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In the years since Barack Obama was first elected president, dozens of books have looked back on his time in office—some that go behind the scenes of Obama’s White House, some that dissect the inner workings of his administration, some that analyze the broader Obama era. There is even a best-selling Obama-Biden detective novel series.
This is something different. In this oral history, you’ll find well-known names from the Obama for America leadership. But you’ll also hear from former field organizers and volunteers as they share what it was like to work deep inside the organization—the moments of joy and terror, inspiration and anxiety, loneliness and fellowship that remain seared into memory more than a decade later. Their voices are only a narrow slice of the six thousand staff, tens of thousands of neighborhood leaders, and millions of volunteers who, not so long ago, in the shadow of an unpopular president, banded together to move the country in a new direction. It would be impossible to include them all, but my hope is that this book offers a portrait of this grassroots movement, one forged when few expected Obama to prevail.
A few standard disclaimers: Because roles evolved as the campaign progressed, the title listed next to each speaker corresponds to the months covered in that chapter. The quotes here are drawn from more than two hundred interviews recorded between September 2013 and June 2015 as well as follow-up sessions in 2019. I’ve removed verbal placeholders (“you know,” “like,” “just,” etc.), condensed quotes, and arranged stories chronologically so the narrative is as clear as possible.
My own voice appears in italics, a reflection of the fact that on this subject, I cannot be neutral. Many of the people included here were strangers when I began this project. Some were former coworkers, roommates, and close friends. One even officiated my wedding. The common thread was having devoted themselves to the election of America’s most unlikely president when the outcome was far from certain.
I chose to present their stories this way in the hope that a constellation of voices might best reflect what so many stressed to me about Obama for America: on every level, the whole was greater than the sum of the parts.
“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
Fall 2004–Spring 2007
In my sophomore year of college, my roommate Sean ordered us matching dark-blue “Barack Obama for Senate” T-shirts. Sean and I were students at the University of Iowa, and because Iowa was a swing state with presidential candidates visiting all the time, it felt like we were at the center of the political world. It was fall 2004, eighteen months after George W. Bush invaded Iraq, and the stakes of that year’s presidential campaign felt life-and-death.
President Bush launching a “preemptive” war in Iraq when I was seventeen is what made me care about politics. As I realized that President Bush’s election had led to people my age being sent to war, I started to follow campaigns in the same obsessive way I tracked baseball box scores as a kid. This was before Twitter, so Sean and I would spend hours refreshing realclearpolitics.com, trying to dissect the latest polls—most of which we did not understand—and speculating about what soon-to-be president John Kerry’s Democratic Senate majority could accomplish.
Even though we watched dozens of races across the country that fall, I didn’t care for most politicians. Obama, who was running for the US Senate in Illinois, was the only one we deemed T-shirt worthy. Everything about him felt different. His Democratic National Convention speech included aspirational language that sounded revolutionary compared to his peers. Obama had spent his twenties as a community organizer, written a memoir that examined his biracial identity and detailed youthful drug use, and been elected the first African American president of the Harvard Law Review. He was young, he was smart, he seemed honest, and unlike nearly every other prominent Democrat, he had been right about the most important policy question in my lifetime: he had opposed the Iraq War before it began. He was also on the verge of becoming only the third Black person elected to the US Senate since Reconstruction.
On election night 2004, Obama’s win was the only bright spot. President Bush won reelection and carried with him into office half a dozen new Republican senators. Even Tom Daschle, the Democratic Senate leader, went down. Against that backdrop, Obama arrived in Washington, where he was greeted as a rising star in a political party desperate for new heroes.
While I was excited about Obama’s ascent, Bush’s reelection left me despondent. I could not understand how a majority of voters thought a man who had entered the White House after losing the popular vote and had started a war based on false pretenses deserved a second term. Further, I couldn’t understand how nearly every Democrat in Congress with presidential ambitions had voted for a congressional war resolution prior to the invasion.
Not knowing where to turn, desperate to do… something… in the aftermath of Kerry’s loss, I dove deeper into political blogs and read every book I could find on presidential elections. Looking at the history of past campaigns, I realized I was in a perfect position to get involved in the next one. I had grown up and gone to college in Iowa City, the most liberal town in Iowa’s most liberal county. Potential 2008 candidates started to visit the home of the first-in-the-nation Iowa caucuses as early as March 2005, quietly exploring presidential runs.
By fall of 2006, my senior year of college, I was attending lots of small local political events, hoping to be inspired. At a Saturday-morning Hawkeye football tailgate, I watched John Kerry politely decline a beer bong (“It was her 21st birthday,” the New York Times reported under the headline “Bong Girl”). At a backyard fundraiser in Waterloo, Joe Biden pulled me close to share a story about working out with Strom Thurmond in the Senate gym. Mark Warner, former governor of Virginia, spent an afternoon shooting hoops with me and a dozen other Iowa college students.
None of them excited me.
The politician I most liked, Obama, was the one who never visited. And so, I assumed, he wouldn’t run for president. At least not in 2008.
Pete Rouse, Obama Senate Chief of Staff: We had a strategic plan for getting established in the Senate. None of it had anything to do with running for president.
By 2004, I’d been Senator Tom Daschle’s chief of staff for nineteen years, ten of those spent with him as Senate Democratic leader. Tom lost his reelection race the same year Obama was elected to the Senate. After the election, Senator Obama asked me to be his chief of staff.
He told me, “I can give a good speech. I know retail politics. I am also aware that I’m coming to the Senate with some notoriety—the only African American, the Boston convention speech. I know that some of my colleagues, including Democrats, are going to be wary of me and concerned about whether I’m going to be a serious senator or a headline grabber. I want to move forward in the Senate, but I want to follow a strategic approach so I can be an effective senator as quickly as possible without ruffling feathers unnecessarily.”
That wasn’t enough for me, though. I had been in the Senate a long time. I was in my midfifties, and I was thinking about moving on to a new phase of my career. So I said, “That’s great. I’m happy to give you advice, but I’m not available to do this.”
Senator-elect Obama countered as follows: “One other thing. You may have heard that I’m thinking about running for president in 2008. That is categorically untrue. Maybe at some point I would consider this down the road—2012, 2016, later if I ever have an opportunity. But now my daughters are too young. My wife would never allow me to do it in 2008. I’m focused on getting established in the Senate.”
So I thought, “Here’s a very smart guy, a very decent guy. He is extraordinarily talented and very important to the future of the Democratic Party. If he’s just looking for somebody to help him get established in the Senate, how hard could this be? I’ll do it for a year and a half, get him going, and then find somebody else to take it from there.”
Nine years later, I left the White House. You just get swept up in it.
Lauren Kidwell, Staff Assistant, US Senate: He was not your typical freshman senator. When I was still a staff assistant working the phones, you would see people come by just to take pictures of the nameplate outside his door.
That first year he turned down a lot of national invitations. Scheduling requests came from people who were not from Illinois. I remember picking up the phone one day, and the woman on the other end said, “Can I talk to the scheduler? I want to invite the senator to something.”
So I went into our normal spiel about how to send the request in writing and cautioned that we don’t accept a lot of invitations.
She was like, “Uh-huh. This is Ethel Kennedy. I’d like to talk to your scheduler please.”
So I put her right through.
I was very junior, so I certainly wasn’t in any inner circle conversations, but from day one, I was opening letters from people around the country saying, “You need to run for president.”
Stephanie Speirs, Senior, Yale University: I wrote a letter to Obama’s senate office when I was in college. Like a lot of people, I first heard of Barack Obama in 2004, from the DNC speech that he gave. I was so struck by the way he talked about government as a force for good and a unifying force, because that wasn’t the era that we were living in under George W. Bush. He talked about how there was more that was common between us than divided us.
In the letter, I talked about how I was really struck by that vision. I was also struck by the fact that he was raised by a single mom who struggled to make ends meet. My own single mom raised three kids on a salary below the poverty line. I, too, was born and raised in Hawaii, where I felt like my story was improbable in any other country than America. Being the child of immigrants, I had a very particular definition of the American dream from my parents—one that Obama also articulated. So for all those reasons, I thought, “One day I want to work for this person in some capacity.”
Alyssa Mastromonaco, Director of Scheduling, US Senate: There was an accessibility to him in the Senate. It was a much more formal place than it is now, and he was someone that everybody felt like they could talk to. Everything you could ever want to do, he got invited to do, so we had to be calculating. He got invited to a bunch of Ivy League and private schools for commencement season, but the big one we did was UMass Boston. UMass Boston had one of the highest percentages of first-time nontraditional students of any school on the East Coast.
Carrianna Suiter, UMass Boston Commencement Audience Member: Senator Obama was my brother’s commencement speaker at UMass Boston. It was such a diverse audience. You had kids who were the first in their families to go to college. You had grandparents and mothers from working families who were graduating. The commencement was outside, in the middle of a storm. Despite the weather, everyone paid attention, everyone listened. Looking around and seeing how enamored of this man people were was incredible. Like he understood what people were striving for.
Jon Favreau, Speechwriter, US Senate: When Hurricane Katrina happened in August of 2005 and Obama started going around the country speaking about it—not just as a failure of ideology but a failure of government standing up for people in the most basic way possible—that cut across party lines. That’s when he started to feel that maybe it was his time to be on the national stage.
All through ’05 and ’06, as he campaigned for other people and at state party conventions around the country, we were crafting a stump speech. It set him up to be seen as a different kind of Democrat—not ideologically but in that he felt that people needed to get involved in politics again. We needed to be honest again. We needed something different. Something outside of Washington. That became his message.
Tommy Vietor, Press Secretary, US Senate: He wrote The Audacity of Hope and did this long book tour. In the ’06 midterms, along with all the travel he was doing, I think he saw the reaction he was getting from other politicians, from candidates and activists. He could tell he was reaching people.
The first sign Obama might be changing his mind about running for president was the announcement that he would travel to Iowa for the Harkin Steak Fry, an annual fundraiser hosted by Iowa Democratic senator Tom Harkin in September 2006.
Alyssa Mastromonaco: Tom Harkin approached Obama on the Senate floor and said, “Every year I host the Harkin Steak Fry. It would really mean a lot to me and the Iowa Democratic Party would raise so much money if you would be our keynote speaker.”
Pete Rouse: Senator Harkin didn’t want to have to choose among his colleagues who were running: Joe Biden, Chris Dodd, John Edwards, Hillary Clinton. Obama was invited as headliner for the Steak Fry because he was the one option who wasn’t a candidate for president in 2008. He initially declined Harkin’s invitation—he didn’t want to generate speculation that he was thinking about running, because at that point he wasn’t. But Senator Harkin continued to argue that he ought to reconsider the invitation, saying, “You’re not running; you’d be perfect.”
Steve Hildebrand, Political Consultant: Pete Rouse called me and said, “Senator Harkin has invited Obama to come to Iowa. Barack’s going to do the steak fry, and we want you to staff him.”
Pete Rouse: Steve Hildebrand was known as the “Iowa guy” from the Gore days. Steve knows all the political people in Iowa.
- "A readable collective chorus of hopeful voices tirelessly promoting Obama's patriotism, moral clarity, and honorable leadership.... As a campaign diary, the book succeeds in gathering representative perspectives from those who participated in its success.... Adulatory reflections on a historic presidency sure to fuel hope for future elections."—Kirkus Reviews
- "They Said This Day Would Never Come tells the story of Barack Obama's historic 2008 campaign through the voices of the people who made it happen, but it's about so much more than one election. It tells a story about the power of everyday people to shape the course of our country and change the world."—Dan Pfeiffer, cohost of Pod Save America and author of Yes We Still Can
- "Chris's book reminds us that politics doesn't have to feel hopeless or slimy if we're willing to put in the effort--this is a beautiful and genuinely moving oral history of how young people who believe in something and are willing to actually DO something about it can change the world."—Amanda Litman, cofounder of Run for Something
- "The Obama campaign of 2007-2008 in Iowa was a wondrous story, authored by a corps of young activists and people hungry for change. In They Said This Day Would Never Come, Chris Liddell-Westefeld brilliantly captures the spirit of that effort."—David Axelrod, director, University of Chicago Institute of Politics and CNN senior political commentator
- "An amazing read in the words of the organizers on the ground who elected Barack Obama president. If you care about bringing about change, there are lessons in this book for you."—David Plouffe, former campaign manager and White House senior adviser for Barack Obama
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- Jan 7, 2020
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