Paradoxically, we have Donald Trump to thank for Crooked Media, the wildly successful progressive media company started by three former Obama staffers. In 2016, as the presidential contest raged and Hillary Clinton’s victory seemed (for many) guaranteed, the three cofounders—Jon Favreau, Tommy Vietor, and Jon Lovett—occupied their time hosting the political podcast Keepin’ It 1600. They figured that once Clinton won, they would possibly continue the show as a hobby, but they had little interest in acting as boosters for the future Clinton administration. After all, they had all worked in the White House already—Favreau as Obama’s chief speechwriter, Vietor as a spokesperson for Obama and the United States National Security Council, and Lovett as a fellow speechwriter.
If anything, they seemed interested in taking their writing chops to Hollywood. Lovett moved to Los Angeles in 2012 to work on a sitcom he helped create for NBC called 1600 Penn, which focused on the antics of an over-the-top but lovable first family (think Modern Family meets The West Wing). The show was perhaps before its time, and NBC pulled the plug after one season. After leaving the Obama administration, Favreau and Vietor started a communications firm and brainstormed projects of their own that never took off.
On election night, Keepin’ It 1600 ran a live stream on its parent site, The Ringer, and the three podcasters narrated the creeping dread and disappointment felt by their listeners. The next day, packed into Lovett’s car on their way to the studio, they ran out of gas. With Lovett sitting in the driver’s seat, Favreau and Vietor pushed his Jeep Grand Cherokee down Sunset Boulevard. For at least two of them, this was rock bottom—but it was also when they first began imagining what would become Crooked Media and its flagship show, Pod Save America.
The biweekly political roundtable, which brought in fellow Obama alum, former senior advisor Dan Pfeiffer, soon spawned two more podcasts: Lovett or Leave It, a live comedy and politics show hosted by Lovett, and Pod Save the World, Vietor’s foreign policy and global politics podcast. Crooked’s portfolio has continued to expand since then— it now includes ten podcasts, a limited-run series, a website, a newsletter, and live shows across the United States and Europe. In the run-up to the 2018 midterms, HBO featured four one-hour Pod Save America specials.
The popularity of the shows has brought the hosts a certain degree of celebrity and an attendant interest in their personal lives. Lovett, for instance, makes up one-half of a media power couple with Pulitzer Prize-winning journalist Ronan Farrow, who, as the son of Mia Farrow and Woody Allen, is no stranger to the spotlight. But perhaps no part of their personal lives has received more attention than the pair of goldendoodles, Pundit and Leo, owned by Lovett and Favreau, respectively.
“I’ve definitely experienced where Leo’s been recognized before me,” says Favreau.
When Crooked first launched, none of the founders took a salary. And the intention is still more about fostering progressive conversations and encouraging activism than generating a profit.
“We started this company because of Trump, sure, but also because I think there was this hunger for a different kind of political conversation that was about how we can help,” says Lovett.
Toward that end, Crooked has taken an active role in helping Democratic campaigns around the country by helping raise candidates’ profiles and boosting grassroots fundraising. For the 2018 midterms, $2.7 million was raised for competitive races and more than 22,000 volunteer shifts were filled across the country, according to numbers provided by the company.
This Saturday, Pod Save America presents a live show cohosted by The Atlantic journalist Jemele Hill at the Greek Theatre—the podcast’s biggest venue of the year. The proceeds from the show will go to four organizations, Vote.org, Election Protection, the National Redistricting Foundation, and Think Social Impact.
“We decided to donate the proceeds from all the tickets to these four organizations that are either helping people register to vote, protecting the right to vote, [or] unfucking the vote that is gerrymandered,” says Vietor. The show will also include musical performances by singer-songwriter Maggie Rogers, rock duo Best Coast, My Morning Jacket front man Jim James, and a comedy set by Amanda Seales.
We talked to Lovett, Vietor, and Favreau about the “D team” in the White House, the recent debates, and the “radicalized” Republican Party. (The interview has been edited for length.)
In the early days of Crooked Media, is it true that you all lived on the same street in West Hollywood?
Jon Lovett: There was a moment where we there was a bunch of us all within a few feet of each other, which you just don’t get an L.A.—
Jon Favreau: Or anywhere. Not as adults.
Lovett: Yeah. You got this little taste of like, oh, when people would live in one small place with people they knew their whole lives, they were happier. Our brains aren’t meant to live this way.
Tommy Vietor: Also, Lovett had this joke where he would come over and he would turn on the fucking Sonos full blast before he walked in.
Lovett: I would play “Ride of the Valkyries” as I entered. So you’d be sitting there and all of a sudden there would just be [mimics the intro of “Ride of the Valkyries”].
Favreau: There was also this situation where the only one of that whole crew who went to a job every day, at first, was my wife [Emily Black]. Emily would come home and the three of us would be exactly as she left us and and she’d ask, ‘OK, did anyone shower today?’
Lovett: I just want to make sure this is in the story: I was actively writing a pilot during those days.
Favreau: “Actively” is doing a lot of work there.
A politics podcast in L.A. doesn’t make obvious sense. Was there ever discussion about going back to D.C.?
Favreau: Not D.C.
Vietor: D.C. is awful. You’re right that on paper L.A. doesn’t make sense. But in practice, being outside of Washington and not getting caught up in that bubble is a very good thing.
Lovett: Honestly, I think we started in L.A. because we lived in L.A., and we were already kind of taking a chance on something and trying to build something from scratch.
Vietor: In D.C., there is a pundit circuit and a conventional wisdom bubble and a group of people that move as an amoeba from place to place and traffic in the same bullshit. Not feeling wedded to that or feeling like you have to do those things is valuable.
Favreau: One of the reasons the Obama campaign was very successful in 2008 is because we had the headquarters in Chicago. You get a sense of outside perspective having a media company outside of the D.C.–New York corridor.
Do you feel like there are disadvantages to being in Los Angeles?
Lovett: I’ll give you one. Jerry Nadler is starting [Mueller] hearings at 8 a.m. [eastern time].
Now that California is in play in the primaries, has that helped you guys get politicians on the show?
Favreau: I think they would’ve come out here anyway for the money, but now they come out for money and a couple of events. They’ll do Kimmel, and they’ll do something else, and then hopefully we can get them in.
Lovett: Yeah. We can draft off of the TV shows. I think, look, California being more important—I think that they’re campaigning here the way they have for years.
[To Lovett:] What prompted you to open up more about your relationship with Ronan Farrow?
Lovett: I don’t know that I have opened up that much. I would say that we don’t talk about it very much, but I’m not going to go out of my way to not talk about it or not make a joke about it. I would say that it’s just about not wanting to focus on it, but not trying to get one over on anybody. You know what I mean?
Favreau: You started going to so many public events together, too. It’s sort of silly to deny it.
Lovett: We never denied it. I guess it’s more that Ronan is someone who had his family life become very prominent. and I think that’s very hard. And so I think it’s really important that the work and the professional aspect of who he is and who I am is what speaks for us. But that doesn’t mean I’m not gonna say his name in an ad read.
You all have operated on the inside of Washington and the inside of the Oval Office to a certain extent. With that perspective, you might be expected to be more inclined to grant the benefit of the doubt or assume good faith. That doesn’t seem to be the case with the current occupants of the White House. Is that because this is such an aberrant administration or … ?
Vietor: I disagree. I do assume good faith, I think. Going from the outside of the White House to inside made me realize the way that the Democratic Party sometimes puffed up Karl Rove was silly—there wasn’t an all-controlling puppet master behind the scenes. Some of the decisions a president makes are not black-and-white and are actually very difficult. But I do think the people that they’ve chosen—like if you choose a guy to lead the intelligence community without ever vetting him and he lies on his resume about his only relevant experience and, apparently, has been on the intelligence committee for less than a year and never shows up. What else do I need to know before giving you the benefit of the doubt there?
“You have a racist buffoon in charge and most of the respectable Republicans have been purged because they’ve criticized Trump at some point…it’s not even like the B team, it’s the D team in there.” —Jon Favreau
Favreau: Yeah. I was talking to a New York Times reporter a couple weeks ago and he said, “People always ask me, ‘Is it so hard to cover the Trump White House—don’t you miss the Obama days?'” And he said, “No, because it was hard covering you guys, because with you guys, people didn’t leak all that much, and it was really hard to find out what was going on behind the scenes.” He’s like everything is out there for everyone to know with the Trump administration. It’s not hard to figure out what’s going on in that White House. You have a racist buffoon in charge; most of the respectable Republicans have been purged because they’ve criticized Trump at some point, and so they can’t work in the White House; and so the people you have left over in that White House are probably the most unqualified for the jobs that they hold of any White House in history. It’s not even like the B team, it’s the D team in there. And so you have a bunch of Twitter trolls and cranks and right-wing website people and Fox News contributors who are running the government right now. I would give people the benefit of the doubt more if it was your typical D.C. people staffing the White House. But this group of lunatics is not that.
You guys have your ear to the ground more than most people. Why haven’t the old-school Republicans from the Trump administration spoken about their experiences after leaving the White House?
Vietor: That’s a really good question. The person I think about a lot is Rex Tillerson. He had enormous stature coming in. He was as humiliated as he could possibly have been to the point of being—the final anecdote we all remember is that he was fired while on the toilet. He doesn’t want to rehab his reputation? Maybe he’s writing a book, I don’t know. I mean, there’s going to be a bunch of people who want—like Nikki Haley, as an example of someone who probably saw some shit, but she wants to run for president someday, so she’s not going to upset the MAGA base. So I get it. There’s the grifters, like a Corey Lewandowski, who got sent packing and humiliated but wants to be able to hawk books and do the Fox News tour.
So let’s talk about the debates. I know that you all had thoughts about the format, maybe some issues with it.
Favreau: Yeah. The way the debates have been set up for a long time are a bad way to pick a president. They are too performative. They don’t allow for actual debate. They allow for the exchange of 30- to 60-second sound bites. They incentivize all the wrong behavior.
Vietor: It’s very weird that something as important as a presidential debate is jammed through the filter of what will make a corporation profits. I think Jake [Tapper] and Dana [Bash] and Don Lemon did a very good job. But the fact that there was a live Powerball-style pick was just to have an hour’s worth of commercials…. It’s strange that the Democratic Party hands over that much power to Turner [Broadcasting System, owner of CNN].
How would you rework it to make it more productive?
Favreau: I think you could have a debate where you have issue experts as the moderators or activists as the questioners—people who have been involved in these issues.
Lovett, you look like you have some thoughts.
Lovett: I always do…. How is having human beings standing on stages side by side with each other bickering elucidating at all? What does it do to show us who’d make a good president? Presidents don’t actually engage in very much one-on-one debate except when they are debating to get the job. But it’s an artifact of a way of thinking about politics. I think it ultimately ends up being helpful, but not because of the format, not because of the debate, but because you learn, despite the format, who these people are.
Tommy: When you think of historical moments in debates that turned the tide of elections, it’s like Reagan saying, “I paid for this damn microphone.” How was that good?
Lovett: Or “I knew JFK, JFK was a friend of mine”—just like zingers.
Favreau: These become moments you view through the lens of history depending on who won, right? Hillary Clinton won all three debates against Donald Trump, and if she won the presidency, we would be looking back at some memorable moment from the debate and be like: That’s the moment that Hillary Clinton clinched the election.
Lovett: All we retained is “No puppet, no puppet.” Obviously the urtext of our era.
Favreau: “I paid for this mic,” “I knew JFK,” and “No puppet, no puppet.”
We’re heading to the next set of debates and obviously a lot of people aren’t going to make it. Who do you wish would make it that probably won’t?
Vietor: Jay Inslee.
Lovett: I agree with that. Jay Inslee was on Lovett or Leave It last night. I think at first he seemed a little reluctant to truly lean into the fact that he was a climate candidate, but the more he’s embraced what was at the core of why he ran, which is climate, I think the more value he’s had in the race. The exchange he had with [Joe] Biden was probably amongst the most substantive of the night, which ultimately boils down to the fact that Biden isn’t setting enough interim targets in his climate change plan. For all of our criticism of debate, pushing Joe Biden to have those steps is the debate we want to have.
So you guys are coming from an administration that a lot of people would describe as straddling Clinton-era neoliberalism but trying to lean a little bit more to the left. But to me it seems as if the company you’ve created is unapologetically progressive and left-leaning, even more so than how I would characterize the Obama administration. Have you guys been pulled to the left, or is it just that outside of the confines of a political environment, you’re able to be yourselves?
Favreau: I would say two things. One, when we were in the White House, we were constrained by what’s possible. And so, to the extent there is a critique from the left about the Obama administration, to me, it has to do with what we couldn’t get done. It has to do with the fact that we had a recalcitrant Republican Congress that wouldn’t let us get anything done, as well as—even when we did have Democratic majorities—we did not have a very progressive Democratic Senate because we had a bunch of red-state Democrats. So we were just boxed in by a lot of things. Because the campaign we ran in ’08 was a campaign against, in the primary at least, neoliberal Clintonism. So, I think, you know—Obama is a progressive guy—but you’re constrained by politics.
Two, which comes a little bit from one, is we’ve learned lessons from how obstructionist and awful the Republican Party was when Obama was president. Obama’s go-to is to try to compromise, try to bring people together. I certainly believe in that, and I still want to believe in that. But I think what has changed is not so much the left, but the fact that the Republican Party has become so radicalized, and if there was a different Republican Party, my preference would be to compromise and work things out.
But it’s hard to compromise with a party that’s become radicalized in a way that we’ve never seen before. And that’s what we have right now.
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