Impolitic with John Heilemann

Latest Episodes:

Ezra Klein: The Year in Politics, Part II Dec 29, 2025

Show notes

John welcomes New York Times columnist and podcasting dynamo Ezra Klein back to the show for the second installment of a two-part, year-end review of the national political scene in 2025

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Jon Favreau & Jon Lovett: The Year in Politics, Part I Dec 26, 2025

Show notes

John welcomes two of the Pod Save America dudes, Jon Favreau and Jon Lovett, to the show for the first installment of a two-part, year-end review of the national political scene in 2025.

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Chris Anderson: Karoline Leavitt Isn’t Rosalia (and Other Inconvenient Truths) Dec 22, 2025

Show notes

John welcomes celebrated photojournalist Christopher Anderson to discuss the controversy over his portraits of Donald Trump’s inner circle in Vanity Fair. Anderson explains his trepidation over taking the assignment and his approach to it once he did; why the outrage over his pictures in some quarters is a result of a growing confusion between political figures and celebrities, the proliferation of photo filters and A.I. image distortion on social media, and a lack of comprehension that photojournalism is, in fact, journalism; and why no one should be shocked that he didn’t conceal signs of Karoline Leavitt's cosmetic enhancements or shoot Stephen Miller as if he were Brad Pitt (beyond the obvious, that is).

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Jordan Klepper: Reiners R.I.P. & The Year in Late Night Comedy Dec 19, 2025

Show notes

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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Rick Wilson: “Strip Club Glitter Never Comes Off” Dec 15, 2025

Show notes

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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Barry McCaffrey: Trump’s War Aims in Venezuela = Maduro Out & Chevron In Dec 12, 2025

Show notes

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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Steven Lepper: Murder Was the Case (Off the Coast of Venezuela) Dec 08, 2025

Show notes

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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Mark Hertling: War Criminal, Cosplay Commandant, or Both? Dec 05, 2025

Show notes

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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Jonathan Karl: Vengeance Is Mine, Sayeth the President Dec 01, 2025

Show notes

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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Jonathan Freedland: The Traitor’s Circle (Live) Nov 28, 2025

Show notes

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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