Yes We (Still) Can: Politics in the Age of Obama, Twitter, and Trump by Dan Pfeiffer is an enjoyable voyage through the Obama years, and chock-full of advice on how to cope with the Trump years. Pfeiffer brings a thrilling view of the 2008 Obama campaign, his time in the Communications Department of the White House, and his life beyond as a pundit and co-host of the hilarious, political podcast Pod Save America. There’s humor and a fire of righteousness to his writing, giving the reader a passionate—and hopeful—view of American politics. Reached by phone on Father’s Day Eve, Pfeiffer put his new baby down for a nap and answered a few questions.
MERCURY: Why did you write a book?
PFEIFFER: When you leave the White House they take your Blackberry, your ID, and then someone from publishing meets you out by the gate to see if you have any interest in writing a book. I was interested in the concept of writing a book for the same reasons that some people run marathons. But it wasn’t until Trump won that I started looking back at my time in the White House and I found forces that Obama was dealing with that I think led to an environment where Trump could win that election. I wanted to look back at those, see how we dealt with them, and do it all in a way that was with a similar tenor of Pod Save America—approachable, nostalgic, and hopefully funny.
Your book is very funny, and at times tender. The footnotes are an interesting additional bonus. Were those added subsequently?
No. I did them in real time. It was an idea from my wife. She suggested the idea of adding in funny asides and additional information.
Do you feel more comfortable now speaking out, instead of trying to represent someone else’s point of view?
Yeah, I think having a podcast where you speak to a large audience for an hour and a half, once a week, makes it easier. It’s also easier now that President Barack Obama isn’t in office. Even in the two years after I left, when he was still in office, every time I opened my mouth I thought about what it would be like for Josh Earnest, the Press Secretary, or Jen Psaki, the Communications Director, to have to clean up some mess. That happened to me all the time when I worked [in the Communications Dept]. Now I can say anything and there are no consequences.
If someone asked you what your favorite job has been so far, would it be one of your political jobs, being a podcaster, or being a television pundit?
Communications Director on the 2008 Obama campaign. That was just a once-in-a-lifetime moment. The friendships I made on that campaign will be the friends I have for the rest of my life. It was an incredibly special thing. And we knew it was special when it was happening.
Do you think the Obama 2008 campaign is a blueprint for what future campaigns can be like or do you think it was a one-time thing?
There’s no doubt that Obama was a singular candidate. There’s no doubt we got a chance to run in what was essentially the perfect moment for a candidate like Obama. Voters were frustrated with the Iraq War, and with partisanship and corruption. We were running a charismatic, politically-talented, inspirational political figure who opposed the Iraq War and was essentially an outsider to politics. And so that was a perfect matching of the man and the moment. That’s not something you can do every time. But the strategic approach we took, the culture we built, and the discipline we applied—I think all of those things can be applied to modern campaigns.
Do you think it’s a waste of time for Democrats to worry too much about what happened in the 2016 campaign?
I think there has to be a balance there. In a campaign that close—decided by 70,000 votes over three states—anything and everything is a deciding factor, right? It’s not just Hillary Clinton because Democrats lost up and down the ballot. We lost Senate seats we absolutely should have won. We lost House seats. We lost governor’s races we should have won. And so the party as itself should look back, and try to get some lessons from it.
You talk a lot about the Administration’s relationship with Fox News in the book. Do you feel like you figured out a way to deal with them? Or is there just no way to deal with them?
In the book, I argue that it’s a waste of time for any Democrats to spend any time on Fox. They’re immune to shame and embarrassment. They make very, very good money doing what they do. You’ll never get a fair deal. But there are ways you can communicate with the people who watch Fox News or the community for which Fox is a major news source.
And we should look at ways to do that. We have to fight back against this massive propaganda machine—of which Fox is the biggest but not the only piece. There’s Breitbart or Sinclair Broadcasting too. It’s a massive apparatus that Trump is directing tweet by tweet, and if we don’t find ways to better combat it we’re going to struggle to win the upcoming elections.
In the book, you put a lot of faith in millenials, and their ability to change how the country works through their votes and advocacy. What do you think candidates should do to give them hope that elections can matter?
The Millennial Generation is one of the most community-involved generations since the Baby Boomers. They care about lots of things, but they’re basically treated like throw away. Too often Democratic politicians are programmed to be like, “Young people! I will talk about student aid!” Which is, of course, an issue. Let’s talk about the "kid issue" right here, and if we don’t get you right away we’re going to move onto the old people. That’s a mistake.
You need to have a serious conversation with them about the issues they care about. Be inspirational. Show why electing one candidate will be better for the country, their community, and their lives than electing the other person. It takes work. It’s one of the hardest things. Barack Obama obviously had a history of showing great appeal to young people. But we also worked hard at organizing, messaging, and advertising. You just have to do it. If we don’t, we will not succeed.
How are you dealing with this administration trying to undo basically everything you guys did over the last eight years of the Obama Administration? I get depressed when I watch the news but I can’t imagine how you guys must feel.
This is one of the things that’s haunted me. I remember our first hundred days in the White House. Basically, every day we would wake up, and undo something George W. Bush did. I think those were the right things to do. “Oh, you guys are against stem cell research? Well, we’ll sign an executive order to make them available.” “Oh, he refused to allow cars to have higher mileage standards? We’ll do that today!” “We’ll outlaw enhanced interrogation techniques or whatever else.”
I did have this vision, even before Trump was nominated, where I thought about a Republican dismantling what we’d achieved. In my vision, it was dark and depressing, and in real life it’s even more dark and depressing.
Do you think President Obama will ever get the credit he deserves for being the kind of president and the kind of man that he is?
Yes, I do. Do I think that the people running around wearing MAGA hats on Fox News or Breitbart will give him that? No. Sorry. But he left with historically high approval ratings, and history will treat him very well. Every day someone like Trump is president, it reminds people how important it was to have a thoughtful, decent man in that office.
You were part of the reason Obama went on Between Two Ferns with Zach Galifianakis. Which, for my own personal point of view, was one of the highlights of the Obama years.Yes.
Do you think if people had seen more of that side of President Obama they would have lightened up on him more?
Maybe. It’s hard to say. That was one of the great challenges we had at the White House. One of Obama’s great appeals to people is that he’s a pretty normal guy, besides the fact that he gets to fly around in Air Force One, and has the nuclear codes.
Behind the White House podium, he was always talking about something very serious, but we tried to find a balance. Do I think more Between Two Ferns appearances would have gotten more Trump supporters to like President Obama? Probably not. But we were always trying to find more time for that.
In the White House, your plans get interrupted on a daily basis. But we’d do March Madness brackets. We loved it. We almost had to cancel a couple of times because there were disasters happening at the exact moment. There was an earthquake near a nuclear reactor, in Japan, one year. You put these things on the schedule, and then you wake up to something that has happened, somewhere in the world, that you’re responsible for. Things like Between Two Ferns or the March Madness brackets or a Buzzfeed video fall off the schedule pretty quick.
Do you have any regrets about the stuff you guys did against Trump during the White House Correspondents Dinner? Do you look back, and think like, “Gee, if we hadn’t done that maybe he wouldn’t have run for president?”
That that speech does haunt people. I was less involved than Jon Favreau, Jon Lovett or others. But I worked on it, too. I can’t fully accept responsibility, but I do wonder, in a Sliding Doors scenario, whether if we had cut this joke or that joke we might be in a different place right now.
I don’t know. It really was funny.
Yeah, in the moment it was great.
You’ve played basketball with President Obama. Who would you compare him to?
Tayshaun Prince. He’s a lefty, savvy. Very smooth J. [Editor’s note for people who know fuck-all about sports: “J” = “jumpshot.”]
What would you tell kids who want to get involved in politics?
If you are looking, in your life, to make an impact in your community, in your country, in the world, there is no better way than getting involved with politics. I always think about what President Obama said after the 2014 election. We had a really tough time. He said, “Never in our lives will we have an opportunity to do as much good, for as many people, as we do right now.” And that’s what you can do if you get into politics. It is fun. It’s where a hard, smart worker is rewarded. Things move so fast, and the country needs you. Absolutely, this is the time to scrub in and try to make a difference.
There’s a lot of anger in this book—and I understand that frustration—but there’s a lot of hope, too. What keeps you hopeful?
Young people keep me hopeful. One of the fortunate parts of the podcast is that I get to go around the country and see people. At the Women’s March, protesting the Muslim Ban at airports, at the March for Our Lives—you meet these young activists. People getting involved with politics for the first time are always inspirational. They’re so different, and the country they see is so different than the country that populists like Donald Trump tell you about.
It’s not inevitable that this is going to turn out well, but we have all the tools and all the people to do it. We just have to do the hard work to organize so we can win in 2018 and 2020. If we work hard, we’ll look back on this very dark era of the Trump presidency as a speed bump on the path to an America, which is a lot more like the one Obama talked about: diverse, inclusive, decent.[An edited version of this interview ran in this week's print issue.]