To The Contrary with Charlie Sykes

Tim O’Brien: When the Law No Longer Matters Apr 15, 2025

Charlie Sykes is joined by Tim O’Brien of Bloomberg Opinion to unpack the chaos of Trump's tariff war, his public humiliation by Vladimir Putin, and his escalating disregard for the rule of law. They discuss how the president’s unchecked impulses are upending markets, weakening U.S. alliances, and threatening legal norms—all while rewarding loyalty and punishing dissent. From stock tips on social media to ignoring Supreme Court rulings, this episode explores what happens when a president governs entirely by id.

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Amy McGarth & Denver Riggleman: Tariffs, Tyranny and Truth in the Barrel Apr 13, 2025

Charlie Sykes is joined by Amy McGrath and Denver Riggleman for a candid conversation about national security, military norms, and the authoritarian threats posed by a second Trump term. They dive into the dangers of loyalty-driven purges, the collapse of soft power, and why some Americans still fall for bizarre conspiracy theories. With bourbon-fueled honesty and bipartisan grit, the trio also preview Amy and Denver's new podcast, Truth in the Barrel.

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Jonathan Allen and Amie Parnes: "Fight" and the Price of Gaslighting Apr 10, 2025

Charlie Sykes talks with Jonathan Allen and Amie Parnes, authors of Fight: Inside the Wildest Battle for the White House, to unpack their explosive behind-the-scenes reporting on the 2024 election. They discuss a Democratic Party in disarray, a media landscape accused of complicity, and the pivotal moments that helped reelect Donald Trump. From Biden’s final days to Harris’s uphill battle, this conversation offers a revealing look at how we got here.

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Peter Wehner: Trump, Denial, and the Collapse of Civic Courage Apr 08, 2025

Charlie Sykes is joined by Peter Wehner to unpack the global economic chaos unfolding under Donald Trump's leadership. They explore the psychological grip Trump holds on his supporters, the failures of institutions to push back, and the dangerous normalization of one-man rule. Together, they reflect on how fear, denial, and the collapse of civic courage have created a moment of reckoning—not just for the Republican Party, but for the country as a whole.

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David French: Tariffs, Sycophants and Signal Apr 06, 2025

Charlie Sykes is joined by David French for a wide-ranging conversation about the alarming trajectory of Trump’s second term—from potential appointments like Pete Hegseth and Kash Patel to the chaos of $6 trillion in new tariffs. They explore the rise of authoritarian instincts, the collapse of due process, and the moral rationalizations enabling Trump's grip on power. Plus: big law caves, Laura Loomer ascends, and Paula White offers angelic blessings—for a price.

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Josh Kraushaar: Elon’s Flameout & the GOP Fallout Apr 03, 2025

Charlie Sykes is joined by Josh Kraushaar to unpack the political aftershocks of Elon Musk’s failed $26 million intervention in Wisconsin’s Supreme Court race. They dig into the GOP’s internal frustrations with Musk, the Trump administration’s growing disregard for due process, and the Democrats’ unexpected resurgence. Plus, the two discuss the rise of Cory Booker, the collapse of institutional resistance, and the dangers of cruelty as political theater.

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David Jolly: Taking Trump's Third Term Seriously Apr 01, 2025

Charlie Sykes and former Congressman David Jolly explore the unsettling prospect of Donald Trump pursuing a third term and the broader implications for American democracy. They examine the collapse of congressional power, the growing influence of Elon Musk in Republican politics, and the corrosive impact of money on elections—including a $100 million Wisconsin Supreme Court race. Jolly also hints at a potential gubernatorial run in Florida and offers sobering insight into the dangers posed by RFK Jr.'s anti-vaccine agenda.

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Jim Acosta: Greenshoots in the Fight for America Mar 30, 2025

Charlie Sykes welcomes CNN veteran and Substack writer Jim Acosta for a weekend conversation on fear, power, and political pushback in the Trump era. They discuss the administration's performative authoritarianism, from mass deportations and censorship to threats against institutions and the judiciary—while also spotlighting signs of resistance, electoral shifts, and green shoots of hope. With humor and urgency, Acosta argues that while Trump wants America to be afraid, the cracks in his facade are beginning to show.

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Anne Applebaum: Signal and the Authoritarian Playbook Mar 27, 2025

Pulitzer Prize-winning author and Atlantic staff writer Anne Applebaum joins Charlie Sykes to unpack the shocking revelations of the "SignalGate" scandal—an alarming breach of national security and a window into the chaos of the second Trump administration. Applebaum explains how the use of unsecured messaging apps, bizarre bravado among senior officials, and a deep-seated hostility toward Europe signal a broader collapse of institutional norms. The conversation also explores how modern autocratic tactics are taking hold in the U.S., and why the erosion of resistance in American institutions should be sounding alarm bells.

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Olivia Troye Has Entered the Chat Mar 25, 2025

Charlie Sykes and national security expert Olivia Troye react to The Atlantic's bombshell report detailing how Trump administration officials accidentally included a journalist in a Signal group chat revealing real-time U.S. war plans. They also examine the chilling erosion of institutional norms—from the revocation of security clearances for dissenters to the shuttering of Voice of America—and question what happens when authoritarian tactics meet amateur hour governance. Plus, they discuss the bizarre return of Trump’s Greenland obsession and the dismantling of Social Security without a single vote.

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Tom Nichols: Why Are We Still Surprised? Mar 23, 2025

Charlie Sykes is joined by Tom Nichols of The Atlantic to discuss the growing normalization of authoritarianism and the failure of America's institutions to push back. They cover everything from Trump’s war on the judiciary to Elon Musk’s growing influence, the alarming capitulations by law firms and universities, and Vladimir Putin's manipulation of global power dynamics. It’s a wide-ranging, sobering, and often darkly funny conversation about why, even after all this time, we’re still capable of being shocked.

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Kinzinger and Sykes: How Putin Humiliates Trump Mar 20, 2025

Former Congressman Adam Kinzinger joins Charlie Sykes for a candid discussion on the state of American democracy, Donald Trump's threats, and the exhaustion of fighting political chaos. Kinzinger reflects on the lessons he's learned since leaving Congress, including the importance of resilience in the face of intimidation and the need to maintain a sense of humor. Together, they break down Trump’s continued fixation on revenge, the GOP’s deference to Vladimir Putin, and why strong leadership is essential for Democrats navigating this critical moment.

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Michael Roth: It's Time for Universities to Stand Up to Trump Mar 18, 2025

Charlie Sykes speaks with Michael Roth, president of Wesleyan University, about the escalating attacks on higher education under Donald Trump’s administration. They discuss the administration’s sweeping funding cuts, threats to academic freedom, and the reluctance of university leaders to push back against government overreach. Roth offers a candid perspective on why he refuses to stay silent and what must happen to preserve the independence of American institutions.

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David Frum: Trade Wars and Turmoil Mar 16, 2025

Charlie Sykes and David Frum discuss the volatile state of the U.S. economy, the Trump administration’s trade war with Canada, and the potential consequences of Elon Musk’s growing influence in government policy. They analyze Trump’s economic policies, including his fixation on tariffs and trade conflicts, and question the administration’s erratic geopolitical maneuvers, from Ukraine to Panama. The conversation also explores the Republican Party’s surrender to Trump’s agenda and the alarming speed of institutional capitulation in American democracy.

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Nicholas Grossman: Why does Trump have a Putin fetish? Mar 13, 2025

Charlie Sykes is joined by Nicholas Grossman, editor of Arc Digital and professor of political science at the University of Illinois, to dissect the latest political chaos. They explore Donald Trump’s bizarre loyalty to Vladimir Putin, the unraveling of U.S. alliances, and the dangerous shift in global power dynamics. From the potential government shutdown to the erosion of democratic norms, this conversation is a deep dive into the troubling state of American politics and its broader implications.

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Reed Galen: The Disconnect Between Voters and the Establishment Mar 11, 2025

Charlie Sykes and Reed Galen discuss the latest political turmoil, including the potential government shutdown, economic uncertainty, and the evolving dynamics within the Republican Party. They examine the rise of authoritarian figures, the state of the opposition, and the disconnect between voters and the political establishment. The conversation also delves into the broader implications of America's shifting global role, the dangers of Trumpism, and how Democrats can counteract the MAGA movement in an increasingly fractured political landscape.

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Jonathan Martin: Are Trump and Musk Breaking Up? Mar 09, 2025

Charlie Sykes sits down with Politico senior writer Jonathan Martin to break down the latest political chaos, including the explosive clash between the Trump cabinet and Elon Musk. They explore the growing tensions within Trump's cabinet, the unpredictability of his policy decisions, and the broader implications for America's allies. Martin also offers insight into the Democratic Party’s struggles, Gavin Newsom’s surprising stance on transgender athletes, and the nervous atmosphere at the recent Munich Security Conference.

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Karen Tumulty: Trump's Delusions Run Into Reality Mar 06, 2025

Charlie Sykes and Washington Post columnist Karen Tumulty react to President Trump's speech to Congress. They discuss the administration’s approach to governance, including its impact on national security, economic policy, and the broader implications of Elon Musk’s influence. Tumulty and Sykes analyze the Republican Party’s response, the weakening of institutional guardrails, and how the media is navigating this new political landscape.

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Susan Glasser: Why Aren’t We in The Streets? Mar 04, 2025

Charlie Sykes and Susan Glasser discuss the significant geopolitical shifts occurring under Donald Trump's presidency, particularly regarding Ukraine and Russia. They analyze the implications of Trump's actions, including his confrontational meeting with Ukrainian President Zelensky, and the broader consequences for American foreign policy and alliances, especially in relation to NATO and Europe.

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Kinzinger-Sykes, Part II: Vindication Mar 02, 2025

Charlie Sykes and Adam Kinzinger discuss the significant shifts within the Republican Party, particularly in relation to Donald Trump's presidency. They explore the betrayal of traditional conservative values, especially regarding foreign policy and support for Ukraine. They also discuss the feelings of isolation and vindication among those who oppose Trump, and the challenges faced by individuals of faith in a politically charged environment. They also critique Elon Musk's influence on government and the potential dangers of drastic cuts to essential services.

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Trump, Vance, and Zelenskyy: A national Disgrace (with Adam Kinzinger) Feb 28, 2025

Charlie Sykes Adam Kinzinger discuss the recent Oval Office meeting between President Trump, Vice President Vance, and Ukrainian President Zelensky. They share their reaction to the treatment of Zelensky, the implications of Trump's actions for U.S. foreign policy, and the shifting dynamics within the Republican Party regarding support for Ukraine.

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Kara Swisher: Bezos throws a tantrum; Musk thinks he’s Jesus Feb 27, 2025

Charlie Sykes and Kara Swisher discuss the evolving landscape of media and the influence of billionaires like Jeff Bezos and Elon Musk, and the future of major media outlets like the Washington Post. Swisher talks the motivations behind these billionaires' actions and their impact on society, emphasizing the need for accountability and the dangers of unchecked power. They also discuss the complex relationship between Trump and Elon Musk, Musk's self-perception as a savior and the potential consequences of his actions on Trump's political standing.

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Paul Rieckhoff: Trump’s Assault on the Military Feb 25, 2025

Charlie Sykes and Paul Rieckhoff discuss the recent UN vote where the United States sided with Russia against a resolution supporting Ukraine. They explore the implications of this decision, the perception of America as the 'bad guy', and the ongoing military purge under Trump's administration. they also discuss the culture of the military, the importance of values in leadership, and the chaos that is unfolding within the military ranks. They also touch on the impact of these changes on veterans and the 9/11 health registry. Plus, the critical role of veterans in politics, the manipulation of media and information by the current administration, and the implications of recent appointments within the FBI. They also highlight the challenges faced by the Democratic Party, including a lack of leadership and strategy, and speculate on Trump's consolidation of power and its potential consequences for the future of American politics.

More information:

Independent Veterans of America: https://independentveteransofamerica.org/

American Veterans for Ukraine: https://americanveteransforukraine.org/

Independent Americans: https://independentamericans.us/

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Ben Wittes: The US Switches Sides in Ukraine Feb 20, 2025

Charlie Sykes is joined by legal analyst Ben Wittes to examine the first month of Trump's second presidency and the shocking realignment of U.S. foreign and domestic policy. They discuss the administration’s abandonment of Ukraine, the erosion of DOJ independence, and the broader constitutional crisis emerging from Trump’s unchecked executive power. With Republican capitulation in Congress and Trump’s open defiance of legal norms, Sykes and Wittes explore the implications for democracy, the judiciary’s role as the last remaining guardrail, and whether Europe can step up as the U.S. retreats from its global leadership.

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Brian Rosenwald: One Month of Trump 2.0 Feb 18, 2025

Charlie Sykes and political historian Brian Rosenwald from the University of Pennsylvania take a look back at the first month of the second Trump administration

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Tim O'Brien: Trump only cares about two things Feb 16, 2025

Charlie Sykes is joined by Tim O’Brien, Executive Editor for Opinion at Bloomberg, for a wide-ranging discussion on Donald Trump’s latest actions and their broader implications. They explore Trump's fascination with power and control, his influence over U.S. institutions, and his ongoing relationship with figures like Elon Musk and Vladimir Putin. The conversation also delves into the fallout from the DOJ’s attempted intervention in the Eric Adams case, Trump's push for tariffs, and the global consequences of his policies.

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Olivia Troye: Standing up to Kash Patel Feb 13, 2025

Charlie Sykes and Olivia Troye discuss the appointment of controversial figures like Kash Patel, the administration’s authoritarian tendencies, and the global implications of Trump’s policies, including mass deportations and weakened alliances. They also explore the growing influence of figures like Elon Musk and Stephen Miller, raising concerns about the long-term consequences for democracy and national security.

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Tom Nichols: Decadent America Feb 11, 2025

Charlie Sykes and Tom Nichols discuss the chaotic first month of Trump’s second term, examining the administration’s internal distractions, its attacks on the rule of law, and the broader implications for democracy. They explore Trump’s erratic priorities—from tariffs and plastic straws to threats against NATO—while considering how authoritarian tendencies are being normalized. The conversation also touches on Elon Musk’s growing influence, the undermining of U.S. institutions, and the dangerous consequences of an increasingly unserious electorate.

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David French: A Constitutional Revolution Feb 09, 2025

Charlie Sykes and David French talk about the chaotic early days of the Trump presidency. They focus on how Trump's actions affected the U.S. Constitution and the balance of power in government. They explain what a constitutional crisis is, how the courts work, and what could happen if people refuse to follow Supreme Court decisions. Their conversation looks at the challenges facing American democracy and why it’s important to understand the laws that limit a president’s power.

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