Dan Pfeiffer was an Obama campaign aide and White House communications director during the years when the definition of communications changed from press relations to ¯\_(ツ)_/¯. Still, when he left the White House exhausted and recovering from a stroke-like condition in 2015, Pfeiffer wasn’t sure he had a book in him.
“I was interested in the idea of writing a book but couldn’t figure out what I could say that would be different than what David Axelrod said in his book or that Barack Obama will write in his book,” Pfeiffer said in an interview with The Daily Beast. “It wasn’t until Trump won that I could look back and see that the story of the forces that led to Trump—fake news, changes in media, the emergence of social media, the Republican Party—was a story that I could tell.”
The book, Yes We (Still) Can: Politics in the Age of Obama, Twitter, and Trump, which in its first week of publication has already jumped into the number one spot on the New York Times bestseller list, is only nominally a campaign and White House memoir. There are wins, losses, and funny anecdotes—like ripping his pants in the Oval Office—but those stories function more as first-person scaffolding for a deep dive into both the social-media world and the organizational dynamics of a successful campaign, White House and new-media startup.
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Pfeiffer is one of the co-hosts of Crooked Media’s Pod Save America podcast and live shows, which will double as part of his book tour over the next few weeks.
How are you handling promoting a book, touring for Pod Save America, and having a newborn?
The baby was born four weeks ago, and I have barely left the house. I’ve been doing interviews and taping podcasts that I can do from home. I’m doing some things for the book and Pod Save America for a few weeks, and then I’m not planning on any more travel until this fall.
You didn’t talk much in the book about travel, but I gather you did a lot of it.
For my last few years in the White House, I went almost everywhere Obama did. That was sort of weird travel because it was a lot of day trips—I’d get up, we’d fly somewhere, and we’d get home late at night. The podcast and the book are different because that’s actually fun travel.
The Obama transition team in early 2009 decided not to nominate Tom Daschle to head Health and Human Services because he had a minor issue about whether a town car service was taxable income. Does that strike you now as—I don’t know—quaint?
That was a heartbreaking situation. I worked on Daschle’s last Senate campaign, a huge core of Tom Daschle’s political team worked for Barack Obama, and we were all very close to him and have a huge amount of respect for him. After he left the Senate, he worked for a few years for a law firm that provided him with a car and driver. He didn’t count that as income at the time, and then he paid back taxes on it.
The whole thing was dumb—not dumb that he did it but dumb that it stopped his nomination when you consider the rampant corruption today. It wasn’t just Republicans who sunk Daschle’s nomination; it was Democrats too. We had 58 Democrats in the Senate—I don’t think Al Franken had won his recount yet—and Daschle was a very popular former Senate Democrat, and Democrats were scared of the politics of it. Republicans applied an entirely different standard for Trump’s nominees.
One idea that runs through the book is that you don’t see Trump as a cause of the crazy things that are happening as much as a byproduct of other causes. That’s not a very optimistic take.
Trump is not the disease of what ails our politics, but he’s a symptom. I think there are two ways to look at this: One is that the Obama era was an aberration between Bush and Trump—that Trump is a reversion to the mean. I tend to take the other view, which is that Trump is the result of changes in politics and media and that this is a speed bump or a sinkhole toward an America of progressive, decent, diverse politics of Obama and not the divisive politics of Trump.
Some of that, I think, will depends on what justice and perception of justice there will be for the things that are happening right now. Paul Manafort, Trump’s campaign chairman, is in jail awaiting two federal criminal trials. I think we’ll look back differently at these years if a lot of Trump’s inner circle winds up going to prison.
I think that’s right. Several Trump people have already pleaded guilty and are cooperating with prosecutors. Absent a spree of pardons, some people are going to serve time for pretty obvious corruption. People are asking all the time: “When is Robert Mueller going to put Trump in jail?” Nixon went down because a number of Republican senators told him that they were going to convict him on the impeachment. There is no world in which that happens with today’s Republican party. They will not do that. The only way Trump will leave office is voters sending him home.
The reason the Obama administration did not go after the Bush administration for war crimes was to avoid a culture of putting your predecessors in jail.
It’s a dangerous world when a new government puts the old one in jail. That’s banana republic stuff. I do worry that the Democratic nominee in 2020 could be the most ethical candidate imaginable, and Trump will investigate him to try and run the same play he ran against Hillary Clinton. These are dangerous times. My hopeful take is that a progressive movement will guide us away from fundamental changes in the nature of our democracy.
Do you read the New York attorney general going after the Trump Foundation as a signal to Donald Trump that he can’t pardon his problems away?
I think that’s very possible. Trump can pardon his kids and Jared Kushner and everyone else out of federal crimes, but they have also likely committed various state crimes. Al Capone did go to jail for tax evasion. The Trump Foundation was clearly a slush fund that Trump used in deeply inappropriate ways.
The civility discussion seems to have two bad answers for Democrats. If you’re civil, Republicans act in bad faith and take advantage of that civility. If you’re not civil, you lose your moral authority. What’s the etiquette here?
I have seen many dumb Washington debates in my time in politics, but this might be the dumbest yet. I don’t care where Sarah Huckabee Sanders eats, and Democrats shouldn’t feel defensive because a private citizen politely asked her to leave a private business. Particularly at a time when we have a pugilistic bully tweeting from the Oval Office. The Morning Joe roundtable doesn’t bestow moral authority, so stop paying attention to pundits.
Sarah Sanders got asked to leave a restaurant and TV execs are going to get pressured not to help Sean Spicer become a TV talk show host. There will be more of these. Civil disobedience is not doing, but this is doing. Should people who work with Trump reap what they sow forever and ever?
Sarah Huckabee Sanders and so many more of Trump’s aides made a decision to lie for a dangerously unfit racist liar, and they should be held accountable. Nothing will be able to remove that black mark from their reputations, but I am more interested in the sort of accountability voters can bring.
I’ll ask this one cold, so feel free to add context: What’s a shitburger?
[Laughs.] A shitburger is what we called something you have to eat that tastes terrible.
It’s a shit sandwich.
Right—a shit sandwich, a poop pie. [Laughs.] Working in the White House during the financial crisis was a shitburger buffet. We would wake up with grand visions about what to do that day, you have a 7:30 a.m. meeting in the White House chief of staff’s office, and here come the shitburgers. Something we didn’t even know was happening would suddenly be the No. 1 concern.
Some company would do something, some agency would do something, there’s a giant hole in the Gulf of Mexico spewing out oil and there’s a camera broadcasting it live on cable TV. That was the nature of the job. Obama would always say that the easy stuff gets done at the agencies, that only the hard stuff would get to the White House.
There are several books coming out right now about truth and falsehood. There’s Amanda Carpenter’s Gaslighting America. There’s a new George Orwell collection called Orwell on Truth. Michiko Kakutani has a book coming out in July called The Death of Truth. You cover a lot of that territory in your book. Do you see a path forward?
We’re in a weird period. If you look at the people most likely to believe conspiracy theories, they’re generally older. They grew up in an era when you could believe that what you read in the newspaper was mostly true. Then Facebook became a primary source of news for a generation that did not grow up with a trust-but-verify approach to what they were reading.
I think a lot about the kids from Parkland, Florida. They’ve very good on the internet. As the younger group of people who have only known a world when anyone could post information online ages into the electorate, we’re going to get past some of this. Millennials are about to be the biggest, most important voting bloc in the country.
If they’ll vote.
If they’ll vote, right. That’s the question. When both parties have to compete for those voters as opposed to Republicans winning by appealing only to older voters, we’ll have a different politics in this country. The internet and social media changed how people consume information faster than the populus was able to learn the rules of those changes.
When the Obama campaign started in 2007, Facebook barely existed and was mostly for college kids. Twitter was mostly for people in the tech industry. Daily newspapers, local newspapers, and the Sunday shows were how most people got information. The iPhone didn’t exist. Instagram didn’t exist. Snapchat didn’t exist. In the last 10 years, we’ve seen as significant a change in how people consume information as the printing press and the telegram. We haven’t caught up to that yet, and I think we will.
I see Twitter putting emphasis now on media brands like ESPN and Buzzfeed News that have good reputations for reporting. Do social media platforms have to fix themselves?
I think so, but each platform is a little different. Facebook’s biggest challenge is that their algorithm favors engagement—likes and shares—so the things that cause the most outrage float to the top. Facebook has to figure out how to show you quality content that keeps you on the platform. Breitbart writes offensive headlines because Breitbart wants you to react, which pushes it around Facebook to more and more people. Facebook has to figure that out.
You have a chapter devoted to the things you learned about running a campaign, and a lot of those things seem applicable to running effective organizations in general. How much did you see rules like “no assholes allowed” translating more broadly?
In any organization—a company, a campaign, the White House—you have to spend time on what your organizational culture is going to be. Barack Obama and David Axelrod and David Plouffe spent real time on the 2008 campaign building a culture. In sports, the most talented player is not a good fit for your team if he disrupts a good organizational culture.
Why does the Trump White House leak so much?
There’s a culture of it. If everyone else is leaking, you’re going to leak too. And there are a lot of agendas. Somebody’s trying to take down Jared Kushner. Somebody else is trying to take down John Kelly. And everyone is trying to protect themselves. There are leaks to knife someone in the back. There are leaks from career public servants who are deeply concerned about what’s happening.
Gary Cohn leaked to show people in Manhattan that he wasn’t part of the bad things that were happening. “I was so upset by the thing Trump said about Najis that I threatened to resign!” He didn’t resign over that, but he wanted people to think he cared. Trump is not loyal to them, they do not trust him, and they do not trust each other. It’s a poisonous culture.
If you were building a Democratic nominee for a 2020 media environment, what kind of characteristics would you want to see?
I would want to see someone who’s very comfortable in their own skin and who’s authentic in person and on social media. I want to see someone who is not afraid to lose; you have to play to win instead of playing not to lose. In terms of the campaign, there are real questions about the efficacy of polling when people don’t have home phones. There are questions about how to translate door-knocking and phone-calling to social media. The best candidate will be one who is willing to question all of the assumptions about how politics has been done to date and willing to take risks.
I’m a little nervous about Obama monetizing himself with a huge book deal and a huge Netflix deal. Where’s community-organizer Obama?
The book will be good. The Netflix deal is going to do good things. When the foundation is up and running in the next few years, it’s going to do good things. Something he’s going to work on very hard at home and abroad is energizing a new generation of young leaders to run for office and get involved in civil discourse and make things better. There are dozens and dozens of Obama alumni who are going to be in Congress and city councils. We might elect a few governors. Obama has been out of office for 18 months, and he’s 56 years old. We haven’t even gotten to the warmups before the first inning of what his legacy is going to be.
