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There was something fitting about the outcomes in Iowa for both parties: the element of surprise, the fundamental way they shifted and shaped the contours of the race ahead. Every presidential contest has its twists and turns, each consequential to some degree. But the 2008 election was a campaign defined by big events, startling revelations, and unexpected episodes that again and again threatened to turn everything on its head. The Reverend Jeremiah Wright. Bill Clinton’s outbursts in South Carolina. Allegations about troubles in the McCain marriage. The epic crisis of the global financial system. The mesmerizing, confounding, deeply polarizing emergence of Sarah Palin. Palin’s public travails and private nightmares, and the unprecedented steps the McCain team took to cope with their superstar. All developments so extravagant and dramatic that they seemed like elements borrowed from a Hollywood screenplay.
And that was fitting, too. More than any election in memory, 2008 was a battle in which the candidates were celebrities, larger-than-life characters who crashed together to create a story uncommonly emotional for politics; a drama rich and captivating and drenched in modern complexities surrounding race, gender, class, religion, and age; a multimedia spectacle that unspooled 24/7 on the Web, cable television, the late-night talk shows, and Saturday Night Live. The drama played out against a backdrop that was itself vividly cinematic: a country at war, an economy on the brink, and an electorate swept up, regardless of party, in a passionate yearning for transformation.
Out in Iowa that January, however, precious little of this was clear. What the candidates knew was that for months, and even years, they’d been working toward that night, positioning, strategizing, calculating. They’d been traversing the country, raising money and cajoling local pooh-bahs, shaking hands and smooching babies. They had no idea what would happen next, where the narrative would take them. Indeed, for Obama and Clinton, the confusion was deeper still: they had no clue that their tale was a love story—or that it had been all along.
PART I
Chapter One
Her Time
THERE WERE THUNDERSTORMS IN Chicago, bringing air traffic to a grinding halt in and out of O’Hare. So Hillary Clinton sat on the tarmac at Martin State Airport, outside Baltimore, eating pizza and gabbing with two aides and her Secret Service detail on the private plane, waiting, waiting for the weather to clear so she could get where she was headed: a pair of fund-raisers in the Windy City for Barack Obama.
It was May 7, 2004, and two months earlier, the young Illinois state senator had won a resounding, unexpected victory in the state’s Democratic United States Senate primary, scoring 53 percent of the vote in a seven-person field. Clinton, as always, was in great demand to help drum up cash for her party’s candidates around the country. She didn’t relish the task, but she did her duty. At least it wasn’t as painful as asking for money for herself—an act of supplication that she found so unpleasant she often simply refused to do it.
As the wait stretched past one hour, and then two, Clinton’s pilot informed the traveling party that he had no idea when or if the plane would be allowed to take off. To the surprise of her aides, Clinton displayed no inclination to scrap the trip; she insisted that they keep their place in line on the runway. The political cognoscenti were buzzing about Obama—his charisma and his poise, his Kenyan-Kansan ancestry and his only-in-America biography—and she was keen to do her part to help him.
“I want to go,” she said firmly.
By the time Clinton finally arrived in Chicago, she had missed the first fund-raiser. But she made it to the second, a dinner at the Arts Club of Chicago, where Barack and Michelle greeted her warmly, grateful for the effort that she’d expended to get there. For the next hour, Clinton worked the room, charming everyone she met, regaling them with funny yarns about the Senate. Then she and Obama raced off to the W Hotel and spoke at a Democratic National Committee soiree for young professionals. The house was packed, Obama rocked it, and Hillary was impressed.
These people know what they’re doing, she said to her aides—then flew back east and gushed about Obama for days. He was young, brainy, African American, a terrific speaker. Just the kind of candidate the party needed more of, the kind that she and Bill had long taken pride in cultivating and promoting. Clinton told Patti Solis Doyle, her closest political aide and the director of her political action committee, HillPAC, to provide Obama with the maximum allowable donation. And that was just the start: in the weeks ahead, Clinton would host a fund-raiser for him at her Washington home, then return to Chicago to raise more money for his campaign.
Clinton’s aides had never seen her more enthusiastic about a political novice. When one of them asked her why, she said simply, “There’s a superstar in Chicago.”
POLITICAL SUPERSTARDOM WAS A phenomenon with which Hillary Rodham Clinton was intimately familiar, of course. She knew the upsides and downsides of it, the pleasure and the pain, as well as anyone in American life. For more than a decade she had been in the spotlight and under the microscope ceaselessly and often miserably, and in the process came to dwell on a rarified plane in the national consciousness: beloved and detested, applauded and denounced, famous and infamous, but never ignored.
Now, at fifty-six and in her fourth year in the U.S. Senate, Clinton was still the bete noire of the Republican right. But she was also one of the most popular Democratic politicians in the country—more so than her party’s presidential nominee, John Kerry, and more so than her husband, whose public image was still in rehab after the Monica Lewinsky imbroglio and the Marc Rich pardon scandal.
The trajectory that delivered Hillary to this place was remarkable in every way. In the White House she had been, from the start, a profoundly polarizing presence. (Much to her bafflement, too; what she’d done to provoke such a lunatic corps of haters was a mystery to her.) Her time as First Lady was marred by a horrid cascade of defeats, humiliations, and conspiracy theories: health care and cattle futures, Vince Foster and Whitewater, Lewinsky and impeachment. Yet somehow Hillary emerged from all of it a larger, more resonant figure. The Lewinsky affair, for all its awfulness, marked a turning point, rendering her sympathetic and vulnerable-seeming, a woman who had behaved with dignity and fortitude in the most appalling circumstances imaginable. Her decision to run for the Senate in New York in 2000 went against the advice of many of her friends; some political prognosticators predicted confidently that she would lose. Instead, she won the race in a canter, by a thumping twelve-point margin. Weeks after Election Day, Simon and Schuster agreed to pay $8 million for her memoirs, at the time the second-biggest advance ever for a nonfiction tome (just slightly less than the sum handed to Pope John Paul II). But when the book, Living History, was published in June 2003, it earned back every penny, selling out its first printing of 1.5 million copies and then some. And the tour to promote it was a sensation, with her fans camping out overnight to get her autograph and the media comparing her to Madonna and Britney Spears.
The Simon and Schuster paycheck allowed Hillary and Bill to buy her dream house in Washington, a $2.85 million, six-bedroom, neo-Georgian manse that was nicknamed after the leafy, secluded street on which it sat: Whitehaven. But Living History did more than that. It sparked the beginning of a flirtation with the idea of running for president in 2004—a flirtation at once serious and so shrouded in secrecy that even the best-informed Democratic insiders knew nothing about it.
It was the book tour that got the ball rolling inside Clinton’s head. Everywhere she went, people kept telling her she should run, that she was the only Democrat with a hope of defeating George W. Bush. And not just people, but important people—elected officials, big-dollar donors, Fortune 500 chieftains. They were in a panic about the party’s extant crop of candidates: Kerry was in single digits in the polls and so broke he would have to lend his campaign money; Dick Gephardt was past his sell-by date, John Edwards was an empty suit, Joe Lieberman a retread. The only one catching on was former Vermont governor Howard Dean, whom the party
bigwigs saw as too hot, too left, and too weak to stand a chance in a general election.
Hillary agreed with all of that, especially the part about Dean’s unelectability. The Bush machine would chew him up and spit him out, then trample on his remains. She also knew that every public poll with her name in the mix had her within striking distance of the incumbent—and trouncing everyone in the Democratic field by thirty points. Oh, sure, her name recognition accounted for much of that lead. Even so! Thirty points! Without lifting a finger!
Hillary was aware, too, that the notion of her running was gaining traction within Clintonworld. For weeks that summer, Steve Ricchetti, who had served as Bill’s deputy White House chief of staff and remained one of his closest political hands, could be heard arguing to anyone in earshot that Hillary faced a Bobby Kennedy moment—in which a terrible war, a torn electorate, and a president who had squandered his chance to unify the nation presented a historic opportunity. Maggie Williams, Hillary’s former White House chief of staff and a paragon of caution, was open to the idea; she saw the nomination and the White House there for the taking. Solis Doyle was more than open: She’d been posting to the HillPAC website a stream of emails from supporters begging Hillary to get in. And now Patti was telling her boss that Mark Penn and Mandy Grunwald said that if Clinton was considering entering the race, some systematic steps were in order, and they were ready to help her take them.
Hillary was surprised. Though both Penn and Grunwald were longtime members in good standing of the Clinton high command, they were currently working on Lieberman’s campaign, Penn as its pollster and Grunwald as its media consultant.
“You know how terribly unethical this is?” Solis Doyle said to Clinton.
Of course she did—but Hillary was interested in their pitch, and she couldn’t help but love the loyalty and devotion it showed to her cause.
Between the public polls and the shenanigans on the website, speculation in the media was mounting about a Clinton bid. Hillary’s public posture was unwavering: not gonna happen. At the New York State Fair in Albany that August she told an Associated Press reporter, “I am absolutely ruling it out.”
But in private, Clinton appeared to be inching closer to ruling it in. Over the next three months, she and her inner circle engaged in a series of closed-door meetings and conference calls to explore the possibility in detail. Even as Penn remained on Lieberman’s payroll, Clinton dispatched him to do a hush-hush poll of voters in Iowa, New Hampshire, and nationwide. (The results did nothing to discourage her.) She enlisted John Hart, a veteran of Bill’s 1992 campaign, to analyze the logistics of a late entry: the filing deadlines, the feasibility of securing sufficient delegates to claim the nomination. (Tough, but doable.) She tasked her message team with devising an answer to explain away the abandonment of the pledge she’d taken during her Senate campaign to serve out her full six-year term. (The circumstances in the country were so extraordinarily dire that she was compelled to run.)
In the end, nearly all her advisers were in agreement: She should do it. Because there was an opening. Because she could win. Because, as Solis Doyle told her, “This could be your time.”
But Clinton was not a woman swayed by dreamy exhortations to seize the moment. She was a rationalist, an empiricist, with a bone-deep instinct to calibrate risk and reward, and a highly developed—maybe overdeveloped—sixth sense about the trapdoors that might lie ahead.
Clinton took her full-term pledge seriously; it was essential to how she had earned the trust of New York voters. Yes, her husband as governor had made a similar vow to the people of Arkansas, then cast it aside before his 1992 presidential race on the grounds that the country’s need for him outweighed the sanctity of his promise. But Hillary worried about betraying the constituents who had given her a home. She also worried about the political price she would pay for doing so. Wouldn’t she get hammered for being dishonest, being cynical, being a rank opportunist? For being . . . well, everything her enemies had said she was lo these many years?
And then there was the possibility that she would lose. The Senate seat gave her a political identity that was distinct and separate from her husband’s. If she ran for president now and lost, she’d be done and dusted in the Senate, she thought. The platform that made her more than just a former First Lady would be undermined.
On the other hand, the potential rewards were obvious, both for her and for the country. The prospect was nearly irresistible: another chance for a Clinton to expel a failed Bush from the White House.
Hillary valued what her team had to say about all this, but she didn’t completely trust it. They had no idea what it was like to be her. Ambition and caution were the twin totems of her psyche, and she was torn between them. She needed more data, more input, more advice—though she was loath to widen the circle much, for fear of the story leaking.
One day late that fall, Clinton summoned James Carville, the architect of Bill’s victory in 1992, to her Senate office. Hillary adored James, had no doubt about his allegiance or discretion—although she hadn’t looped him in until now. Having advised against her Senate run, Carville was feeling a little gun-shy, so the counsel he offered was hedged. But Hillary seemed to have the bit between her teeth. I think I can do this, she said. None of these guys who are in the race can beat Bush, and I think he can be had.
Carville sat there thunderstruck. When the meeting was over, he walked out the door and thought, Shit, she may run!
Clinton also put in a call to her old friend Tom Vilsack, the governor of Iowa. On November 15, she was scheduled to visit Vilsack’s state for the annual Jefferson-Jackson Dinner in Des Moines. The J-J was a big deal every year, but on the eve of the Iowa caucuses in a presidential year, it was the biggest deal in Democratic politics. All the major candidates showed up, kicking off the Iowa homestretch, giving speeches they hoped would provide a rush of adrenaline to carry them across the finish line. Hillary had been invited to deliver the keynote and serve as emcee, an honorary role reserved for a Democratic heavyweight who was not in the hunt for the party’s nomination.
Clinton had heard through the grapevine, however, that Vilsack thought she should be running. On the phone, Vilsack said it was true—and then practically begged her to get into the race. The party had to thwart Dean, Vilsack told her, and she was the only one who could do it. “This is going to be a holy war, and we need our A team on the field,” Vilsack said, “and you’re our A team.”
Flattered but conflicted, intrigued but not convinced, Clinton arrived at the J-J Dinner in a haze of ambivalence. And then uncorked a scathing denunciation of Bush—“He has no vision for a future that will make America safer and stronger and smarter and richer and better and fairer”—that whipped the crowd into a lather.
In retrospect, Kerry’s performance that night, strong and spirited, would be seen as the start of his comeback. Edwards did fine, too. But Hillary’s speech outshone all the rest, and she knew it. As she watched her fellow Democrats work the room—pretenders one and all, free of gravitas or panache, let alone any hope of beating Bush—she thought, These are our candidates for president?
With the filing deadlines for key primaries looming in December, decision time was upon her. Hillary called together the innermost members of her inner circle for one final meeting at the Clinton home in Chappaqua, in the Westchester County suburbs of New York. Around the table were her husband; their daughter, Chelsea, and Chelsea’s boyfriend; Williams and Solis Doyle; and two Clinton White House stalwarts to whom Hillary was close: Evelyn Lieberman, the sharp-eyed former deputy chief of staff famous for having banished Lewinsky from the West Wing to the Pentagon, and Cheryl Mills, the diamond-hard lawyer who had defended Bill in his impeachment trial.
One by one, Hillary polled the group, listening carefully to what each of them had to say. These were the people whose opinions meant the most to her. Solis Doyle and Williams were in favor, as they had been all along. Lieberman and Mills were down with the prog
ram, too. And so was Bill. He had no doubt that Hillary would make a better president than anyone who was running. Just as important, he was sure that she could win.
But Hillary discovered that there was one dissenter in the room. Chelsea believed that her mother had to finish her term, that she’d made a promise and had to keep it, that voters would be unforgiving if she didn’t.
Try as she might to convince herself otherwise, Hillary thought her daughter was right. After months of weighing the pros and cons, gaming out the decision from every angle, she simply couldn’t get past the pledge. All the artful answers in the world wouldn’t satisfy her own conscience or drown out the bleating of the anti-Clinton chorus and their amen corner in the press that would greet her if she launched a last-minute campaign. Hillary could hear it now: ambitious bitch, there she goes again, dissembling, scheming, shimmying up the greasy pole with no regard for principle.
“I’d be crucified,” she told Solis Doyle.
Clinton’s decision to forego the 2004 race would prove fateful. It is impossible to know whether Hillary would have won either the Democratic nomination or the White House—although the strategists behind Bush’s reelection considered her formidable in a way they never did Dean or Kerry. But her entry would have scrambled the Democratic race severely. By closing a door, she opened another, inadvertently setting off a chain reaction that would have enormous consequences for her deferred ambitions. The absence of Clinton in the race left the road clear for Kerry to stage his surprising resurgence. The stunning victory over Dean in Iowa. The landslide in New Hampshire. The knockout blow on Super Tuesday that sealed the nomination and put Kerry in a position to make a decision as unlikely as it was momentous: the tapping of an unknown Illinois state legislator to give the keynote address that summer at the Democratic National Convention.