INTRODUCTION

January 2014

“So, Chris, I want to hear more about this project,” Barack Obama said as Marine One lifted off the runway.

Staring back at the forty-fourth president of the United States, seated in his helicopter, I felt a familiar anxiety set in. When I first started organizing for Obama in 2007, the campaign leadership drilled into everyone that our most precious resource was the candidate’s time—every minute he attended to staff could mean one less minute persuading an undecided voter or inspiring a potential volunteer. If you wanted to contribute to the organization’s success, you should never divert focus from those two goals. This lesson had been so deeply ingrained in me that even after nearly seven years of working for Barack Obama, I never felt at ease interacting with him.

So I always tried to keep my interactions as brief as possible. My job at the White House was to handle “the Book”—a black leather binder embossed with a gold presidential seal that functioned as the president’s nightly homework assignment. The Book contained all the memos, national security directives, draft remarks, schedules, constituent letters, and other documents deemed worthy of the president’s attention. Upon delivery, President Obama would confirm receipt with a nod, thanks, or sometimes—referencing the intense expression I wore nearly every time I entered his personal space, my attempt at professionalism—“you’re still looking really serious, man.”

I had never expected to have a front row seat to the Obama presidency. When I signed up to volunteer for him in my hometown, Iowa City, on the day then-Senator Obama announced his campaign, I assumed he would lose. Nearly two years later, I joined hundreds of other former organizers in following the new president to Washington, looking to be a part of the administration we had played a small, collective role in bringing about.

Through a mix of timing, luck, and privilege, I had landed this West Wing position, where I saw up close how the government documents a president’s time in office. Every staffer’s email is public record, every photo is archived, and every piece of paper is preserved under the Presidential Records Act. These materials are eventually administered by the National Archives and Records Administration and become primary sources for future generations. Sometimes I would imagine historians reading the Book decades later, trying to reconstruct Obama’s eight years.

But as he entered his second term, it occurred to me that comparatively little had been done to document the campaign that put Obama in the White House. Aside from memoirs by the campaign leadership, few had recorded what it felt like to live through the experience in their own words. The reflections of organizers and volunteers—the majority of the people who made up the effort to elect America’s first Black president—would likely be lost to history.

Only five years after his inauguration, the victory that had seemed so improbable at the outset was becoming more inevitable in the retelling. The outcome of the 2012 campaign had already reshaped the meaning of 2008, a trend likely to accelerate with each passing election cycle. Friends’ oft-told campaign stories began to strain credulity, omitting moments of hardship or doubt. It was easy to see how decades of nostalgia might erode the details and reduce their recollection of the experience to “2008? It was great… we changed the world.”

That’s why this was my final trip as a White House staffer. With no other appointments demanding the president’s attention, I’d been given a chance to tell him about the project that compelled me to leave three years before the end of his term.

“Well, sir, it’s an oral history project to document your 2008 campaign,” I said. “I’m leaving to collect interviews with alumni, starting in Iowa.”

In the early days, presidential campaigns attract dreamers.

Every four years, ordinary Americans invest their hopes for the future in a new candidate for president. Despite the stereotype that politics is a cynical quest for power, for thousands of volunteers and activists, campaign fieldwork is an earnest act of blind faith—the belief that your labor might alter the trajectory of the most powerful country on earth.

Nowhere is that sense of possibility greater than in Iowa. The Iowa caucus is an election process different from other states. The caucuses reward grassroots activism, local organization, and community deliberation while offering everyday people the chance to rigorously vet each candidate. Although its predominantly white, older, and rural population doesn’t much reflect the diversity of the national electorate, as host of the first primary contest, Iowa is where presidential dreams take root or die.

It was in Iowa, during his first trip as a presidential candidate, that Obama referred to himself as “an imperfect vessel for your hopes and dreams.” That was especially true for a group Obama called “the kids”—the young volunteers and staff who joined his campaign from far-flung parts of the country in 2007 when he was still an underdog down twenty points in the national polls.

I was one of them. Over the course of eleven months, more than two hundred of us embedded across ninety-nine Iowa counties to build an organization of local volunteers. Our mission was to finish first in Iowa in hopes of proving that Obama could remake the electorate by attracting new voters and that an overwhelmingly white state would support a Black candidate for president.

On January 3, 2008, Obama’s victory in Iowa shocked the country, validating a risky campaign strategy and providing momentum for the remaining primary contests. But to Obama, the experience was more than just another campaign win. It was a test of his most fundamental belief about democracy: that in the face of long odds, ordinary people can bring about change.

Primaries are often covered as national competitions, but they are also sequential, and each one counts in its own way. When the Iowa caucuses ended, Obama’s organizers took what we had learned and went national. Most of us joined up with counterparts in other early states—New Hampshire, Nevada, and South Carolina—hopscotching across the country every few weeks through a new primary.

That summer, transitioning to the general election, volunteers and staff set up shop in areas uncontested by national Democrats for decades—longtime conservative strongholds like Indiana, Virginia, and North Carolina—to register new voters and build neighborhood volunteer teams. By the end, six thousand organizers were managing tens of thousands of trained volunteer leaders. And on November 4, 2008, that work culminated in Barack Hussein Obama—a Black man campaigning to lead a nation founded, in part, on the principles of white supremacy—earning more votes for president than any candidate in American history.

When President Obama is asked about his 2008 campaign, this is who he talks about: his volunteers and his organizers. Many of the people I met over those twenty-one months were natural organizers. I was not. I would equate long hours with productivity, skipping meals only to binge on cinnamon rolls and cake when my blood sugar dropped. The basic duties of a campaign organizer—cold-calling strangers and showing up at their door—made me deeply uncomfortable.

But the cause was all-consuming. Raw enthusiasm eventually infused me with a self-confidence I’d never had before, and it proved contagious around volunteers. “We’re making history,” Iowa state director Paul Tewes, a veteran campaigner, kept telling us. I believed him. Later, when I was working in North Carolina during the general election, I would tell volunteers that knocking on twenty doors could be one of the most important achievements of their life. Every action carried outsize weight. Nothing seemed small.

In the years that followed, I met hundreds of staff and volunteers whose path to joining up had required more sacrifice than mine. It had been easy for me to sign on because it started in my backyard, but I wanted to understand what inspired so many other people to uproot their lives on behalf of an unlikely cause. To know what lessons their experience could offer future generations and how these bit players formed the foundation of the most successful grassroots campaign in modern American history.

So I set out to track down the alumni—the staff and the volunteers, the young people and the young at heart, those who toiled in the campaign’s Chicago headquarters and its local field offices. I wanted to document how they went from wanting something to be different to pulling it off. To capture their spirit and their effort as proof that what happened once could happen again.

As Marine One touched down on the White House lawn, President Obama turned to me and said, “Well, if you want, when you’re ready, let me know and I’ll do an interview with you.”

More than a year later—after nearly two hundred interviews—I took him up on that offer. In the Oval Office, he described what kept him going during the early months of the campaign, when he was widely expected to lose:

It was really the team on the ground—and I would include the volunteers with that—those staff and volunteers that carried us in those early months at a time when we were still honing our message and I was still finding my way as a candidate.

When I was their age, I had become a community organizer, not even really knowing exactly what that meant and not necessarily being as good at it as any of them were. But it was based on a premise that drew from my reading of the civil rights movement and my reading about the union movement and the women’s suffrage movement. This vision of a politics from the bottom up. And so often electoral politics was something completely removed from that. It’s money, and it’s TV ads, and it’s positioning, and it’s talking points. And somehow the process of people becoming involved and determining their own destiny—that got lost.

And what I saw with both the staff and the volunteers was this almost organic process of people organizing themselves. And I was the front man, but they were the band… when you saw folks like this work, you just didn’t want to screw up. You wanted to make sure that you were worthy of these efforts. And I really wanted to win, for the staff and volunteers, as badly as I wanted to win for myself.

This is the story of his team on the ground—from Iowa to the inauguration—as told by those who lived it.

The 2004 Campaign: The Illinois Primary; From Crowded Field, Democrats Choose State Legislator to Seek Senate Seat

—New York Times, March 17, 2004

As Quickly as Overnight, a Democratic Star Is Born

—New York Times, March 18, 2004

Barack Obama Named Keynote Speaker at 2004 National Convention

—NBC Today Show, July 15, 2004

“Skinny Kid with a Funny Name” Makes Good

—CNN, July 30, 2004

Bush Wins Second Term

—Guardian, November 3, 2004

Convention Star Obama Wins Illinois Senate Seat

—New York Times, November 3, 2004

Republicans Enlarge Senate Majority: GOP Majority Now Includes 55 Senators

—Sabato’s Crystal Ball, November 4, 2004