HOLLYWOOD, California—“Like the new place?” Jon Favreau asks, greeting me at the door to the new Crooked Media offices. “The old one was a real shithole.”
With its glass-paneled conference rooms, polished cement floors and exposed Edison light bulbs hanging from the ceiling, the new spot fully completes the former Obama communications staffers’ long transition from White House grandeur to tech-bro minimalism.
The first thing you see when you enter the new offices is a full neon recreation of George Washington wearing earbuds—the logo for their wildly popular Pod Save America podcast, which launched the week before President Trump’s inauguration and has been going strong ever since. This Friday night, HBO will premiere the first of four live Pod Save America specials leading up to the midterm elections on November 6th.
Gathered around a small coffee table in their corner office are Favreau, Lovett and their third Crooked Media co-founder Tommy Vietor. Lovett’s infamous Goldendoodle Pundit and her half-brother Leo, who belongs to Favreau, are also present. Along with their Pod Save America co-host Dan Pfeiffer, who’s on speakerphone, the guys all spent time working behind the scenes in President Obama’s White House. First with their podcast and now the series of HBO specials, they have become celebrities in their own right. “Finally,” Lovett says, cracking up the room.
On the door behind Vietor are four columns of color-coded sticky notes, one for each of the cities they will visit over the next four weeks. After Miami, they will go to Austin to help drive enthusiasm for Beto O’Rourke’s longshot Senate bid against Ted Cruz. Pittsburgh has been crossed out in favor of Philadelphia. (The venue there wasn’t up to fire code.) The tour will end in Irvine, California, just a few days before the election.
Before HBO came calling, the team had always planned to spend the month leading up to the midterms touring battleground states and putting on live shows. “It worked out very well that HBO said, cool, we’ll film them,” Favreau says. Joining them on the road will be fellow members of the Crooked family, including Daily Beast contributor Erin Ryan, former Bernie Sanders spokesperson Symone Sanders and others.
Given how fast the news cycle moves these days, the bulk of the live shows’ content won’t be determined until the hours before they go on stage. “There’s just no other way to do it,” Favreau says. There are some issues like health care or tax reform that they know will be key in certain races, but otherwise the daily onslaught of news provides them with “plenty of material.”
Just before we sit down for our interview, HBO sent out an announcement that Florida’s Democratic gubernatorial candidate Andrew Gillum will be a guest on the Miami show. But the guys caution that with Hurricane Michael barreling toward the Panhandle, its possible the Tallahassee mayor won’t make it. “We’ve all worked for politicians and when there’s a storm we wouldn’t advise our bosses to go on a show,” Favreau explains.
Even though Gillum could use the platform to raise awareness about relief efforts, Vietor says, “we wouldn’t be dicks about it if he couldn’t make it.”
“Disagree,” Lovett jokes. “I will hold a grudge forever.”
At their live shows across the country over the past 18 months or so, Pod Save America has helped elevate little-known Democratic politicians into bona fide rock stars. This includes figures from Ralph Northam in Virginia to Kyrsten Sinema in Arizona. But none has received a bigger ovation from their crowd than Beto O’Rourke.
When I ask whether O’Rourke will appear on their October 19th show from Austin, Vietor says, “That would be the hope.”
“It would be cool if Beto showed up,” Lovett adds with a laugh, quick to point out that the Texas Democrat actually appeared on his live podcast, Lovett or Leave It, before he went on Pod Save America at SXSW. Lovett got O’Rourke to help facilitate a game of “Cruz or Crockett” in which the candidate read a series of quotes aloud and an audience member had to determine whether they were said by Ted Cruz or Davy Crockett.
While the guys are all-in on O’Rourke, he was noticeably absent from a recent list of endorsements by their former boss Barack Obama. Responding to the media backlash, Lovett immediately jokes, “Obama hates Beto O’Rourke and hopes he loses. That’s why he left him off, because he hates him and wants him to lose.”
Nervous laughter around the room gives way to the real explanation from Vietor. “Beto doesn’t want any outside endorsements,” he says, pointing out that the candidate said as much after a town hall event last week. “I don’t even think Biden is going to Texas.”
“If I were on his campaign, I would say no Obama, no Biden, no Hillary,” Favreau adds, stressing that O’Rourke is running a “very smart campaign” that is rightly keeping the focus local.
Meanwhile, President Trump has vowed to hold a rally for Cruz at the “biggest stadium” in Texas. “I know we don’t make predictions, but I will make one prediction,” Lovett says, “My prediction is that Donald Trump will not be able to stop himself from making fun of Ted Cruz. Remember with Chris Christie and the Oreos? That’s what’s coming for Ted Cruz.”
“And in that way, Donald Trump is a little like all of us,” Pfeiffer jokes from the phone.
Over the past couple of years, HBO has made a few attempts to turn podcasts into television shows, some more successful than others. Bill Simmons, who helped launch the Pod Save America precursor Keepin’ It 1600 at his website The Ringer, tried and quickly failed to translate his popular podcast into Any Given Wednesday in 2016. This past winter, 2 Dope Queens hosts Jessica Williams and Phoebe Robinson had a better go of it when they produced four live specials for the network. That is clearly the model being emulated here.
“If we had only been in the studio for the last year and a half and then we were doing a show, I’d be a little more anxious about what it might look like to make that transition,” Favreau says. “What we’re benefiting from is that we’ve done these live shows so often.”
Aside from the HBO specials—and the ten podcasts that are currently being produced by Crooked Media—their big focus this fall has been Vote Save America, a national, interactive online platform where people can make sure they’re registered to vote, download annotated ballots (“in plain English”) and sign up for volunteer shifts in their area. So far, they’ve had over 132,000 people pledge to vote through the site and driven volunteers to sign up for more than 6,000 shifts.
“When we started this whole project, we were like, is there a place where you can register to vote, check if you’re registered, get involved somehow and then actually know what you’re voting on?” Favreau says. “And there was no place that does all those things.”
There is plenty of talk during every election cycle about how this is the most important election of our lifetimes, but as an organization, Crooked Media clearly believes it about this year’s midterms. In 2016, they were urging listeners not to “bed-wet” over the prospect of Hillary Clinton losing to Trump, but they are not taking anything for granted in 2018.
If the Republicans win again this year, Pfeiffer says, “It will reinforce the idea that everything they’ve done thus far is right and the lesson there for them is that there is no accountability for bad actions, criminal or otherwise.” If they win again, he predicts Special Counsel Robert Mueller will be “gone” and the Trump family will be “in the National Treasury stuffing their pockets,” adding, “the prospects of what could happen are horrifying.”
Their official website describes Pod Save America as a “no-bullshit conversation about politics” that “breaks down the week’s news and helps people figure out what matters and how to help.” And it’s true that their discussions contain none of the “both sides” false equivalency that has become the standard on much of cable news.
Favreau calls their unabashedly progressive approach “liberating,” explaining that “the only challenge is when we get asked, ‘Aren’t you contributing to the tribalism and partisanship?’”
From their time in the White House, they know plenty of people who serve as talking heads on networks like CNN—Dan Pfeiffer included. “It’s sometimes harder to be yourself,” Favreau says. “You have to coldly analyze politics and pretend you’re not someone with an opinion.”
“There is no shortage of people who are intellectually dishonest across the spectrum,” Lovett adds, “but I think on the left, whether it’s us or Rachel Maddow or Chris Hayes, yeah they have a point of view, yeah they have policy preferences, but I think there’s a sincerity to how they approach things.”
“The right just doesn’t have as much of that,” he continues. “The country would be a better place if Sean Hannity was more like Rachel Maddow, but he’s not. Rachel Maddow respects her audience. Sean Hannity hates the people who watch his show. Rachel Maddow treats the people who watch her show with respect. Sean Hannity treats the people who watch his show like dogshit.”
As Pfeiffer sees it, news consumers go to CNN or The New York Times for something “very different” than what they get when they download Pod Save America. “What Crooked Media does is fill a huge vacuum. There has never been smart, entertaining, activist media on the left,” he says. “That was a hole that needed to be filled, both because there’s a market for it, but more importantly, it’s a huge problem for progressives that we are massively outgunned in the media space.”
A recent article by Dan Zak in The Washington Post seemed to equate what Pod Save America is doing on the left to what former Breitbart editor Ben Shapiro is doing on the right with his podcast. The headline read, “The battle in your ear buds: The bros of political podcasting and their quest to reinvent punditry.”
“Cool piece,” Favreau says, sarcastically.
The big difference between what Crooked Media and conservative websites are doing, Vietor says, is that Breitbart, The Federalist and The Daily Caller are all “propped up by right-wing billionaire money.”
“Soros keeps sending pallets of cash, but we send ‘em back. We don’t want them,” Lovett chimes in, jokingly referring to President Trump’s favorite liberal boogeyman.
While those sites aim to “inflame tensions and scare people,” Vietor says Democrats “don’t get motivated that way.”
“Their political goal has basically been reduced to owning the libs,” Favreau says of right-wing media figures. “All of their content is trolling. It’s not even like they’re saying, ‘Go support Donald Trump’s immigration policy’ or ‘Build the wall,’ all the stuff they used to do in 2016. Now it’s pretty much just like, ‘The left-wing is horrible, let’s embarrass them, let’s piss them off, let’s play victims.’” He finds it hard to imagine anyone on the right encouraging people to knock on doors for conservative candidates. “That would be the equivalent of what we do, but we don’t see that,” he says.
The guys are well aware that they are almost exclusively reaching like-minded listeners with their podcast, but they hold out hope, however unrealistically, that the HBO shows could have a wider reach.
“To listen to a podcast you have to search for it, seek it, spend time with it,” Vietor says. “There’s going to be someone wearing a MAGA hat who’s flipping around on HBO and sees this show. Maybe they’ll despise it but the odds of you listening to a podcast you despise are probably pretty low.”
Imagining the elusive Trump-loving HBO subscriber, Lovett jokes, “I come here for Ballers and Insecure, not this political claptrap!”