Crooked Media

Crooked Media is an American political media company. It was founded in 2017 by Jon Favreau, Jon Lovett, and Tommy Vietor, all former top Barack Obama staffers and co-hosts, with Dan Pfeiffer, of the Keepin' it 1600 podcast.

The company's offerings encompass a network of podcasts; a news and opinion website; live shows and tours; and a social media and live streaming presence. It aims to foster open conversation between liberals and support grassroots activism and political participation.

The company's flagship podcast, Pod Save America, airs twice weekly and averages more than 1.5 million listeners an episode. In Fall 2018, four Pod Save America one-hour specials aired on HBO.[2] By November of its first year, the podcast had been downloaded over 120 million times, and 175 million times by February 2018.[3][4]

The company is headquartered in Los Angeles, California.[5]

Crooked Media
Crooked media logo
Crooked Media logotype
Type of site
News and political commentary
Available inEnglish
Created byJon Favreau (Co-founder), Jon Lovett (Co-founder), Tommy Vietor (Co-founder)
EditorBrian Beutler (Editor-in-Chief)
Key peopleSarah Wick (COO), Tanya Somanader (CCO)[1]
LaunchedJanuary 2017


Favreau, Lovett, Vietor, and Pfeiffer hosted The Ringer's Keepin' it 1600 political podcast from March 2016 until December 2016.[6]

After Donald Trump's victory in the 2016 Presidential Election, Favreau, Lovett, and Vietor decided they wanted to do podcasting and activism on a full-time basis. In an interview with Recode's Kara Swisher, Vietor explained that “If Hillary had won, we probably would’ve kept doing this as a hobby... But when she lost, I think we all had this existential crisis, where it didn’t feel right to wake up every day and obsess about politics and what’s happening in the country, and then go to work doing something else.”[5]

The quartet ended Keepin' it 1600 in December 2016. Favreau, Lovett, and Vietor formed their own company, Crooked Media, and, the following month, launched a new podcast called Pod Save America.[7] Pfeiffer opted not to join the company, and instead co-host the Thursday edition of the show.[8]

Crooked Media is named after a favorite term used by President Trump. When asked whether he thought Crooked Media was a 'media company', Favreau said, “I don’t know if it’s a political movement or a media company.”[9]

The company announced a major expansion in October 2017 with the launch of, a text journalism site helmed by Editor-In-Chief Brian Beutler, a former New Republic senior editor. The expansion introduced the 'Crooked Contributors' network—a diverse group of journalists, activists, organizers, policy experts, campaign veterans, and comedians who will be featured in podcasts, videos, and articles produced by the company.[10]

The company is not raising money from outside investors; instead using advertising revenue to fund the business.[5]


Alyssa Mastromonaco (Hysteria), Ana Marie Cox (With Friends Like These), Blair Imani (Hysteria), Brittany Packnett (Pod Save the People), Clint Smith III (Pod Save the People), Dan Pfeiffer (Pod Save America), DeRay Mckesson (Pod Save the People), Erin Ryan (Hysteria), Grace Parra (Hysteria), Ira Madison III (Keep It), Jason Kander (Majority 54), Jon Favreau (Pod Save America/The Wilderness), Jon Lovett (Pod Save America/Lovett or Leave It), Kara Brown (Keep It), Kiran Deol (Hysteria), Louis Virtel (Keep It), Megan Gailey (Hysteria), Samuel Sinyangwe (Pod Save the People), Tommy Vietor (Pod Save America/Pod Save the World), and Ziwe Fumudoh (Hysteria).


Crooked Media produces and distributes a range of podcasts.

Pod Save America

An American progressive political podcast "for people not yet ready to give up or go insane." Pod Save America airs twice weekly, with the Monday edition hosted by Favreau, Vietor, and Lovett, and the Thursday edition by Favreau and Pfeiffer. Pod Save America is noted for its focus on activism.[9][11][12]

Pod Save the People

Hosted by organizer and activist DeRay Mckesson,[13][14] Pod Save the People talks about culture, social justice, and politics by exploring the history, the language, and the people who are shaping the struggle for progress — and talking about the steps that each individual can take to make a difference.[15]

Pod Save the World

Hosted by Vietor, a former national security council spokesman in the Obama administration. Pod Save the World attempts to discuss foreign policy and international relations in a relatable and down to earth way. The show brings listeners behind the scenes into White House Situation Room meetings and secret negotiations through a series of conversations with people who were there. The podcast also focuses on what listeners can do to make an impact on global events.[16]

Lovett or Leave It

Hosted by Lovett, former speech and joke writer for President Obama. Lovett or Leave it is a recording of a weekly live show and features the eponymous host dissecting the news with a panel of guests. The show features a variety of games, as well as one-on-one interviews that center around the week's news and American politics.[17]

With Friends Like These

Hosted by political journalist Ana Marie Cox. With Friends Like These delves into social, cultural, and, to a lesser extent, political issues through in-depth interviews. Namely, how to bridge divides in our society and approach through conversations with peers. Cox focuses on attempting to have difficult conversations in a public space.[12]

Crooked Conversations

Hosted by members of the company's 'Crooked Contributor' network. Crooked Conversations features deeper dives into topics less tied to the latest headlines.[18]

Majority 54 With Jason Kander

Hosted by former Missouri Secretary of State Jason Kander. Majority 54 explores how Democrats can talk to Trump voters about divisive issues.[19]

Keep It

Hosted by culture critic and columnist Ira Madison III. Comedians, journalists, actors, musicians, activists, politicians, and others join Madison for a conversation at the intersection of pop culture and politics.[20]


Hosted by Erin Ryan and a rotating set of women including Alyssa Mastromonaco, Blair Imani, Grace Parra, Kiran Deol, Megan Gailey, and Ziwe Fumudoh.[21]

The Wilderness

Hosted by Jon Favreau, it is a docuseries about the Democratic Party.[22]


Crooked Media embarked on its first tour, Pod Tours America, in fall of 2017. The tour featured live versions of Pod Save America and Lovett or Leave it, and appearances from McKesson, Cox, various members of the 'Crooked Contributors' network, and special guests.[23] Live shows are recorded and released as podcasts.

A second tour, Pod Tours the World, was announced for 2018, with live shows in Stockholm, Oslo, Amsterdam, and London.[24]


Unlike more traditional media organisations, Crooked Media engages directly in political activism, including advocating for policies and candidates, supporting get out the vote efforts, raising money, and driving phone calls and demonstrations.[3]

During its first year, it partnered with progressive advocacy group MoveOn to send nearly 2,000 Pod Save America listeners to Republican town-hall meetings, with Swing Left to raise over a million dollars for challengers to House Republicans in the 2018 midterm elections, and with Indivisible to drive phone calls in favor of the Affordable Care Act. In the 2017 Virginia elections, the company lent its support to Democratic candidates across the ballot, including Lt. Gov. Ralph Northam in the state's governor race.[3]

Towards the end of 2017, the company launched "The Crooked 7" in partnership with Swing Left, a new initiative to raise money to flip seven California House districts held by Republicans in the 2018 midterm elections.[25] All seven California districts targeted flipped to Democratic control after the 2018 midterms.


The company's podcasts regularly sit near the top of the iTunes list of most popular podcasts.[9] The New York Times has called Crooked Media 'the left's answer to conservative talk radio'.[3] Pod Save America was called "the nation’s most popular political podcast" by Newsweek.[12] Reviewing the first episodes of the company's flagship podcast, The Guardian noted: "Pod Save America's commentators are sparky and funny—and they have a habit of talking a whole lot of sense."[26]


  1. ^ "Team - Crooked Media". Retrieved November 8, 2017.
  2. ^ "- HBO Announces Pod Save America Podcast Specials". HBO.
  3. ^ a b c d Zengerle, Jason (2017-11-22). "The Voices in Blue America's Head". The New York Times. ISSN 0362-4331. Retrieved 2017-12-22.
  4. ^ "'Pod Save America' Getting HBO Treatment With Election Specials". The Hollywood Reporter. Retrieved 2018-02-09.
  5. ^ a b c "Crooked Media's founders aren't paying themselves anything". Recode. Retrieved 2018-01-02.
  6. ^ "'Keepin' It 1600' Hosts Launch New Podcast 'Pod Save America' Via DGital Media". All Access. Retrieved 2017-12-22.
  7. ^ "'Keeping It 1600' Podcast's Obama Alums Launch New Show and 'Crooked Media' Company". The Hollywood Reporter. Retrieved 2017-12-22.
  8. ^ Hartmann, Margaret. "Keepin' It 1600 Crew Launches New Podcast, 'Crooked Media' Company". Daily Intelligencer. Retrieved 2018-01-02.
  9. ^ a b c Rutenberg, Jim (2017-03-20). "Opposition and a Shave: Former Obama Aides Counter Trump". The New York Times. ISSN 0362-4331. Retrieved 2017-06-13.
  10. ^ "Crooked Media expands from podcasts to text, with a new site and plans for investigative reporting". Nieman Lab. Retrieved 2017-12-22.
  11. ^ Gillies, Craille Maguire (January 18, 2017). "Pod save America: 12 podcasts to get you through the Trump presidency". The Guardian.
  12. ^ a b c "Crooked Media Fights Trump with "Pod Save America"". Newsweek. 2017-03-26. Retrieved 2017-06-11.
  13. ^ "Crooked Media Launches Pod Save the People | Podcaster News". Retrieved 2017-05-18.
  14. ^ S, Darren; Reporter, s BuzzFeed News. "DeRay Mckesson Is Going To Host A Crooked Media Podcast". BuzzFeed. Retrieved 2017-05-18.
  15. ^ "Pod Save The People Archives | Crooked Media". Crooked Media. Retrieved 2018-01-02.
  16. ^ "Pod Save the World by Crooked Media on Apple Podcasts". Apple Podcasts. Retrieved 2017-06-11.
  17. ^ Verdier, Hannah (2017-03-30). "Lovett or Leave It: the Pod Save America crew take the political panel show and make it funny". The Guardian. ISSN 0261-3077. Retrieved 2017-06-11.
  18. ^ "Crooked Media Announces New Site, Podcast & Store". Publishing Executive. Retrieved 2018-01-02.
  19. ^ "Majority 54 with Jason Kander Archives - Crooked Media". Crooked Media.
  20. ^ "Keep It Archives - Crooked Media". Crooked Media.
  21. ^ "Hysteria". Crooked Media. 2018. Retrieved July 18, 2018.
  22. ^ "The Wilderness". Crooked Media. 2018. Retrieved July 18, 2018.
  23. ^ "Pod Save America announces nationwide tour". Consequence of Sound. 2017-08-16. Retrieved 2018-01-02.
  24. ^ "Pod Save America and Lovett or Leave It are coming to London in January, here's how to get tickets". The List. 2017-12-01. Retrieved 2018-01-02.
  25. ^ "'Pod Save America' about to take its next step". San Francisco Chronicle. Retrieved 2018-01-02.
  26. ^ Verdier, Hannah (2017-01-26). "Pod Save America – the podcast that won Obama's last interview". The Guardian. ISSN 0261-3077. Retrieved 2018-01-02.

External links

Alyssa Mastromonaco

Alyssa Mende Mastromonaco (born February 22, 1976) is a Senior Advisor and spokesperson for NARAL as of July 2018. She was previously the President of Global Communications Strategy & Talent at A&E Networks and the Chief Operating Officer of Vice Media. She is also a contributing editor at Marie Claire magazine. She previously served as White House Deputy Chief of Staff for Operations in the administration of President Barack Obama from 2011 to 2014. She was the youngest woman to hold that position. In 2005 Mastromonaco was hired as then Senator Obama's Director of Scheduling.

Ben Rhodes (White House staffer)

Benjamin J. Rhodes (born November 14, 1977) is a writer and political commentator. With Jake Sullivan, he is the co-chair of National Security Action, which promotes progressive foreign policy as an alternative to the Trump administration's approach. He contributes to NBC News and MSNBC regularly as a political commentator. He is also a Crooked Media contributor, and co-host of the foreign policy podcast Pod Save the World.In 2018, Random House published The World as It Is, a New York Times bestseller and revelatory behind-the-scenes account of Barack Obama's presidency. George Packer in the New Yorker called the book "the closest view of Obama we’re likely to get until he publishes his own memoir." In the New York Times, Joe Klein wrote, "His achievement is rare for a political memoir: He has written a humane and honorable book." Rhodes has written opinion articles for newspapers and magazines including the New York Times and The Atlantic.During the Obama administration, Rhodes led the secret negotiations with Cuba that resulted in the December 17, 2014 announcement by President Obama and Raúl Castro that the two countries would normalize relations. Rhodes traveled to Canada and the Vatican for talks with Cuba about a prisoner exchange that led to the release of Alan Gross and a U.S. intelligence asset, along with the decision to re-establish diplomatic relations between Cuba and the U.S. In his book, Rhodes revealed that his negotiating counterpart was Alejandro Castro, the son of Raúl. Rhodes was the U.S. government representative at the funeral for Fidel Castro in 2016. Rhodes has been critical of the Trump administration's approach to Cuba.Rhodes was featured in the HBO documentary The Final Year, along with John Kerry, Samantha Power and Susan Rice. The documentary portrays the events of Obama’s final year in office, with a focus on his foreign policy team.

Daniel Pfeiffer

Howard Daniel Pfeiffer (born December 24, 1975) is an American activist, podcaster, and former Senior Advisor to U.S. President Barack Obama for Strategy and Communications.Pfeiffer was a long-time aide to Obama, serving in various press and communications roles throughout his 2008 campaign for the Presidency, on his presidential transition team, and in the Obama White House. He co-hosts the Pod Save America podcast with Jon Favreau, Jon Lovett, and Tommy Vietor. In 2015, Pfeiffer joined CNN as a political contributor.

DeRay Mckesson

DeRay Mckesson (born July 9, 1985) is an American civil rights activist, podcaster, and former school administrator. Mckesson is a supporter of the Black Lives Matter movement, often on social media outlets such as Twitter and Instagram, and has been active in the protests in Ferguson, Missouri, and Baltimore, Maryland. Mckesson has also written for HuffPost and The Guardian. Along with Johnetta Elzie, Brittany Packnett, and Samuel Sinyangwe, Mckesson launched Campaign Zero, a policy platform to end police violence. He is currently part of the Crooked Media and hosts a podcast of the same name Pod Save the People.On February 3, 2016, Mckesson announced his candidacy in the 2016 Baltimore mayoral election. He finished with 3,445 votes (2.6%) placing sixth in the Democratic Party primary on April 26.Mckesson is the author of On the Other Side of Freedom: The Case for Hope, a memoir about his life and time as a Black Lives Matter organizer.

Ira Madison III

Ira Madison III (born July 28, 1986) is an American TV writer and podcaster. A former critic at The Daily Beast, GQ Magazine, and other publications, Madison is currently the host of the Crooked Media podcast Keep It! and a writer on Daybreak, an upcoming Netflix original show.

John F. Solomon

John F. Solomon is an American media executive and columnist. He is currently vice president of digital video and an opinion contributor for The Hill. He is known primarily for his tenure as an executive and editor-in-chief at The Washington Times. He has been accused of biased reporting in favor of conservatives, and of repeatedly manufacturing faux scandals.

Jon Favreau (speechwriter)

Jonathan Edward Favreau (born June 2, 1981) is an American political commentator and the former Director of Speechwriting for President Barack Obama.Favreau attended the College of the Holy Cross, graduating as valedictorian. In college, he accumulated scholastic honors, and took part in and directed community and civic programs. After graduation, he went to work for the John Kerry presidential campaign in 2004, working to collect talk radio news for the campaign and was promoted to the role of Deputy Speechwriter. While working for the Kerry campaign, he first met Barack Obama.

In 2005, Obama's communications director Robert Gibbs recommended Favreau to Obama as a speechwriter. Favreau was hired as Obama's speechwriter shortly after Obama's election to the United States Senate. Obama and Favreau grew close, and Obama referred to him as his "mind reader." He went on the campaign trail with Obama during his successful presidential election campaign. In 2009, he was named to the White House staff as Director of Speechwriting.In January 2017, he co-founded liberal media company Crooked Media with fellow former Obama staffers Tommy Vietor and Jon Lovett, and began co-hosting the political podcast Pod Save America with Vietor, Lovett and Dan Pfeiffer.

Jon Lovett

Jonathan Ira Lovett (born August 17, 1982) is an American screenwriter, speechwriter, television producer, and podcaster. After working as a speech and joke writer for President Barack Obama and Hillary Clinton, Lovett co-created the NBC White House sitcom 1600 Penn, and served as a writer and producer on the third season of HBO's The Newsroom. He is a founder of Crooked Media and currently hosts the podcasts Pod Save America and Lovett or Leave It.

Keepin' it 1600

Keepin' it 1600 was an American political podcast produced by The Ringer and hosted by former Barack Obama staffers Jon Favreau, Tommy Vietor, Jon Lovett, and Dan Pfeiffer.

Lovett or Leave It

Lovett or Leave It is a weekly podcast hosted by speechwriter and screenwriter Jon Lovett. It is produced by Lee Eisenberg and distributed by Crooked Media. The theme song is by the band Sure Sure. Lovett has described the show as a way to talk about politics in plain language and has called the discussion "very loose."

North Reading, Massachusetts

North Reading (pronounced, as is with Reading as North REDD-ing) is a town in Middlesex County, Massachusetts, United States. The population was 14,892 at the 2010 census.

Pod Save America

Pod Save America is an American liberal political podcast produced and distributed by Crooked Media. The podcast debuted in January 2017 and airs twice weekly, with the Tuesday edition hosted by former Barack Obama staffers Jon Favreau, Tommy Vietor, and Jon Lovett, and the Thursday edition by Favreau and Dan Pfeiffer.It is the flagship podcast of Crooked Media, a media company founded by Favreau, Vietor, and Lovett. The show averages more than 1.5 million listeners an episode, and had been downloaded more than 120 million times by November 2017.Four Pod Save America one-hour HBO TV specials aired in fall 2018 to cover the U.S. midterm elections.

Pod Save the People

Pod Save the People is an American political podcast produced and distributed by Crooked Media and hosted by organizer and activist DeRay Mckesson with weekly appearances by Samuel Sinyangwe, Clint Smith, and Brittany Packnett.Mckesson talks about culture, social justice, and politics by exploring the history, language, and people who are shaping the struggle for progress — and talking about the steps that each of us can take to make a difference. When asked about the podcast's purpose, Mckessen said: "It is about creating space for conversation about the most important issues of the week. It is also about making sure people have the information they need to be the most thoughtful activists and organizers".Notable guests have included Edward Snowden, Senator Cory Booker, and singers John Legend and Katy Perry.

Pod Save the World

Pod Save the World is a weekly foreign policy podcast produced and distributed by Crooked Media, and hosted by former White House National Security Council spokesman Tommy Vietor.Vietor is joined each week by a guest to discuss foreign policy and international relations. Notable guests have included former National Security Advisor Susan Rice, former White House Chief of Staff Denis McDonough, and U.S. Senator and Vice Presidential Candidate Tim Kaine.New episodes initially debuted on Wednesday; towards the end of 2017, this changed to Friday.

While other Crooked Media podcasts tend to focus heavily on domestic issues within the United States, Pod Save the World discusses global issues and international relations, with a focus on civic involvement.Vietor describes the podcast as a "no bullshit" approach to global news that tries to make complicated issues seem relatable and simple to understand.

Running with Beto

Running with Beto is a 2019 documentary film following Beto O'Rourke's campaign in the 2018 United States Senate election in Texas. The film is set to debut at the 2019 South by Southwest (SXSW) Film Festival and will premiere on HBO sometime in spring of 2019.

Swing Left

Swing Left is a progressive political group that was created following the election of Donald Trump in 2016. The group's founders come from multiple different sectors – tech, marketing, media, and the arts – to create an easier way for Democrats to volunteer in their nearest swing district. Its initial mission was to win a Democratic majority in the House of Representatives in 2018 by building a grassroots network of volunteers and donors in targeted swing districts across the United States.Since its launch on January 19, 2017, Swing Left has recruited 300,000 volunteers and raised over $2 million in grassroots donations. It has partnered with Daily Kos and ActBlue with the goal of raising $100,000 for each of its targeted swing districts.In May 2017, Onward Together cited Swing Left as one of the groups whose work it would support.In December 2017, Crooked Media announced a joint fundraising initiative with Swing Left called the Crooked Seven, to raise money for the eventual Democratic challengers of seven Republican-controlled House districts that Hillary Clinton won in 2016.

The President Show

The President Show is an American comedy television series that premiered on April 27, 2017 on Comedy Central. The show was created by Anthony Atamanuik who also stars as Donald Trump, the President of the United States, alongside Peter Grosz as Mike Pence, the Vice President.

The Ringer (website)

The Ringer is a sports and pop culture website and podcast network, founded by sportswriter Bill Simmons in 2016.

Tommy Vietor

Thomas Frederick "Tommy" Vietor IV (born August 31, 1980) is an American political commentator and podcaster. He is a former spokesperson for President Obama and United States National Security Council from 2011 to 2013. He is a founder of Crooked Media and currently hosts the podcasts Pod Save America and Pod Save the World.

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