How a Group of Former Obama Staffers Is Helping Lead a New Age of Activism

On the Wednesday before Inauguration Day, after holding his final press conference, President Obama sat down in the Roosevelt Room for the last interview of his presidency. “Let me just preface this by saying,” he told his interviewers, “I cannot believe that people actually listen to you guys.”

Those guys are Jon Favreau, Jon Lovett, and Tommy Vietor, all former communications aides in the Obama White House. And despite their onetime boss’s deadpan faux-skepticism, people do listen to them. Over the course of last year’s election season, their podcast, Keepin’ It 1600, attracted hundreds of thousands of listeners.

1600 was a side project. Had Hillary Clinton won the election, as the hosts (along with millions of other Americans) assumed she would, the show would have stayed that way. But in early January, Favreau, Vietor, and Lovett announced that they would be shuttering 1600 to launch a new company, Crooked Media, and a new podcast — one that’s remarkably similar to 1600 with one very important difference: This time the goal is to make sure that people do more than just listen, an ambition that’s laid out in the new show’s wryly cocky title: Pod Save America. The show debuted on January 9; by the following day, Pod was the number one podcast download on iTunes. By the time the Pod guys sat down to interview Obama ten days later, the first three episodes had racked up a total of a million listens. Apparently America agreed it was in need of saving.

In the heady early days of the Obama administration, the economy was in free fall but hopes were high, with progressives looking eagerly to the president to begin enacting the agenda he had campaigned on. Favreau, Vietor, and Lovett were part of the team that was going to help him sell it. Favreau, Obama’s head speechwriter, had been with the new president since his days in the Senate. Lovett joined Favreau on the White House speechwriting staff after working on Clinton’s losing primary bid. Vietor, who had been with Obama since his 2004 Senate campaign, served as assistant press secretary and then national security spokesperson. The “Obama Bros,” as Politico has called them, were young — all in their mid-twenties at the time — driven, and bro-ish, making headlines when, for example, a photo emerged of Favreau and Vietor engaging in some shirtless day-drinking in a Georgetown bar.

Eventually, all three left the White House for the private sector — Lovett in 2011 to get into television (he co-created the short-lived First Family–hijinks sitcom 1600 Penn) and Favreau and Vietor in 2013 to found Fenway Strategies, a California-based communications firm. Bill Simmons approached Favreau and Dan Pfeiffer, another former Obama adviser, about hosting a show for his new media company, The Ringer, in March of last year, when the podcasting world was seeing an explosion of new shows focusing on election coverage. But the podcasting listenership hadn’t quite caught up. This was a month in which the front-runner for the Republican nomination boasted during a primary debate about the size of his penis. Yet on the day 1600 launched, not a single politics podcast managed to crack the top ten on iTunes. (As I write this, fully half of iTunes’ top ten podcasts are explicitly political.)

From the beginning, the vibe of 1600 was jocular and frank, offering an insider-y perspective that even other increasingly popular shows, such as 538‘s politics podcast, couldn’t provide. As the election bore down the show attracted a devoted stable of listeners who found solace in hearing Favreau and Pfeiffer (and eventually Vietor and Lovett, who signed on as co-hosts) analyze the latest polling numbers, riff on the increasingly perverse developments of the race, and provide reassurance that Clinton had this one in the bag. Then Trump won, and suddenly lighthearted punditry didn’t seem like enough.

“It started on election night,” Favreau told me. “We were all pretty shocked, like everyone was, and pretty down. The next day, Tommy, Lovett, and I got together and asked, how do we actually get back into the game here?” The answer, they decided, started with the podcast. After the election, the 1600 team was contacted over and over by listeners who wanted to know what they could do. “We didn’t have a good answer,” Favreau said, “but we thought, let’s use the podcast to figure that answer out. And let’s move it into something even bigger.” Who better to rally progressives to push back against an executive and a Congress poised to systematically dismantle the Affordable Care Act and other accomplishments of the Obama administration than the team that helped sell those initiatives to the public in the first place? “Look, all of us have worked in communications and speechwriting,” Favreau said. “We have a unique ability to talk about what’s the most effective message to counter Trump’s agenda.” After all, it might not be a coincidence that the last time Favreau and the others were in the political game, progressives actually managed to win a few battles.

Over the past three months, as the initial disbelief at the election outcome has given way to a dark comprehension of what’s in store, many have come to believe that traditional media are incapable of addressing an administration that lies without shame and seems determined to doublespeak the country into believing that facts are unknowable. The deep distrust of the “liberal media” that Trump has strategically cultivated among his supporters hasn’t helped. The result has been an increasing polarization in how Americans consume their news, with both sides ultimately left unsatisfied. As Obama himself put it during his Pod Save America interview, “My instinct is everybody hates the media right now, everybody knows that the political culture doesn’t work. So that has to be an opportunity. There’s got to be a way in which we can create a virtual public square that feels better for people.”

In a way, it’s this opportunity that the Crooked Media guys want to harness. And they’re not alone. The past year has seen the emergence of a handful of openly left-leaning, activism-oriented podcasts that are aiming, in their own ways, to take advantage of the intimate, conversational nature of the medium to guide listeners through an unprecedented political era shaping up to be so grotesque it’s difficult to even wrap one’s mind around. Last week the website Jezebel launched its first podcast, Big Time Dicks, hosted by Joanna Rothkopf and Prachi Gupta, which looks at the policies being created at all levels of government that will harm women and people of color. “I do feel that Donald Trump, the big dick, has empowered politicians all across America to be at their most dickish,” Rothkopf told me.

Another new show, The FourFiftyOne, bills itself as “a podcast for the resistance.” Co-host Summer Brennan, a journalist and former U.N. communications consultant, says she started the show (with journalist Jesse Hirsch and musician Jonathan Mann) to combat the hopelessness she saw in the wake of the election and to provide “a place for people to check in with other Americans, and non-Americans, who are concerned about what’s going on.” The first few episodes of The FourFiftyOne, which launched in December, have revolved around earnest, shell-shocked conversations about the news of the week, followed by interviews with activists, academics, and legislators (the Brooklyn congresswoman and fierce Trump resister Yvette Clarke dropped by on a recent episode). The point, Brennan says, is less to tell listeners exactly what to do than to point out the different ways other people and groups are pushing back against Trump, and to “help people feel less alone.”

Comforting listeners is not the goal of Chapo Trap House, a far-left satirical politics podcast that launched last March and picked up a cult following over the course of 2016 as its hosts mercilessly mocked not just Trump and the right wing but also what they saw as the hackish incompetence of the Clinton campaign and the depravity of the liberal establishment. The Chapo hosts initially wondered whether the show could survive under a Trump presidency — how do you parody someone who’s already a parody of himself? — but in fact their listenership has gone up since the election. “With the hard right in control of every lever of power,” says co-host Will Menaker, “I have to take that seriously as someone who has a platform that is not inconsiderable.”

Menaker still sees comedy as the primary mission of the show, and there are no plans to alter the tone (or lay off on Democrats). But there will be more emphasis on grassroots organizing and on supporting an affirmative political vision for the left that can stand in opposition to both the hard-right agenda and milquetoast “Cory Booker 2020” centrism. “There are lots of things happening on an issue-by-issue basis,” says Menaker, “whether it’s Fight for $15 or Black Lives Matter or single-payer healthcare or a universal basic income — these are issues that expand the aperture of what is considered possible or realistic in the American political system. Which we’re in desperate need of.” Already, the Chapo hosts have heard from listeners who say that the show inspired them to join the Democratic Socialists of America. “One of the things we’ve been trying to emphasize is getting people who have been brought up on the internet to the mindset that what they do online does not count as politics,” says Matt Christman, another Chapo host. “And that includes listening to our show.”

Translating an online listenership into IRL civic activity is part of the mission of Crooked Media, too (though it’s unlikely the Pod guys will be driving listeners to the nearest DSA meeting). “Everything is in the very early stages,” Favreau said, explaining that they wanted to launch with Pod right away so as not to miss the news coming down in the early days of the Trump administration. For now, they’re funding the show with their own money and through native ads for things like razors and suits, and operating with a staff of zero, partnering with podcasting network DGital Media (which works on podcasts ranging from Kara Swisher’s business/tech Recode Decode to sports entries like UFC Unfiltered) to produce the show. But the plan is to grow a network of political podcasts hosted by “a diverse range of voices” — Favreau, Vietor, and Lovett are very much aware that they are three white guys who live in California — and eventually expand into video and written content. (Pfeiffer is a co-host on Pod Save America, but he’s holding on to his day job at GoFundMe and isn’t tied to Crooked Media.)

Most importantly, Crooked Media’s output won’t just assume a progressive perspective — it’ll also have a progressive agenda. The biggest difference between 1600 and Pod Save America, said Favreau, is that “we wanted to make this more activist in nature.” A main component of their strategy will be telling the PSA audience about concrete steps they can take to push back against the right-wing agenda. “As we grow this,” Favreau continued, “we want to keep in mind that the purpose is not just to inform people and entertain them, but keep inspiring action,” beginning with rallying listeners to apply pressure to their congressional representatives to save Obamacare.

Given the rudderless state of the Democratic Party at the moment, I asked Favreau whether he or the others had ever considered getting back into the political game directly — say, helping some up-and-coming progressive politician become the next Barack Obama. “All of us did that for so long,” he replied. “Who knows in the future, but it seemed like the podcast gave us a connection with people. It felt like we were helping to persuade people, and also offer progressive leaders and activists and organizers a platform to talk about the Democratic Party vision, or the progressive movement vision, and there aren’t a lot of places to do that in the media right now.”

As Vietor put it, “A lot of times you watch cable news and you feel like you got dumber, you got more cynical.” A panel full of flacks from opposing camps come on to deliver their talking points, spin the day’s news to fit whatever narrative they’re trying to sell, and see who can shout the loudest for seven minutes before it’s on to the next panel. “[Listeners] want people who are gonna be honest with them and be authentic and admit when they fuck up,” said Vietor, “but also draw from their own experiences, as imperfect as they may be, to help them understand what’s going on.”

About that fucking up: The Pod guys’ transition into full-time media activism hasn’t come without some self-reflection. Like many of us, they didn’t see any way Trump could possibly win and spent much of the election season reassuring listeners that Clinton had it locked up, going so far as to label those who feared otherwise as “bedwetters.” A week after the election, journalist Nicholas Quah, who writes a weekly podcast-focused newsletter called Hot Pod, posed a provocative question: “Did the election podcast glut of 2016 fail its listeners?” Quah’s post jumped off a Tweetstorm from Forward writer Josh Nathan-Kazis essentially arguing that the trust listeners had placed in shows like 1600, all of which got this election so spectacularly wrong, points to a sort of self-reinforcing groupthink that the medium can enable. “The conceit of such shows is to give listeners a sense of what journalists or experts are talking about in spaces separate from the performed professionalism of the public platform,” Quah observed. “The basic idea in these setups is to engender trust in the people and the process, not just the product. But when the people and the process fail, the cut feels so much deeper, and it is incredibly hard to win that trust — that sense of comfort and safety (which is perhaps the problem?) — back.”

For the Pod guys, part of re-establishing that trust means drawing back from the data game that pundits, over the past few years, had increasingly come to rely on as a kind of infallible crystal ball. “There is a lesson that we learned from way back in the 2008 campaign that we sort of unlearned as time went on,” Favreau said. “The story of the 2012 campaign was the rise of data. Back in ’08, the story was Obama’s message and the story he told. People say politics is an art and a science, and I think in 2016 we leaned a little too much on the science and not enough on the art.”

So one rule for the new show: no more predictions. But there’s also the slightly stickier matter of authenticity. Part of the appeal of 1600, and now Pod Save America, is how candid it feels — the sense that you’re eavesdropping on a conversation among Washington insiders who know how the game is played. Which you are. But you’re also listening to skilled PR professionals, and in an election season where you’ve got a dog in the fight, and particularly one in which the other dog is Donald Trump, the line between frankness and persuasion can get a little blurry. (An October story in Politico described the 1600 guys as “wingmen for Clinton’s official spin shop.”) And in the first 1600 episode after the election, stunned by what had just taken place, Lovett acknowledged that while he and the other hosts had always been honest on the show, what their listeners had heard hadn’t necessarily been the full story. “There has been a difference, I think it’s fair to say, between what we’ve said to ourselves and what we’ve said on this podcast,” he admitted. “There are two ways to be honest, and one is to be honest about the things that are easier to talk about and the other is to be honest about the things that are harder to talk about….We made our choices about the things we talked about, and we need to face up to the fact that the things we didn’t talk about” — specifically, Clinton’s liabilities as a candidate — “kept millions of people home.”

It wasn’t exactly a mea culpa — the three hosts that day went on to agree that the final throes of a high-stakes presidential race aren’t the best time to start picking apart your candidate’s flaws. But now, with the Democrats in shambles and competing visions for the direction the party should take, Lovett says the show won’t hesitate to confront topics and questions that might be a little uncomfortable. “Moving forward, we’re going to be honest about the places where we think the Democratic Party has weaknesses, where the liberal side is making mistakes,” he told me. “This was a crazy, overdetermined election — problems in the way it was covered, crazy leaks that led to nothing. And then there were mistakes and problems on the Democrats’ side that we have to address if we want to come back from this period of time where we’re basically in the wilderness.”

But even as the left tries to put its political house in order, there’s work to be done on the ground now, and there’s a difference between #resistance and actual resistance, whether in Washington or on Fifth Avenue or at the nearest international airport. Quah’s observation that the feeling of “comfort and safety” that political podcasts offer listeners may have been problematic during the election season also has some bearing on the current moment: At a time when the political landscape (and the country, really) seems utterly alien to many Americans, a desire to feel less alone — to know that you’re not crazy, that there are people out there who feel the same way you do — is undoubtedly one of the forces driving newly dispossessed listeners to their lefty podcast of choice. But if effective dissent against Trump’s agenda is the goal, it’s not inconceivable that the clubby, intimate nature of podcasting could have the opposite effect of the one intended — lulling audiences into feeling like they’re engaging in a movement just by listening.

This point isn’t lost on Favreau. “We’ve tried to make sure, in almost every episode, we tell people to go do something,” he said. “This idea of ‘Well, I listened to a political podcast or I watched a political show, and that’s my engagement for the day and I’m good to go…’ ” He paused. “That’s not gonna do much.”