Crooked Media, the liberal political media company founded by former Obama staffers Jon Favreau, Jon Lovett, and Tommy Vietor, is primarily built around its popular talk-radio-style podcast, Pod Save America. But today, the team is adding another shot to its game with the release of a new podcast documentary called The Wilderness, led and hosted by Favreau, that they’re describing as being about the history and future of the Democratic Party.
“Most political news today is about why Donald Trump is bad, and I don’t think we talk enough about the party that needs to beat him — its strengths, its weaknesses, and how it’s changed over time,” Favreau told Vulture in an email, when asked about the purpose of the project. “What does the Democratic Party stand for in 2018? How did we lose nearly 1,000 seats over the last decade, and how do we make sure that never happens again? I wanted to talk about these questions with as many people as possible in a format that allows for more nuance and reasonableness than Twitter or cable.”
The first four episodes of The Wilderness dropped this morning, and they attend to a big, complicated question: How did the Democratic Party screw up the 2016 presidential election so badly? The opening volleys evoke the Pod Save America team’s mea culpa episode right after the election back when they hosted Keepin’ It 1600, though with the considerably more robust contextual substance that comes with leaning into the documentary format. From the upcoming chapters listed posted on Crooked Media’s website, the series will be laid out across 15 installments, all of which trend towards an even larger question: How, exactly, is the Democratic Party working to pull itself back from the brink of political oblivion?
To that end, The Wilderness is driven by a cacophony of interviews that Favreau conducted with a wide range of people: politicians, political operatives, activists, analysts, and writers, many of whom will be familiar to those who are already followers of Crooked Media. As a whole, the podcast is structured in a manner not unlike a guidebook, with each chapter built around a different focus: How do you fix what’s wrong with the Democratic Party? How democratic should the Democratic Party be? How can Democrats break through in today’s media environment? Favreau notes that the chapterized structure was part of the team’s effort to make the podcast more accessible to those who aren’t immediately super-immersed in the nitty-gritty of American politics.
“Historical context is so important to the political debates we’re having, and it’s especially helpful to all the people who just started paying attention to politics when Trump was elected — and that’s an audience I’m hoping to reach with this series,” he wrote. “I also wanted to make sure we covered the major areas and issues the party needs to focus on, which is why there are 15 chapters in the series. And while they’re meant to be listened to as a whole, most chapters can also stand on their own if people have a special interest in, say, immigration, or media, or foreign policy.”
The documentary format marks a stylistic departure for Crooked Media, which has primarily built its podcast network out of conversational or interview-style programming. To make the jump between genres, the team struck a collaborative partnership with Two-Up Productions, the shop behind the popular fiction podcasts Limetown and 36 Questions.
The Wilderness extends what has already been a very busy year and a half since Favreau, Lovett, and Vietor launched Crooked Media in early 2017. This February, HBO announced that the premium cable company had struck a deal with Crooked Media to produce a series of hour-long specials that will follow the trio as they host live tapings on the campaign trail in the run-up to the midterm elections. That deal runs alongside the company’s ever-expanding lineup of liberal-to-progressive-leaning political podcasts, which now includes shows featuring The Daily Beast editor Erin Gloria Ryan (Hysteria), the activist DeRay Mckesson (Pod Save the People), and Missouri Secretary of State Jason Kander (Majority 54).
New episodes of The Wilderness are scheduled to come out every Monday, with the final chapter slated to drop slightly over a month before the midterm elections.