Hildebrand had not even seen Obama’s 2004 convention keynote. A few months before the steak fry, in fact, he had met with Hillary and offered to work for her—but she brushed him off. Hildebrand returned to South Dakota and grew angry at what he saw as Clinton’s weaseling over the Iraq War. So when Rouse asked him to accompany Obama to Harkin’s event, Hildebrand was game. He knew that his presence in Iowa at Obama’s side would set off alarm bells in the political sphere, that he was being used as a tool. The Obama people are fucking with the Clintons, he thought. And that was just fine with him.
The scene that greeted Obama in Indianola was pure pandemonium. Nearly four thousand people showed up that day at Balloon Field; for a typical steak fry, the number was fifteen hundred. The crowd had its share of college kids from Drake and Iowa State, and was so thick on the ground and eager to get close to Obama that he could barely move. His speech never quite gelled, but the crowd didn’t seem to notice. Afterward, as Obama made his way down an endless rope line, with cameras capturing his every move, fans thrust copies of Dreams from My Father at him to autograph. “Thank you for giving us hope,” one person told Obama.
Hildebrand was thunderstruck. It reminded him of the images of the Clinton-Gore bus tour after the convention in 1992—the rabid, spontaneous enthusiasm, the palpable sense of connection, the future-is-nowness of it. As they walked to the parking lot afterward, he asked Obama, “How do these people know so much about you?”
“I don’t know. The convention speech, and then it just grew from there.”
“Is it like this in other places?”
Obama shrugged and said, “It’s like this everywhere we go.”
The following morning, Hildebrand received an email from Solis Doyle: “Saw your name in The New York Times. Hope you don’t make any decisions before we have a chance to talk.”
Hildebrand laughed. Hillary Clinton? Please. His decision was already made. He would do whatever it took to get Obama in the race, then elect him president.
THE OBAMA BOOK TOUR was purposefully structured to approximate the rigors of a presidential campaign. Gibbs wanted to give his boss a taste of what nonstop life on the road would be like. Each day of the tour would be in a different city and have three elements: a book signing, a political event, and a thank-you get-together for his donors. Because Obama had missed his deadline repeatedly, the publication date of The Audacity of Hope had been pushed back to October 17, shortening the tour to just a week—and also putting the book in direct competition with John Grisham’s first nonfiction opus, The Innocent Man, which hit the shelves the same day. The Grisham title entered the bestseller lists at number one, with Obama’s at number two. When Obama learned of the rankings, he was peevish, a little whiny. “But I want to be number one,” he complained.
In Chicago, Jarrett threw Obama a book party at the home of her parents. It was pouring rain, and despite a tent in the backyard and umbrella-toting underlings, many of the attendees got soaked, their shoes ruined by the mud. Jarrett introduced Obama and spoke about Audacity’s final chapter, in which he wrote about the stress that the demands of his career put on his marriage, the disruptions to his family life. As Jarrett went on, talking about the sacrifices his wife and girls were making, she saw that Obama was crying—to the point where he couldn’t manage to speak when it came his turn. Michelle walked over, put her arm around him, and began to cry as well.
Even Obama’s closest friends had never seen him choke up in public before. He’s not emoting about the past, Jarrett thought. He’s emoting about the future. About the fact that the sacrifices he’s imposed on his family are only just beginning.
On October 22, Obama returned to Tim Russert’s set for another appearance on Meet the Press. The day before, he’d ridden down from Philadelphia in a limousine with Axelrod and Gibbs. Axelrod warned Obama that Russert would surely revisit his unequivocal reaffirmation from earlier that year that he would “absolutely” not be on the national ticket in 2008. It took no great genius to see the question coming: Obama’s face was on the cover of that week’s Time, beside a headline that read “Why Barack Obama Could Be the Next President.” Axelrod, impersonating Russert, intoned, “And so, Senator, here’s the tape. Is that still your position?”
Here was the question that had tied Hillary Clinton in knots in 2003, that twelve years earlier had caused her husband to stage a contrived tour around Arkansas to solicit a release from his pledge not to run for president. But Obama hardly gave the conundrum a moment’s thought. He couldn’t see any point in shilly-shallying over what was patently true. “I’m gonna tell him no,” he said to Axelrod and Gibbs. “I think it’s best to say I’m reconsidering.”
A few minutes later, Obama was on the phone with Michelle. Following previous orders, Gibbs whispered urgently, “Tell her about tomorrow!” But Obama already had. Michelle wasn’t pleased with what her husband planned to say—she had serious doubts about the notion of a presidential bid—but she was under no illusions about what was going on inside her husband’s head.
Obama’s new answer on Meet the Press—Russert: “It’s fair to say you’re thinking about running?” Obama: “It’s fair, yes”—set off a firestorm in the press, all right. A firestorm of febrile excitement over the possibility that he was running, and of analysis about what it might mean and how it might play out. Few in the media seemed to notice or care that Obama had broken his pledge, preferring instead to praise his candor.
With Obama now leaving the door ajar (even if only “a bit,” as he said on the air), an even greater frisson suffused his homestretch campaigning in the two weeks before the midterms. He was often doing four events a day, hopscotching from state to state to raise last-minute cash for incumbents and challengers alike. The punishing schedule made Obama grouchy. “Why the fuck am I going to Indiana?” he squawked to Hopefund’s political director, Alyssa Mastromonaco.
“There are three candidates, and they’re running out of money. If we can go and raise $200,000 at this fund-raiser, we’ll keep them on the air through Election Day,” she retorted.
“Really?” Obama asked skeptically, but then agreed to go. (All three candidates won.)
On the Sunday before the midterms, Obama attended church in Tennessee with Democratic congressman Harold Ford, Jr., the African American Senate candidate there, whose campaign had been rocked by a negative TV ad that fanned fears of miscegenation, a reminder to Obama that race was still a combustible electoral factor. He did stops in Illinois, Ohio, and Iowa—where Hildebrand could be found handing out hundreds of unauthorized “Obama for President” buttons that he’d had made up—and traveled to St. Louis to campaign for Claire McCaskill.
At that last stop, thousands of people lined up for hours outside the World’s Fair Pavilion to hear Obama speak. Among those onstage was former Missouri senator Tom Eagleton, who had briefly been George McGovern’s running mate in 1972 and was among the party’s most beloved figures. Dressed in yellow pants and a green crew-neck sweater, Eagleton was nearly eighty years old and in poor health; this would be his last major public appearance before his death.
But Eagleton desperately wanted a gander at Obama. When the event was over, he approached McCaskill and marveled, “I haven’t seen people want to touch someone that way since Bobby Kennedy.”
ON NOVEMBER 8, the day after the Democrats routed the congressional GOP, retaking control of Congress and repudiating George W. Bush, Obama drove to the brick building in the River North neighborhood of Chicago that housed the offices of Axelrod’s consulting firm. He was there to have a private lunch with Bill Daley. Daley was the seventh and youngest child of the storied Chicago mayor Richard J. Daley; his brother, Richie, currently occupied City Hall. A banker now, Bill Daley had served as the secretary of commerce in Bill Clinton’s second term. Daley knew the Clintons well—how ruthless they were, how crazy their world was, and how vulnerable Hillary might be to the right kind of nomination challenge.
All of which was w
hy Obama was meeting Daley that day. The midterms were past, it was time to get serious about “the options,” and Obama wasn’t wasting a moment. “Yeah, you gotta run,” Daley told him right off the bat. “Why not? What have you got to lose? Can you win? I think you can. You know, who knows? You don’t know, but why wouldn’t you? What’s the negative here? What are you gonna wait for?”
Obama brought up the issue of money: Could he raise enough to be competitive? “I don’t think money’s your problem,” Daley said. Judging by his performance the past two years, Obama was a money magnet, and one who might be able to change the game by tapping into small donors to an unprecedented degree. Daley, in fact, suggested that Obama could afford not to rush into the race. Maybe he should take a little more time, prepare himself better for what a challenge to Hillary would entail.
“You don’t understand,” Daley said. “Running around doing fundraisers for other people is not running for president. These people, the Clintons, for thirty-five years, this is what they do. You’ve done this now for a couple of years. This is their life. This is, like, 24/7 for them. Hillary knows where she’s going for lunch next March, okay? It’s a very different thing here.” What Daley was thinking was, Be ready, because the shit’s gonna come at you big-time.
Daley was struck by how much consideration Obama already seemed to have devoted to his hypothetical candidacy. To the suggestion that he hang back, Obama responded that he didn’t have the luxury of time; if he dawdled, Hillary would lock up too many big donors and key operatives. Obama was clear about something else, which also struck Daley—for its chutzpah.
“If I can win Iowa,” Obama said, “I can put this thing away.”
Yet for all his bravado, Obama was still ambivalent about getting into the race, for reasons personal and political. The personal ambivalence was complex and nebulous, but could be resolved down the road. The political ambivalence was more pressing and revolved around one question: Could he and his advisers chart a plausible pathway to victory?
The cartographic endeavor began in earnest a few hours after his lunch with Bill Daley ended. The setting was the same: the fourth-floor conference room in Axlerod’s office. On the table were cookies, bottled water, and soda. Around it were the members of Obama’s personal and professional brain trust: Michelle, Jarrett, and his close friend, Marty Nesbitt; Axelrod, Gibbs, Rouse, Mastromonaco, Hildebrand, and Axelrod’s business partner, David Plouffe. Over the next few hours, Obama received from the group what amounted to a crash course: Presidential Politics 101—the logistics, the mechanics, the calendar, how the whole thing worked. His knowledge about the topic was limited (alarmingly so, thought some at the table), his initial questions rudimentary. How much of his time would be required? How often would he be on the road? Michelle asked if he could come home every weekend—or at least every Sunday—to be with his family.
“Yes, he can have Sundays off,” Hildebrand blurted out.
Bullshit, thought Mastromonaco. Crazy, thought Gibbs. Almost to a person, the Obama brain trust was determined that their boss understand how hard running for the White House would be, that none of the bitter realities of the process be sugarcoated. Axelrod and Rouse had long wondered if Obama had the requisite inferno raging in his belly. They wanted him to enter the race eyes wide open, both for his own sake and so there would be no recriminations later.
Hildebrand didn’t care one whit about raising Obama’s consciousness. He wanted him, needed him, to run. He was so enamored of Obama that he was willing to say just about anything to get him in, no matter how nonsensical. Sundays off? Sure! We’ll do things differently, we’ll use the Web, we’ll make it work, he assured Obama.
No, we won’t, Plouffe cut in. And no, you can’t come home on Sundays.
Rail-thin, pretense-free, incapable of artifice, Plouffe had run winning campaigns at the senatorial, congressional, and gubernatorial levels, as well as worked on two prior presidentials. He knew the score. You have two choices, he told Obama. You can stay in the Senate, enjoy your weekends at home, take regular vacations, and have a lovely time with your family. Or you can run for president, have your whole life poked at and pried into, almost never see your family, travel incessantly, bang your tin cup for donations like some street-corner beggar, lead a lonely, miserable life.
That’s your choice, Plouffe explained. There’s no middle ground, no short cuts—especially when you’re running against Hillary Clinton.
The estimability of the putative Clinton endeavor hovered over the discussion, weighing on Obama. But the people around the table were no rookies at this game; if you had to start from scratch, they were among the best in the business to start there with. Their attitude toward the Clinton machine was clinical and uncowed. The machine was real, but it could be broken down into two constituent parts: personnel and money. Axelrod assured Obama that there were plenty of top-flight players in the party who wouldn’t be working for Hillary, especially in the four states that would kick off the nomination contest: Iowa, New Hampshire, Nevada, and South Carolina.
Iowa loomed large in Axelrod’s mind. Twenty years earlier, when he worked for Paul Simon’s underdog campaign, the Illinois senator lost the caucuses to another candidate from a neighboring state, Missouri congressman Dick Gephardt, by just one percentage point. The lesson for Axelrod was that proximity mattered; that having Chicago as his home base would allow Obama to penetrate Iowa more readily and thoroughly than his would-be rivals, including Clinton. Focusing on Iowa and the other early contests also addressed the second of Hillary’s advantages. Though she would likely raise a ton of dough, nobody doubted that Obama could come up with enough to match her in the first four, modest-sized, states.
Obama himself had been fixated on Iowa since the steak fry. He had a good feeling about the place, but that wasn’t enough. If the Hawkeye State was going to be so crucial to his chances, he wanted details. Much of November would be spent gathering them, with Hildebrand quietly dispatched to Iowa to do reconnaissance.
One night later that month, Hildebrand’s phone rang in Sioux Falls, waking him from a sound sleep. Obama was on the line. For the next forty-five minutes he quizzed Hildebrand about every conceivable Iowa-related topic: how he would fare against Edwards in rural counties; the impact of media coverage spilling over from Illinois into the Iowa communities along the Mississippi River; which local officials they could expect to bring on board as endorsers. Hildebrand told him that he, Michelle, and the girls would all have to spend a lot of time in Iowa—and also that the catalyst for winning there would be bringing new voters into the process. If we run a traditional campaign, Hildebrand said, we’re doomed.
Axelrod had a complementary view, which he laid out for Obama. In every election, Axelrod argued, the incumbent defines the race, even if he isn’t on the ballot. Which meant 2008 was going to be defined by Bush. And given the enmity that the president had inspired in the Democratic Party, Axelrod went on, the overwhelmingly liberal primary and caucus electorate would be hungry for a candidate representing the sharpest possible departure from 43: one who promised to be a unifier and not a polarizer; someone nondogmatic and uncontaminated by the special-interest cesspool that Washington had become; and, critically, someone seen as a staunch and principled opponent of the war raging in Iraq. Now, who had a better chance of being that someone—Hillary or Barack? The question answered itself.
Axelrod’s contention was bolstered by a conversation that Obama had with Rahm Emanuel. Emanuel, an Illinois congressman and another of Axelrod’s clients, was one of the shrewdest and most aggressive pols of his generation. He was also a veteran of the Clinton White House, intimately aware of how the former First Couple operated. They’re gonna do what they gotta do to win—and this is not patty-cake, Emanuel told Obama. But could they be had? They could be had. There’s a soft underbelly with them.
The contours of Hillary’s vulnerabilities were revealed in detail by polling and focus group testing in Iowa that the Obama brai
n trust secretly commissioned a few weeks later, near the end of 2006. Though the polling put Obama in third place behind Edwards and Clinton, he was within striking distance of both. Not bad, considering that Edwards had been practically living in Iowa for two years already and that Clinton was . . . well, Clinton.
More striking were the focus groups, which were conducted in Des Moines and Cedar Rapids. Almost uniformly, the people in the groups reacted favorably to Obama—to his 2002 speech opposing the war, his rhetoric of change and unity, his freshness and sense of promise. Rarely did they express grave misgivings about his race or his exotic background. The more they knew about his biography and bearing, the more they liked him. In one of the sessions, after watching a video clip of Obama, a white woman said, “There’s something about that guy; that’s the guy I want. I can’t even put it into words.”
Observing from behind a two-way mirror, Axelrod was floored. “We can’t forget that woman,” he said to his colleagues. “We have something special here. I feel like I’ve been handed a porcelain baby”—something very, very precious, but very fragile.
The results of the focus groups were equally encouraging when it came to Clinton. She was well known, well liked, and well respected, but inspired nagging doubts. She registered with participants as status quo, as the past and not the future; she stirred up memories of the partisan bickering of the nineties, the Clinton-Gingrich contretemps, Monica, and impeachment. Her standing among women was much stronger than it was among men, but there was no sweeping feminist imperative to support her. “I do want a woman to be president of the United States,” one female voter said, “but not this one.”
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