How He Did It

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!"