In retrospect, Jon Stewart probably quit the business at just the right time. The current era has banjaxed the late-night comedy set, serving up explosions of absurdity that soar beyond the reach of the kind of parody that thrived in the Bush and Obama years. The surviving bits of his Daily Show's sensibility and aesthetic have often filtered into the space between straight news and outright comedy, paired with a strand of earnest, outright activism to deliver mainstream liberals the news and action items they need in a way that does not make people want to shut the blinds and house some Xanax. It’s the old combo of broccoli and desert, delivered via podcast. If you’re looking for the center of this brand of political communication in the year 2020, you might find it in and around Pod Save America.
It’s the flagship podcast from Crooked Media, founded by three Obama administration alums—Jon Favreau, Jon Lovett, and Tommy Vietor—after their spell hosting a 2016 campaign program on Bill Simmons’ podcast network. They set out on their own after Trump’s election, and since the early days of 2017, the project has evolved substantially. They’ve assembled a formidable slate of podcasts featuring projects like Hysteria!, a pod hosted by Erin Gloria Ryan and another Obama alum, Alyssa Mastromonaco, which features exclusively women guests. The outfit has also become a genuine proposition when it comes to political organizing.
Their campaign to stop the deranged Republican pursuit of Obamacare repeal—they called one iteration “Repeal and Go Fuck Yourself”—kicked off a now characteristic strategy to forward progressive goals: bring attention to a cause with catchy byphrases, get people motivated to take action, and raise some money. Ahead of the 2020 cycle, they’ve certainly done that: under the umbrella of Vote Save America, they raised $32 million last quarter, the lion’s share of which flowed into their Get Mitch or Die Trying fund backing Democratic candidates in competitive races who, together, could flip the Senate and pull Mitch McConnell out of the Majority Leader’s chair. 300,000 people have checked their voter registration through the initiative, and 50,000 have registered to vote. Their Fuck Gerry(mandering) program also reflects the Democratic Party’s newfound focus on downballot races after the party lost 900 state legislature seats throughout the Obama era.
I spoke with Favreau, Lovett, and Vietor about what kind of changes they’ve seen in the party since their old boss left office, and the key factors in the looming 2020 contest. But first, we had to tackle Donald Trump’s no good, very bad week. The conversation has been edited for length and clarity.
Esquire: As former White House staffers, could you ever have conceived of a week like the one we've just seen, and the succession of fuck-ups that we have witnessed?
Jon Favreau: No! Like, not as former White House staffers, as current human beings. I cannot, I'm at a loss for words over the last week. Just when you think things can't get any fucking weirder, Trump comes through.
Esquire: Obviously the COVID outbreak is an issue, but also Wednesday, he announced that there would be no stimulus deal and seemed almost eager to take the credit for that.
Tommy Vietor: Yeah, until he changed his mind like what, four hours later and demanded a standalone bill.
JF: And [Thursday] morning, the White House said no, the deal is still off. I think killing the stimulus bill might have been one of the dumbest moves in politics that I have seen in a long time. Like, not that I expected that they would come to a deal, but I expected that maybe the deal would fall apart and then Republicans and Democrats would both blame each other. And then he just like jumped in and was like, I'm to blame! I'm to blame for making sure that nobody gets any additional assistance between now and the election in the middle of a fucking recession. I'm to blame!
[Editor’s note: The White House is now making noise that Trump is once again interested in striking a deal with Speaker Nancy Pelosi. The Republican Senate is less interested.]
Jon Lovett: There’s a lot of people being like, oh, he's on steroids. Well, it's not like his tweets are normally cogent, but I will say, jumping up to raise his hand to say, “It's my fault there's no stimulus,” is not very like him. He's not a big fan of taking responsibility, so maybe it is the steroids.
TV: It's a big deal that he has COVID, but I think it's almost getting lost that the White House has hosted multiple superspreader events that have now not only gotten the president sick, it's also gotten the First Lady sick, although he never mentions her. It got like, what, a dozen or more White House staffers, like almost, like nine military leaders, the Chairman of the Joint Chiefs, they all have to quarantine because of this superspreader event that he did with Gold Star Families. There's just many different levels of irresponsibility here.
Esquire: I think one of the underrated parts of this administration is the total lack of professionalism. When you worked in this setup, there must have been a tightly managed structure. What do you see now?
JF: I mean, chaos. There could be a whole bunch of professional people who work there, but it all comes from the top, right? You have a bunch of fucking goobers from the Fox News universe who work there, you have some like traditional establishment Republicans, you have some non-partisans, career staff that are there. But none of them can do anything without Donald Trump approving it, and he's a mess, right?
JL: There was some Trump campaign goon on background [quoted anonymously] who yelled at Axios about Mark Meadows screwing it up as if this is like some finely honed operation until butter fingers Mark Meadows messed it all up. What are they talking about? Like, we've been through so many Chiefs of Staff, so many different members of the team. It doesn't matter, it doesn't matter. There's a malevolent incompetent goober at the top, and everything is in chaos.
Esquire: We talk about the disaster of the last, well, years, but also the last week or so. But four years ago today, the Access Hollywood tape dropped and the whole world concluded Trump was finished. There are a lot of differences now, but what can we learn from what happened after that?
JF: In 2016, the the story was Donald Trump was out on the campaign trail saying a bunch of racist, sexist, horribly offensive things almost every day, and I think that offensive words have a different effect on voters than when you're president, and as a result of your policies, and as a result of your neglect as a leader, the entire country is suffering through a pandemic that's out of control and a very deep recession. I don’t think Trump getting COVID himself is necessarily going to affect voters’ lives, but it reminds voters that this man has not paid attention to or taken seriously a pandemic that we're still suffering through right now. Now who knows what will happen in the election, of course, but I do think it's very different to be upset at him because of an offensive thing he said or did in the past.
Esquire: Does it feel like nobody’s taking anything for granted this time?
TV: Certainly, there’s a big group of Democrats who are seething with this election, and who are doing things they've never done before, like donating money to candidates up and down the ballot, to volunteering their time on a regular basis. I mean, not to pivot to Vote Save America, but you know, raising $35 million online for US Senate candidates doesn't just happen because of Trump. It's because you have an electorate that has been paying incredibly close attention to this race for four years. You know, like we didn't get 300,000 people in our Adopt-A-State program because people just suddenly woke up to him. We've all been suffering through this for so long, and I do think people are more motivated this cycle. There was a lot of complacency at the end of 2016 because everyone just assumed she was gonna win. Myself included.
JF: You can see from the polls this time around, when you ask the question, “Who do you expect to win?” In 2016, many, many, many more people expected Hillary Clinton to win, which says something about the complacency. Now, even with the polls the way they are, people are still more likely to say that Donald Trump is gonna win, or at least it's much closer.
Esquire: Yeah, I think James Comey thought she was going to win. Critics pointed to the 900 state legislature seats lost under Obama and said Democrats don’t look down-ballot. It seems like with campaigns like Fuck Gerry(mandering), you’re encouraging people to see those smaller races as part of a larger project.
TV: I think that's well put. It is a larger project. This is the second Fuck Gerrymandering fund we have put together. The first was focused on Virginia. We were also able to raise $2 million for Fair Fight, which is Stacey Abrams’ organization to stop voter suppression and help people get to the polls. I think people understand that there's a lot of pieces to this. It's not just Trump versus Biden. It's state legislatures. It's redistricting. It's voter access. It's fighting back against voter suppression laws. People are really taking a big picture, hopefully long term look at what it means to be a citizen this cycle. The project will be how do you sustain that, and how do you make this a regular part of peoples' lives, and that's something that we think about a lot.
JL: You can say that there was complacency, and you can look at Trump winning as part of that. I think you can look at people seeing a victory of Barack Obama as a sign that things would change, not that they had to be responsible for changing them. And my hope, the thing that keeps me hopeful even through all this chaos in these dark times, is just this idea that there's a possibility that if everybody pays attention, everybody gets involved, everybody does their part in this election, there'll be a moment where we'll be able to defeat Trump, remove him, and then you'll still have everybody paying attention. You'll still have everybody involved, but it won't just be about trying to remove the worst human being we've ever had in this job, but also doing some real good and achieving some real progressive policy changes.
Esquire: How else have Democratic politics changed in the last four years? What are the issues? What’s the message focused on? Are they doing a better job speaking to the issues working-class people have?
TV: I do think Democrats have done a very good job focusing on healthcare, and the Republican attempts to rip it away, to get rid of the Affordable Care Act, both in Congress and in the courts. And the other recent development is Democrats understanding in a really visceral way the importance of judicial nominees, and I think that was the big takeaway after RBG's death, and all the money that was raised.
JF: We just had an election in 2018 where I think that the Democratic victory there was certainly fueled in no small part by anti-Trump sentiment, but it was also fueled by every single Democrat up and down the ticket running on healthcare, right? And so, it happened in 2018, it worked, and now we're in the last couple weeks of an election where again we're focusing on healthcare, sadly because of a pandemic, but also because he's, I mean look how fast Democrats moved from, Oh, he's gonna nominate this Supreme Court Justice, what are we gonna do, to, we're gonna make this whole nomination fight about the Affordable Care Act. And everyone's on the same page.
Esquire: On the Supreme Court seat, do you think the Democrats in the Senate are doing everything they can on that?
JF: I think we have limited tools—I mean, we're activists, but we're also former staffers, and we know the rules to the Senate. There is a certain amount that Democrats can do to gum up the works and try to delay this hearing, or delay the nomination, but at the end of the day, Mitch McConnell has majority, he has the numbers, and any rule that we bend, or any tactic that we use to slow it down, he can change the rules.
TV: Yeah. There's a lot of armchair Twitter Senate rule experts, but that's the thing that everybody has to understand: You can slow things down and you can delay, but ultimately McConnell can just write his own rules and it sucks.
Esquire: Speaking of McConnell, his opponent, Amy McGrath, has raised an unbelievable amount of money, but it does not look like she’s going to win. Would people be better served taking a more holistic approach, like your program, which is concerned about all these Senate races that could at least remove him from majority power?
JL: I don’t know. We chose to do a fund focused on the races we thought, where the money would go the furthest and do the most good to do the most important thing, which is remove Mitch McConnell from office. I understand the rage that people feel towards McConnell and the desire to give him a really good fight in Kentucky and while it's a really, it's a long-shot bid, I do understand why people would want to support it, but I think we made a choice and our choice was to think about how to make sure dollars would go the absolute furthest. That's what we do with Get Mitch, that's what we do with the Gerrymandering fund, that's what we're doing in our House fund. We go to people with a lot of asks, and we want them to trust that when we ask them to put their money behind something, that we've tried our best to figure out where those dollars can do the most good right now. I don't think that means we need to like criticize where other people put their money.
Esquire: On the money issue, too, it's been sort of a longstanding liberal-left priority to try to get the money out of politics. Obviously right now, this is sort of a unique threat to the republic, all hands on deck. But do you guys have any concerns about the amount of money flowing through politics, and specifically Democratic politics, these days?
TV: I mean, I think the system is the system and it's bipartisan, one, but two, it's an abomination, you know? Citizens United was one of the most damaging decisions the Supreme Court has made, and that's a pretty long list. So yeah, I'm very concerned.
JL: When I saw the news that Mike Bloomberg was putting $100 million in Florida, I thought, “Thank God. That's incredible.” Like that could make all the difference. And then I also thought, “Wow, wouldn't it be nice if the outcome in our elections didn't hinge on the mercurial spending habits of various billionaires set against each other in a war for control of democracy.” I think that would be a nice change.
JF: I will say like the silver lining of this election was, we saw two major presidential campaigns, one which was the runner up in the primary, Bernie Sanders, like basically run a campaign based solely on small dollar donations. So like, it's possible, right? Like it's possible to run a very expensive campaign fueled by small dollar, grassroots donations and not have these billionaires at war with each other.
Esquire: I’ve noticed you guys try to distill your campaigns down to--I won't call it a catch phrase, but a slogan or something that people can latch onto. Is that how you think about it?
JL: When we talked about naming them like, whatever, the Fuck Gerrymandering fund or Get Mitch or Die Trying, I think what we've tried to do is to make sure people—this is a really hard time for people. It's a really dark time for the country. But there's value to translating that into defiance and even humor, and trying to find the joy in the fight and trying to remember there's a bunch of other people who feel the same way as you who have the same sense of what's broken, are angry about the same stuff, find the same stuff ridiculous. If we can tap into that by giving these things kind of catchy names that make fun of the situation even as we're fighting so hard to get out of it, there’s value to that.
Esquire: How would you guys describe yourselves? You do some things that are journalism, but you also engage in activism.
JL: You’re more introspective than us.
TV: The day-one description of Crooked Media, when it was the three of us sitting in somebody’s kitchen kicking around the idea, was: entertain, inform, inspire action. Because we felt like you'd watch an hour of cable coverage in 2016 and you wouldn’t really learn anything. You would really hate watching Jeffrey Lord or whatever sordid assholes were forced upon you, and then you would be despondent at the end if you didn't really understand how you could fix this broken world you'd just been hearing about for a couple hours.
Esquire: What are you concentrating on with less than a month left?
TV: A lot of it's just really basic. You know, like make a plan to vote, vote as early as you can, think of five friends who live in states where there's up for grabs races, reach out to them, get them to vote. We’re going to roll out a ballot tool that will allow you to look at your ballot, see what candidates are on it, see what ballot measures are on it that you'll be voting for before you can go to the polls. I don’t know if you’ve ever voted in California, but the ballot is incredibly long and it's complicated and these ballot initiatives are written in a way that it's designed to give you absolutely no information about what you're actually voting on.
Esquire: Yeah, I'm in New York where they sent everyone in Brooklyn the wrong ballots.
TV: Oh my god, I know. I know.
JL: Trump retweeted Rebecca Traister, that's how I found out.
JF: The messaging on that has evolved, right? For a while it was like, vote by mail seemed like it could be the only safe way to vote. Now I think the messaging is, if you have early voting in your state, just go as soon as you can. Like, bank your vote.
TV: One thing, it sounds trite, but just asking people to post information on their social media feeds about Joe Biden and his plans is actually very important. So we've made a lot of great Instagram-sized comparisons on the issues. Billie Eilish and her brother Phineas posted one of the cards on climate change the other day. Jon Favreau continues to do Instagram Lives with as many Kardashians as he can.
JF: Just doin' my part. No, the issue comparison, it's the most shared piece of content that Vote Save America has made which just goes to show you the hunger out there for an actual discussion about and a comparison of both candidates on the issues. Everyone in our audience has I’m sure made up their minds, but everyone has social networks and to go to those social networks and to share Joe Biden content. It helps combat everything that's going on on Facebook, right, where the top 10 shared stories on Facebook are like the Trump campaign and Ben Shapiro and all these right-wing websites. It's important that progressives can just play on that field and flood the zone with a lot of our own content.
TV: I'd love to meet an undecided Pod Save America listener.
JF: Me too. I was about to say like all of our audience, and I was like, I guess? Who's undecided listening to us?
JL: We got a comment on our podcast from Ken Bone.
TV: I can't believe that fucking guy is coming back into our lives. He tweeted who he's voting for. No one gives a shit, Ken Bone. You're a creepy weirdo who lives in Illinois, it doesn't matter.
Esquire: It's funny you mention Facebook because to me one of the most surreal experiences you can have is checking in to one of these hearings in Congress where Jim Jordan or Ted Cruz will talk about how conservatives are oppressed on Facebook. It's beyond comprehension when you look at what actually is traveling on Facebook.
JL: It's almost like it's not on the level.
TV: Yeah, lots of credit to Kevin Roose at the New York Times for posting every day what is the most popular content. Takes you about a week to realize that it's a platform for right-wing propaganda, and then adjacent to that is all the QAnon, like truly crazy stuff. So yeah, it's very bad.
Esquire: You’re right to say it’s not on the level, but do you worry about our ability to piece things back together someday? I almost feel like people are speaking a different language when I watch some of these things. “Bruce and Nelly Ohr,” this cast of characters from Sean Hannity's show
JF: Yeah. We're very worried. The question we get a lot is like, if Trump loses, like what happens to Crooked Media? What happens to Pod Save America? If Trump loses, the battle isn't over by any means. Trumpism lives on in the form of Fox and Ben Shapiro and all this shit we're talking about. All the misinformation, all the conspiracies, it's like just traveling through social media every single day, and we have to have an apparatus on our side to battle that, right?
JL: It took decades for enough rot and mistrust and propaganda to make it possible for someone as obviously monstrous and unfit as Donald Trump to become President, and it won't be resolved when he leaves. It will take a very long time for us to fight our way out of this.
TV: The problem with Facebook is that Mark Zuckerberg was so easily brow-beaten by those bad-faith Republican attacks that he is now in a place where he’s more worried about being called partisan than he is about having blatantly false information all over his site. And I think that's a huge structural problem, that's a huge Facebook problem. I think it's gonna have to be fixed through regulations, cause I don't think we can trust the people inside these companies to do it on their own.
JL: Tommy, are you saying right now that you don't have faith that the Facebook review board that's gonna be set up just after the most important election in our history is gonna be up to the task? Is that what you'd have us believe?
TV: I mean, just yesterday they banned QAnon stuff, right? There was a guy involved in an armed confrontation on the Hoover Dam in July of 2018 because he thought QAnon sent him there, and it took them until this week to do something about it.
JL: Yeah, fixing this is, Facebook just hired a new Global Vice President for putting the toothpaste back in the tube.
Esquire: Do you think the Democratic Party is growing more attuned to this as well? I saw that House report on the tech monopolies this week, but do you think they're getting more of a handle on this problem?
JL: I think that the Democratic party is like, on this and on everything, not a monolith. I think there is a very big difference between, say, how Dianne Feinstein sees this issue and how someone like AOC sees this issue. That said, I think what we have seen over the last couple years is a general growing consensus about a combination of threats that are not about left versus right, but about preserving democratic institutions and democratic values versus incredibly powerful and dangerous anti-democratic forces. I think we're at the beginning of that fight, I think these issues are actually really hard. Even if you understand why what these platforms have done is so dangerous, even if you believe we need to do something as a country to address these issues, I think how we address it is a very, very hard problem.
You see someone like Trump saying, “Repeal Section 230.” And other conservatives, future Trumpists, trying to find a simple way to talk about this, too, because they understand that it's a big war to come. But I think we're at the very beginning. Look, this is one of the great shifts in human society. We're at the very beginning of understanding how we grapple with systems like Facebook and Twitter when what we have seen, study after study around the world, that they have encouraged extremism and radicalization, and in some places serious violence and chaos.
Esquire: You mentioned Dianne Feinstein, and this is not just the Democrats, because I remember a couple years ago Lindsay Graham would brag that he'd never sent an email. But is there an issue with the age of congressional leaders and their ability to govern?
JF: Yes. I think the last four years have taught us that everything is a-okay.
JL: Look, I'll only vote for somebody if I know they saw Chinatown in theaters.
TV: Oh man. Yeah, remember when Ted Stevens describing the internet as “a series of tubes” was funny, and then all of a sudden it's like, oh shit, we're living with this. We're living with the legacy of 80-year-olds trying to figure out how to regulate social media companies. That's not good.
JF: I will say, in fairness, you have politicians like Bernie Sanders and Elizabeth Warren who are up there, who very much get this shit, and you have younger politicians who do not at all. But generally, I think when you look at Congress and you look at the overall age, it is hard to conclude that it's not problematic that you have so many people that are that far removed from the experiences of the largest generations in the country right now.
JL: And I think like regardless, and without even making a judgement of any of these politicians, I think it speaks to a larger issue if, as a country we're not elevating younger leaders to kind of slowly take the reins. I think that speaks to something else that is broken, something that's missing, some set of incentives that make going into politics so heinous and so difficult. You see the way it rips people's lives apart, you see the amount of fundraising that's required, you see how vicious it becomes. We don't want to live in a world where the only people willing to run for office are people like Ted Cruz.
JF: Yeah, I mean you can be young and an ignorant douche too. Ted Cruz is a good example.
JL: It's happened.
TV: I mean, Josh Hawley.
Esquire: So, what would your guys, if you were working Joe Biden's campaign, what would your closing argument be for the next month?
TV: Don't touch me until you wash your hands.
JF: It seems like there is a moment at one of those debates where Trump is throwing a tantrum, screaming, and Biden just sort of looks at the camera like Jim from The Office style and is like, do you really want four more years of this? Is that what you want? For all that we have said about how important it is for Joe Biden to reach voters with his agenda, let them know what he stands for, it ultimately is, for a lot of people, a referendum on Donald Trump. What has united a lot of the country, from people on the far left to the center right, is the idea that everyone's just fucking exhausted of dealing with Donald Trump. I think when people are casting their ballot, that's what they're gonna think about. Do I really want four more years of this bullshit?
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