Chapter 1
How He Did It
A team of NEWSWEEK reporters reveals the secret battles and private fears behind an epic election.
Published Nov 5, 2008
From the magazine Newsweek issue dated Nov 17, 2008
This is part one of a seven-part in-depth look behind the scenes of the campaign, consisting of exclusive behind-the-scenes reporting from the McCain and Obama camps assembled by a special team of reporters who were granted year-long access on the condition that none of their findings appear until after Election Day.
Barack Obama had a gift, and he knew it. He had a way of making very smart, very accomplished people feel virtuous just by wanting to help Barack Obama. It had happened at Harvard Law School in the mid-1980s, at a time when the school was embroiled in fights over political correctness. He had won one of the truly plum prizes of overachievement at Harvard: he had been voted president of the law review, the first African-American ever so honored. Though his politics were conventionally (if not stridently) liberal, even the conservatives voted for him. Obama was a good listener, attentive and empathetic, and his powerful mind could turn disjointed screeds into reasoned consensus, but his appeal lay in something deeper. He was a black man who had moved beyond racial politics and narrowly defined interest groups. He seemed indifferent to, if not scornful of, the politics of identity and grievance. He showed no sense of entitlement or resentment. Obama had a way of transcending ambition, though he himself was ambitious as hell. In the grasping race for status and achievement—a competition that can seem like blood lust at a place like Harvard—Obama could make hypersuccessful meritocrats pause and remember a time (part mythical perhaps, but still beckoning) when service to others was more important than serving oneself.
Gregory Craig, a lawyer in Washington, D.C., was one of those Americans who wanted to believe again. Craig was not exactly an ordinary citizen—he had served and worked with the powerful all his life, as an aide to Sen. Edward Kennedy in the 1980s, as chief of policy planning at the State Department in the Clinton administration and as a lawyer hired to represent President Clinton at his impeachment trial in the U.S. Senate in 1999. He had seen the imperfections of the mighty, up close and personal, and by and large accepted human frailty. But, like a lot of Americans, he was tired of partisan bickering and yearned for someone who could rise above politics as usual. A 63-year-old baby boomer, Craig wanted to recapture the youthful idealism that he had experienced as a student at Harvard in the 1960s and later at Yale Law School, where his friends included Bill Clinton and Hillary Rodham. In the late fall of 2003, he was invited to hear a young state senator from Illinois who was running for the U.S. Senate. Craig was immediately taken with Barack Obama. "He spoke 20 to 30 minutes, and I found him to be funny, smart and very knowledgeable for a state senator," Craig recalled. Craig was so visibly impressed that his host that evening, the longtime Washington mover and shaker Vernon Jordan, teased him, saying, "Greg has just fallen in love."
It was true. Craig read Obama's book "The Audacity of Hope," which, Craig said, "floored me," and later chanced to ride with Obama on the Washington shuttle. He read Obama's earlier autobiography, "Dreams From My Father," and was "blown away," he recalled. "In my judgment, he showed more insight and maturity than Bill Clinton at the age of 60 in terms of understanding himself." In November 2006, Craig sat next to George Stevens, an old friend of the Robert Kennedy clan, at another Obama speech. Stevens leaned over to Craig and said, "What do you think of this guy for president? I haven't heard anybody like this since Bobby Kennedy." Craig instantly replied, "Sign me up." Stevens and Craig approached Obama coming out of the speech and asked, "What are you doing in 2008?" Obama gave them a big grin and said, "Oh, man, it wasn't that good." But before long Craig and Stevens were raising money for Obama's political-action committee, the Hope Fund. Obama was amused by the devotion of the two old Kennedy hands. After a while, every time he saw the two men he would say, "Here come the Kool-Aid boys."
That December of 2006, Obama told Craig and Stevens, "Lay off me for a while. I've got to talk to Michelle." Obama went off to Hawaii with his wife and two girls for the holidays. "I thought, 'We're dead'," recalled Craig. "He's not going to be able to do it."
Craig was not wrong to be pessimistic. Obama could marshal a lawyerly set of arguments about how he could win, that the country was at a "defining point" and that Obama was the best hope to bring change. "I, I, I actually believe my own rhetoric," Obama stammered, uncharacteristically, in an interview with NEWSWEEK in the spring of 2008. But Michelle was not eager to subject her family to a process that was dangerous and ugly—uplifting and history-making, maybe, but also a potential family wrecker. Her kids would be given cute names by the Secret Service ("Radiance" and "Rosebud," as it turned out), but their lives would never be the same.
Obama had been warned. That November of 2006, at dinner at a fancy Italian restaurant in Washington, former Senate majority leader Tom Daschle had reminded Obama that he had never really been attacked before. "I told him he should think about how he might react if his wife was attacked—the emotional discipline it takes," recalled Daschle. At about the same time, with his fellow Illinois senator, Richard Durbin, Obama had talked about the physical risks. At a political event at the Union League Club in Chicago before Thanksgiving, Obama told Durbin that many of his African-American friends were advising him not to run, some of them because they were afraid he would get killed. (Durbin shared their fears and began lobbying to get Obama put under Secret Service protection. In May, eight months before the first primary, the Secret Service would begin standing watch over Obama, the first time such protection had been extended to a candidate so early in the process.)
Michelle Obama was worried about her husband's safety, but was also seized with a kind of free-floating anxiety, recalled Durbin. Even after she said yes, she asked Durbin, "They're not setting him up, are they?" The "they" was all the people who were urging Obama to run. Michelle wondered at their motives.
Obama understood his wife's fears and even, to some degree, shared them, but he had a way of turning empathy into persuasion. "Her initial instinct was to say no," Obama recalled. "She knew how difficult it was for me to be away from the girls, she feels lonely when I'm not around, so her initial instinct was not to do it. And I think she also felt that, you know, the Clintons are tough, and that I would be subject to a lot of attacks." So that Christmas season, 2006, Michelle and Barack went for some long walks on the beach in Hawaii, where they were visiting his grandmother, and "just talked it through. It wasn't as if it was a slam-dunk for me," said Obama. "I think part of the reason she agreed to do it was because she knew that she had veto power, that she and the girls ultimately mattered more than my own ambitions in this process, and if she said no we would be OK." Michelle was able to extract a promise: if he ran, her husband would have to quit smoking.
In some ways, running for president was a preposterous idea for someone who had served as a two-term state legislator and had spent only two years in the United States Senate. But Obama, a careful student of his own unique journey, could see the stars coming into alignment—the country was exhausted by the Iraq War (which he, alone among leading candidates, had opposed as "dumb" from the outset). As Obama saw it, the conservative tide in America was ebbing, and voters were turning away from the Republican Party. People were sick of politicians of the standard variety and yearned for someone new—truly new and different. Another politician with a superb sense of timing, Bill Clinton, perfectly understood why Obama saw a golden, possibly once-in-a-lifetime, opportunity. The former president believed that the mainstream press, whose liberal guilt Clinton understood and had exploited from time to time, would act as Obama's personal chauffeur on the long journey ahead. "If somebody pulled up a Rolls-Royce to me and said, 'Get in'," Clinton liked to say, with admiration and maybe a little envy, "I'd get in it, too."
Barack Obama can be cocky about his star power. On the eve of his speech to the Democratic convention in 2004, the speech that effectively launched him as the party's hope of the future, he took a walk down a street in Boston with his friend Marty Nesbitt. A growing crowd followed them. "Man, you're like a rock star," Nesbitt said to Obama. "He looked at me," Nesbitt recalled in a story he liked to tell reporters, "and said, 'Marty, you think it's bad today, wait until tomorrow.' And I said, 'What do you mean?' And he said, 'My speech is pretty good'."
Obama's 2004 convention speech launched him into the strange world of celebritydom; he acquired the kind of aura that can transform a skinny, scholarly man with big ears into a sex symbol. Eureka Gilkey, one of Obama's aides, recalled going with him when he made a speech to the Democratic National Committee shortly after he began his campaign. Obama was mobbed outside the bathroom. "These were DNC members; they're supposed to be jaded by politicians," recalled Gilkey. "Not trying to tear their shirts off. I remember going home that night, and my boyfriend saying, 'What is that purple bruise on your back?' I had bruises on my back from people pushing and shoving, trying to get to [Obama] … I remember grabbing women's hands because they were trying to pull his shirt from his pants. I couldn't believe it."
Obama was growing accustomed to adulation. Greg Craig was not the only old Kennedy hand to fall in love. At Coretta Scott King's funeral in early 2006, Ethel Kennedy, the widow of Robert Kennedy, leaned over to him and whispered, "The torch is being passed to you." "A chill went up my spine," Obama told an aide. The funeral, he said, was "pretty intimidating."
Obama understood that he had become a giant screen upon which Americans projected their hopes and fears, dreams and frustrations. Maybe such a person never really existed, couldn't exist, but people wanted a savior nonetheless. As a bestselling memoirist he had created a mythic figure, a man named Barack Obama who had searched and quested and overcome travails, who had found an identity and a calling in public service. Obama recalled that he often joked with his team, "This Barack Obama sounds like a great guy. Now I'm not sure that I am Barack Obama, right?" He added, pointedly, "It wasn't entirely a joke."
In the first quarter of 2007, Obama put the political world on notice when he raised $24.8 million, more money than any other Democrat except Hillary Clinton, and drew huge crowds at his early rallies. But he was a tentative, awkward presence in the endless Democratic debates through the spring and summer of 2007. He didn't really seem to have his heart in it; he appeared to lack the required, almost pathological drive to be president. The campaign strategist, David Axelrod, told Obama he worried that the candidate was "too normal" to run a presidential campaign, and Obama began wondering himself. He missed going to the movies and reading a book and playing with his kids. He worried about "losing touch" with "what matters." To a NEWSWEEK reporter he said, "I'm not trying to say that I'm some sort of reluctant candidate—obviously this is a choice I made. But there was some tension there in my own mind." He seemed so distracted in one debate that one of his rivals, former senator John Edwards, came up to him during a break and scolded him, "Barack … you've got to focus."
Obama bridled at the sometimes mindless rituals and one-upmanship of a national political campaign in the age of cable news. He resented the pressure he felt to declare, as he put it to NEWSWEEK, that you "want to bomb the hell out of someone" to show toughness on terrorism. He was surprised when Hillary Clinton refused to shake his hand on the Senate floor after he declared his candidacy. And he was upset with his own campaign after a low-level staffer referred in a press release to Clinton as "(D-Punjab)" because of her ties to supporters of India. "I don't want you guys freelancing and, quote, protecting me from what you're doing," he lectured his staff. "I'm saying this loud and clear—no winks, no nods here," he said, irritated to take the heat for a clumsy dirty trick he had not known about and would never have authorized. "I'm looking at every one of you. If you think you're close to the line, the answer isn't to protect me—the answer is to ask me."
Obama was something unusual in a politician: genuinely self-aware. In late May 2007, he had stumbled through a couple of early debates and was feeling uncertain about what he called his "uneven" performance. "Part of it is psychological," he told his aides. "I'm still wrapping my head around doing this in a way that I think the other candidates just aren't. There's a certain ambivalence in my character that I like about myself. It's part of what makes me a good writer, you know? It's not necessarily useful in a presidential campaign."
These candid remarks were taped at a debate-prep session at a law firm in Washington. The tape of Obama's back-and-forth with his advisers, provided to NEWSWEEK by an attendee, is a remarkably frank and revealing record of what the candidate was really thinking when he took the stage with his opponents.
On the tape, after Obama's rueful remark about the mixed blessings of his detached nature, there is cross talk and laughter, and then Axelrod cracks, "You can save that for your next memoir."
Obama continues: "When you have to be cheerful all the time and try to perform and act like [the tape is unclear; Obama appears to be poking fun at his opponents], I'm sure that some of it has to do with nerves or anxiety and not having done this before, I'm sure. And in my own head, you know, there's—I don't consider this to be a good format for me, which makes me more cautious. When you're going into something thinking, 'This is not my best …' I often find myself trapped by the questions and thinking to myself, 'You know, this is a stupid question, but let me … answer it.' Instead of being appropriately [the tape is garbled]. So when Brian Williams is asking me about what's a personal thing that you've done [that's green], and I say, you know, 'Well, I planted a bunch of trees.' And he says, 'I'm talking about personal.' What I'm thinking in my head is, 'Well, the truth is, Brian, we can't solve global warming because I f–––ing changed light bulbs in my house. It's because of something collective'."
Obama was refreshingly honest with his aides, who chuckled over his remarks, but he was no Happy Warrior, and his detachment deflated his staff a bit. His campaign headquarters at 233 North Michigan Avenue in Chicago was high tech—lots of flat screens, more cell phones than regular phones—but earnest and nerdy. (A large hand-lettered sign stuck on the bathroom door instructed staffers to BRING BACK HOTEL SHAMPOOS AND SOAPS FOR DONATIONS TO SHELTERS.) A former Clinton staffer, accustomed to the earthy chaos of the Clinton war room (where, in legend at least, James Carville refused to change his lucky underwear), found it a little soulless. A newcomer to the campaign in September 2007, Betsy Myers—sister of former Clinton press secretary Dee Dee Myers and a former Clinton White House staffer herself—hoped that Obama, in town overnight, might come to headquarters to cheer the staff. "But he didn't," she recalled later that fall. "He went to the gym instead." She paused as she recollected. "He hasn't been in the headquarters in months. A lot of these people are young and really look up to him, and it would have meant a lot to them if he'd stopped by." Another pause. "Nobody would have had to tell Bill Clinton to stop by if he was just a couple of blocks away. You would have had to physically drag Bill Clinton out of there."
The low point, Obama later recalled, came in September and October, when he trailed Clinton in the national polls by 20 to 30 points. His staff was complaining that he lacked "energy." But Obama wasn't that worried. He trusted his chief strategist, Axelrod, a former newspaperman with a melancholy look, an ironic air and a clear sense of what to do: make the campaign about change, and make Hillary Clinton out to be more of the same. A veteran of numerous state, local and national campaigns, Axelrod, at 52, was an idealist who liked to read old Bobby Kennedy speeches in his spare time but who was well versed in gut-cutting politics, Chicago style. Axelrod had suffered in his own life (his father committed suicide; one of his children was severely epileptic), and he kept a certain detachment. He was courtly and gentle, not at all the more typical hit-'em-again macho political consultant. He liked Obama in part because he could see that the candidate was unusually intelligent (especially, in his experience, for a politician coming out of the Illinois Statehouse), and because Obama seemed uninterested in and unimpressed by the mindless tit-for-tat of modern political campaigning. Axelrod was, like Obama, self-contained. He did not use an office at the gleaming high-tech headquarters but rather worked from his own low-key office and spent much of his time at a greasy deli called Manny's. Axelrod was a seer and a good listener, though not much for glad-handing and schmoozing.
To run things, Obama counted on David Plouffe, who was calm and a little nerdy himself. (Staffers joked that Plouffe's range of emotions ran all the way "from A to B.") Plouffe reflected the cool self-discipline of the candidate, and the two of them set the ethos of the campaign, which staffers dubbed "No-Drama Obama." Plouffe also had a clear and simple plan: concentrate on four early states—Iowa, New Hampshire, Nevada and South Carolina. Clinton might be ahead in the national polls, but Obama knew he was raising record amounts of money—and, even better, in small amounts over the Internet, which meant that donors would not get tapped out. The campaign had 37 field offices in Iowa. No other campaign was so well organized.
Obama had laid out his vision for the campaign on the day after the midterm elections in 2006. The Democrats had routed the Republicans in Congress, and Obama sensed that the moment had arrived for an unconventional campaign that would take advantage of voter disenchantment—not just with the Republicans but with politics as usual. He had met in a small, dimly lit conference room in the office of Axelrod's consulting firm in Chicago with his inner circle: Michelle, his friend Marty Nesbitt, Axelrod, Plouffe, Robert Gibbs (who would handle communications), Steve Hildebrand (Plouffe's deputy), Alyssa Mastromonaco (director of the advance teams) and Pete Rouse, Tom Daschle's former chief of staff and a Capitol Hill insider. Valerie Jarrett, a close Obama family friend who was closely connected with Chicago Mayor Richard M. Daley, joked about the decidedly unfancy setting. There were cookies, bottled water and canned soda—"whatever kind of pop you wanted," Jarrett said with a laugh as she later recounted the scene. "This is David Axelrod."
Obama spoke first. "I just remember him saying that if he were to do this, he wanted to make sure that it was a different kind of campaign and consistent with his philosophy of ground up rather than top down," Jarrett recalled. As a community organizer in Chicago in the '80s, Obama had been influenced by the teachings of Saul Alinsky, a radical with a realist bent who once wrote, "Any revolutionary change must be preceded by a passive, affirmative, non-challenging attitude toward change among the mass of our people." Obama knew he had a knack for finding non-threatening ways to make people accept change—to begin with, his own skin color. As Jarrett recalled, Obama insisted that he wanted to run a grass-roots campaign because he had seen it work as a community organizer, and he wanted to try to take the model and go national. Rouse, the old Washington hand, had a slightly different recollection of the meeting: the grass-roots model wasn't really a choice. It was a necessity. Hillary Clinton would have the establishment behind her, which meant that she'd have the early money (or so it was thought), the endorsements and a national organization.
For the meeting, Rouse had prepared a list of six questions. The third question was: "Are you intimidated about being the leader of the free world?" Obama had a ready answer: "Who wouldn't be?"
Thus, in a dim room in Chicago, was launched one of the most formidable political operations ever seen in American politics. But its potential was not obvious at the time. Obama fretted about his showing in the early going, particularly his shaky debating skills. "It's worse than I thought," he told Axelrod after he watched the videotape of one dismal performance in the summer of 2007. But he felt he was learning on the stump—at his own pace and in his own way. Obama was a relentless self-improver: "I'm my own worst critic," he told NEWSWEEK, but he was also a loner who needed to step back away from the others, to look more closely at himself. He wasn't chilly, exactly, but for a politician he was astonishingly inner-directed, and that could make him seem remote. He felt a little overprotected by his handlers, who would signal from the back of the hall that he had time for only one or two questions from the public—and none from the press. Obama began ignoring the signal from Gibbs, his communications director, instead taking three or four more questions from the crowd, though he still kept his distance from reporters. (Curiously, though Obama drove his rivals mad by receiving reams of mostly friendly publicity, he was not well liked by reporters, many of whom found him chilly and guarded. He was more popular with editors, who regarded him as a phenomenon.)
On the stump, he decided to experiment, to try loosening up a little. Speaking to an African-American crowd in Manning, S.C., on Nov. 2, he began to riff, using the call-and-response cadence of a black preacher. Addressing the doubts among some blacks about whether the country was ready to vote for an African-American, Obama said, "I just want y'all to be clear … I would not be running if I weren't confident I was gon' win!"
There was a rousing chorus of "Amen!" and cheers from the audience.
"I'm not interested in second place!" More cheers, and a big grin from Obama … he could feel the crowd's energy.
"I'm not running to be vice president! I'm not running to be secretary of something-or-other!" They were like old friends now, Obama and the crowd … this was fun!
But then Obama got carried away with himself and violated a cardinal rule of braggadocio in the black community: don't get too high and mighty.
"I was doing just fine before I started running for president! I'm a United States senator already!"
In an instant the crowd went quiet—and that should have been his cue … but Obama plowed ahead.
"Everybody already knows me!" A lone shout went up from the audience.
"I already sold a lot of books! I don't need to run for president to get on television or on the radio …"
Silence.
"I've been on Oprah!" That seemed to get the crowd back, but Obama knew he had almost lost them altogether.
Obama studied himself and learned, just in time. The annual Jefferson-Jackson Day Dinner in Des Moines on Nov. 10 was a crucial beauty pageant before the real contest, the caucuses on Jan. 3. Obama's Iowa organization made sure to pack the hall and drown out the supporters of all the other candidates. Because the candidates were not allowed to use teleprompters, Obama spent hours memorizing the words and perfecting his delivery. The speech was a good one, ripping George W. Bush and taking down Hillary (a little more subtly), and it built into a crescendo as Obama told the story of how, on a miserable morning when he faced a small, bored crowd in Greenwood, S.C., a single black woman in the audience had revived his flagging spirit by getting the crowd to chant, responsively, "Fired up!" "Ready to go!" Slipping from an easy, bemused tone to a near shout, Obama egged on the overflow crowd at the J-J dinner. "So I've got one thing to ask you. Are you FIRED UP? Are you READY TO GO? FIRED UP! READY TO GO!" The Washington Post's David Broder, the Yoda of political reporters, was watching and understood that Obama had found the Force. The speech became Obama's standard stump speech, and in the weeks ahead it never failed him. Broder described the effect of Obama's thumping windup: "And then, as the shouting became almost too loud to hear, he adds the five words that capsulize the whole message and sends the voters scrambling back into their winter coats and streaming out the door: 'Let's go change the world.' And he sounds as if he means it. In every audience I have seen," Broder reported on Dec. 23, a week and a half before the Iowa caucuses, "there is a jolt of pure electrical energy at those closing words. Tears stain some cheeks—and some people look a little thunderstruck."
For someone who had reportedly coveted the White House for years, who had long plotted with her husband to take back the presidency and restore the Clinton imperium, Hillary Clinton was slow to actually declare for the nomination. "We utterly squandered '05 and '06 in terms of her running for president," recalled one Clinton adviser. For someone who was known as a fierce battler, who was in fact courageous in adversity, she was oddly detached and conflict-averse as a boss. There were moments when it seemed she wasn't all that eager to give up her solid, useful life as a U.S. senator to pursue the Clinton destiny, at least as it was understood by the press and by the former president.
On a cold midmorning in January 2007, Hillary sat in the sunny living room of her house on Whitehaven Street in Washington, a well-to-do enclave off Embassy Row where she lived with her mother and, on occasion, her husband. She was finishing a last round of policy prep with her aides before getting on a plane to Iowa for her first big campaign swing. In a moment of quiet, she looked around the living room and said, to no one in particular, "I so love this house. Why am I doing this?"
Her policy director, Neera Tanden, and her advertising director, Mandy Grunwald, laughed, a little too lightheartedly. Clinton went on. "I'm so comfortable here. Why am I doing this?"
Tanden spoke up. "The White House isn't so bad," she said.
"I've been there," said Clinton.
For most of her political life, and for most of the campaign to come, Hillary Clinton was a stubborn fighter. She was a very able lawmaker; indeed, she was more dutiful and effective in the Senate than Obama was. But she was, to a degree not generally recognized at the time, not a strong manager. She was unable to control her own staffers, who from the very first skirmish with the Obama forces showed questionable judgment and mutual distrust.
In late February 2007, Maureen Dowd of The New York Times ran a much-noticed column, an interview with David Geffen, a big-time Hollywood producer. Hollywood money had always flowed into the Clinton coffers, but Geffen had just given a big fundraiser for Obama. Geffen explained why, using code that anyone could understand: "I don't think that anybody believes that in the last six years, all of a sudden Bill Clinton has become a different person."
To say that Geffen's remark struck a raw nerve in the Clinton camp is a mild understatement. "We're just praying that Bill behaves," a Clinton staffer told a NEWSWEEK reporter that winter. She clasped her hands and bowed several times. Other staffers dryly referred to the private plane owned by supermarket magnate and playboy Ron Burkle, Bill Clinton's friend and traveling buddy, as "Air F––– One."
Geffen's remarks to Dowd, which were sure to ricochet around the political world by lunch, presented the Clinton war room with its first real challenge. Howard Wolfson, Hillary's bulldog spokesman, had read the column by 5 a.m., called her by 6 and summoned a crisis conference call by 7. By the time most Americans were arriving at work, Wolfson had put out a statement calling on Obama to denounce Geffen's statement and return the money from the fundraiser. The Obama war room responded with a not-so-subtle crack about selling the Lincoln Bedroom in the Bill Clinton administration. The Clintonites were delighted—as they saw it, the Obama team had taken the bait and fallen into a trap. Wolfson issued a press release: "Obama Embraces Slash & Burn Politics: by refusing to disavow the personal attacks …" It was an all-hands-on-deck moment, with every staffer in the Clinton war room on the phone with a reporter, pushing the story.
It was exciting. Combat! First blood! But lost in all the frantic Googling, Nexising and IMing was the larger picture. By overreacting, the Clinton campaigners drew attention to their own misgivings about the former president's behavior and to Obama's status as a legitimate contender who could raise big bucks from the Clintons' own base. Obama himself floated coolly over the whole flap, telling a reporter, "It's not clear to me why I should be apologizing for someone else's remarks. My sense is that Mr. Geffen may have differences with the Clintons, but that doesn't really have anything to do with our campaign."
Before too long, reality set in among Clinton's staffers, and the finger-pointing began. According to other staffers, Mark Penn, Hillary's prickly chief strategist, had been all for the assault on Obama, but when he saw it backfiring he told Bill Clinton that he had not been involved, that it was Wolfson's fault. With Hillary Clinton, he suggested that perhaps Wolfson, who was cast in the press as a hit man out of "The Sopranos," wasn't up to the job of chief spokesman in a presidential campaign. For good measure he took a swipe at Grunwald, officially the campaign's chief ad person, though Penn regarded himself as the campaign's true image maker. "You have to fix this," said Hillary. Penn nodded. "We have to make him think that he's in charge of communications," Penn said conspiratorially, "the same way we made Mandy think she's in charge of ads."
The story, while byzantine, was a perfect microcosm of the campaign to come: a Hollywood mogul uses a famous columnist to revive old rumors of the candidate's husband's infidelities; the candidate's campaign panics and ends up aggravating the problem; the campaign's chief strategist washes his hands of the whole situation, and when the candidate tells him to "fix it" he sees an opportunity to undermine two other top staffers—without fixing anything.
Crisis, chaos, deceit and subterfuge. After eight years in the Clinton White House, it was all familiar to Hillary—a world she had bravely struggled in but not against; it was the only world she really knew.
The Clinton campaign blew through cash: fancy hotels like the Bellagio in Las Vegas and the Four Seasons everywhere; thousands of dollars on flowers and valet parking; and one memorable $100,000 grocery bill at a Des Moines supermarket. Hillary never spent a night in a motel in rural Iowa if she could possibly avoid it. She preferred to overnight in the Presidential Suite in the Des Moines Embassy Suites and to fly alone in private jets, without the press or staff. Her campaign manager was her former White House scheduler, Patti Solis Doyle, who had coined the term "Hillaryland" to describe the circle of women loyalists around Hillary and referred to Bill's circle of advisers as "the White Boys." Chief White Boy was Penn, who, during the dark days of 1994, had come into the Clinton White House with Dick Morris, the secretive and now shunned former adviser. Penn and Solis Doyle barely spoke. More important, Penn, who was in charge of polling data, shared his findings with Bill Clinton—but often kept them from Solis Doyle and the other advisers (who naturally assumed he was hiding any results that didn't jibe with his strategy).
Penn especially did not get along with Harold Ickes, a top aide from the White House days. The two men were a volatile match. Penn's social skills were limited; Paul Begala, another old Clinton hand, privately joked that Penn had Asperger's syndrome, because he was narrowly smart and generally clueless. Ickes was a labor lawyer with a spectacularly foul mouth, even by campaign standards. By midwinter, an account of Penn and Ickes screaming the F word at each other would make it into The Washington Post. Campaign manager Solis Doyle seemed overwhelmed by it all. Her door was often closed, and she sometimes did not return phone calls. The New Republic reported campaign gossip that she was inside her office watching soap operas. (Actually, she was answering e-mails until the early hours of the morning.)
The campaign seemed to lurch from message to message, in part because Penn wanted to go negative against Obama, and Solis Doyle, Wolfson, Grunwald and Ickes wanted to "humanize" Hillary. "She's not going to go around talking about feelings," Penn would sneer. Solis Doyle, who liked nicknames and acronyms, dubbed Penn "the Chairman of the Kill Him Caucus." Hillary was unable to choose between the two approaches. Ads attacking Obama or softening Clinton were made—and then put on the shelf while her advisers bickered. Hillary's lame first campaign slogan, designed by default and by committee, was "I'm in It to Win." ("No s–––," Ickes muttered to a NEWSWEEK reporter.)
Clinton liked to describe her campaign as a "team of rivals," borrowing from the title Doris Kearns Goodwin used for her book on Abraham Lincoln and his strong-willed and disputatious, but ultimately triumphant, Civil War cabinet. A top adviser may have more accurately captured the spirit of the Clinton campaign when remarking to a NEWSWEEK reporter, "It was a terribly unpleasant place to work. You had seven people on a morning call, all of whom had tried to get someone else on the call fired, or knew someone on the call tried to get them fired. It was not a recipe for cohesive team building."
Throughout the fall of 2007, Clinton was hailed as "inevitable" by a good portion of the press corps. Even so, her campaign was suffused with a sense of grievance—that Obama was getting a free ride and that reporters were itching for her or her husband to trip up. At a debate in Philadelphia in late October, Hillary, looking sick and exhausted, stumbled on a question after parrying with her opponents for more than an hour. Asked whether she supported New York Gov. Eliot Spitzer's plan to allow illegal immigrants to apply for driver's licenses, she answered yes, no, maybe. Sen. Chris Dodd, then John Edwards, pounced. The Clinton campaign posted a video it dubbed "Piling On," a rapid-fire montage of the men onstage attacking Hillary in the debate. The press accused her of playing the victim, which just heightened the sense among the Clintonites that she was a victim—of a double standard that judged women more harshly than men, especially one particular black man. The feeling deepened a couple of weeks later when Obama, at another debate, botched the same question on immigration and went unscathed by the press.
The Clintonites were not entirely wrong about the press. At the final Iowa debate, on Dec. 13, Obama was asked how he could really present himself as the candidate of change when so many of his advisers had worked in the Clinton administration. As he professorially cleared his throat ("Well, you know, I …"), a sharp laugh erupted from Hillary, who exclaimed, "I want to hear this!" Obama allowed himself a bit of drollery, remarking, "Well, Hillary, I'm looking forward to you advising me as well." Reporters watching in the press area began debating whether Clinton's laugh was really a "cackle" and cracking jokes about "Cruella de Hil."
Obama was starting to feel confident, even cocky again. During December, he took Oprah Winfrey with him as a kind of warmup act, and crowds by the tens of thousands began turning out in the early-winter chill. Winfrey spoke of reading "The Autobiography of Miss Jane Pittman," how the enslaved Pittman was searching for "the One," the child savior who would lead her people to freedom. "Well, I believe, in '08, I have found the answer to Ms. Pittman's question. I have fo-o-u-und the answer! It is the same question that our nation is asking: 'Are you the one? Are you the one?' I'm here to tell y'all, he is the one. He is the one … Barack Obama!!" Waiting backstage, Obama peered out at the crowd of 30,000 and did a little dance with Michelle. At a huge rally with Winfrey in South Carolina, Obama cast off his habitual reserve and shouted so loud his voice cracked. "I just want to know, ARE YOU FIRED UP? READY TO GO! F-I-I-RED UP? READY TO GO!! F-I-I-RED UP READY TO GO FIRED UP READY TO GO FIRED UP READY TO GO …" again and again, until Stevie Wonder came blasting from the speakers: "Here I am-m-m-m ba-a-a-by, signed, sealed, delivered, I-I-I'm yo-o-o-u-u-urs!!!"
Obama was not given to shows of emotion. But at the last debate he was asked an innocuous question about his New Year's resolution, and he launched into standard-issue boilerplate about being "a better father, better husband. And I want to remind myself constantly that this is not about me, ah, what I'm doing today. It's an enormous strain on the family … a-a-a-nd …" He paused, and for the briefest moment there was a hitch in his voice before he continued, "Y'know, yesterday I went and bought a Christmas tree with my girls, and we had about two hours before I had to fly back to Washington to vote …" Valerie Jarrett, the family friend who had become one of his closest political advisers, thought Obama was going to tear up. She had seen it before, at a book party for "The Audacity of Hope" in 2006, when Obama had started to say he was sorry to have been away from his family so much during his campaign for the Senate, and began crying so hard he couldn't go on. Obama was remarkably self-contained, but he was also palpably emotionally attached to his family. Jarrett knew that he had not been able to keep his promises to Michelle about getting home to see her and the kids, and that the strain was starting to show.
At 6 p.m. on Jan. 3, 2008, the night of the Iowa caucuses, Obama, Jarrett and Plouffe drove to one of the canvass locations, a large high school in Des Moines. The parking lot was packed. The three of them just looked at each other, Jarrett recalled. The crowd, mostly white, many wearing Obama T shirts, swirled around them. Obama thanked a young Asian boy for coming out to vote—it was his first election—and when Obama turned away, Jarrett noticed that there were tears streaming down the boy's face. Obama seemed reasonably relaxed to Jarrett. He went off to dinner, but his staff didn't pay him much attention. Their heads were all lowered as they peered at their BlackBerrys, looking for early voting returns.
Over at Clinton headquarters, the preternaturally optimistic Terry McAuliffe, a longtime Clinton fundraiser, thought his candidate would win by 10 points. Nearly everyone had told him so, though Penn, holding close the polls, had hedged with a lot of caveats and footnotes. At 8 p.m. McAuliffe stood in the middle of the campaign boiler room and boomed, "How are we doing?" Wolfson, the spokesman, walked by on the way to get a piece of pizza. "We're getting killed," said Wolfson. "We're going to get killed. We're going to get our asses kicked."
The Clintonites had vastly underestimated the turnout. Penn had originally figured 90,000 Iowans would turn out on a snowy night (the pollster/strategist later boosted the number to 150,000). On the night of Jan. 3, 250,000 came to stand around in crowded gyms and be herded into preference groups for one candidate or another. Some 22 percent were under the age of 25, an unusually high percentage from an age group not known for voting. Hillary won just 5 percent of their votes.
An aide approached McAuliffe and said the president wanted to see him. McAuliffe was escorted to the Clintons' suite by a Secret Service agent. He found Bill Clinton watching a bowl game on TV. The ex-president seemed perfectly relaxed and jovial. "Sir," said McAuliffe, "have you heard the news?" "What news?" Clinton asked. "We're going to get killed," said McAuliffe.
"What!" exclaimed Clinton, who then called out in a loud voice, "Hillary!"
Hillary emerged from the bedroom. McAuliffe recalled: "Nobody had told them. He thought he was going to have a beer with me and watch the game." Suddenly there was pandemonium. Grunwald and Penn appeared, then Solis Doyle and Wolfson and Neera Tanden, the policy director. "How did this happen?" the Clintons demanded. A squabble broke out when Grunwald showed some negative ads on her laptop that had been made—but never aired. Penn insisted that the argument—that Obama had overstated his antiwar credentials—had tested well; it was the ads themselves, made by Grunwald, that were no good. Now President Clinton wanted to run the ads. "Let's go," he said, giving a thumbs-up. But Hillary asked, "Where are we going? It's just throwing stuff against the wall."
The plane flight back to Manchester after midnight was grim. "Mark, we lost women," McAuliffe said. Penn just shrugged his shoulders. At a senior staff teleconference in the morning, Hillary, who had slept no more than an hour, asked for ideas. There was an awkward silence. So she held for a bit, then asked for input. Again, silence. "Well, I want to thank you all," she said. "It's been really great talking to myself." Then she hung up.
Less than 24 hours before the New Hampshire polls opened on Tuesday, Jan. 8, she was sitting in a strip-mall coffee shop in Manchester, talking to about 16 voters, when someone asked, "My question is very personal: How do you do it? How do you do … how do you keep upbeat and so wonderful?" Hillary answered, "It's not easy, it's not easy, and I couldn't do it if I just didn't passionately believe it was the right thing to do. I have so many opportunities from this country …" Her voice cracked. "I just don't want to see us fall backwards. You know, this is very personal for me …"
In the bus afterward, she ranted at one of her aides, "We never should have gone to Iowa. I knew it. I knew we never should have gone." Now she fretted that she had doomed herself with a "Muskie moment," referring to the late Ed Muskie, the once front-running senator from Maine who had doomed his 1972 presidential campaign by welling up at a campaign event in New Hampshire. Penn had warned her not to show vulnerability. "I've been so wound up in doing the commander-in-chief thing," she said. Later that afternoon she stopped in at her Manchester campaign headquarters, where staffers were buzzing about how she had become choked up at a coffee shop. It played well, they assured her. Hillary thanked them. "Don't expect that too often," she said dryly.
Obama's strategist David Axelrod was on the campaign bus when word came that Clinton had teared up, experienced some sort of breakdown. Some of Obama's aides began chortling about an Ed Muskie moment, but when Axelrod went online and saw a video feed of the incident, he had an uneasy feeling. "Everybody said, 'Oh, Ed Muskie and all that'," Axelrod later recalled. "But it didn't come across that way to me at all. It came across as a moment of humanity from someone who badly needed to show one."
Obama was making a triumphal march across the state. The press (once so sure of Clinton's "inevitability") sensed History in the Making, the first black presidential nominee. Several journalists brought their families to Obama campaign rallies to bear witness. But on Jan. 5, at the last debate, Hillary was asked why voters felt that Obama was a more likable figure. "Well, that hurts my feelings," she responded. "But I'll try to go on. He's very likable. I agree with that. I don't think I'm that bad." Obama, barely looking up while he took a note, remarked, "You're likable enough, Hillary."
On Election Day, undecided women voters broke almost entirely Clinton's way. That night, in the press-filing center, New Yorker writer Ryan Lizza was putting the finishing touches on a 10,000-word story on Rocket Ship Obama. "I think I'm f–––ed," he said. "I have to write a completely different story."
Obama was sitting in a coach's office in a high-school gym when the results came in. Axelrod knocked on the door, and Obama stepped outside into the hallway. "It doesn't look like it's going to happen," said Axelrod. Obama closed his eyes and leaned against the wall. He inhaled, exhaled.
"This is going to take a while, isn't it?" he asked.
"I think so," Axelrod answered.
Next: McCain, adrift if not sinking, finds a new narrative: the comeback.
