To The Contrary with Charlie Sykes

After the midterm wave, Bloomberg Opinion columnist Timothy O’Brien, author of TrumpNation, joins Charlie to discuss how a cornered Trump may respond, why corporate America and Silicon Valley are bracing for subpoenas, why the big Republican spending didn’t work, how moderate Democrats powered the win, and what it means for the 2028 race.

Note: This episode was recorded minutes before President Trump named Stephen Miller as his new Chief of Staff.

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The day after America sent a devastating rebuke of Donald J. Trump, I break down the shocking wins in deep-red states, the rise of new Democrat leaders like James Talarico, Jon Ossoff, and Annie Andrews, and the question facing Republicans: will they keep falling in line behind Trump, or finally have the backbone to stand up to him?

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On Election Day, Charlie Sykes and political historian Brian Rosenwald of the University of Pennsylvania give you an hour-by-hour guide to election night. They cover when the polls close, the Senate and governor’s races that could signal a wave, how to read the results as they come in at different points of the night, and Rosenwald’s final predictions for the House, Senate and Governorships.

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Three days before the midterms, Harry Litman of the Talking Feds podcast joins Charlie to discuss how far the Trump administration could go to interfere with the election, the court battles over certification, record early voting, the pundit fixation on Alaska, and the races to watch from Texas to Kansas to Georgia.

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Retired federal judge Jeremy Fogel of the Article III Coalition joins Charlie to discuss threats against judges, DOJ’s challenge in Alaska, the “creeping” defiance of court orders, Supreme Court term limits and court packing, and what happens to the republic when one of the three branches is under attack.

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As Trump and the Republicans make their closing arguments, New York Times columnist David French joins Charlie to discuss the backlash to the Ramaswamy ad, whether Texas is really in play, the DOJ’s Alaska lawsuit, Pete Hegseth’s reported Senate ambitions, and how corruption could shape the vote.

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Ten days before the midterms, journalist Tara Palmeri (The Red Letter, The Tara Palmeri Show) joins me to unpack the backlash over the Ramaswamy ad targeting Amy Acton. Plus, GOP insiders are bracing for a wipeout, their search for fall guys and the art of the grift continues with Jared Kushner’s Middle East slush fund.

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Less than two weeks before the midterms, economist Justin Wolfers (University of Michigan, Platypus Economics) joins Charlie to explain why consumer sentiment is at a record low, how tariffs and immigration crackdowns eroded trust in Trump’s economy, and why October giveaways may not work.

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Two weeks before the midterms, the host of the Fast Politics podcast, Molly Jong-Fast joins Charlie to unpack Trump’s Putin pivot, Elon Musk’s election spending, the White House infighting, and the post-election chaos that lies ahead. Plus: what Democrats do with power, and the rising stars to watch for 2028.

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Charlie Sykes sits down with political scientist and writer from The Atlantic, Tom Nichols, as they discuss midterms and possible battleground states to look out for, Trump's latest actions in Ukraine, and the motives of the current administration before election day.

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Three weeks before the 2026 midterms, Charlie Sykes talks with former Congressman Adam Kinzinger about where the race really stands, how the political spending of trillionaires like Musk is dangerous, and Trump’s latest moves on Ukraine. They also ask why so few Republicans will speak out against clear violations of the Constitution.

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Three weeks before the 2026 midterms, Charlie and Daniel Drezner dig into Trump’s Russia dealings, Marco Rubio’s rebrand, and what’s really driving the race for Congress. Is the blue wave real, or are Democrats headed for another heartbreak?

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On today’s episode, Charlie sits down with journalist, David Frum to discuss the US’s status in the world economy, how the Trump administration compares to other historically corrupt administrations and the new rules of American politics approaching the midterms.

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On today’s episode, Charlie flies solo to dive into Thom Thillis’ recent debate gone wrong with Stephanie Ruhle, Trump’s publicly funded PSA video, the importance of staying vigilant against misinformation as citizens and more.

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On today’s episode, Charlie sits down with journalist and author, David Corn about the long-standing influence of Russia on American politics, Putin’s long-game with Trump and their dangerous decades-long relationship that’s shaped recent history and threatens democracy.

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On today's episode, Charlie Sykes sits down with author and journalist, Jonathan Rauch to discuss a potpourri of topics, from Pete Hegseth’s recent War Department speech, AI advancement and risks and the moral dilemmas surrounding the death penalty.

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On today’s episode, Charlie is joined by author and historian, Timothy Snyder. Charlie and Timothy discuss the relevance of Timothy’s book, “On Tyranny,” what citizens are called to do in the face of an all-powerful oligarchy and the unmasking of Trump’s true character.

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Why do powerful people fold when it matters most? Charlie Sykes sits down with journalist and author Jacob Weisberg to discuss his explosive new book, Profiles in Cowardice — a deep dive into eight influential figures who chose silence, self-interest, and appeasement over standing up to Trump.

Weisberg unpacks what separates courage from cowardice, why institutions built to check power so often buckle under pressure, and how fear and neediness can undo even the wealthiest and most powerful people in America. It's a candid conversation about principle, complicity, and what it really costs to say no.

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Topics discussed: cowardice in leadership • institutional weakness • political courage • Trump-era enablers • standing on principle

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Susan Glasser, author of "Letter from Trump's Washington" in The New Yorker joins Charlie to discuss Trump breaking the law again, the GOP's midterm panic, the President's shameful groveling to a communist dictator, and much more.

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Paulina Borsook predicted Silicon Valley's authoritarian turn back in the 1990s — we revisit her book "Cyberselfish" and how eerily right she was. Then I break down Trump's controversial statements at the United Nations, his attack on the First Ammendment, and what it all means for American democracy.

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Is there a secret formula for Democratic victories in deep red states? Former Alabama Senator and current candidate for Governor, Doug Jones joins me to discuss his fight against the Republican machine, the attack on voting rights, and the Trump effect on races throughout the country. 

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Charlie flies solo this episode to break down the biggest headlines in current events, dig into where the midterms actually stand right now, and get personal about the toll — both individual and societal — of a decade shaped by Trump.

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Founder of Protect Democracy and winner of the MacArthur genius grant, Ian Bassin joins Charlie for a wide-ranging discussion about important reads, how technology shapes society, post-Trump America, and the weird new FBI rule about bestiality. 

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World renowned tech journalist Kara Swisher joins Charlie to explore the complex issues surrounding AI development, the role of regulation, and the global implications.

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Author of Kill Switch and Supermajority, Adam Jentleson joins Charlie for a deep dive into what it will take for Democrats to win and keep power, the weird machinations of John Fetterman, and who would make the strongest candidate to beat back whoever is Trump's successor.

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John Avlon — journalist, author, and political commentator — joins Charlie to reflect on the lessons of 9/11 as its 25th anniversary approaches, break down the emerging 2028 Democratic field, and unpack Trump's strange fixation on movie-villain imagery.

A conversation about memory, politics, and power you won't want to miss.

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Professor of Strategic Studies and host of The Phillips's Newsletter Podcast, Phillips O'Brien joins Charlie to talk about Trump's strange love for Russia, the decline of U.S. influence in Europe, and the Donald's infatuation with building monuments to himself.

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Former University of Montana President and Green Beret Seth Bodnar is running for Senate as an Independent. He joins Charlie to talk about Hegseth's military purge, Canadian tariffs, and why neither party is what America needs.

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Economist Justin Wolfers joins Charlie to break down Trump's trade war with Canada, the controversial oil deal with Venezuela, and concerns over politicizing the U.S. Census Bureau.

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Congressman Jake Auchincloss joins Charlie to discuss a wide array of topics, including the future of the Democratic Party, how they can become the party of ideas again, and which MAGA disciples face a reckoning after the November elections. 

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Author of Doomsday Scenario blog and former editor of Politico Magazine, Garrett Graff joins Charlie to talk about the emerging battle against AI data centers, the current political landscape, and Trump's weak sauce threat against Canada to change the name of Lake Ontario to Lake America. 

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Charlie talks about yet another war Trump has started that no Americans wanted and author, historian and elections expert, Brian Rosenwald joins him to break down where all the important midterm races stand.

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The Atlantic'sTom Nichols joins Charlie to talk about the frightening delusions of the Trump team, his human binky Natalie Harp, and Congress shirking its most basic responsibilities.

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Charlie goes solo today to discuss Trump cozying up to another despot, pumping the brakes on data centers and who the hell is Natalie Harp.

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Harry Litman, host of the Talking Feds podcast, joins Charlie to talk about Trump's continued warping of reality, Blanche showing the era of DOJ impartiality is over, and the possibility the Republicans in Congress will refuse to seat a newly elected Democratic member on January 3rd.

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Ed Luce from the Financial Times joins Charlie to talk about today's political climate, the undeniable reality of global warming and the existential threat of AI. 

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The co-founder of Third Way, Matt Bennett joins Charlie to talk about the DSA's stunning defeat in Wisconsin, their agenda to destroy the Democratic Party and why electability still matters.

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The Atlantic's Peter Wehner joins Charlie to talk about Trump's desperate attempts to remain relevant, his miscalculations about Iran, and MAGA's obsession with Anthony Fauci.

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The Atlantic's Anne Applebaum joins Charlie to discuss Trump's sale of early access to Truth Social posts, his doubling down on the reflecting pool vandalism lie, and the Ceuta border crisis and how the far right has weaponized it.

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New York Times Opinion writer David French joins Charlie to discuss Trump's unprecedented corruption, the Todd Blanche Attorney General nomination now in limbo, and Anthony Fauci's Senate hearing. 

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Tara Palmeri, host of The Tara Palmeri Show and author of the newsletter "The Red Letter," joins Charlie to unpack Trump's attack on Kaitlan Collins at the White House Correspondents' Dinner, Todd Blanche's role in the Epstein cover-up, and Lindsey Graham's fraught legacy.

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Nicholas Grossman, editor of Arc Digital and professor of international relations at the University of Illinois, joins Charlie to discuss Trump's frenzied posting of AI slop about Iran, the bizarre White House Correspondents' Dinner, and the global implications of the newly announced Saudi nuclear deal.

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Jonathan Rauch is a Brookings Institution Senior Fellow and a contributing writer at The Atlantic. In this episode, he joins Charlie to explain how the "postmodern right" thinks it can manipulate reality, how Trump's people thought they could change civil society — and why all of this is failing. They also discuss the continuing casualties from the war with Iran, Trump's obsession with numbers, and Lindsey Graham's legacy.

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In this special solo episode, Charlie answers your questions about the latest crisis in US-Canada relations, Jay Clayton's confirmation hearing, and the US-Saudi nuclear deal. 

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Ben Wikler served as the chair of the Democratic Party of Wisconsin for six years. In this episode he joins Charlie to talk about his new book This Is the Plan: How to End America's Meltdown and Save Democracy. Inevitably, they also talk a lot about Wisconsin politics.

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Michael Tomasky is the editor of The New Republic and author of a new book titled Killing Baby Hitler.It's part sci-fi thriller, part satire and even though it takes place in the future and the past, it tells us a lot about the present. 

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On today’s episode, Charlie welcomes back friend of the show and former US Representative, Adam Kinzinger. The two discuss Graham’s passing and his legacy in relation to Trump, Trump’s mysterious upcoming broadcast on Thursday and the latest on the Iran War.

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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 discuss the economic and political implications of current global events, AI advancements, and Trump's corruption. 

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Atlantic writer Tom Nichols joins Charlie to discuss the Maine Senate election fiasco, Trump's antics at the NATO summit, and the Administration looking for a plan C in Iran. 

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Retired Lieutenant General Mark Hertling served as commanding general of the U.S. Army in Europe during the Obama administration. He's also the author of “If I Don’t Return: A Father’s Wartime Journal.” In this episode, he and Charlie discuss the conflict with Iran, Trump insulting our NATO allies, Ukraine's struggles, and Pete Hegseth's unusual leadership style.

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Legal analyst and Talking Feds host Harry Litman joins Charlie to talk about the state of American democracy 250 years after independence, recent Supreme Court decisions and their implications, and Trump's unparalleled corruption.

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For the 4th July we're re-running Charlie's conversation with 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.

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On today’s episode of “To the Contrary,” Charlie welcomes back journalist and author of “The Red Letter,” Tara Palmeri. They discuss Trump’s obsession with image leading up to the 4th of July holiday, immigration and Palmeri’s recent interview with Congresswoman, Kat Cammack. 

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Peter Wehner, a contributing writer at The Atlantic and a senior fellow at the Trinity Forum, joins Charlie to talk about Trump's recent Supreme Court wins and losses, Trump's state fair fiasco, and the consequences of cultural degradation.

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Jamil Smith is a columnist at The Guardian and a lecturer at the UC Berkeley Graduate School of Journalism. In this episode, he joins Charlie to discuss what America's upcoming 250th birthday means to them, the latest Supreme Court decisions and their implications, and Trump's obsession with voter suppression.

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Peter Suderman is the features editor for Reason, a free market libertarian magazine. In this episode he joins Charlie to discuss the decline of libertarian influence in the Republican Party, the relationship between government power and corporate influence, and the rise of progressive candidates following the recent elections in New York.

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Sofia Kinzinger was a WH staffer under Trump during his first term. In this episode, she talks to Charlie about what it was like, and about her journey and political awakening. They also discuss JD Vance's book launch and the future of the Republican Party.

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Ed Luce from the Financial Times joins Charlie to discuss the deal with Iran, the Netanyahu-Trump fallout, and Elon Musk's obsession with Britain.  

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Yoni Appelbaum, historian and deputy executive editor at The Atlantic, joins Charlie to go over what we know — and don't know — about the deal with Iran and what it all means for US interests in the region. They also discuss Appelbaum's latest article, in which he argues that the US has lost the ability to agree on a shared national story and, as a result, has largely stopped trying to tell one — in schools, universities, and public life.

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Atlantic writer Tom Nichols joins Charlie to catch up on Trump's zigzagging on Iran, discuss Elon Musk's new status as a trillionaire, and unpack the absurdity of Pete Hegseth.

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In this special To the Contrary episode, Charlie sits down with Danielle Crittenden, whose daughter Miranda died suddenly two years ago. Crittenden recently published Dispatches from Grief: A Mother's Journey Through the Unthinkable. They discuss life after loss, how to talk about grief, and the awkward moments that arise when you tell others you've lost someone you love.

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Legal analyst and Talking Feds host, Harry Litman, joins Charlie to dissect Trump's brief interview with Meet the Press, his legal battles over the slush fund, and the DOJ declaration that Trump has the right to bulldoze the Statue of Liberty. 

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On today’s episode of “To the Contrary,” Charlie sits down with journalist and author of “The Red Letter” Substack, Tara Palmeri. The two of them discuss Main’s messy Senate race, Trump’s behavior with female reporters in the Oval Office and CBS’ continual crumble. 

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Jonathan Rauch is a Brookings Institution Senior Fellow and a contributing writer at The Atlantic. In this episode, he joins Charlie to talk about Trump's-now-killed slush fund, U.S.-Israel relations, and the war with Iran.

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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.

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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.

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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.

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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.

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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. 

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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.

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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. 

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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.

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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.

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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.)

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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.

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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. 

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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.

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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.

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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. 

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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.

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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." 

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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.

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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.

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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.

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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.

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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. 

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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.

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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.

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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.

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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.”

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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.

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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.

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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.

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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. 

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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. 

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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.

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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.

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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.

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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. 

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