Republicans have an “asshole advantage” when it comes to the types of tactics they’re willing to engage in to consolidate power. What level of assholery should Democrats undertake in order to fight back? That’s the question Dan Pfeiffer, co-host of Pod Save America and former adviser to President Barack Obama, attempts to answer in his new book, Un-Trumping America: A Plan to Make America a Democracy Again.

Pfeiffer lays out a playbook for Democrats to combat Donald Trump and the Republican Party in the 2020 election, as well as what to do after.

“The Republican path to power is to surf a wave of cynicism because they know their base will turn out,” he says. “We depend on less frequent voters. And so if you can turn this thing into a cynical shitshow, then their voters will come, ours won’t, they will win. That’s how they won in 2016.”

There have long been questions about how Democrats need to approach politics, tactics-wise, and whether the “when they go low, we go high” mantra needs replacing. Democrats may not need to get into the trenches, but there are structural overhauls that would significantly level the playing field: eliminating the filibuster in the Senate, adding Washington, DC, as a state, and ending the Electoral College, among others.

“For too long, Democrats, myself included, have been too shy about pushing for reforms and ideas that increase our political power,” he says.

I recently spoke with Pfeiffer about how Democrats can regain power pre- and post-Trump as well as Sen. Bernie Sanders’s rise, former New York Mayor Mike Bloomberg’s multi-million-dollar campaign, and why Pfeiffer’s old boss is, thus far, sitting the election out.

Our conversation, edited for length and clarity, is below.

Emily Stewart

Okay, so it is looking like Bernie Sanders is the frontrunner. Who is the moderate closest to taking him on? To me, it just feels like Democrats are afraid they’ll lose and are going in every direction.

Dan Pfeiffer

Most Democratic primary voters exist in a state of paranoid paralysis where we can’t really figure out who the “best” candidate to take on Trump would be, and I put myself in my category.

We have these two problems, which is we believe that Trump is an existential threat to the country and the planet, and 2016 undermines so much of what we thought we understood about politics. So we don’t know who or what to trust. We don’t trust our own guts. People wake up every day, they say, “Maybe Bernie is the most likable candidate,” and then by lunch they’re like, “Well, maybe it’s Klobuchar.” And by mid-afternoon snack time, it’s, “What if it’s Warren.” And then rinse and repeat every single day.

This whole situation massively advantages Sanders, because he has the highest core of any of the candidates. He has the most dedicated group of supporters, which is getting him to somewhere between 25 and 28 percent in the early states and potentially nationally. And if that’s the case, he’s both vulnerable in the sense that if you’re only getting the 25 to 28 percent, one person can clearly beat you, but no one can decide who that person is. And it’s not clear to me that the process is going to winnow itself to that point in time for there to be a two-person race between Bernie Sanders and someone else.

Emily Stewart

Should Democrats be afraid of a Bernie nomination? You have James Carville out here sounding the alarms about him, some Democrats worrying about some of his supporters turning voters off or harassing people, like what happened with the Nevada culinary union. How does he expand his support?

Dan Pfeiffer

If the question comes down to can Bernie Sanders when the White House, the answer is yes. And I think that is true of every other candidate who is currently in the top five, plus Bloomberg. Every one of them can win. This is going to sound like a cop-out, but this is really more a product of whatever humility I’m trying to bring to this after getting 2016 wrong. The campaign is likely to be decided among 100,000 to 300,000 votes over four states. And so once you get to that, anyone can do it.

Sanders definitely has vulnerabilities. Trump is going to call every Democrat a socialist, but it’s easier to respond to that if you have not self-identified as that for decades. And Sanders is going to need a better answer for that than he has put forward to date.

I think the Sanders supporters issue is both legitimate and blown out of proportion. If you go to a Bernie rally, it feels like it could be an Obama ’08 rally or a Warren ’20 rally. It’s just a bunch of voters of all ages. And so we’re obviously talking about a very specific, very vocal, very online part of Bernie’s support.

Bernie has been the candidate most vocally and most prominently in every speech saying that he will get behind the Democratic nominee if it’s not him. Now that’s obviously easier to say when you’re winning than when you’re losing. But I think Bernie Sanders himself and some of the top leadership of his campaign recognize that some Democrats that Bernie Sanders is going to need to win — both in the primary and the general — view he and his campaign as divisive, so they’re trying to address it.

I read some of the emails that were put out by the Culinary Union, and they’re quite disturbing. And I know many people, particularly women and people of color, who have been on the receiving end of very aggressive attacks. Certainly some of these people are anonymous trolls with three followers, and some of them are prominent supporters of the Sanders campaign with pretty large followings. I’m not sure it’s a fatal problem in the general election, but I think it would be in the best interest of the Sanders campaign to try to do more if possible.

Emily Stewart

So to pivot a little, why isn’t Obama or Obama-land weighing in more? Barack Obama has not endorsed Joe Biden. What’s going on?

Dan Pfeiffer

This is a very traditional role for a former president, and I think that particularly after 2016, it is Obama’s view that the best thing for the party is to let the voters decide and not have major figures trying to put their thumb on the scale, particularly early in the process.

Also, Obama-land generally quite basically encompasses most people who’ve worked in Democratic politics at some level in the last decade. Many of them are working for various candidates — Joe Biden, Elizabeth Warren, Bernie Sanders, Pete Buttigieg. Others of us have a podcast where we made a decision to be neutral.

It’s not obvious who the “most electable candidate” was. I can make a case for and against all of the major candidates. We know a lot of them. We’ve known them for a long time, and I’d take any of them, right? So let the process play itself out.

Emily Stewart

How do you think about Mike Bloomberg, then? Here’s a guy who’s basically like, “Hey, I have all of the money in the world,” and wants to be president. Is that fair?

Dan Pfeiffer

Bloomberg’s path is real, but narrow. He can only win the nomination if he is one-on-one with Bernie Sanders very soon. It doesn’t work with anyone else, I think. And so if somehow Biden or Buttigieg emerge as the new front runner because of what happens next or even Warren, the door closes on Bloomberg. But his team is very, very smart. They have unlimited resources, and they are spending at such an aggressive level that it is possible.

If he’s the nominee, I certainly think he can win, but he’ll have real challenges with the Democratic base. He’s been standing outside the process and hasn’t had to face, until recently, real questions about some of his policies in New York. And we’ll see what happens if and when he gets on a debate stage how he handles that.

He’s sitting as the billionaire generic Democrat right now, which is ironic considering he’s a former Republican mayor of New York. Everyone likes everyone until some flaw is exposed and then they panic and move to someone else. And right now, all they’re seeing is positive messaging from Bloomberg. It is a fascinating experiment in what you can do with unlimited resources in politics.

Emily Stewart

So to pivot to the book, there’s this ongoing debate among Democrats about how “low” they should go in combating the Republican Party. You talk about Republicans having what you call an “asshole advantage,” basically, the types of tactics they’re willing to engage in to gain power, and get into the question of what Democrats should do. What level of “assholery” should Democrats embrace?

Dan Pfeiffer

There still remains among some parts of elected Democrats a naiveté about who the Republicans are and how we got to this moment. This is a core of the Biden argument, that Trump is this aberration, that if we get rid of him, Republicans will somehow resort to something more normal or less terrible.

And I just do not believe that to be the case. Trump is the logical extension of what Republicans have become. And all the incentives that made someone like Trump act the way he does and get to the point where he is will remain true. Republicans are in a position where they need to double down on a diminishing white base and with racial fear-mongering continue push policies that limit the political power of people of color in order to hold on to power.

The point for me of writing the book was to try to lay out a path where Democrats could take on what I think is the fundamental strategy of the Republican Party, which is minority rule, in a way that is aggressive but consistent with our values. There’s nothing wrong with Democrats pushing ideas like getting rid of the filibuster or adding Washington, DC as a state that increase our political power. For too long, Democrats, myself included, have been too shy about pushing for reforms and ideas that increase our political power.

Emily Stewart

A lot of these things are difficult to achieve. In a tactics level, are Democrats equipped to do it, given where the party is right now?

Dan Pfeiffer

That’s the question: Are we as a party tough enough to take on Trump? I think the answer to that is yes. In the Obama years, we took on the Karl Rove machine that had killed Democrats for much of the century and won twice. And took on Fox News and all of that. So it is possible.

I don’t think the problem is that Democrats haven’t been “tough enough” or “mean enough.” The question of can you be as big an asshole as Trump is the wrong question, because we just have different strategies.

The Republican path to power is to surf a wave of cynicism because they know their base will turn out. We depend on less frequent voters. And so if you can turn this thing into a cynical shit show, then their voters will come, ours won’t, they will win. That’s how they won in 2016.

We have to be tough, and we have to be smart, but we also have to be inspirational. We have to give people a reason to believe that their vote is going to count, and that it’s going to matter.

This is going to take a long time. Much in the way in which Bernie Sanders and the progressive left has moved the Overton window on policy issues like universal health care, free college, etc., I think the Democrats also need to move the Overton window on democratic reforms. We have to be aggressive about what we push for, and maybe we’ll get all of them, maybe we’ll get some of them. But if we don’t start fighting for it, we’re going to get none of it.

We have spent so much time in 2020 arguing about what we’re going to do about health care and almost no time arguing about how we’re going to do it. What is your plan, Bernie Sanders, Elizabeth Warren, Pete Buttigieg, whoever else, to get this done in a world in which the filibuster exists? We have to deal with structural democratic reforms to have a chance to have a progressive policy in this country that reflects a progressive majority.

Emily Stewart

Do you think the American public cares enough? We just got through impeachment, and it kind of landed like, eh. There were not people in the streets. Some people are very comfortable and look at the last four years and think it wasn’t that bad, though obviously that’s from a privileged position.

Dan Pfeiffer

A lot of white people, particularly white men of means in this country, are very insulated from the worst parts of Trump’s policies. They may even have gotten a tax cut. And so they don’t necessarily always bring the same urgency to the matter as people whose reproductive freedoms are at risk or whose family and friends and community are at risk of deportation or are being targeted with anti-LGBTQ policies. That is certainly true.

The high levels of interest in this election speak to the fact that an overwhelming majority of the American people on both sides think this is an incredibly important election and understand there are very high stakes.

It certainly did not manifest itself in the street protests. And I think that comes from two things, and this is just a guess on my part. One is that there was so much of that in the first couple of years of the Trump administration, the March for Our Lives, the Women’s March, the airport protests. Another is that what ended up being the thing that really mattered in the ability to at least put some checks on Trump was an election, and we’re sitting in an election year.

There may be a sense of exhaustion that we can’t really force these Republicans to do anything they don’t want to do through civil disobedience, and so the best way to do it is through electoral action. And there is just an incredibly high interest level and donations and volunteers with all the grassroots groups, which are positive signs.

I do worry, if Democrats don’t win the election, what message it will send to the people who’ve gotten so engaged since 2016. Do they check out because they feel like it wasn’t worth it? And that’s what puts us in a very dangerous position.

It’s also on the Democratic nominee to raise the stakes for this election and make people understand why it matters so much. We have to do that. If we make it about small things, we’re going to get a response that is commensurate with a typical election as opposed to the one that most of us think is perhaps the most important in our lifetimes.

Emily Stewart

Do you think that voters care about policies?

Dan Pfeiffer

Some do. There are some voters for whom there are red line litmus test issues. But, generally, voters are less ideological than political types like ourselves think. We think there’s a liberal lane and a moderate lane, and then you realize that when Elizabeth Warren lost support in New Hampshire, most of that support seemed to either go to Amy Klobuchar or Pete Buttigieg as opposed to Bernie Sanders. When Biden lost support, a lot of that went to Sanders.

And so as your colleague, Ezra Klein, wrote in his book, [Why We’re Polarized], politics is much more about identity than ideology. A good campaign and a good candidate uses policy to tell a story about values. The most important question that a lot of voters take into the ballot box with them is: Who is this person fighting for? Are they fighting for me or are they fighting for others?

Policy is a proxy for values and character. And then you get into the White House and everyone, including your voters, holds you to account for whether you’re going to pass something you talked about on the campaign trail.

Emily Stewart

In your book, you talk about birtherism and wonder whether Democrats would have been better able to push back on that if they had the technological tools we have today. That struck me, because I sort of think it would be the opposite. With the levels of disinformation and misinformation we’re seeing right now, how would it not be 100 times worse? And Democrats don’t seem especially prepared for the onslaught.

Dan Pfeiffer

If we had had the capacity to, at scale, get counter information out, I don’t think we would have stopped what is now the MAGA base from believing that Obama wasn’t born in the United States. But we were doing hand-to-hand combat with Democrats in Iowa, who loved Obama, but were afraid they would find out later he was ineligible for the presidency because he was born in Kenya.

That was all happening with right-wing radio, some Fox News stuff, and email forwards. If we’d the ability at scale through Facebook and other social media to push back in a targeted fashion, that could have helped with Democratic, independent, and some Republican voters. We wouldn’t have stopped it at its root, because long before Facebook showed up and made everything worse, conspiracy theories have had a long history in American politics and particularly on the far right.

Are Democrats prepared to take on disinformation? No, but they’re at a massive disadvantage: Facebook controls this more than anyone else, and they’ve decided that they will be a disinformation platform. We are fighting this with both hands tied behind our back.

A lot of the party, particularly in how we think about reaching voters, is still more old world than new world. And we have to think more creatively about what it means to communicate in the social media age. The view of how we get our message out is still very traditional press heavy. We spend all this time thinking about where we’re going to get the story placed and what interview we’re going to do instead of how we get a piece of information or content from the interview to the voters we care about.

But digital is not the solution to all of our problems. We already have a huge infrastructure disadvantage to the Republicans because in some cases it’s we haven’t been focused on it enough. In other cases, it’s simply a dollars issue. It’s not that no one had the idea that we should have ads to give air cover to vulnerable Democrats on impeachment. It’s that there wasn’t money for it. We barely have enough money to be running anti-Trump ads in Wisconsin. And so we exist in a massive funding infrastructure disadvantage, which is broader than technology, but also includes technology.

Emily Stewart

And instead you’ve got two Democratic billionaires running for president.

Dan Pfeiffer

Yes, exactly. That is exactly right. Their billionaires pay for party infrastructure, our billionaires run for president. It’s a real disadvantage.