The Audacity to Win: The Inside Story and Lessons of Barack Obama's Historic Victory

by David Plouffe

  “I wished you had been here tonight,” he said. “We’ve come a long way.”

  “I’ll be there with you the night we win.”

  J-J Day marked the beginning of the stretch drive in Iowa. Had the caucuses been held that day, I think we would have finished a close second to Clinton with Edwards posting a surprisingly poor third-place showing. But we had two months left to close the gap, and all of our pacing, spending, advertising, and strategy were predicated on trying to be at our strongest point on January 3. Our candidate was really hitting his stride and had just delivered a closing argument to voters as he began to crisscross Iowa at a breakneck pace. I would say we were anxious but optimistic.

  In early December on a Saturday night (the night of yet another debate, the Black & Brown Presidential Forum in Iowa, which is a mainstay and a must-attend), all thoughts turned to the Des Moines Register poll, which was scheduled for release in the next day’s paper.

  The Register may have the biggest impact of any paper in the primary process, and its poll has tremendous influence beyond Iowa’s borders. It is regarded as one of the most accurate polls in caucus history, and its results not only shape the press narrative about who has momentum and who is stalled or fading, but they also have a real impact on the ground in Iowa. Local officials endorse based on it, potential caucus-goers weigh it in pledging their support, and it can provide a motivational boost to an organization—or sink its hopes.

  Generally, polls are a dime a dozen in a presidential race, and the sheer number of them makes each one seem less important. But the release of the Register poll is considered an event. Time stops and waits for the results.

  My first experience with the poll was in 1990 when I was working on Tom Harkin’s Senate race. This was before the Internet, so if you wanted the scoop on the poll you had to go down to the Register’s loading docks around midnight and persuade one of the truck drivers to give you a copy before he left on his route. Harkin’s campaign manager called me into his office on a Saturday afternoon and told me to stay out of the bars that night and instead to go down to the Register building at midnight, get a copy of the paper, and then call him at home (cell phones were just large, toaster-sized oddities in those days) to give him the results and read him the story—then he would call the senator.

  Sounds pretty pro forma and uneventful, but to a wet-eared twenty-three-year-old kid it was a high honor; it made me believe I must be doing a good job to be trusted with such an important task. Since then I have never seen a Register poll without thinking of that night and of how seemingly insignificant moments like that can have an outsized impact on your professional trajectory. Now I got to play the old hand: I told our mostly under-thirty staff about how we used to get the Register poll down at the docks because there was no Internet, and they would roll their eyes and look at me like I had escaped from the set of Cocoon.

  The Register poll updates about every couple of months during the campaign season, and the previous results had been released in October, showing us at 22 percent, with Clinton at 29 and Edwards at 23. In the “when it rains it pours” category, we happened to be holding our National Finance Committee meeting (all of our top fund-raisers from around the country) in Iowa on the very Sunday that the poll came out.

  I had half joked to our finance staff that we should buy up and burn every copy of the Register at the airport and all the convenience stores along the route to our meeting. The Register polls are always blared across the paper’s front page, and the October poll edition had pictures of Clinton, Edwards, and Obama with their polling number and arrows for whether they were up or down from the last Register poll in the summer.

  In that poll we were down a few points, Edwards was steady, and Clinton was up. So all of our donors were greeted with a big down arrow next to the picture of their candidate in the biggest paper of the one state we told them mattered most. Unsurprisingly, the meeting that followed was one of our roughest moments with donors pre-Iowa.

  But we were in a very different place now, thanks to our continued organizational efforts, Clinton’s gaffes, and our knockout showing at the J-J dinner. So as we awaited the results of the December poll, we had a lot to be optimistic about.

  The Black & Brown debate on Saturday night was uneventful. It was only telecast on HD Net, which we did not get in the campaign office, so our finance staff found a nearby donor who did; he and his wife graciously opened up their home, ordered food for everyone, and went out for the evening, allowing us to turn the apartment into our rapid-response war room. About twenty staffers gathered around the TV; the HDNet feed went out once or twice so we had to listen over streaming audio on a laptop. It was a pretty bush-league moment for a major campaign.

  The debate was sleepy, but just as it was ending, the Register poll posted online: Edwards, 23 percent; Clinton, 25; Obama, 28.

  “We’ve taken the lead!” yelled Bill Burton, our press secretary, and all of our press and research staff roared at the news.

  This result was a bit rosier than our internal polling, which showed us even more closely bunched together, but it captured what would happen if turnout was high and more independents and Republicans showed. More than any other poll, the Register’s closely matched our field data and the voter ID work we were doing, which was far more voluminous than any poll’s sample size.

  This was a trend throughout the campaign. While our conventional polling always showed a tight race, our field data would suggest that if we turned out our supporters, we might be heading to a terrific outcome.

  When I walked out of the donors’ apartment that night in December, encased in the glow of the favorable Register poll, it was snowing lightly, just a gorgeous midwestern night. I decided to walk the forty-five minutes back to our apartment, enjoying the snow, the city, and the fact that, finally, we were getting out of the penalty box.

  We were less than a month out from the caucuses when we finally deployed our ace in the hole—the big O.

  Oprah Winfrey publicly indicated her support for Obama early in 2007 and had opened her Santa Barbara home in the fall for our largest fund-raiser to date; we raised over $4 million in one evening.

  There was a lot of intrigue about how else we might use her, and a lot of back and forth in the press over whether she would help or hurt. While she was a popular figure, endorsements rarely cause people to support a candidate. There was also the question of whether Winfrey’s endorsement would feed into the notion that Obama was more celebrity than serious contender. Time’s political analysis was typical of the doubts that many pundits shared about her impact. Its story before the trip was titled “Why Oprah Won’t Help Obama.”

  “[D]on’t expect [the Oprah] events to do anything productive to allow Obama to get over the biggest hurdle standing between him and the White House,” the article read. “American voters are not looking for a celebrity or talk show sidekick to lead them. Obama is an intelligent and thoughtful potential president, but Winfrey’s imprimatur is unlikely to convey those traits to many undecided voters.

  “In that respect, Winfrey’s events might even be—dare it be said—counterproductive.”

  These were not unimportant concerns to us. We wrestled with the question of celebrity and stature, but decided to plow forward with an aggressive Oprah plan for two main reasons.

  First, her numbers among noncore caucus-goers and primary voters in the early states were even higher than among the general population. We tested this thoroughly before deploying her. We thought some high-profile campaigning with Oprah could reach some of these voters in a more compelling way than the traditional messengers and methods would.

  Second, we thought it would simply be a great way to gather huge numbers of people, many of whom would otherwise never come to a political event. We would be able to collect their contact information and also get to make a direct pitch—always the most effective form of communication—to a mass of important voters. To reach an unorthodox electorate I thought we
needed to try unorthodox tactics.

  We decided to devote a whole weekend in early December to campaigning with Oprah. Barack, Michelle, and Oprah would do two events in Iowa, one in New Hampshire, and one in South Carolina.

  While much of the national commentary focused on images, we became increasingly focused on raw numbers. About thirty thousand people attended the two Iowa events, in Des Moines and Cedar Rapids. That’s almost 25 percent of the total turnout for the 2004 Iowa caucuses!

  The South Carolina event was also a huge lift. We drew an enormous crowd to a football field, over thirty thousand people. A huge percentage of the crowd was African American women, a demographic in which Hillary was clobbering us in South Carolina. Not after Oprah. We never trailed in that cohort again.

  Some ugliness broke out right after that, which provided real drama for the last and by far the most important debate before the Iowa caucuses.

  The Des Moines Register debate is a hallowed event that has a history of being a difference maker in the caucuses. John Edwards gave his best debate performance of 2004 in this debate, and Dick Gephardt, probably his worst; Edwards’s ascendancy and Gephardt’s decline in the closing weeks of the primary campaign can be at least partly attributed to how they fared here.

  Bottom line: Iowa caucus-goers pay attention to this one. It would take place on December 13, just twenty-one days before the caucuses.

  Two days before the debate, Bill Shaheen, husband of former New Hampshire governor Jeanne Shaheen and cochair of Hillary’s New Hampshire campaign, was quoted in the Washington Post talking about the vulnerability Obama’s admitted teenage drug use would present in a general election. Shaheen wondered if Obama’s candor on the subject would “open the door” to further questions. “It’ll be, ‘When was the last time? Did you ever give drugs to anyone? Did you sell them to anyone?’ Shaheen told the Post.

  These comments created a furor, and it was clear as soon as this broke that Shaheen would have to go. Rather than aggressively distancing themselves from the comments, the Clinton campaign simply let Shaheen resign, saying he didn’t want to be a distraction. They said he was not speaking for the campaign and that they did not authorize these comments. It was a very conventional way of handling a situation like this, almost giving the appearance of a wink and a nod. From a strategic viewpoint, I thought they should have more forcefully criticized Shaheen’s comments.

  Both Clinton and Obama were in Washington casting a vote the morning of the Register debate, a rarity in the closing months of the campaign. They were both needed on what was thought to be a close and important vote, so both broke campaign schedules, traveled to D.C., and then headed back to Iowa for the debate.

  In a tableau that might seem excessive to many, both candidates had large private planes idling at Washington’s National Airport ready to take them to the debate. Our caravan got there first, and Obama, Axelrod, Gibbs (who had traveled back to D.C. with Obama to do some last-minute rolling debate prep), and our traveling team boarded the plane. Hillary’s motorcade pulled up to her plane a couple of minutes later, and her traveling aide came over to speak to us. Reggie Love went down the steps to see what was up and was told Clinton wanted a moment with Obama.

  He reported that back, and a minute later Obama bounded down the steps. The two rivals met on the tarmac between the planes.

  I was sitting on a plane at Chicago O‘Hare, about to fly to Iowa to join up with the traveling team when Axelrod called me. He didn’t even say hello. “Barack and Hillary are talking on the tarmac,” he said breathlessly. “Hillary’s arms are waving wildly and it looks heated.”

  “Sir?”

  I looked up to find a flight attendant standing in the aisle next to me. “Sir, we’re taking off. Please turn off your phone.”

  Unbelievable. But I did as she said. “I’ll call you with more,” said Ax just before he hung up. And then my plane was taxiing down the runway and we were off. For me it was the longest hour of the whole campaign.

  When I landed, they were still in the air, so I stayed on tenterhooks until they got to our greenroom at the debate site. When the traveling party barged in, it was storytelling time. Obama came up to me immediately. “You won’t believe it,” he said.

  “I want to hear it all,” I told him.

  Obama re-created the conversation, with Axelrod and Gibbs piping in and Ax helpfully performing pantomime as appropriate.

  The guts of the encounter were this: Hillary began by graciously apologizing for Shaheen’s comments and saying they were not authorized by her or her campaign.

  “I appreciate that, Hillary,” Barack replied, “and I don’t believe you encouraged that behavior. But we all have to take responsibility for the tone of the campaign and the signals that we send.”

  And with that, Clinton began gesticulating wildly and even shaking a bit (which Axelrod role-played while Obama was recounting the conversation)

  and said that it was not her campaign that put out the D-Punjab memo, or that was talking about trust and character. Obama gently put his hand on her arm to calm things down and said, “I said we all have responsibility, not just you. Let’s both tell our campaigns to try to be more careful.”

  Then it was over, and both candidates headed for their planes.

  “For the first time, I saw a glimpse of recognition and deep concern in her eyes,” said Obama, bringing the recap to a close. “I think she may finally realize that this could be a battle and that Iowa is a jump ball. I’d still rather be her than us, but we’re in their heads for the first time.”

  Hillary’s trepidation had a strong effect on Obama. Clinton was a smart, tenacious candidate who was quick on her feet and highly knowledgeable. And she was the only one in the race with a margin for error. He’d always been deeply impressed by her political skills, but I believe the tarmac exchange gave Obama a real boost of confidence. It might have been the first time he saw her as beatable.

  We were minutes before our most important debate to date, but the atmosphere in the greenroom was light and jocular. One bonus in the Register debate: they assign the biggest greenroom to the candidate in first place in the last Register poll. So we had some fairly spacious digs. It sounds completely dumb, but the competitive juices were flowing so aggressively that even having a bigger greenroom was something to be celebrated. “Screw ‘em and their small-ass rooms,” you’d say of your rivals. “Serves them right for sucking wind in the polls.” Stupid stuff, but it carried a charge.

  When Obama left for the stage, Ax, Gibbs, and I huddled and agreed he was in a great frame of mind. We thought we’d have a very good debate.

  We did. The key moment of the debate, shown repeatedly on the news, was a smart question the moderator asked Obama about how he could be trusted to deliver on change when many of his foreign policy advisers had played key roles in the Clinton administration.

  Before Obama answered, Hillary could be heard laughing very loudly and saying, “I want to hear that.”

  Obama didn’t miss a beat. “Hillary, I’m looking forward to you advising me, as well,” he said, smiling.

  Fucking home run.

  After the debate, all the campaign advisers made the usual media rounds to explain why their candidate won. This is usually a complete waste of time, but if your opponents are out there you always feel you need to make your pitch as well. It’s a fairly rote exercise, and usually the key reporters are already off writing their stories and putting together their TV packages, so you end up spinning to Swedish TV and other, even more minor outlets.

  Right after the debate, Mark Penn was being interviewed on MSNBC along with Edwards strategist Joe Trippi, and he was asked about Bill Shaheen’s comments. As he parroted the line that their New Hampshire chair was not speaking for the campaign, he managed to slip in the word “cocaine,” as in “I think we’ve made clear that the issue related to cocaine use is not something that the campaign was in any way raising.”

  It was breathtaking, ev
en for Penn. Trippi was standing next to Penn and when he heard this, he interrupted Penn. “I think he just did it again. He just did it again,” Trippi piped in. “Unbelievable. This guy has been filibustering on this. He just said ‘cocaine’ again.”

  It wasn’t Trippi’s axe to grind but he seemed genuinely outraged. This exchange was also looped on cable news, making our banner news cycle even sweeter and piling more grief on camp Clinton.

  As we were leaving the debate site (word of the Penn cocaine comments had already spread like wildfire), I told Axelrod, “If we needed any more incentive to win, we just got it. What Penn did is despicable and he’s got to be beat.”

  “He’s everything we are running against,” Ax replied.

  We were now in two-minute-warning time. After a year of preparing, caucus day was nearly upon us. Our internal numbers told us we had momentum and Clinton was stagnant. Signs were that they now thought so, too, but their execution left a lot to be desired. Two instances of their getting tough ended up backfiring on them and landing right in our message wheelhouse.

  Obama kept returning to the idea that he was not running because he thought this was owed to him or because he harbored a lifelong ambition to be president. He was in the race because he thought at this moment he might have something unique to offer the country in terms of leadership; there was no master political game plan at work. And then unexpectedly we got two Christmas gifts from the Clinton campaign.

  The Clinton people decided to send out a memo—written quite seriously—which highlighted a remark made by one of Obama’s grade school teachers in Indonesia, to the effect that while in kindergarten Obama had written an essay stating he wanted to be president. The point, apparently, was that Obama was being disingenuous about his lack of ambition, because he had clearly harbored dreams of being president dating back to when he was five years old.