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Authors: John Heilemann

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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 program, 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.

THE SELECTION OF OBAMA had yet to be announced when Bill Clinton rolled into Chicago on July 2, 2004. The former president was passing through on the book tour for his memoir,
My Life
, which was burning up the bestseller lists even more scorchingly than his wife’s had done—a million copies sold its first week on the street. The weather was oppressive that day, criminally muggy, and Clinton was ridiculously overscheduled. So, by the time Bill arrived at his last event, an Obama fund-raiser at the home of billionaire real estate mogul Neil Bluhm, he was exhausted, cranky, and feeling every bit his age. But after heading upstairs at the Bluhm house to freshen up and meet Barack and Michelle, he rallied and gave a juicily Clintonian introduction for Obama, praising his potential to the heavens. When Clinton was done, Obama stepped up and responded with a self-deprecating reference to his meager income relative to the piles of dough that Clinton’s book was hauling in: “My life would probably be a lot better if I was just finishing up this book tour,” Obama deadpanned.

Clinton laughed and then, being Clinton, reclaimed the floor.

“Sonny,” he declared, “I’d trade places with you any day of the week!”

The poignancy of Clinton’s comment would be hammered home all too soon. On the Monday night of the Democratic convention in Boston, the former president turned in a triumphal performance—and then saw his speech rendered a footnote to history the next evening by Obama’s keynote, which catapulted Barack into the stratosphere. A month later, Clinton, after complaining of heart pains and shortness of breath, underwent an angiogram that revealed arterial blockages of such magnitude (90 percent in several places) that his doctors scheduled him for surgery. On September 6, he was subjected to a quadruple bypass, his breastbone cut open, chest pulled apart, heart stopped for seventy-three minutes. His recovery would be slow, arduous, and beset by complications. In some ways, he would never be the same again.

From his hospital bed, Clinton consulted by phone with Kerry, who for months had seen his prospects minced by the Bush campaign and its conservative-media allies. Kerry had handed the Republicans ample ammunition to paint him as an effete, patrician, liberal flip-flopper—and, more disastrously, had failed to push back against the Swift Boat Veterans for Truth, who challenged both his veracity and his war record. The advice Clinton gave him was rudimentary: more economy, less Vietnam; “Bush fights for Halliburton, John Kerry fights for kids.”

Even in his sick and weary state, Clinton could see the election slipping away. In late October, fresh out of the hospital, looking pallid and gaunt and sounding winded, he made a last-ditch effort to help save his party’s standard-bearer, speaking in front of a crowd of one hundred thousand at a Kerry rally in Philadelphia. “If this isn’t good for my heart,” he declared, “I don’t know what is.”

Hillary did her part for Kerry, too, crisscrossing the country on his behalf in the campaign’s closing days. But she felt little sympathy for him. She had nothing but contempt for Democrats who allowed their public images to be mangled and their characters maligned by the right-wing freak show. This was why she’d thought so little of Dean and why she’d always had doubts about Kerry. She detected a strain of Al Gore in the nominee: a passivity, a weakness, an inability to wield the blade in self-defense, let alone pounce at the right moment to carve up an opponent. She sensed that he lacked the hardness needed to survive the combination meat grinder/flash incinerator that postmodern politics had become—a hardness that had come to her unbidden, but that she now wore like a badge of honor.

The verdict on Election Day was, for Hillary, stark confirmation of these home truths. Another honorable Democrat destroyed, another winnable election lost. But it was also, of course, a kind of blessing: 2008 would now be an open-field run. After two Bush terms, her party would rally behind her—naturally, happily, eagerly. She would have a full term in office as a well-regarded senator under her belt. The pledge would be behind her.

Up in Chappaqua a few days after the election, surrounded by her team, Clinton began the process of positioning for the future. Ever circumspect, she claimed she wasn’t yet fully certain that she would be gunning for the White House, but everyone took those assertions as pro forma, as Hillary being Hillary. They harbored no doubts that she believed 2008 would be her time.

But Election Day 2004 had delivered something else as well: a blowout Senate victory for Barack Obama. The superstar in Chicago was on his way to Washington.

OBAMA AMBLED DOWN THE fourth-floor hallway in the Russell Senate Office Building looking for his destination: SR476. It was February 1, 2005, a little less than a month after he’d been sworn in as the third African American senator since Reconstruction, and he was still learning his way around Capitol Hill. His own quarters were a block away, in the larger, more modern, and less prestigious Hart Building. Russell was the tank where the big fish swam—Ted Kennedy, John Kerry, John McCain. It was also where Hillary Clinton occupied the suite that had once belonged to the legendary New York senator Daniel Patrick Moynihan, and it was Clinton whom Obama was coming to see on that cold, clear winter day.

He needed help. The past six months had been sheer mayhem. One day, Obama was a promising but obscure politico with a funny name and an uphill fight to win the Senate race into which he’d leapt. The next, his life was swept up in a whirlwind of nearly unfathomable force. His oration at the Democratic convention—with its stirring calls to unity and common purpose, its rejection of false distinctions between red and blue America, its rejection of “the politics of cynicism” and embrace of “the politics of hope”—had not only struck a chord with countless Democrats but turned him into a worldwide celebrity. Suddenly, Obama was recognized everywhere he went. Crowds waited for him outside his favorite restaurants in Chicago, swarmed around him on the streets. Suddenly, he was on the cover of
Newsweek
and the set of
Meet the Press.

Precious few people in any walk of life could even faintly comprehend what had happened to him and what it meant. But Hillary would understand completely. Obama’s view of her husband was complicated; there was much about Bill Clinton and the creed of Clintonism that he admired, but also much that gave him pause. His feelings about Hillary were, however, more straightforward. He’d liked her from the moment they met. Obama was wonkier, more enthralled by policy, than most people understood, and he saw in Hillary a kindred spirit. He thought she was tough, smart, ballsy, and knew how to win. A number of Obama’s campaign aides had worked for John Edwards before he folded his 2004 campaign, and Obama enjoyed razzing them about what would happen if Clinton and Edwards squared off for the Democratic presidential nomination in 2008. “Hillary’s gonna kick your guy’s ass,” he’d say.

Obama also was impressed with how Clinton had handled her transition from the White House to the Senate back in 2001. He knew that his megawatt status could prove problematic in the upper chamber, a hidebound institution where seniority determined power, prestige, and privilege—and where noses easily went out of joint. He wanted Hillary’s assistance in navigating the minefield stretched out before him.

They sat together for about an hour that day, amid the tchotchkes and the photos on Clinton’s canary-yellow office walls—a picture of Bobby Kennedy, another of her and Bill in the Oval Office, a composite shot of Hillary with her hero Eleanor Roosevelt. Clinton believed that success in the Senate required the sublimation of the ego (or a credible facsimile thereof ). And the advice she offered Obama based on that theory was clear and bullet-point concise: Keep your head down. Avoid the limelight. Get on the right committees. Go to hearings. Do your homework. Build up a substantive portfolio. And never forget the care and feeding of the people who sent you here.

Clinton appreciated that Obama had sought her counsel, seemed to see him as a budding protege, wanted to take him under her wing. During that first year together in the Senate, he would approach her often on the floor (something he did with other colleagues only rarely), and she always took time to chat with him quietly, to try to steer him in the right direction. At one point, Obama gave her a gift: a photograph of him, Michelle, and their two young daughters, Sasha and Malia. From then until the day she left the Senate in 2009—through all the rivalry and rancor that eventually developed between them—Hillary displayed it prominently in her office.

Clinton’s staff, however, looked on Obama with a somewhat more jaundiced eye. In the early months of 2005, any number of stories in the press noted approvingly his adherence to the “Clinton model” of cautious advancement. But Hillary’s people thought Obama’s conduct was nothing like their boss’s in her first years in the Senate. Instead of shying away from the national media, he seemed to be courting it, giving innumerable interviews and being trailed constantly by photographers and camera crews.

One day that spring, Hillary’s personal aide, Huma Abedin, and another Clinton staffer were loitering just off the Senate floor when they ran into Obama, who greeted them casually: “Hey, what’s going on?”

“I saw your picture on a magazine cover,” Abedin said, gently chiding him. “It was nice.”

To which Obama replied without irony, “Oh, which one?”

The point was made.

HE COULD COME ACROSS as cocky, that was for sure—and not just to people outside his circle. He was smarter than the average bear, not to mention the average politician, and he not only knew it but wanted to make sure that everyone else knew it, too. In meetings with his aides, he exerted control over the conversation by interrupting whoever was talking. “Look,” he would say—it was his favorite interjection, almost a tic—and then be off to the races, reframing the point, extending it, claiming ownership of it. “Whose idea was that?” was another of his favorites, employed with cheery boastfulness whenever something he’d previously proposed had come up roses. His calmness and composure could veer into the freakish, and sometimes concealed his gaudy confidence in himself. But not always. A few hours before his high-stakes convention keynote, a
Chicago Tribune
reporter asked him if he was nervous. “I’m LeBron, baby,” Obama replied. “I can play on this level. I got some game.”

The self-assurance had been there as long as anyone could remember, alongside the ambition. When Obama started dating a young Chicago lawyer named Michelle Robinson, in the summer of 1989, he mentioned to her brother, Craig, that he might one day want to run for Senate, “possibly even for president.” Craig replied, “Okay, but don’t say that to my aunt Gracie,” attempting to save the poor schlub from embarrassing himself. (Aunt Gracie was the least of Obama’s worries; his new girlfriend disdained politics as a cynical game. “[Craig] should have said, ‘Don’t tell Michelle,’” Mrs. Obama later recalled.)

The 2004 convention keynote and its aftermath moved the possibility of an Obama run for the White House out of the realm of pure theory. The buzz about it had started the moment he climbed down from the stage. David Axelrod and Robert Gibbs, who had piloted him to his Senate win and remained his two main political advisers, both discussed it, but believed it was at least eight years down the road.

Obama agreed. “There’s a lot of speculation about what will happen in 2008,” he told his new Senate chief of staff, Pete Rouse, right at the start of 2005. “I can assure you there’s no way that I’m running—I have two small kids and I’m not that presumptuous.”

But for a man who disclaimed any short-range designs on the Oval Office, Obama surrounded himself with a striking number of adjutants whose eyes had long been on that prize. Axelrod, fifty, a former political journalist with a walrus mustache and a world-weary manner, had made the switch to advising candidates in 1984. In 1988, he worked on Illinois senator Paul Simon’s presidential run; he consulted secretly with Al Gore on a possible 2004 bid, then joined Edwards’s campaign that year. His resume was studded with other clients with national ambitions: Senator Chris Dodd, Tom Vilsack, and Hillary Clinton. In the trade, Axelrod was known for being interested less in policy than in softer qualities of character and biography. His central gift was a grasp of the power of narrative—his ability to weave his candidate’s beliefs and background into an emotionally compelling bundle. In Obama, whom he’d met in 1991 and had guided ever since, Axelrod saw qualities that the nation was hungry for: optimism, dynamism, outsider status, an aversion to hoary ideological dogmas, a biography that radiated the possibility of overcoming divisions and the capacity for change.

Gibbs, too, saw in Obama a figure of national stature. Having worked on Kerry’s presidential campaign in its early stages before losing his job in a campaign purge, he had signed on to Obama’s Senate race in no small part because he viewed the candidate as a guy who was going places.

And then there was the latest addition to Obama’s inner circle. Pete Rouse was a round man in his late fifties with a head of thick salt-and-pepper hair, a gruff manner, and a voice that sounded as if he gargled with gravel. The consummate insider, he had come highly recommended by Tom Daschle, after many years as the former Senate majority leader’s chief of staff. Obama had bonded with Daschle the previous fall, when Daschle was on his way to being defeated for reelection in South Dakota, and had been conferring with him ever since. Rouse would be the first of the Daschle Mafia—arguably the only collection of Washington talent to rival the Clinton apparatus—to gravitate toward Obama, most of them hoping to work for a future president.

Obama made it plain to Rouse that his focus was on the Senate, however. He wanted to be effective and strategic, to move ahead as quickly as possible without ruffling feathers, to project an image of diligence and humility. But unlike Clinton, whose national profile was already as capacious as it could get before she arrived in the Senate, Obama wanted to take advantage of his newfound prominence to build a larger brand. His staff was fielding three hundred speaking invitations a week. Grassroots liberal activists, conservative columnists, and his party’s leadership all wanted a piece of him.

Together with Axelrod and Gibbs, Rouse developed a strategic plan to capitalize on this outsize interest. The plan—which Rouse and the rest ingeniously dubbed “The Plan”—called for Obama to dive neck-deep into fund-raising for his Senate colleagues. (They’ll be coming for you anyway, Rouse told him, so you might as well volunteer.) To give major speeches on national policy: energy, education, economics. To travel abroad as a member of the Senate Foreign Relations Committee to build his credibility on international affairs. To expand his political horizons aggressively and systematically.

Obama put his shoulder to the wheel, but he found many aspects of his new life frustrating, starting with the Senate itself. The glacial pace, the endless procedural wrangling, the witless posturing and pettifoggery, the geriatric cast of characters doddering around the place: all of it drove him nuts. To one friend in Chicago, Obama complained, “It’s basically the same as Springfield”—the Illinois capital where he had toiled in the state senate—“except the average age in Springfield is forty-two and in Washington it’s sixty-two. Other than that, it’s the same bullshit.” After enduring an unceasing monologue by Senator Joe Biden during a committee hearing, Obama passed a note to Gibbs that read, “Shoot me now.” Time and again after debates on the floor, he would emerge through the chamber’s double doors shaking his head, rolling his eyes, using both hands to give the universal symbol for the flapping of gums, sighing wearily, “Yak, yak, yak.”

Obama’s frustration was magnified by the fact that he was living apart from his wife and daughters. He didn’t doubt the decision that he and Michelle had made to keep their home in Chicago; his spouse had her own career in the city; her mother lived nearby; the girls were happy, grounded, in a wonderful school. But Obama missed them all terribly and questioned whether the separation was worth it when all he seemed to be doing in the Senate was nibbling around the edges.

Then, in late August 2005, Hurricane Katrina happened—and brought Obama to a different place. For weeks afterward, he was downcast and angry at the scale of the failure of George W. Bush and his administration. He started speaking about an “empathy deficit” crippling the country, about the severity of the problems that America faced and the epic failure to confront them. Slowly, subtly, tentatively, Obama seemed to be trying on the mantle of a national leader.

Obama’s aides were laboring mightily to further that impression, sending him from one end of the country to the other—Virginia, New Jersey, Texas, Arizona, Tennessee—for fund-raising or political events right before and after the off-year elections of 2005. By the end of the year, Obama was exhausted and annoyed: he’d missed three weekends at home in a row, and weekends were sacrosanct to him. Michelle was even more irritated. “It’s a tough choice between, do you stay for Malia’s basketball game on Sunday or do you go to New Jersey and campaign for [then-senator Jon] Corzine?” she said to a reporter at the time, her voice dripping with sarcasm. “Corzine got it this time around.”

Gibbs was in charge of Obama’s schedule and well aware that he’d screwed up. So he was bewildered when Obama came to him in November and indicated he might like to speak at the Florida Democratic Party convention on December 10. Florida senator Bill Nelson had asked Obama three times to attend; three times, Obama had said no. The tenth was a Saturday, and not just any Saturday, but one on which Malia had a dance recital in Chicago. But here was Obama, toying with going to the Sunshine State anyway.

“What do you have in mind?” Gibbs asked his boss.

“I’ve got some stuff I’d like to try out,” Obama said. “I want to see what the reaction is.”

What Obama wanted to try out was an honest-to-goodness stump speech full of sweeping national themes, crafted by him, Axelrod, and his precocious twenty-four-year-old speechwriter, Jon Favreau. And he was so intent on going to Florida—Florida!—that he was willing to leave his daughter’s recital, drive out to the airport, catch a charter plane, fly down to Lake Buena Vista, address the crowd, and jet back to Chicago the same night.

Huh
, Gibbs thought.
Interesting.

On the appointed evening, Obama took the podium in a cavernous ballroom at a Walt Disney World hotel. Edwards and Vilsack—both potential candidates for 2008—had spoken earlier that day and garnered respectful receptions. The crowd was maybe a thousand strong, overwhelmingly white. As Obama unfurled his speech, a narrative about the transition from the twentieth century into the twenty-first and the inability of a generation of leaders to realize that the world had changed, people in the audience began shouting, “You should run!”

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