, unlike many of his other friends, she pulled no punches. “She’s blunt,” he explained, “so she can tell me things that maybe other people are afraid to tell me.”
In this case, she was not about to reassure him. When she had first heard Barack’s name, she thought it sounded “weird and off-putting.” The similarity between his name and that of a hated international terrorist could not, she told him, be “a good thing.”
Just days after 9/11, Barack went ahead and had a long-ago scheduled lunch with a leading media consultant for Democratic candidates, Eric Adelstein. Both men had been thinking that Barack should consider making a run for statewide office—maybe the U.S. Senate—but now, in Adelstein’s words, the “political dynamics” had changed. “Hell of a thing, isn’t it?” he told Barack as he held up the front page of the Chicago Tribune with Osama Bin Laden’s picture on it. “Really bad luck. You can’t change your name, of course. Voters are suspicious of that kind of thing.”
Barack considered the possibility that, at age forty, he was stopped in his tracks. He looked with envy at younger politicians who, simply by virtue of their names, faced a more promising future.
When Michelle called, near tears, to say that their babysitter had quit to return to nursing, Barack tried to reassure her. “Michelle’s thinking to herself, ‘What am I going to do?’” Barack remembered, “because she had depended so heavily on this person to kind of hold it together. And she was, frankly, mad at me. Because she felt as if she was all alone in this process.”
Barack knew that as long as he stayed in politics the demands on his wife and young daughters would only get worse. Perhaps it was time, he thought, to finally focus on his family—to get that job in the private sector that would finance the cost of child care, private school tuition, and, eventually, college.
It was around this time that he was interviewed for a three-hundred-thousand-dollar-a-year job running the Joyce Foundation, where he had been a board member for seven years. Barack nearly bolted at the last minute; he simply did not want the job.
“What is wrong with you?” Dan Shomon asked when Barack told him how he felt. “This is a dream. You can build up money, build up relationships, and run again.” Michelle’s reaction to the news was one of quiet resignation. She knew all too well that her husband, despite his recent doubts about ever being able to overcome the Osama-Obama curse, was far too ambitious to quit as a mere State Senator.
Barack was no longer certain that his name would keep him from higher office. He had been making inquiries of his powerful, well-connected friends in Chicago—chief among them Mayor Daley—and he was convinced that Illinois’s incumbent Republican Senator, Peter Fitzgerald, was vulnerable.
The Dartmouth-educated scion of a wealthy banking family, Fitzgerald had unseated one-term Senator Carol Moseley Braun in 1998. He repeatedly ran afoul of his own party’s leadership on a wide range of issues, including the authorization of federal funds to build an Abraham Lincoln Presidential Library in Springfield and the fifteen-billion-dollar post-9/11 airline bailout. Fitzgerald was, in fact, the only U.S. Senator to vote against the bailout.
Because of his maverick, go-it-alone stance both in Washington and in Illinois, Fitzgerald’s approval ratings were approaching record lows. GOP leaders were threatening to put up candidates to challenge him in the primaries. Barack was convinced that Carol Moseley Braun’s Senate seat could be reclaimed for the Democrats in 2004—and that he was just the man to do it.
“I want to be a Senator,” Barack told his friend and Michelle’s former boss Newton Minow.
“But you are a Senator,” Minow replied.
“I mean a U.S. Senator,” Barack said.
Minow didn’t take much convincing. “Chief Justice Oliver Wendell Holmes once described Franklin Roosevelt as having ‘a first-class temperament and a second-class intellect,’” Minow said. “Barack has a first-class temperament and a first-class intellect. It was a very, very, very long shot. But I told him to go for it.”
Few others were as encouraging. Marty Nesbitt, Valerie Jarrett, Jeremiah Wright, most of his poker-playing friends in Springfield—even the heavy-hitting fund-raisers, academics, foundation board member types, and Lakefront liberals who for years had been kidding him about running for President—seemed taken aback by his chutzpah. A few, including Nesbitt, actually laughed in his face.
Gradually, however, he managed to persuade them that he could mount an effective campaign—provided he could find a way to raise ten million dollars. With that kind of backing, which he believed he could raise from the well-heeled friends he had cultivated for years, he insisted, “I guarantee you I will win.”
There were those, even among his supporters, who felt the former president of the Harvard Law Review might not be enough of a street fighter to win a knock-down, drag-out U.S. Senate race. “I’ve seen a lot of tough guys get knocked down and stay down,” Denny Jacobs said. “I’ll take the resilient guy who gets knocked down and gets right back up. It’s going to be the hardest thing in the world to defeat Barack Obama. He just keeps getting right back up.”
While nearly everyone thought Barack was at best a long shot (“I remember thinking he had a snowball’s chance in hell,” Toni Preckwinkle said), several friends appealed to him to reconsider for strictly personal reasons. Dan Shomon knew that Barack already felt “tremendous guilt” over not spending more time with his children. “It burns a small hole in his heart,” he said, “every night when he is not with them.”
“You will destroy your marriage,” another friend told him. “Look what you’ve put Michelle through already. She is really pissed off at you as it is. Don’t do this.”
Barack turned steely. “I’ve made up my mind,” he said. “I’m running.”
He would, of course, be far more diplomatic when broaching the subject with his wife. “Politics has been a huge strain on you,” he told Michelle, “but I really think there is a strong possibility that I can win this race…if you are willing to go with me on this ride, and if it doesn’t work out, then I will step out of politics.”
Michelle studied his face. “Just this one last time,” he pleaded. “I think I can do this…. Just give me one more shot. It’ll either be up—or out.”
At this point, Michelle was primarily concerned with one thing: “How are we going to make it—I mean, financially?” she asked. They were still deeply in debt—in part due to his failed congressional race two years earlier. If he lost, that debt would deepen. In the unlikely event that he won, then they would have two residences to maintain—one in Chicago and one in the nation’s capital. “It’s just killing us,” she told him. “How will you afford all this?”
“I guess,” Barack replied matter-of-factly, “I’ll just have to write another book.”
Michelle, aware that his first book had taken Barack five years to write and wound up selling a modest ten thousand copies, shook her head in disbelief. “Oh, another book…. Snake eyes there…yeah, you just go ahead write that book, Jack.”
Then Michelle collected her thoughts and sighed. “Okay,” she said. “Whatever.”
Barack looked at her quizzically. “Okay?” he asked.
“Yeah, we’ll figure it out,” she said with a shrug. “We’re not hurting. Go ahead.” Barack waited for the inevitable zinger. “And,” she said, grinning, “mayb
e you’ll lose.”
Michelle had, in fact, found a way to come to terms with the “huge strains” Barack’s political ambition had taken on their marriage. “This was the epiphany,” she later recalled. “I am sitting here with a new baby, angry, tired, and out of shape. The baby is up for that four o’clock feeding and my husband is lying there, sleeping.” It was then that she realized if she simply left the condo at 4:30 A.M. and went to the gym for her workout, Barack would have “no choice but to get up.”
The first time she disappeared after Sasha’s 4 A.M. feeding, Barack didn’t notice until 8 A.M., when he finally stumbled out of bed and realized he’d been left in charge of the kids. From that point on, whenever Barack was in town, Michelle tiptoed out of the apartment before sunrise, headed for a workout with her personal trainer. “I would get home from the gym, and the girls would be up and fed,” she recalled. “That was something I had to do for me.”
It was then that Michelle made the conscious decision that she would be the one to adjust to the circumstances he created—and not vice versa. “The big thing I figured out was that I was pushing to make Barack be something I wanted him to be for me,” she explained. “I believed that if only he were around more often, everything would be better. So I was depending on him to make me happy. Except it didn’t have anything to do with him. I needed support. I didn’t necessarily need it from Barack.”
Michelle decided to approach the problems in her marriage the way she would approach the problems she faced daily at work. “I had to change,” she said. “So how do I stop being mad at him and start problem solving, and cobble together the resources? I also had to admit that I needed space and I needed time. And the more time that I could get to myself, the less stress I felt.”
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