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Authors: John Heilemann

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Reines read her the quote verbatim: “I think he’s been a great leader, but I don’t want my daughter near him.”

The phone went quiet. Hillary was speechless. A few more seconds passed, and then finally came her voice, hot with fury.

“Fuck her,” Hillary said—and then called Solis Doyle and summarily canceled the fund-raiser.

MCCASKILL WOULD AGAIN APOLOGIZE to Hillary and Bill, writing them letters, begging their forgiveness and forbearance. What she said had been stupid, hurtful, insensitive. But the truth was that McCaskill meant it, just as she’d meant her earlier prediction of the damage to Democrats across the country if Hillary won the nomination. McCaskill was in the market for a different horse—and now, like many other Democrats, she thought she saw one in Obama.

Inside Hillaryland, the notion that Obama might enter the race seemed remote to almost everyone. Harold Ickes, a fabled Democratic operative and longtime adviser to the Clintons, was so dismissive of the idea that he offered to bet Solis Doyle $50,000 that it would never happen. Penn, too, was sure Obama would stay out; that was the skinny he was hearing from inside the Illinois senator’s orbit.

Hillary, for her part, had no idea what Obama would do, though she knew that he wouldn’t be swayed by the argument that his experience was insufficient. “No one ever thinks they don’t have the experience to do this,” she told one of her aides. “No one thinks that way. He wouldn’t have gotten to this point and then said, ‘Oh, I don’t have the experience.’ You don’t think about your weaknesses. You think about your strengths.”

But Obama’s strengths didn’t strike her as especially intimidating, and whether he took his weaknesses seriously or not, they were many and glaring. Sure, he had a great deal of potential, but it was just that—potential. He had no fund-raising network, no tangible accomplishments in the Senate. The speeches he gave—oh, they were pretty, but so what?
You don’t change people’s lives with words
, Hillary thought.
You change them with committed effort, by pushing through the opposition. You change them with a fight.
That was how you won elections, too. With a fight. In his entire career, Obama had yet to be hit with a single negative ad. How would he ever withstand the sheer, unrelenting hell of a presidential race: the constant pummeling by his opponents, the withering scrutiny and X-ray intrusions of the media?

But even as most of Clintonworld dismissed Obama, one dissenter stewed. All that talent. The antiwar credentials. The desire for something different in the country. The combination could be deadly, Bill Clinton kept saying. This guy could be trouble.

OBAMA FLEW OUT OF Washington on August 18, 2006, and arrived the next morning in Cape Town, South Africa, to start his two-week tour of the continent—and the two-and-a-half-month rocket ride that would carry him to the day of the midterm elections. “Rocket ride” was Gibbs’s term, and he wasn’t exaggerating. The period would include the publication of Obama’s second book,
The Audacity of Hope
, the national book tour to publicize it, and a marathon stretch of campaigning for Democratic candidates from coast to coast. Everyone around Obama understood that the interval would be pivotal to his decision about running for president, which he had consciously put off until November. But most of them assumed that in the end, however tempting he found the idea, practicality would prevail.

The Africa trip turned out to be a revelation for both Barack and Michelle. The last time he had been there was fourteen years earlier, with a pack on his back and not much more than a packet of cigarettes in his pocket. Now, from Chad to Ethiopia to Djibouti, and especially in his father’s Kenyan homeland, he was treated like a head of state—or Muhammad Ali in Zaire for the Rumble in the Jungle. In Nairobi, thousands lined the streets and stood on rooftops chanting, “Obama biro, yawne yo!”—“Obama’s coming, clear the way!” The crowds were bigger than any he had experienced since the Democratic convention, but unlike that audience, the African throngs were there for him and him alone. Michelle found the spectacle discomfiting. “Part of you just wants to say, ‘Can we tame this down a little bit?’” she said at the time. “Does it have to be all this? This is out of hand.”

But what Michelle saw as overwhelming, her husband viewed as possibility. He began to entertain the notion that he’d tapped into something remarkable; that by virtue of what he represented, he might be able to effect change on a global scale. It was heady and humbling at the same time, nothing short of an epiphany.

When Obama got home, he had one event on his calendar before the madness of the book tour began: the 29th Annual Harkin Steak Fry. And in its way, it was an even bigger deal than the Africa trip. Taking place every September in Indianola, Iowa, the steak fry was a political fair sponsored by Senator Tom Harkin and attended by hundreds of the state’s hardcore Democratic activists—and was thus a coveted speaking venue for any aspiring presidential candidate. Eager to avoid an awkward choice between Clinton, Edwards, Warner, or Vilsack, Harkin offered Obama the keynote slot on the assumption that he wasn’t running. Obama’s advisers were fully aware that if he accepted, the political world would erupt with speculation about his intentions.

“You have to understand what this is going to indicate to a lot of people,” Gibbs told Obama, in a meeting with the senior staff. “They’re going to think you’re running.”

“I understand,” Obama said.

The truth was, he was ready to stir the pot. Going to the steak fry didn’t commit him to anything. The media might whip itself up, but attending the event would let him take the temperature of Iowa activists—another important data point for decision time after the midterms. Obama was intent on not being sloppy about it, not showing too much or too little leg. “If we’re gonna do this, we have to do it right,” he said, then glanced around the room. In case he wasn’t being sufficiently clear, he added, “Don’t fuck this up.”

Obama, though, was the one to blunder. After the press reported that he’d agreed to keynote the steak fry, Michelle’s phone started ringing off the hook, with people calling about her husband’s first foray into Iowa. But Michelle was totally in the dark—and now steamed at him. Obama walked into his Senate office looking sheepish.

“Next time I decide to make a big announcement,” he said to Gibbs, “would you remind me to tell Michelle?”

Not screwing up the steak fry itself would require staffing Obama well. And Pete Rouse had an idea—one that made sense on the merits and was sure to draw attention. They would add Steve Hildebrand to Obama’s traveling party.

Among Democratic insiders and political reporters, Hildebrand was renowned. A grassroots-organizing savant with close ties to three foundational Democratic factions—women’s groups, gay activists, and labor—Hildebrand was yet another former Daschle staffer, which was how he and Rouse were friends. But his claim to fame was having helped deliver the Iowa caucuses for Al Gore in 2000. Goateed, tattooed, and openly gay, Hildebrand was the rare top-shelf national operative who lived outside the Beltway (and way outside, in Sioux Falls, South Dakota). Even rarer, he was passionate about issues and had a romantic streak about politics as wide and verdant as a Paris boulevard.

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 why 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.

BOOK: Game Change
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