Crooked Media
Crooked Media is an American progressive political media company built around podcasts, digital journalism, live events, and civic activism.
Last updated August 22, 2026
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Overview
Crooked Media is an American progressive political media company founded in 2017 by Jon Favreau, Jon Lovett, and Tommy Vietor, former senior Barack Obama administration staffers who had previously co-hosted the political podcast Keepin' It 1600. The company began as a podcast venture and developed into a broader media and activism platform focused on center-left politics, public affairs, culture, social justice, and political participation. Its flagship program, Pod Save America, launched in early 2017 and became the foundation of the company's audience and identity. Hosted primarily by Favreau, Lovett, and Vietor, with Dan Pfeiffer participating in the Thursday edition, the show combines political analysis, reporting, humor, interviews, and appeals for civic engagement. Crooked Media subsequently built a network of programs addressing subjects including foreign policy, law, climate, health care, culture, sports, religion, workplace issues, and British politics. Notable series have included Pod Save the People, Pod Save the World, Lovett or Leave It, The Wilderness, Strict Scrutiny, Pod Save the UK, Hysteria, What a Day, Offline, This Land, and Wind of Change. The company expanded beyond audio in October 2017 with Crooked.com, a digital journalism and opinion site led initially by editor Brian Beutler. The expansion also introduced the Crooked Contributors network, bringing journalists, activists, organizers, policy specialists, campaign veterans, and comedians into the company's publishing and programming ecosystem. Crooked Media's business model has primarily relied on advertising and audience-supported media activity rather than a publicly traded structure. Live performance is another important part of the brand. Crooked Media has produced tours featuring live versions of its podcasts, including Pod Save America and Lovett or Leave It. The tours have taken the company's political-comedy format to venues across the United States and, in 2018, to international cities including Stockholm, Oslo, Amsterdam, and London. The company also uses video, social platforms, and livestreaming to extend podcast programming and political commentary. Crooked Media is distinctive because it combines media production with organized political participation. Through Vote Save America and related initiatives, it has encouraged voter registration, turnout, volunteering, donations, attendance at public meetings, and support for progressive candidates and causes. Its election-related work has included collaborations with MoveOn, Swing Left, Indivisible, Fair Fight, and Data for Progress. These activities position the company between a conventional political publisher, a podcast network, and a civic-engagement organization. The company is headquartered in Los Angeles. Its stated or evident audience is primarily center-left and progressive listeners in the United States, although its programs and tours have developed an international reach. Crooked Media's name references a phrase associated with Donald Trump and reflects the founders' deliberately irreverent approach to political commentary. The company remains best known for translating Democratic campaign and government experience into accessible political media while encouraging listeners to participate directly in elections and public life.
History
Crooked Media emerged from a podcasting partnership among Jon Favreau, Jon Lovett, and Tommy Vietor, three former senior Obama administration staffers. The trio, together with Dan Pfeiffer, had hosted Keepin' It 1600 for The Ringer from March through December 2016. During 2016, Favreau, Lovett, and Vietor began treating podcasting and political activism as a full-time pursuit. They formally established Crooked Media in January 2017, and launched Pod Save America the following month. Pfeiffer did not become a company founder but continued as a recurring co-host, particularly on the show's Thursday edition. The new company adopted a name derived from a phrase associated with Donald Trump. The choice signaled an intentionally partisan, humorous, and confrontational editorial identity. From the outset, Crooked Media was more than a conventional audio publisher: its hosts connected political discussion with persuasion, volunteering, donations, and participation in public events. Pod Save America quickly became the company's anchor, using former campaign and government insiders to explain current politics in an informal style while directing listeners toward civic action. In October 2017, Crooked Media broadened its scope through the launch of Crooked.com, a text-based news and opinion operation led by Brian Beutler. The company also created Crooked Contributors, a network of journalists, activists, organizers, policy experts, campaign veterans, and comedians who could appear across podcasts, articles, and video. This expansion helped establish the company as a multi-format progressive media outlet rather than a single-show podcast business. Crooked Media continued to build a large podcast portfolio. Pod Save the People addressed social justice and politics through the perspective of organizer DeRay Mckesson. Pod Save the World examined foreign policy with Tommy Vietor and Ben Rhodes. Lovett or Leave It converted a weekly live format into political comedy and commentary. Other programs covered the Democratic Party's future, the Supreme Court, climate change, health care, culture, sports, religion, workplace questions, online life, and international affairs. The network also produced documentary and investigative series, including This Land, Wind of Change, and The Wilderness. Live tours became a major audience and revenue extension. The first Crooked Media podcast tour took place in fall 2017 and combined live versions of Pod Save America and Lovett or Leave It with appearances by other hosts and guests. A subsequent 2018 tour included European dates, demonstrating that the company's audience extended beyond its American political base. Video, social media, and livestreaming further allowed the company to distribute clips, interviews, and event material outside conventional podcast feeds. Political activism became institutionalized through Vote Save America, a label used for Crooked Media's voter-turnout initiatives and political action committee. The company worked with organizations such as MoveOn, Swing Left, Indivisible, Fair Fight, and Data for Progress. Its activities have included encouraging attendance at Republican town halls, raising funds for competitive races, coordinating volunteers, supporting voter registration, and promoting ballot initiatives. During the 2018 midterm cycle, Crooked Media reported raising $2.7 million and directing 22,000 volunteers toward competitive races. In 2019 it launched the F*ck Gerry(mandering) Fund with Data for Progress. During the 2020 cycle, Vote Save America raised substantial funds for Democratic candidates and connected listeners with campaign and grassroots organizations. By 2024, the activism program was emphasizing down-ballot races, ballot measures, voter registration, and recurring support for grassroots groups in battleground states. This reflected the company's broader strategy of treating its audience as an organized civic community rather than only as consumers of political commentary. The company has remained privately held and headquartered in Los Angeles. Its continuing development has centered on expanding podcast genres, building live and video formats, and combining progressive editorial programming with direct political participation.
- 2024
Vote Save America emphasizes down-ballot organizing
[1]The civic-engagement program prioritizes competitive congressional races, ballot initiatives, voter registration, and battleground-state grassroots organizations.
- 2022
Strict Scrutiny joins the network
[1]Crooked Media acquires the Supreme Court-focused legal podcast Strict Scrutiny.
- 2019
F*ck Gerry(mandering) Fund launches
[1]Vote Save America and Data for Progress establish a fund supporting closely contested Virginia races and anti-gerrymandering work.
- 2018
Pod Save America appears on HBO
[1]Four one-hour Pod Save America specials air on HBO during fall 2018.
- 2017
Crooked Media is founded
[1]Favreau, Lovett, and Vietor establish Crooked Media as a political podcast and activism company.
- 2017
Pod Save America launches
[1]The flagship podcast begins broadcasting and becomes the central audience and editorial property of the company.
- 2017
Crooked.com launches
[1]Crooked Media expands into written journalism, opinion, video, and a contributor network.
- 2017
First podcast tour
[1]The company stages its first live tour, featuring Pod Save America, Lovett or Leave It, and other contributors.
- 2016
Founders host Keepin' It 1600
[1]Jon Favreau, Jon Lovett, Tommy Vietor, and Dan Pfeiffer host the political podcast Keepin' It 1600 for The Ringer before forming Crooked Media.
Products and positioning
A progressive, personality-driven political media and civic-engagement platform that combines podcast entertainment, news analysis, activism, and live events.
Political podcast · 2017
Pod Save America
Crooked Media's flagship progressive political podcast is hosted primarily by Jon Favreau, Jon Lovett, and Tommy Vietor, with Dan Pfeiffer co-hosting a weekly edition. It mixes news analysis, interviews, political humor, and practical appeals for activism and persuasion. The show has also produced special series on subjects such as presidential caucuses and vice-presidential selection.
Civic-engagement program and political action committee
Vote Save America
Vote Save America organizes Crooked Media's election-related activism. Its activities have included voter registration, volunteer recruitment, fundraising for candidates and causes, support for ballot initiatives, and partnerships with progressive organizations. It functions as a bridge between the company's media audience and campaigns or grassroots groups.
Social-justice and politics podcast
Pod Save the People
Hosted by organizer and activist DeRay Mckesson, Pod Save the People examines social justice, culture, politics, and the ways these areas intersect. It extends Crooked Media's political coverage beyond electoral strategy into movement issues and public-policy debates.
Foreign-policy podcast
Pod Save the World
Hosted by Tommy Vietor and former deputy national security adviser Ben Rhodes, Pod Save the World focuses on international relations, diplomacy, national security, and foreign-policy developments.
Live political-comedy podcast
Lovett or Leave It
Jon Lovett's weekly live show uses panels, interviews, games, and audience interaction to examine American politics and the news. It is one of Crooked Media's clearest examples of combining political commentary with stand-up and variety-show conventions.
Legal podcast · 2022
Strict Scrutiny
Strict Scrutiny follows the United States Supreme Court and analyzes constitutional law, judicial decisions, and the court's political and institutional significance. Its hosts include Leah Litman, Melissa Murray, and Kate Shaw.
Digital news and opinion platform · 2017
Crooked.com
Crooked.com was launched as the company's written-journalism and opinion operation. It brought together articles and commentary from a contributor network of journalists, activists, organizers, policy experts, campaign veterans, and comedians.
Marketing campaigns
- 2024Battleground grassroots support
United States
Vote Save America emphasized fundraising and volunteer direction for competitive down-ballot races, ballot initiatives, and voter-registration work in battleground states.
- 2020Vote Save America election program
United States
The program raised money for Democratic candidates, recruited volunteers, and partnered with Fair Fight on voter-suppression and turnout-related work.
Outcome. The program became Crooked Media's most extensive election-cycle civic-engagement operation.
- 2019F*ck Gerry(mandering) Fund
United States
Vote Save America and Data for Progress directed listener donations toward 14 closely contested Virginia races as part of an anti-gerrymandering effort.
- 20182018 midterm organizing
United States
Crooked Media worked with organizations including Swing Left and Indivisible to raise money and recruit volunteers for competitive races and progressive causes.
Outcome. The company reported raising $2.7 million and directing 22,000 volunteers to shifts in competitive races.
- 2017Early voter and political activism initiatives
United States
Crooked Media used its new podcast audience to encourage political participation, including activism around public meetings and electoral organizing.
Outcome. Established the audience-to-activism model later formalized through Vote Save America.
Brand decisions
2026
Agreement for Crooked on MS NOWStrategyBackground
Crooked Media sought additional television distribution for its political programming.
Action taken
The company announced an agreement with MS NOW for a weekly compilation program scheduled to begin February 28.
2022
Add Strict Scrutiny to the podcast networkM&ABackground
Crooked Media continued expanding into specialized political and public-affairs coverage.
Action taken
The company acquired the Supreme Court-focused podcast Strict Scrutiny.
Aftermath
The acquisition strengthened Crooked Media's legal and constitutional-policy programming.
2017
Expand from podcasting into a multi-format media companyStrategyBackground
After launching Pod Save America, Crooked Media sought to broaden its reach and reduce dependence on a single podcast through journalism, contributors, video, live events, and social distribution.
Action taken
The company launched Crooked.com and the Crooked Contributors network.
Aftermath
Crooked Media developed a wider portfolio spanning audio, written commentary, video, livestreaming, and live performance.
2017
Launch Pod Save AmericaProduct launchBackground
The founders needed a new home for their political podcasting after Keepin' It 1600 ended.
Action taken
Crooked Media launched Pod Save America with Favreau, Lovett, and Vietor as principal hosts and Pfeiffer as a recurring co-host.
Aftermath
The program became the company's flagship property and a major channel for political commentary and activism.
Recent events
- Unconfirmed
Crooked Media acquires FiveThirtyEight Politics podcast[2]
Reported:
Crooked Media inked a deal to acquire and revive the "FiveThirtyEight Politics" podcast hosted by Nate Silver, Clare Malone and Galen Druke, ahead of the 2026 midterm elections.
Crooked Media and Acast announce partnership[3]
Reported:
Crooked Media announced a partnership with podcast platform Acast.
Sources3 sources
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