By Dan Pfeiffer
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From Obama’s former communications director and current co-host of Pod Save America comes a colorful account of how politics, the media, and the Internet changed during the Obama presidency and how Democrats can fight back in the Trump era.
On November 9th, 2016, Dan Pfeiffer woke up like most of the world wondering WTF just happened. How had Donald Trump won the White House? How was it that a decent and thoughtful president had been succeeded by a buffoonish reality star, and what do we do now?
Instead of throwing away his phone and moving to another country (which were his first and second thoughts), Pfeiffer decided to tell this surreal story, recounting how Barack Obama navigated the insane political forces that created Trump, explaining why everyone got 2016 wrong, and offering a path for where Democrats go from here.
Pfeiffer was one of Obama’s first hires when he decided to run for president, and was at his side through two presidential campaigns and six years in the White House. Using never-before-heard stories and behind-the-scenes anecdotes, Yes We (Still) Can examines how Obama succeeded despite Twitter trolls, Fox News (and their fake news), and a Republican Party that lost its collective mind.
An irreverent, no-BS take on the crazy politics of our time, Yes We (Still) Can is a must-read for everyone who is disturbed by Trump, misses Obama, and is marching, calling, and hoping for a better future for the country.
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
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.
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.
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 elected.
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.
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.
“Who wants to volunteer to be Vice President Bush?”
About ten hands went up.
“Who wants to be Michael Dukakis?”
One hand went up.
I’m not exactly sure why I volunteered. Maybe I thought being on TV would be cool.4 I did enjoy debating or, as my mom would call it, being a “smart aleck.”5 There is a famous story in my family about a seven-year-old me finding out that Santa wasn’t real and turning it into a debate about the existence of God. I stand by my view then that if Santa, the Easter Bunny, and the Tooth Fairy—all magical entities, never seen by people—were fake, I was right to ask the question. My mom disagreed.
Either way, I definitely did not think it through before I raised my hand. But now I was Michael Dukakis for the whole world or at least the whole of Japan to see. My parents were lifelong Democrats whose views had been shaped growing up in the South during the heyday of the civil rights movement and going to college in 1968, when activism against the Vietnam War swept the nation. We talked about politics and world events at the dinner table in part because my dad’s job allowed us to see a lot of the world outside the United States. Prior to living in Japan, we had also spent three years in São Paulo, Brazil. My parents had ingrained in my younger brother and me the idea that Democrats were right and Republicans were wrong.6 At this point, I had a very simple understanding of our two-party system: Republicans liked war and hated poor people.7 Democrats hated war and liked poor people. I also knew that Democrats did not win elections very often. As for Dukakis himself, he was a mystery other than the fact that he was a Democrat, was losing, and once looked ridiculous riding in a tank.
I leaped into preparation. I didn’t know a lot about life, but I knew enough to be aware that embarrassing yourself on TV was something you don’t quickly live down in the cutthroat world of middle school. And beyond my own social standing, I hated losing in anything and everything.
When I was about ten or eleven, my family got the board game Trivial Pursuit and we would all play it together. Other than being able to answer some of the sports questions and some of the easiest questions on subjects like history that I studied in school, I was completely flummoxed. The questions were about books, movies, television shows, and events that happened long before I was born. I was bad at the game and I hated constantly losing.
I took matters into my own hands.
When my parents weren’t looking, I would take the cards with the questions from the box and go into my room and memorize the answers. I would read each card several times, repeating the answers to myself before moving on to the next card. I did this almost every day for weeks until the next family game night, which went something like this:
“What Byzantine city was renamed Istanbul after being captured by the Ottoman Empire?”
And so it went. I answered the next ten or so questions without getting one wrong—including one about what movie won the Best Picture Oscar in 19448—and won the game in record time. My parents couldn’t tell if I was a remarkable genius or an inveterate cheater. By the end of the game, they were either sending me to juvee or early enrolling me in Yale.
I stand by the idea that this was in no way cheating (my dad disagrees9), but it definitely revealed my combination of nerdiness, obsessive compulsion, and competitiveness, which would define much of my adult life and help push me toward a career in politics.
This was the level of preparation that I brought to the role of Michael Dukakis. Because I lived in Japan and the Internet wasn’t yet invented, the only way to learn about Dukakis was to go to an actual library and look at old newspapers and magazines. I printed reams of articles and made flashcards of the candidate’s positions. My dad would quiz me at the dinner table about the finer points of Dukakis’s policy papers.
Heading into the debate, I was very confident. The role of Bush was being played by one of the smartest girls in our class, but I was sure there was no way she knew more or was better prepared for the debate—I could memorize an entire set of Trivial Pursuit cards.
I was right. I knew more about the issues and positions of both candidates. And in what should be an object lesson for generations of Democrats, I still got killed.
While I was trying to explain how Dukakis’s plans were better for the middle class, my opponent was hammering me over the head claiming Dukakis was soft on crime, soft on the Soviet Union, and wanted to raise people’s taxes.
I pushed back on those accusations with facts about Dukakis’s plans, but I was on the defensive for much of the debate. It didn’t matter that I was right on the facts; her message was much more compelling than my policy details. This is a lesson that I would need to relearn many times in my career.
After we’d finished, our civics class held a mock election based on what they’d seen in the debate. I lost by a margin not dissimilar to the ass kicking that the real Dukakis received in the real election.
A couple of years after my less than stellar performance, my family moved back to Delaware so that I could go to high school in the United States. When it came time to think about college, I didn’t really know where I wanted to go to school. All I knew was that I wanted to get out of Delaware. After living in Tokyo, life in the second-smallest state in the Union—one best known for being the home of tax-free shopping—had started to feel suffocating.
I ended up at Georgetown University in Washington, DC.
I was pleasantly surprised when I was accepted. I wasn’t great about turning my homework in on time, so my high school GPA was a little below their standards. Before the beginning of my freshman year, I went to an event for incoming students hosted by a local alumnus to introduce us to our new classmates and learn more about the school. When I introduced myself to the host, he said, “Dan Pfeiffer? I remember your application.”
“Oh?” I responded.
“I have been serving on the acceptance committee for many years and I have never seen a report on an alumni interview like yours. It’s why you got in.”
Part of the application process involved an in-person interview with a local alumnus. These are usually scheduled for forty-five minutes or so. Mine lasted almost two hours. My bullshit abilities were at peak performance this day. We talked about everything—politics, the Gulf War, civil disobedience, the novel Catch-22, and what I learned about the world from living abroad. Everything I had ever read, experienced, and memorized came in handy that day.
I didn’t think much of it at the time, but it was now clear that I might have just conned my way into college. I was immediately scared shitless that people would figure out that I didn’t belong as soon as I stepped on campus.
This was the kick in the ass I needed. After gliding through high school doing just enough to do fine, I arrived at college with a chip on my shoulder to prove that I belonged and a strong desire not to flunk out.
Don’t get me wrong, I had a lot of fun in college, but I never skipped a single class in four years—no matter how tired, sick, or hungover I was, I dragged myself to class. I couldn’t control how smart I was or how hard the classes were, but I could give myself the best chance to succeed by being the guy who went to class every day.10
This was the same approach I’d taken in my decidedly mediocre high school basketball career.
- On Sale
- Jun 19, 2018
- Page Count
- 304 pages