Crooked Media

Crooked Media
Crooked Media · Public domain · source
Name	Crooked Media
Type	Private
Industry	Media
Founded	2017
Founders	Jon Favreau, Jon Lovett, Tommy Vietor, Daniel Pfeiffer
Headquarters	Los Angeles, California; New York City, New York; Washington, D.C.
Products	Podcasts, live events, digital content

Crooked Media is an American media company and podcast network founded in 2017 by former political staffers and speechwriters. The company produces political commentary, interview programs, and cultural podcasts, expanding into live events, video, and digital organizing. Its emergence linked content production with progressive activism and modern podcast monetization, drawing attention from commentators across United States media, political, and academic institutions.

History

Founded in 2017 by former Obama administration staffers and speechwriters Jon Favreau, Jon Lovett, Tommy Vietor, and Daniel Pfeiffer, the company grew out of post-2016 electoral activism connected to the aftermath of the 2016 United States presidential election. Early operations connected to networks of alumni from the Barack Obama White House and liberal think tanks such as the Center for American Progress and the Brookings Institution. Initial publicity followed appearances at venues like the New York International Fringe Festival and collaborations with hosts who had backgrounds at outlets including The New Yorker, The Washington Post, MSNBC, The New York Times, and Vox. The network expanded through partnerships with platforms such as iHeartMedia affiliates, distribution on Apple Podcasts, and advertising relationships with firms servicing the NPR and Gimlet Media audiences. Growth involved recruitment from institutions including Harvard University, Columbia University, and Georgetown University and events hosted near hubs like Silicon Valley, Hollywood, and Capitol Hill.

Podcasts and Programming

The flagship program launched early, featuring hosts with prior roles in the White House and Department of State, and spawned a slate of shows covering politics, culture, and sports. Programming has included interview formats with guests from institutions like United Nations, NATO, European Union, and personalities from the Academy Awards, Pulitzer Prize winners, and Tony Awards participants. The network’s roster drew contributors from newsrooms such as CNN, Fox News, Bloomberg, Politico, ProPublica, and The Atlantic, as well as commentators from National Public Radio and public intellectuals affiliated with universities like Yale University, Princeton University, Stanford University, Oxford University, and Cambridge University. Special series have featured guests with histories at the Supreme Court of the United States, former members of Congress including from the United States House of Representatives and United States Senate, and analysts from the Federal Reserve and Brookings Institution. Sports-adjacent episodes have hosted athletes with ties to the National Football League, National Basketball Association, Major League Baseball, and United States Soccer Federation.

Political Activities and Advocacy

Beyond audio, the company engaged in advocacy and get-out-the-vote operations, coordinating with nonprofit groups like Organizing for Action, MoveOn.org, and labor organizations including the AFL–CIO and Service Employees International Union. Campaign activities intersected with progressive political campaigns in states such as Pennsylvania, Michigan, Wisconsin, and Florida, and with ballot initiatives in jurisdictions like California and New York State. The network’s initiatives partnered with advocacy groups addressing issues before bodies like the United States Congress, the Supreme Court of the United States, and state legislatures. Collaborations included public information campaigns during elections overseen by the Federal Election Commission and civic education work with nonprofits similar to Common Cause and League of Women Voters.

Business Model and Funding

Revenue sources combined advertising, subscription content, live ticket sales, and branded partnerships with firms active in digital advertising markets such as Spotify, YouTube, Facebook, Twitter, and premium platforms like Patreon. The company monetized through dynamic ad insertion, sponsorships from corporations in sectors represented by Amazon (company), Netflix, Apple Inc., and consumer brands that advertise on networks like iHeartRadio and SiriusXM. Financial support and seed investment came from private founders and venture-stage media investors alongside partnerships with podcast networks similar to Wondery and Audible. The company explored direct-to-consumer models analogous to those used by The New York Times and The Washington Post with membership tiers and donation campaigns resembling mechanisms used by nonprofit media organizations such as ProPublica and Mother Jones.

Reception and Criticism

Reception mixed across political and media observers from outlets such as The New York Times, The Washington Post, Variety, The Atlantic, and The New Yorker. Supporters compared its influence to progressive media platforms like HuffPost and Slate, while critics likened its partisanship to legacy outlets aligned with political movements associated with figures like Bernie Sanders and organizations such as Democratic National Committee. Coverage in trade publications including Adweek and Nieman Lab evaluated its advertising efficacy and audience metrics against competitors like Radiolab, Serial (podcast), and This American Life. Legal and ethical scrutiny from commentators addressed conflicts of interest paralleling cases in media history involving outlets such as Fox News and MSNBC, and debates considered comparisons to activist media campaigns run by groups like MoveOn.org.

Key Personnel and Contributors

Founders Jon Favreau, Jon Lovett, Tommy Vietor, and Daniel Pfeiffer anchored programming alongside a rotating roster of hosts and guests drawn from institutions including Hillary Clinton’s 2016 campaign staff, former officials from the Department of Justice, and commentators who previously worked at Slate, The Daily Show, The Colbert Report, and Late Night with Seth Meyers. Regular contributors and guests have included elected officials from the United States House of Representatives and United States Senate, former cabinet members with ties to the Department of State and Department of Defense, journalists from The Guardian and Reuters, legal analysts from the American Civil Liberties Union and Heritage Foundation-adjacent scholars, and cultural figures from the Academy of Motion Picture Arts and Sciences and Recording Academy. Production and executive teams included professionals with backgrounds at Sony Music Entertainment, Warner Music Group, Endeavor, and public relations firms operating in Los Angeles and Washington, D.C..

Category:Podcast networks Category:Political media in the United States