Yes We (Still) Can

  Copyright © 2018 by Daniel Pfeiffer

  Cover design by Jarrod Taylor

  Cover images: Obama, Trump, basketball hoop © Getty Images; floor © Alamy

  Cover copyright © 2018 by Hachette Book Group, Inc.

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  First edition: June 2018

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  Library of Congress Control Number: 2018932320

  ISBNs: 978-1-5387-1171-2 (hardcover), 978-1-5387-1172-9 (ebook)

  E3-20180511-NF-DA

  Contents

  Cover

  Title

  Copyright

  Dedication

  Epigraph

  Introduction

  Chapter 1: Started from the Bottom

  Chapter 2: How Not to Lose a Campaign

  Chapter 3: Telling the Country and Other Tales of Presidential Communications

  Interlude 1: Something Pants-Splittingly Funny

  Chapter 4: The New Media Wasteland

  Chapter 5: Fighting Fake News

  Interlude 2: My Beautiful, Dark, Twisted (White House) Fantasy

  Chapter 6: Fox (and Friends) Is Destroying America

  Chapter 7: The Republicans Go off the Deep End

  Chapter 8: Tweeting While Rome Burns

  Chapter 9: From 1600 Penn to Keepin’ it 1600

  Interlude 3: Advice You Can Believe In

  Chapter 10: The 2016 Campaign Clusterfuck

  Chapter 11: Thanks, Obama (Seriously)

  Acknowledgments

  About the Author

  Twelve Mission Statement

  Newsletters

  To Howli, who is simply the best.

  We know the battle ahead will be long. But always remember that no matter what obstacles stand in our way, nothing can stand in the way of the power of millions of voices calling for change.

  —Barack Obama, “Yes We Can”

  speech, January 8, 2008

  Introduction

  If You’re Reading This, It’s Too Late

  My final visit to the White House during the Obama era was not at all what I’d imagined it would be.

  Over the years, I had often thought about the moment when this chapter in my life and the country’s history would come to a close. I imagined it to be bittersweet, but more sweet than bitter. I imagined it to be the triumphant end to a great era in American history—one that would be talked about with the reverence reserved for the great presidents.

  This was the last day of the Obama presidency. But I wasn’t headed back for a raucous good-bye party or even a sheet cake in the Roosevelt Room to pat ourselves on the back for years of good work.

  We weren’t celebrating at all. We were about thirty-six hours from Barack Obama, our first African American president, leaving and Donald J. Trump, racist reality TV star, assuming the presidency. Sure, I had thought about the possibility that Obama would be replaced by a Republican. It wasn’t just possible, but historically probable. But I had never imagined something like this.

  Donald Trump in the White House was worse than my worst nightmare.

  And to make this visit even more surreal, I was back at the White House to interview President Obama. For a podcast. A medium I barely knew existed when I first met him back in 2007.

  I walked into the West Wing this one last time with my Pod Save America cohosts, Jon Favreau, Tommy Vietor, and Jon Lovett, all of whom had been with me on Day 1 of the Obama presidency.1

  There is something powerful about walking through the doors of the White House—even if you do it every day for six years—but this time felt even more consequential. This was the last time I would walk into a White House staffed by friends and colleagues—people with whom I had shed blood, sweat, and tears in the service of making Hope and Change a reality. This was the last time I would walk into a White House where Barack Obama was president.

  This might be the last time I ever walked into the White House period—the place that had been my home for almost my entire thirties; the place where I had experienced tremendous triumph and tragedy; the place where I had met and fallen in love with my wife.2

  I am proud to say I never took working in the White House for granted. But up until this moment, it had never occurred to me that I might never again walk through those doors.

  We arrived just in time for Obama’s final press conference as president. This felt fitting. I hate press conferences. Sure, presidents taking questions from reporters is an important part of the democratic process. But I hate everything about them. I hate the process of preparing for them. I hate the questions that are asked. And I hate watching them. When I worked in the White House, I couldn’t bear to be in the room when they happened. They made me too anxious, and I would watch in my office. I told people I did that so I could consume the press conference like the public—see how it played on TV. That was bullshit. I just wanted the ability to yell at the TV like a crazy, basement-dwelling C-SPAN viewer.3

  On this day, I ostensibly had to watch in preparation for our pod interview, which would immediately follow the press conference. Even though I had no skin in this game, I was freaked out for the whole press conference, unable to sit still, and yelling at the TV when I thought the questions were inane or the answers too long. A fitting end to my role in Barack Obama’s dance with the White House Press Corps.

  I was mostly anxious about the interview. It was going to be his final interview as president of the United States, and this was a big deal for Pod Save America, which had just launched less than two weeks earlier.

  Interviewing a president is hard. I have seen experienced, world-famous journalists melt the moment they walk into the Oval Office. We weren’t experienced and we certainly weren’t journalists. Our familiarity with the subject added to my anxiety. I know all too well how busy a president is—even on his or her last day in office. During my years working with Obama, one of the things I brought to the table was a finely honed sense of the exact moment when Barack Obama was tired of doing the thing he was doing. In staff meetings and prep sessions, I could always tell when Obama’s brain had started to move on to the next item of his never-ending to-do list. It was often my role to bring the meeting or interview to an end before the length of the meeting exceeded Obama’s patience.

  I dreaded the idea of seeing that switch flipped before we were done. The last thing I wanted to do was be yet another annoying thing on his schedule. I had been the one to ask the president if he would do the interview, so I felt particularly tied to its success.

  Or failure.

  We had been working on questions for weeks. Obama is by his very nature a storyteller, so I went looking for the perfect anecdote to set him up to put the Obama era in perspective and explain how and why we ended up with someone like Donald Trump as president.

  When I left the White House in 2015, President Obama gave me a collection of photos from our time together, dating back to the early days of the campaign,4 as a farewell gift.

  One of the first photos in the book is from an early 2007 campaign trip to New Hampshire. Neither Obama nor I have any gray hair, and we both look so young. We are smiling and laughing—blissfully unaware of all that is to come—as we head into one of the endless series of meet and greets with voters that define the early days of presidential campaigns.

  Each photo in the album is attached to a different moment in the Obama era—the good times and the bad; the funny and the sad; our successes and our failures.

  I never found the magic question for the interview, but I did find the seeds of this book.

  Reader Beware

  First, let’s talk about what this book isn’t.

  It’s not a history of the Obama years, because I’m not a historian.

  It’s not the inside account of the moments that will fill the history books, because that’s Barack Obama’s story to tell (and he will tell it much better).

  And finally, it’s not a “tell all” filled with gossipy scoops about the Obama White House, because I’m not an asshole.

  Instead, Yes We (Still) Can5 is a look back at my experiences on the Obama campaigns and in the White House to try to better understand the current state of politics and look at where we go from here. Much like Pod Save America, it’s a no-bullshit conversation about politics in the era of Obama, Trump, and Twitter.

  As I was doing my deep dive through the Obama years, I kept finding examples of Barack Obama trying to navigate the very forces that created an environment where someone like Donald Trump could be elec
ted.

  For eight years, Barack Obama dealt with:

  A dystopic, anything-goes media environment upended by the emergence of the Internet

  An intellectually bankrupt and increasingly rabid Republican Party

  A right-wing propaganda machine embodied by Fox News

  The rising tide of fake news and conspiracy theories

  The emergence of social media platforms such as Twitter that reward the loudest voices and penalize thoughtfulness and analysis

  It became clear to me in those dark days after the election that embedded in the successes (and failures)6 of our battles against these forces were lessons about how Democrats can ultimately defeat Trumpism.

  This account is my best recollection of what happened and what people said. I didn’t take notes or keep a diary, because at the time I had no intention of writing a book, but I like to think I have a good memory. I threw in some of my favorite fun stories, just cuz.

  Finally, this book is also an argument to young people that politics is something very much worth engaging in. It’s fun, fulfilling, and really damn important. We need another generation of young people to get in the game. Barack Obama inspired millions of young people to believe in the value of being part of something larger than themselves. As the rapidly emerging gray hairs of myself and my former 2008 colleagues show, that generation is now older. It’s time for a new generation to step up and take charge of our future.

  I started writing this book in the days after that final presidential encounter with Obama. I didn’t know what I was writing when I started; I just knew I wanted to say something about how we got to this moment in politics and how we could get past it. I was worried that it would be a depressing exercise, the equivalent of wallowing at home looking at photos of an ex after a bad breakup.

  But it wasn’t.

  Not at all. Quite the opposite actually. I was inspired by something Obama said in the Pod Save America interview.

  Toward the end of the interview, Jon Favreau asked Obama,

  “Mr. President…you’ve talked a lot about how we’re all trying to get our paragraph right in history. What do you hope that paragraph says about you?”

  The president replied, “When I think about what will most gratify me, it will be if, twenty years from now, I can look back and I can say, wow, look at all these people who first got involved—maybe even when they were too young to vote—in government, politics, issues, nonprofits, public service, and that wave just kind of—a cleansing wave washes over the country. And if that happens, then the details of how we dealt with climate change, or whether the individual responsibility mandate on the Affordable Care Act was the right approach or not—that becomes less important. Because if we’re getting the broad direction right, this is a pretty ingenious country, full of ingenious people, and we’ll figure it out. And that’s what I want—is I want everybody to feel like we can figure this out if we just don’t waste a lot of time doing dumb stuff.”

  The idea of Trump and his coterie of Internet trolls, self-dealing Wall Street tycoons, and unrepentant racists wandering the halls of the White House doing dumb, mean shit is hard to stomach. Not a day has gone by since the 2016 election when I haven’t been angry about the result and sad for the country.

  My hope in writing this book is to show that it doesn’t have to be this way. That if we learn the right lessons and, most important, people—especially young people—get involved in politics, we can ensure that Donald Trump is an aberration. A speed bump on the path to the America we all hoped for in 2008.

  But it’s up to us.

  Yes we (still) can.7

  1 As is well known by all Friends of the Pod, Tommy and Favreau were original Obama campaign staffers while Lovett worked for Hillary in ’08. We forgave him, but never stopped making fun of him.

  2 You will meet her later—she’s awesome.

  3 Or the forty-fifth president of the United States.

  4 Obama also gave me—a rabid Georgetown University basketball fan—a basketball autographed by Georgetown legends Patrick Ewing, Alonzo Mourning, and Dikembe Mutombo.

  5 I am going to make the parentheses thing a thing. Just watch.

  6 See footnote 5.

  7 Not giving up the parentheses thing.

  Chapter 1

  Started from the Bottom

  I don’t believe in fate. But if I did, I would say it was fate that I ended up meeting Barack Obama at the exact moment when I most needed to meet someone like Barack Obama.

  Since I don’t believe in fate, I will chalk it up to being one lucky SOB.

  I walked into my first meeting with Barack Obama in early 2007 with a good deal of skepticism. Ostensibly, I was there for him to interview me for a potential presidential campaign, but I wanted to see if Barack Obama, the man, matched up to Barack Obama, the hype. I was pretty skeptical that a rookie politician espousing a gauzy but vague message of hope and change had what it took to survive the brutal freak show of presidential politics.

  Frankly, on paper it was insane that he was considering running for president. But that’s why I was there.

  I went into that meeting with a hard-earned cynicism from a decade in Democratic politics filled with defeats, disappointments, and a growing disillusionment. I was on the verge of quitting politics and trying my hand at something new—I had even started studying for the GRE and was looking at applying to grad schools.

  Instead, I walked out of that meeting with a new job and a new reason to hope.

  The rest is history, but I almost missed it.

  This is embarrassing to admit now, but when the rest of the world was falling in love with Barack Obama in 2004, I wasn’t paying any attention to him.

  In fact, I didn’t even watch the famous 2004 convention speech that skyrocketed Barack Obama into national politics. I didn’t watch it in the days after when it was the talk of everyone in politics. And I didn’t watch it in the ensuing two years when I was working in the Senate and seeing Obama on the weird Senate Subway,1 which takes senators and their aides from their office buildings to the Senate Chamber.

  In 2004, I was working day and night on Senate Minority Leader Tom Daschle’s reelection campaign in South Dakota, and due to the obsessive tunnel vision that campaigns give you, I was paying very little attention to anything that wasn’t in the Sioux Falls Argus Leader newspaper.

  When Dreams of My Father, Obama’s memoir, was rereleased to rave reviews in 2004, I didn’t read it.

  When The Audacity of Hope, Obama’s instant best-seller of a follow-up book, was published, I didn’t read it.

  The first time I heard the name Barack Obama, I was sitting in the backseat of an SUV driving around rural South Dakota with my boss, Senator Daschle. Senator Jon Corzine of New Jersey, who was heading up the Senate Democrats’ campaign committee, called Daschle to check in. After the call, I asked Daschle what Corzine had wanted and he said, “Jon has just met the most impressive candidate who is running in the Illinois primary. His name is Barack Hussein Obama.” Daschle went on to convey Corzine’s assessment of Obama’s immense charisma, smarts, and oratorical skills, as well as Obama’s unique background.

  “Sounds amazing. Too bad he has no shot,” I responded.2

  Who Am I? Why Am I Here?3

  My first encounter in politics was one befitting a Democrat: I got my ass kicked.

  It was 1988, I was in seventh grade, and it was in Tokyo.

  My family was living in Japan because my dad worked for DuPont and had been assigned to a four-year stint in the Tokyo office. I was attending the appropriately named American School in Japan, being that it was an American school that was most certainly in Japan. My civics teacher opened up class one day with an announcement.

  A Japanese television network was doing a special on the American election, and as part of their programming, they wanted to put on a mock presidential debate with two students playing the roles of then vice president George H. W. Bush and Massachusetts governor Michael Dukakis. The debate would be carried in part on local Japanese television.

  The teacher asked for volunteers and said the class would vote to choose the debaters.