Pfeiffer - Yes We (Still) Can

If Youre Reading This, Its Too Late

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

Over the years, I had often thought about the moment when this chapter in my life and the countrys 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 historyone that would be talked about with the reverence reserved for the great presidents.

This was the last day of the Obama presidency. But I wasnt 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 werent 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 wasnt 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.

There is something powerful about walking through the doors of the White Houseeven if you do it every day for six yearsbut this time felt even more consequential. This was the last time I would walk into a White House staffed by friends and colleaguespeople 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 periodthe 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.

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 Obamas 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 couldnt 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 publicsee 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.

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 Obamas 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 werent experienced and we certainly werent journalists. Our familiarity with the subject added to my anxiety. I know all too well how busy a president iseven 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 Obamas 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 Obamas 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, 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 laughingblissfully unaware of all that is to comeas 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 erathe 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, lets talk about what this book isnt.

Its not a history of the Obama years, because Im not a historian.