To The Contrary with Charlie Sykes

John Avlon is chair of Citizens Union, former editor-in-chief of The Daily Beast and former chief speechwriter for Mayor Rudy Giuliani. In this episode, he joins Charlie to discuss Trump's UFC cage, Rudy Giuliani's fall from grace, and John Cornyn's scorpion fable post. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 2 June 2026

Miles Taylor is a former DHS official during Trump's first term and the founder of Defiance.org. He joins Charlie to discuss how the administration's changes to the green card process reveal that Trump's immigration stance was never about those who entered the country illegally — but about all immigrants. They also cover artists pulling out of the Freedom 250 concert and Trump's potential role in the 60 Minutes shake-up. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 30 May 2026

Former Congressman and children’s book author, Adam Kinzinger, joins Charlie to discuss the ridiculousness of the UFC Octagon project on the WH lawn, Megyn Kelly's shock at Trump's corruption, and Texas election. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 28 May 2026

Justin Wolfers is a professor of economics at the University of Michigan and author of the Platypus Economics Substack. In this episode, he joins Charlie to make the case against big tech moguls, discuss the price tag of Trump's Iran adventure, and talk about how crony capitalism is reshaping America. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 23 May 2026

Phillips O'Brien is a historian and Professor of Strategic Studies at the University of St Andrews, Scotland. In this episode, he joins Charlie to discuss Trump's corruption, his desperate Iran's gambit, and his weak position in global politics.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 21 May 2026

Nicholas Grossman, editor of Arc Digital and professor of international relations at the University of Illinois, joins Charlie to discuss the new levels of corruption Trump and his family have descended into. They also discuss Trump's visit to China, his Iran conundrum, and whether Cuba is next. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 19 May 2026

Tim O'Brien, Senior Executive Editor at Bloomberg Opinion, joins Charlie to discuss the President's recent China visit, the poor state of American democracy, and Trump's golden phone scam.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 16 May 2026

David Frum of The Atlantic joins Charlie to discuss Trump's China visit, his ignorance on oil and the global economy, and the Democrats' missteps heading into the midterms. The conversation also turns personal: Frum reflects on loss and his wife's new book about their family's journey through grief after losing their daughter. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 14 May 2026

On today’s episode, Charlie welcomes Gal Beckerman, a staff writer at The Atlantic and author of the book, “How to Be a Dissident.” The two walk through Gal’s book which outlines the simple but difficult steps anyone can take to avoid falling mistakenly in line with a political system that’s going off the rails. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 9 May 2026

On today's 'To the Contrary" podcast, Charlie is joined by NYT contributor Molly Jong-Fast to discuss the latest developments: the GOP's billion dollar ballroom; stunning new polling on the Trump-as-Jesus meme; this week's TACO on Iran, and why the abortion issue has exploded back onto the political scene. (They also talk about Molly's cameo in the new "Devil Wears Prada 2" movie.) Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 7 May 2026

On today’s episode, Charlie welcomes attorney, NYT Best-selling author and CEO of the Foundation for Individual Rights and Expression (FIRE), Greg Lukianoff. Charlie and Greg discuss the ways Trump is weaponizing the FCC to skirt free speech and how his efforts fit into the larger nuances of 1st Amendment rights in the US today. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 5 May 2026

The New Yorker's Susan Glasser joins Charlie to discuss Trump's war on free speech and press freedom, US relations with Ukraine, Russia, and China, and Trump missing the point of King Charles' speech.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 2 May 2026

Peter Wehner, a contributing writer at The Atlantic and a senior fellow at the Trinity Forum, joins Charlie to dissect King Charles' historic address to Congress and Trump's feud with the pope. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 30 April 2026

The Atlantic's Anne Applebaum joins Charlie to discuss the fallout from the White House Correspondents' dinner, Victor Orbán's defeat, and why Trump wants to talk about his ballroom and his triumph arch rather than Iran. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 28 April 2026

Economist Justin Wolfers joins Charlie to rage about Trump's Fed chair nominee. They also discuss the importance of Fed independence, prediction markets, and private credit markets.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 25 April 2026

Former Congressman and now children’s book author, Adam Kinzinger, joins Charlie to discuss gerrymandering, the state of Congress, and what should the next President do to make sure there isn't another Trump-style presidency in the future. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 23 April 2026

Tom Nichols, Atlantic staff writer and author of The Death of Expertise, joins Charlie to discuss the anti-vax movement, the continuing crisis with Iran, and why Trump and his cabinet are "melting down."  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 21 April 2026

On today’s episode, Charlie sits down with former Under Secretary of State for Public Diplomacy and Public Affairs, former Managing Editor of TIME, and author, Richard Stengel. The two discuss the Trump administration’s ever-worsening performative piousness, how the Iran “deal” is just a recovery of Trump’s own doing and how the US’s global reputation is changing for the worse. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 18 April 2026

Legal analyst and Talking Feds host, Harry Litman, joins Charlie to break down the Justice Department's efforts to vacate January 6 convictions for far-right extremists as well as its surprising position on the Presidential Records Act. Also in the episode: JD Vance's latest bizarre comments, the administration fight with the Pope, and the Epstein scandal. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 16 April 2026

Ian Bassin is Co-founder and Executive director of Protect Democracy and a 2023 recipient of the MacArthur Genius Grant. He joins Charlie to discuss what are the lessons from Viktor Orbán’s defeat in Hungary's elections, global authoritarian trends, and the importance of coalition-building in defending democracy. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 14 April 2026

Sarah McLaughlin is a Senior Scholar of Global Expression at FIRE (Foundation for Individual Rights and Expression), and author of Authoritarians in the Academy. She joins Charlie to explore the global threats to free speech, especially with recent developments in Turkey, the UK, and Australia, and their implications for free expression in the US. Also, Charlie summarizes one of the strangest weeks we've witnessed. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 11 April 2026

Scott MacFarlane recently left CBS News and joined Substack as well as MeidasTouch. In this episode, he tells Charlie about his transition from traditional to independent media and what drove his decision. They also discuss whether the Iran deal is a strategic failure, the new acting US Attorney General, and the ongoing court cases involving Trump's ballroom and Kennedy Center.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 9 April 2026

Sarah Fitzpatrick is a staff writer at The Atlantic, where she covers national security and the Department of Justice. She joins Charlie to talk about why the Jeffrey Epstein scandal is here to stay, digest Trump's "Open the f***in' strait" post, and discuss the effects of gutting expertise within the Pentagon. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 7 April 2026

New York Times Opinion writer David French joins Charlie to discuss the beginning of "the great Trump purge," which started with the firing of Pam Bondi but is now rippling through the Pentagon and the military. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 4 April 2026

In this solo episode, Charlie answers listeners' questions on Trump's order on mail-in voting, the reports on Pete Hegseth's war stock, the future of NATO, and more.  We decided to release this episode earlier than usual because of Trump's address to the nation. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 1 April 2026

Retired Lieutenant General Mark Hertling served as commanding general of the U.S. Army in Europe during the Obama administration. In this episode, he tells Charlie that it's very difficult for the military to draft a campaign plan for Iran when the end state goal is unclear. He also discusses his new book: “If I Don’t Return: A Father’s Wartime Journal.” Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 31 March 2026

Jonathan Rauch is a Brookings Institution Senior Fellow and a contributing writer at The Atlantic. In this episode, he makes the case that the Trump administration is, as a whole, psychotic, erratic, and unpredictable. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 28 March 2026

Phillips O'Brien is a historian and Professor of Strategic Studies at the University of St Andrews, Scotland. In this episode, he joins Charlie to discuss the different ways Trump could operate in Iran right now and the biggest obstacle to it all — the fact that Trump is only motivated by personal gain and that many people have given up. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 26 March 2026

Former Congressman and Substack superstar, Adam Kinzinger, joins Charlie to discuss the economic implications of the Iran war, Trump's response to the death of Robert Mueller, and ICE deployment at airports. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 24 March 2026

On today’s episode, Charlie welcomes author, journalist, political commentator and former Congressional candidate, John Avlon. The two discuss the stark contrast between the decorum of past presidents and Trump, along with the broken incentive structures at the heart of the American political system, and how all this has brought political extremists to the forefront of American politics.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 21 March 2026

Ed Luce from the Financial Times joins Charlie to discuss his recent phone call with the president, Trump's obsession with the British Prime Minister, and whether the US is opening another front in Cuba.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 19 March 2026

Trying to make sense of Trump's incoherent approach to war and peace with the New Yorker's Susan Glasser, one of the nation's foremost Trumpologists. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 17 March 2026

Economist Justin Wolfers joins Charlie to explain the impact of rising oil prices but also to remind us that there are much deeper questions that need to be asked. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 14 March 2026

Molly Jong-Fast, host of the Fast Politics podcast and a contributing NYT Opinion writer, joins Charlie to discuss the miscalculations of the Iran war, the newly-streamable docu-bribe Melania, and Trump's troubles in Texas. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 12 March 2026

Author and Senior Editor of Arc Digital, Nicholas Grossman, joins Charlie to discuss the White House's "hype videos" concerning the War in Iran, the economic consequences of the conflict and how the SAVE act may affect the upcoming midterms.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 10 March 2026

In this solo episode, Charlie is recapping the long awaited firing of Homeland Security Secretary. He also answers the questions you sent us on a wide range of current issues. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 7 March 2026

Josh Barro, co-host of Central Air and author of the Very Serious Substack, joins Charlie to discuss a wide range of political news: the Iran war, the Texas primaries, Anthropic, and Trump’s tariff obsession. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 5 March 2026

The Atlantic's Anne Applebaum joins Charlie to try to figure out why we're at war with Iran. Is it about Trump's friends and business partners in Gulf states and Israel? Was Iran a long-term obsession of Trump? Or is it just the ultimate wag-the-dog move for him at this moment? Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 3 March 2026

The Atlantic writer, Tom Nichols, joins Charlie to discuss the rise of extremist ideologies within the Republican Party, the Epstein files, and whether we're going to war. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 28 February 2026

Voters have soured on Trump, but polls suggest they still have their doubts about Democrats. Long time Democratic strategist and president of The Searchlight Institute, Adam Jentleson, joins Charlie to discuss past mistakes and the challenges now facing the Democratic Party. Also, Trump's State of the Union, and Senator John Fetterman. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 26 February 2026

Jamil Smith, a columnist at The Guardian, and lecturer at the UC Berkeley Graduate School of Journalism, joins Charlie to discuss the State of the Union, Trump's blatant racism, and the latest environmental policy shift you probably didn't hear about.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 24 February 2026

Former Congressman and now children’s book author, Adam Kinzinger, joins Charlie to discuss Lindsey Graham’s behavior at the Munich Security Conference, the Trump administration inching closer to a conflict with Iran and how all this foreign policy affects the political landscape at home.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 21 February 2026

Tara Palmeri, host of The Tara Palmeri Show and the author of the newsletter “The Red Letter”, joins Charlie to discuss the latest on the Epstein scandal that shadowed almost every aspect of the second Trump presidency. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 19 February 2026

Susan Glasser of The New Yorker joins Charlie to talk about Trump's attempt to arrest and indict six sitting members of Congress, Marco Rubio in Munich, and DHS asking tech companies to expose the personal details of "anti-ICE" social media accounts.  Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 17 February 2026

David Frum of The Atlantic joins Charlie to break down the shifting public opinion on Trump, Pam Bondi’s congressional testimony, and how AI is changing us. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 14 February 2026

Reporter Ashley Parker spent eight years at The Washington Post before joining The Atlantic. She’s been watching the recent moves by owner Jeff Bezos and the paper’s leadership, and explains to Charlie why she believes they may be leading the paper toward its demise. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 12 February 2026

Peter Wehner, a contributing writer at The Atlantic and a senior fellow at the Trinity Forum, joins Charlie to explain why some evangelicals see Trump as a defender of their values. Also: Bad Bunny. Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 10 February 2026

Following Jeff Bezos's gutting of the Washington Post, economist Justin Wolfers joins Charlie to try to unpack billionaires' actions. Also, how's the American economy really doing these days? Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 7 February 2026

Garrett M. Graff, a contributing editor at WIRED and former editor of POLITICO Magazine, joins Charlie to try to answer that question. Also (not unrelated): where did the Proud Boys go? Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 5 February 2026

Legal analyst and Talking Feds host, Harry Litman, joins Charlie to talk about Trump shutting down Kennedy Center, the release of 5-year-old Liam Ramos, and the dire state of the U.S. Attorney office for the District of Minnesota. To read Litman's piece on the Kennedy Center: Trump Meets Lincoln, Doesn’t Recognize Him Hosted on Acast. See acast.com/privacy for more information.

Transcribed - Published: 3 February 2026