The ‘Keepin’ It 1600’ Guys Launch Crooked Media to Counter Trump

Jon Favreau, Jon Lovett, and Tommy Vietor are leaving The Ringer’s ‘Keepin’ It 1600’ to launch a new media company that aims to challenge Trump.

Crooked Media

With Donald Trump about to enter the White House, they just don’t feel like “keepin’ it 1600” anymore.

Just before Christmas, former Obama administration staffers Jon Favreau, Jon Lovett, and Tommy Vietor recorded what would become the final episode of their popular 2016 campaign podcast Keepin’ It 1600 for Bill Simmons’ The Ringer network. Today, they are back with a new podcast—Pod Save America—and this time it is under the banner of their new company, the pointedly titled Crooked Media.

Along with former Obama communications director Dan Pfeiffer, who will appear weekly on Pod Save America but does not have a stake in Crooked Media, the Keepin’ It 1600 guys were a vital voice on the left leading up to the election. But like so many others, they did not see the election of Donald Trump coming and consistently urged listeners not to “bed-wet” over the slim possibility that Hillary Clinton could lose.

They have some regrets.

Looking back at the podcast’s initial run, Favreau says, “One thing we wished we had done slightly differently—in addition to political analysis and punditry and all that good stuff—we wish we had done a little more advocacy, encouraged more participation and activism and used it as a platform to lift up all of the young progressives’ voices that are out there.”

Calling from Los Angeles, Favreau, a sometime Daily Beast contributor, says he and the two other guys were spending their Sunday “running around like crazy realizing that we decided to launch a media company.”

“If Hillary Clinton had won the election, like we all wrongly prognosticated, I think all of us would have been content to keep doing this as a hobby,” Vietor, who served as a spokesperson for Obama, adds. “But that night changed things for a lot of people, us included. I woke up feeling like sitting on the sidelines wasn’t an option anymore. I wanted to be part of whatever is going to happen over the next four years to preserve the things we fought for at the White House.”

Vietor is moving from San Francisco to Los Angeles for the project and, along with Favreau, will hand over control of Fenway Strategies, the speechwriting company they started a few years back, to existing staff, who will run day-to-day operations. Beyond the new podcast, they want to build out the company to include additional podcasts, streaming video, and written content.

So far, they have not taken any outside funding and are building the platforms entirely on their own. “We are coming into this with a lot of humility and an understanding that there’s a lot we don’t know,” Vietor says.

Despite their collective experience at 1600 Pennsylvania Avenue, none of the three guys say they were on track to go work in a Hillary Clinton administration had she been elected. “I would have been inclined to feel comfortable that Obama’s legacy and the things we worked on were safe,” Vietor says. “It’s not helpful or practical or accurate to think that the only way you can be engaged in politics is by living in Washington. In fact, the most important work is going to happen outside of that city.”

Had things turned out differently, Favreau says, “We’d probably still be at The Ringer and we’d be doing podcasts as a part-time job as we all were in 2016. Trump winning changed everything. It was a wake-up call.”

It was also the event that precipitated their split from Bill Simmons, who scored a major coup when he helped them launch Keepin’ It 1600 in March of last year, giving his new site an important voice in the 2016 election. “The Ringer’s great, but we need to have the freedom to make this our own,” Lovett says of the move.

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“And Bill thought that made sense, too,” Favreau hastens to add, saying Simmons “encouraged” them to strike out on their own once they decided to move in a more activist, less journalistic direction. “For us, politics is not a passive thing that you consume,” he says. “It has to be active. You can’t just scroll through Twitter, you actually have to do something.”

They are very aware, as Vietor puts it, that Trump is going to be able to “swamp you every time with a single tweet.” So, they have decided to take a page out of his playbook and try to “reach voters directly” without filtering their message through a larger media lens. The “intimate” nature of podcasts and Facebook Live allow for this direct connection.

In the same way President Obama fears watching his legacy get upended, they see in a Trump presidency the likely reversal of the policies they spent the past eight years communicating to the American people. And just as Obama may no longer be content to go relax on a beach in Hawaii, they felt it would be an abdication of responsibility to merely comment on the news in their spare time.

Favreau, who’s been helping out with the creation of Obama’s new foundation from afar, does not expect the media to be the president’s primary focus after he leaves office, as some reports have suggested. Nor will he be joining their effort directly.

“He did just send over his CV and it looks great,” Lovett, who worked on Hillary Clinton’s 2008 campaign before joining the Obama White House, jokes of his former boss. “He doesn’t have any direct media experience, but he’s interacted with a lot of reporters. I think he gets the medium.”

“I don’t think they have any media plans in place right now,” Favreau says, on a more serious note. “But the overall mission of the foundation, which is to get people involved in civic life and get people engaged in politics, I think we would very much like to be the media company version of that. So it’s certainly inspired by a lot of what Obama has talked about in terms of the media over the last several months.”

The most popular episode of Keepin’ It 1600 was the one that went up “the morning after Hillary almost won,” as Lovett puts it, wryly. “That was a real test for us, which was to be open and vulnerable and honest and sincere. And talk about the future and our own anxieties and concerns and hopes,” he continues. “It was the moment we realized we wanted to be doing something more than what we had been doing before the election.”

Deciding to call their venture Crooked Media was the result of “10,000 text messages back and forth between the three of us,” Vietor says of the “tongue-in-cheek” moniker. “We take this work very seriously, we take the issues very seriously. We don’t take ourselves seriously.” It is their attempt to “take back” a phrase that Trump used to smear the press during his campaign—and will no doubt continue to wield as a weapon against his critics once in office.

“One lesson from Donald Trump is, name things after something Donald Trump says and you’ll get attention,” Favreau adds, laughing. “We didn’t want to send a message that we’re starting this company only in opposition to Donald Trump. It’s much bigger than that. But I think that Trump obviously looms large for us and everyone else right now.”

“We’re doing this because we care about these issues and we care about talking about these issues in a way that would perhaps bother somebody like Donald Trump,” Lovett says. “And maybe earn the name ‘Crooked Media’ from him.”

“In the battle between Donald Trump and the media, we are firmly on the side of the media,” Favreau insists. He rejects the type of news analysis that “hides behind the veneer of objectivity” saying, “we’re always going to be Obama guys, we’re very open and honest about that.” But that doesn’t mean they can’t have “open and honest” conversations with people who have different views.

As for what listeners can expect from Pod Save America, Favreau says he hopes they can “pierce the bubble” that separates left from right in America by engaging in casual, long-form conversations in a podcast setting, as opposed to the type of cable news shout-fests that were a staple of the election cycle. “We are not going to have people on who have been known to just lie constantly all the time,” he says, “but if you have opposing views, I want to have those conversations.”

“We have a hard ban on devious morons,” Lovett adds, laughing. Would that standard apply to someone like Kellyanne Conway, for example? He just sighs and says, “She’s so busy!” Informed that she will be on with Seth Meyers’ show this week, he jokes, “Maybe she’ll say something true.”