The Democratic Party has some figuring out to do between now and 2020—what lessons to take from 2016, how to govern if they win the House of Representatives in November, who to run against Donald Trump in 2020, what kind of campaign that should be. Big, consequential stuff.
Fairly early in Crooked Media’s new podcast series The Wilderness about the future of the Democratic Party, there’s an episode called “The Nightmare” about the 2016 election. Jon Favreau, the former Obama speechwriter and Crooked Media co-founder who hosts the series, talks to journalist Rebecca Traister about the optimism of Barack Obama’s second inaugural, about “life, liberty, and the pursuit of happiness” as the story of America.
“Those were back in the hopeful days before Trump,” Favreau says in the episode. There are no lights or cameras, just two politically astute vets of the Obama years talking into microphones. “It’s because we’re on the brink of getting to that next place that we are being hit so hard,” Traister says. “That’s exactly what we’re in the midst of right now. And it’s not because it’s impossible to get to that next step. It’s because it’s really possible.”
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I hear all of this as I’m running on an outdoor loop at the YMCA a mile from my home, and the experience is like being on a conference call with the two of them. They’re talking, and I’m listening. The show has the same factual foundation and the same politics as Crooked Media’s popular Pod Save America, but it’s a few clicks removed from the news cycle. Other big thinkers—historians, sociologists, political observers—weigh in. A hopeful sense runs through the show that Democrats are still in the woods but have a few trails to follow.
The Wilderness premiered July 16 on podcast platforms and will drop weekly installments on Mondays through the end of September. If you hadn’t considered that one of the battlegrounds for 2020 will be your earbuds, start considering it. Favreau sat down with The Daily Beast to talk about the new series.
The obvious outlets for this kind of project are a book or a Netflix-style documentary series. Other than the fact that you’re running a podcast company, why does this make sense as a podcast series?
I thought about doing a traditional documentary. Having seen those and been interviewed for those, I think people are more candid when they don’t have a bunch of cameras pointed at them. When you’re sitting around a table chatting or talking to someone on the phone, it’s a much different interaction. And I’m too lazy to write a whole book. [Laughs.] Looking back at the series, I feel like I wrote enough voiceover to fill up a book.
You’re trying to reach young voters and people with influence in the Democratic Party, and I suspect those people will experience a podcast much differently—in their car, on the morning run, etc., than watching a documentary on TV.
I think that’s right. Pod Save America has a big audience of political junkies like us, but there’s another big audience of people who did not pay attention to politics before Donald Trump became president. We think about those people a lot. We meet them at our live shows. To tell a story about the Democratic Party, I quickly realized it would require history and context for people who haven’t paid as much attention to politics. A lot of the upcoming episodes tackle separate issues like immigration, foreign policy, the economy, etc. The first half of each of those episodes is about the political decisions that led to today, and the second half is about where we go from here.
Aren’t you talking mostly to people who are already with you on these issues?
I talked to Cornell Belcher, who was one of President Obama’s pollsters, and he pointed out that 12 percent of Obama voters in 2008 were first-time voters. That’s a significant number. If we really want a blue wave in 2018 that will flip the Senate and give Democrats a strong majority in the House, we have to bring in voters who haven’t voted before or haven’t been active in politics before.
If Republicans hold the Senate and keep at least a narrow majority in the House, will they have a good basis to claim victory in the midterm elections?
Yes. If Republicans hold the House, for sure. I think the Senate is more of an uphill climb for Democrats, but I think we have a good chance of taking the Senate.
The Supreme Court confirmation hearings in September will be one of the last big things that happens before the midterm elections. Will that more energize Democrats or Republicans?
I tend to think it will be a big rallying point for Democrats. One of our problems over the last several years is that we don’t have as many voters as Republicans who vote based on the Supreme Court. Donald Trump putting out a list of proposed justices during the campaign was one of the things that rallied a lot of the Republican base that wasn’t necessarily happy with him during the campaign. It’s not just the Supreme Court—it’s state legislators, governors, Congress, local elections. Democrats have focused too much on the presidency and not enough on the other levers of power.
After I listened to the first 10 minutes of the first episode of The Wilderness, about election night in 2016, I texted your publicist “first 10 minutes” followed by that green, sick-face emoji. She texted me back: “It gets better.” Why did you want to start with that?
[Laughs.] I’m a “hope” guy, and the thrust of the series was always going to be hopeful and inspirational. From a storytelling perspective you have to earn that, and I think we needed to remind people how bad that election night was.
Episode 3 is about the various factors that went into Clinton losing the election—James Comey, Russian interference, Hillary fatigue, etc.—and I wondered how much any of that stuff matters going forward. Does sorting through all that really help Democrats in 2020?
I think about 2016 in terms of factors that we couldn’t control and factors that we could have controlled. Hillary Clinton faced a certain amount of sexism, and it was a factor in why she lost. We have to confront that challenge, but it’s not something we can fix overnight. We can fix how Democrats communicate their message in a fractured media environment. Democrats can propose a policy agenda bold enough and progressive enough for the current moment. There are lessons in 2016 about what we should do differently in 2018 and 2020.
If 2020 shapes up as a question about whether to nominate a moderate or a progressive—which I don’t necessarily think will be the question—is that a proxy for whether voters think the election will be more about swing voters or more about turnout?
In Episode 4, I sat down with Obama-Trump voters from outside of Detroit who were white 40- to 60-year-olds, and I sat down with younger, more diverse voters outside of Houston who either didn’t vote in 2016 or voted for a third-party candidate. The same issues motivated both of those groups. Democrats have a problem if they think the issue is centrist positions vs. liberal positions. Inequality has been on the rise for decades, people are having difficulty paying for basic necessities, and they’re seeing a political system that doesn’t work.
Republicans say, “Government doesn’t work and is not the answer to your problems, so we’ll just cut taxes and fight culture wars.” Democrats believe that government can make a difference, but it’s a problem for Democrats that Washington is just people yelling at each other. Big, bold, progressive, economic solutions will appeal to middle-aged voters in the Midwest and to young, diverse voters in Texas who thought Bernie Sanders seemed interesting but then didn’t vote in 2016.
So you would look at an issue like Medicare for everyone in terms of how it works as a positive issue rather than how to present it in a way that minimizes the Republican response to it?
I do. I don’t fear that at all. Republicans have demagogued Democratic positions and been so hyperbolic in their attacks going back to the beginning of the Obama years. They called the Affordable Care Act socialized medicine and a government take-over. They have nowhere to go on Medicare for all beyond the exact same attack.
Republicans will demonize whatever you say, so say what you actually want to do?
They’re going to demonize whatever you say, they will do it unfairly, and they will not care when the fact-checkers point out that they are lying. Those hyperbolic attacks by Republicans liberate Democrats to say what they actually believe will fix the problems. If you’re a Democrat who believes that Medicare for all won’t actually work and you’d rather have a public option, or if you think we need to reform ICE rather than abolish it, there should be space within the Democratic Party for people to propose what they actually believe.
The Democrats who run for president will be looking for areas of disagreement the way Obama and Clinton disagreed on the individual mandate in healthcare in 2016.
Democrats tend to have big slogans—“change” or “opportunity”—and a laundry list of small, incremental policy positions. What we often lack are ideas—goals—with simplicity and clarity like Medicare for all or debt-free college that go beyond gauzy talk about equality and prosperity.
I listen to Pod Save America fairly regularly, and sometimes it’s just too much. Sometimes, there’s just too much happening, and I can’t deal with it. Do you go through that?
With the outrage?
With the outrage. With just the news. Are there days when you just say “fuck politics” and go to a baseball game?
I’m a masochist. I’m a junkie. I have a hard time tearing myself away from Twitter. There are days when I feel like the hill is steeper than other days. [Laughs.] The day Justice Kennedy announced his retirement was bad. Some days are dark. I don’t think I would feel as hopeful as I do if I hadn’t worked for Barack Obama. I never saw him freak out or get too worried. Even during the worst of the financial crisis, he told us we had to take the long view on these things. The only thing we can do is work to try and make it better.
Jon Meacham said recently in an interview on WNYC about his book [The Soul of America] that Joe McCarthy had a national approval rating in the 30s during the McCarthy hearings. We’ve always had one-third of the country that didn’t want change, didn’t want minorities in their restaurants, didn’t want women in their workplaces.
That is a big reason why I wanted to do this series. There’s hope in the realization that we’ve always had these fights. We think: “How did we get here. This is the worst that things have ever been.” And when you go back into history, there was no Golden Age for the Democratic Party ever.
LBJ had big majorities in 1964 and ’65 and passed Medicare, the Civil Rights Act, the Voting Rights Act—and Vietnam ran him out. FDR had his great moment with the New Deal and World War II, but—oh, by the way—that didn’t include African-Americans. There was no moment when the full promise of the Democratic Party for everyone actually happened. Recognizing that, there’s hope that this could really happen.
You talk in one of the early episodes about the rally in Philadelphia the day before the 2016 election. The Obamas and the Clintons were there, and they talked emotionally about those kinds of goals.
I started that story with what Obama had told me he wanted in the speech for the second inaugural—that the entire history of the United States was about trying to live up the ideals of the opening lines of the Declaration of Independence about “life, liberty, and the pursuit of happiness.”
You have a Pod Save America series coming to HBO this fall. Is that a variation of the podcast?
We originally thought that we would spend the fall doing live shows like what we’ve been doing for the last year in swing districts and swing states to help Democrats take back the House and the Senate. When we talked to HBO, the thought was to do a series of specials about the live shows. We’re still figuring out what that’s going to be, but our hope is to tell the story of the 2018 election and the sleeping giant that Trump has awakened with all of the activism that’s happening on the ground.
Does that make Crooked Media more of an advocacy group than a news organization?
We’re sort of a political-media hybrid organization. I think the difference is that news—whether it has a conservative bent or a progressive bent or is right down the middle—tells you everything that’s wrong with the world today. We go the extra step and tell people what they can do to change it.
Are you the Fox News of the left—a political organization with a newsy delivery?
Fox News was founded on the lie that it’s “fair and balanced.” We don’t pretend to be that. We’re Obama staffers. You know what our views are. We want to be as honest as possible about the facts we provide and what we believe. We’re trying to tell people that you can do something about this, and these are the organizations you can work with, and you can actually make a difference.
One of the names that jumped out at me from the list of people you talked to for upcoming episodes is Ruy Teixeira, who’s an expert on Latino demographic change. The success that Republicans are having state by state seems to run against the idea that the country is becoming more ethnically diverse. What did he tell you about that?
My college thesis was about his book with John Judis, The Emerging Democratic Majority, which famously argued that demographics was destiny for the Democratic Party. He now thinks they may have overstated it a bit. [Laughs.] They didn’t know that the Democrats’ share of non-college-educated, white vote would go as low as it has gone. After the first black president left office, we didn’t think that the share of white voters would go lower for Hillary Clinton than it did for Barack Obama. It did.
The predictions they made about how college-educated whites, Latinos, African-Americans, and women would continue to drift toward the Democratic Party turned out to be correct. If the national popular vote winner had the power in this country, it wouldn’t be as much of a worry, but the Electoral College and gerrymandered states have made the math such that Democrats need to win back some of the non-college-educated white voters. Not as much as you’d think from the prevailing narrative, but Democrats can win back some of those voters without giving an inch on the fight for racial justice and equality.
And 2020 is a census year, so big wins in Pennsylvania, Virginia, and several other states would mean undoing the gerrymandered districts in those states.
That’s right, and that’s huge. The challenge will continue to be the Senate. By 2040, 70 percent of the country will live in 30 states. Democrats will likely have to get rid of the filibuster to have an operating majority because it will be difficult to ever get to 60 Democrats again.
Do you foresee doing this going forward rather than running a presidential campaign or running for Congress in 2020?
Yeah, for sure. I never imagined this is what I’d wind up doing. I don’t think Tommy Vietor or or Jon Lovett or Dan Pfeiffer thought this is what we’d be doing either, but it’s the most fun I’ve had since the early days of the Obama campaign in 2008. Our role is helping amplify the progressive voices that are out there and to—as we always say here—inform, entertain, and inspire action. That feels more right to me than jumping into another campaign.
