Yes We (Still) Can

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.

Mine.

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?”

“Constantinople!”

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.