John welcomes The Daily Show’s Jordan Klepper back to the show for a fond remembrance of the lives and legendary film and television careers of Rob and Michele Singer Reiner. Klepper also discusses his latest Daily Show special, which took him from Mississippi to Norway to Portland, Oregon, where he took part in a naked anti-ICE protest and got pepper-sprayed in the process; the challenges of finding the funny amid the fear and loathing that have typified the Trump 2.0 era; and the sword of Damocles that hung over late night comedy in the year of Jimmy Kimmel’s suspension and Stephen Colbert’s cancellation.

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John welcomes lapsed Republican strategist and Lincoln Project cofounder Rick Wilson back to the show to discuss the mounting signs that, less than one full year into his second term in office, Donald Trump has reached his sell-by date – and the implications of Trump's political decline for the MAGA-fied Republican Party.

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John welcomes retired four-star U.S. Army General Barry McCaffrey to discuss the rapidly escalating conflict between America and Venezuela. McAffrey argues that Donald Trump appears to be hellbent on regime change in Venezuela; that his stated motivations related to narco-terrorism make virtually no sense at all; and that his primary motivations instead revolve primarily around seizing the South American country’s oil reserves. McCaffrey also assesses the recently unveiled official U.S. National Security Strategy, the elements of which he regards as ranging from incoherent to farcical to flat out “horrifying.”

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John welcomes retired Major General Steven Lepper, a former Deputy Judge Advocate General of the U.S. Air Force, to discuss the legal dimensions of the Trump administration’s Venezuelan boat strikes. Lepper contends that there is no basis in domestic or international law for any of the 23 boat strikes and 87 related fatalities that have taken place so far; that the now infamous second strike on September 2 is more likely to have been straight up murder than a war crime on the part of Pete Hegseth (and others in the chain of command); that the firing of the top Army, Air Force, and acting Navy JAGs early in Trump’s second term was the first sign of an concerted and ongoing effort remove the rule of law from the armed forces; and that the boat-strike scandal portends more (and worse) lawless military orders to come.

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John welcomes retired Lieutenant General Mark Hertling to discuss the Trump administration’s air strikes against alleged Venezuelan drug boats and the mounting charges that Defense Secretary Pete Hegseth may be guilty of a war crime – or just plain murder. Hertling, who served as commander of U.S. Army Europe among other posts, offers a withering perspective on Hegseth’s explanations of his role in the disputed strike and his leadership of the Pentagon writ large; a stark assessment of where the metastasizing story is headed next; and a fraught view of the fragile state of civilian-military relations in Trump 2.0.

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John welcomes ABC News chief Washington correspondent Jonathan Karl to discuss his new book, “Retribution: Donald Trump and the Campaign That Changed America.” The author of three previous bestsellers about 45/47, Karl describes how Trump has – and hasn’t – changed in the 30-plus years since the two first met; how Trump's desire for vengeance against his political foes became the driving force of his 2024 campaign and has dominated his second term in office; and his complex love-hate relationship with the press (with Karl as a prime example). Karl also weighs in on how much sway Steve Bannon actually has with Trump, and Nancy Pelosi's behind-the-scenes role in ending Joe Biden’s reelection campaign.

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In this special episode taped live onstage in New York, John interviews his pal Jonathan Freedland – Guardian political columnist and co-host of the Unholy podcast – about his new book, “The Traitor’s Circle: The True Story of a Secret Resistance Network in Nazi Germany – and the Spy Who Betrayed Them.” Freedland, the author of nine thrillers under the pen name Sam Bourne, describes how "The Traitor's Circle," like its predecessor “The Escape Artist,” marries rigorous research with the techniques of genre fiction to create a serious work of historical non-fiction that reads like an Agatha Christie mystery. The two also discuss how pop culture has processed the Holocaust, from “Shoah” to “The Odessa Files” and “Inglorious Bastards.”

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John welcomes former Republican consultant, Lincoln Project/Lincoln Square bigwig, and bestselling author Stuart Stevens back to the show to discuss Donald Trump’s sudden political senescence. Stevens discusses the emerging dynamics and incentives driving GOP congresspeople to break with Trump; the continued risks he poses to American interests at home and abroad, especially in connection with Ukraine; and the vast talent gap between the two parties when it comes to the 2028 presidential race—and the particular problem Republicans are facing in the form of a de facto frontrunner, J.D. Vance, whom Stevens sees as “super creepy.”

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John welcomes Tim Miller, host of The Bulwark Podcast, back to the show to discuss the signs this week that Donald Trump’s fabled base — and broader political coalition — may be starting to unravel. Tim dissects the two main stressors creating fissures within MAGA: Trump's efforts to deep six the Epstein files in the face of his coalition's concerns about pedophilia among the political and financial elite; and the normalization of anti-Semitism on the right as personified by Groyper godfather Nick Fuentes. Tim and John also wax lyrical about the band of this moment, Geese, and ponder the possibility of a previously unreported anatomical commonality between Trump and Epstein.

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John welcomes Democratic congressman Pat Ryan—a 43-year-old West Point grad and Iraq War vet whose 14-point victory in his deep purple upstate New York district in 2024 elevated him to national rising-star status—to discuss the lessons of his party’s off-year election gains and signs that Donald Trump’s lame duck era is at hand. Ryan also explains his crusade to end the scourge of sports TV blackouts in the age of streaming, and why it’s not merely good policy and good politics, but the kind of effort that could help Democrats regain entry into the manosphere.

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John welcomes four-time Pulitzer Prize-winning investigative reporter Carol Leonnig to discuss her new book with Aaron C. Davis, “Injustice: How Politics and Fear Vanquished America’s Justice Department.” Leonnig, a 25-year Washington Post veteran now serving as a senior MSNBC correspondent, explains how Donald Trump’s first-term impairment of the DOJ, followed by Merrick Garland’s failure to meet the moment after January 6, not only let Trump evade legal accountability but set the stage for his radical second-term subversion of the department’s role and the rule of law itself. She also weighs in on Trump’s recent spate of pardons and maladroit handling of the Epstein files, as well her own scoop regarding Tom Homan and his cash-filled Cava bag.

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