Impolitic with John Heilemann

John is joined by former Department of Homeland Security chief of staff Miles Taylor to discuss the recent executive order by Donald Trump directing federal law enforcement agencies to investigate Taylor (for unnamed and unknown crimes) and his fledgling efforts to fight back. Taylor—who rose to prominence during Trump's first term with a New York Times op-ed and No. 1 bestselling book, written under the pen name Anonymous, that detailed a “quiet resistance” within the administration—describes the financial, professional, emotional impacts of being declared “guilty of treason” by Trump for no specified reason aside from having publicly criticized him; the legal countermeasures Taylor plans to undertake; and the wider political implications of his case. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by former CEO of UBS Americas and Democratic mega-donor Robert Wolf to discuss the exit of Elon Musk from the White House and Donald Trump’s latest economic-policy gyrations. The recipient of three presidential appointments from Barack Obama and one from Joe Biden, Wolf explains why Musk’s foray into government was always bound to end in tears; why Wall Street's TACO (Trump Always Chickens Out) meme perfectly captures the financial world’s view of the president's feckless approach to trade and tariffs; and why the state of the economy is even more precarious than it appears. Wolf also reflects on his own role in aiding and abetting Biden’s bid for reelection despite doubts about his ability to serve a second term. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by Parkland survivor, gun control activist, and embattled DNC vice chair David Hogg to discuss the controversies swirling around him and what his party needs to do to fix itself. Hogg explains the rationale behind his plan to spend $20 million through his Leaders We Deserve PAC to elect younger candidates who embrace a combative anti-MAGA stance; why that plan includes backing primary challenges to ossified, ineffective Democratic incumbents; and the ensuing rage among much of his party’s establishment, which he sees as fueling a campaign to oust him from DNC role and “destroy my reputation.” To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by Mark Whitaker to discuss his new book, “The Afterlife of Malcolm X: An Outcast Turned Icon’s Enduring Impact on America.” A former editor in chief of Newsweek, Washington bureau chief for NBC News, and managing editor of CNN Worldwide, Whitaker lays out the two narrative threads at the heart of his book: the first, a deep exploration of the unsolved mystery over who killed the revolutionary Muslim minister and progenitor of the Black Power movement; and the second, a rich exegesis of Malcolm’s lasting political and cultural influence. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by CNN's Jake Tapper and Axios's Alex Thompson to discuss their scoop-filled, headline-spawning, controversy-stirring new book, "Original Sin: President Biden's Decline, Its Cover-Up, and His Disastrous Choice to Run Again." Jake and Alex explain the nature and central players in the concealment of the decline in President Biden's mental acuity during his time in the White House; how the lack of transparency about his health and cognitive fitness before leaving office have lent credence to the profusion of conspiracy theories following the disclosure this week of his prostate cancer diagnosis; and the impotence of a Democratic Party convinced that the stakes of the 2024 election were existential and yet unable to acknowledge Biden's age-related political liabilities before it was too late. The authors also address some of the controversies that have arisen surrounding the book and their reporting methods in the wake of its publication. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Pablo Torre, ESPN and MSNBC commentator and host of the Edward R. Murrow Award-winning video podcast Pablo Torre Finds Out, is back with John to weigh in on an assortment of red-hot stories at the intersection of sports, culture, and politics: from the backlash in Canada against Wayne Gretzky over his association with Donald Trump and the reinstatement of Pete Rose by Major League Baseball (and Trump’s rumored role in the decision) to the calamitous collision between Bill Belichick’s private and public lives. Plus, Pablo reflects on the death row drama unfolding around Dallas Cowboys superfan and dubiously convicted supermax inmate Charles Flores, the coverage of which recently earned PTFO a Peabody Award nomination. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by former Florida Republican congressman David Jolly to discuss Donald Trump’s trip to the Mideast and the naked corruption on display in his embrace of a $400 million 747 gifted by Qatar to serve as a new Air Force One; disarray among House Republicans over the “one big, beautiful bill," and Jolly’s defection to the Democratic Party ahead of an all but certain run for governor in the Sunshine State in 2026. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by the Oscar and Emmy Award-winning documentarian Davis Guggenheim to discuss his new film for Apple TV +, “Deaf President Now!” Davis lays out the story behind the movie, which revolves around a student protest that erupted over eight days in 1988 at Gallaudet University in Washington, DC, the world’s only university for the deaf, and explains why it stands as “the greatest civil rights movement in history you’ve never heard of.” Davis also retraces his storied career as a non-fiction director, connecting the dots between his past films, from “An Inconvenient Truth” and “Waiting for ‘Superman’” to “He Named Me Malala" and "Still: A Michael J. Fox Movie”—and reveals why getting fired by Denzel Washington from “Training Day” changed his life, and for the better. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by Atlantic staff writers Ashley Parker and Michael Scherer to discuss their new cover story on the remarkable political resurrection that returned Donald Trump to the White House and imbued him with a patina of invincibility—and the recent signs that this veneer is starting to crack. Parker and Scherer weigh in on Trump’s tete-a-tete with Canada’s new prime minister, Mark Carney; the differences between his first and second-term states of mind; and whether becoming an avatar of tariff-induced austerity is a good look for him. They also opine on whether Trump’s talk about reopening Alcatraz is serious, yet more trolling, or a sign that he’s been watching too many old movies on cable. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by hedge fund manager Anthony Scaramucci to discuss the first White House personnel shake-up of Donald Trump’s second term and the culture of sycophancy in his cabinet. Scaramucci — who served a famously shambolic 11-day stint at Trump’s communications director in 2017 — offers his take on why Mike Waltz lost his job as national security adviser, Marco Rubio was chosen as his replacement (at least for now), and Trump, contrary to his reality-tv persona, is actually terrible at firing people. Scaramucci also weighs in on Trump’s trade war, arguing that his recent remark about America's children having to settle for “two dolls instead of 30” was a clear sign that his former boss is moving inexorably towards caving on his tariff agenda. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by Semafor editor-in-chief Ben Smith to discuss the role of private group chats in pushing Silicon Valley's politics to the right—and many of its most powerful figures into the arms of Donald Trump. Ben lays out how dozens of hush-hush Signal and WhatsApp groups emerged during Covid among the tech elite in reaction to what its members saw as the stifling woke conformity of social media; the seminal role of venture capitalist Marc Andreessen in seeding these forums; and how their influence now flows through X, Substack, and podcasts, making them the "dark matter of American politics and media." Ben also contends that, 100 days into his second term, Trump is starting to feel the pull of political gravity; that Semafor, which he cofounded three years ago, still retains the vaulting ambitions the company famously trumpeted at launch; and that the recent tumult in financial markets has elevated "Margin Call" from a cult classic to the greatest Wall Street movie of all time. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

On the eve of Donald Trump’s 100th day back in office, John is joined by his Puck Political Superfriend and partner Peter Hamby to look back on what 45/47 hath wrought since January 20 — what has mattered and what hasn’t; the most truly surprising, most entirely predictable, and most grievously overlooked developments and storylines; and both the state of the Democratic Party generally and the broader anti-Trump resistance specifically — as Trump 2.0 got underway with a bang (really more of a eardrum-shredding sonic boom) and not a whimper. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by Susan Morrison, articles editor of The New Yorker, to discuss “Lorne: The Man Who Invented Saturday Night Live,” her biography of SNL creator and producer Lorne Michaels. Morrison argues that no one has done more to shape modern America’s sense of humor than Michaels, an enigmatic Canadian about whom most Americans know nothing; and that while Michaels a figure of enduring obsession among comics, he remains a mystery to them as well. Morrison lays out the singular combination of qualities (tastemaker, talent-spotter, task-master, raconteur, adrenaline junkie) that makes Lorne Lorne—and reveals that, yes, in fact, he was the inspiration for Dr. Evil. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Imagine if you could ask someone anything you wanted about their finances. On What We Spend, people from across the country and across the financial spectrum are opening their wallets—and their lives—to tell you everything: what they make, what they want, and—for one week—what they spend. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by a pair of former GOP panjandrums turned NeverTrump stalwarts — attorney George Conway and political strategist Stuart Stevens — to discuss the Kilmar Abrego Garcia case and Donald Trump’s efforts to turn the U.S. into a police state. Conway and Stevens argue that the guardrails preventing that outcome are banged up but still holding; that the real test of them will come when (not if) the administration defies the Supreme Court even more flagrantly than it has already; and that Harvard is offering the kind of a master class in resistance to MAGA bullying that many of the nation’s top law firms have been too gutless and/or greedy to provide. They also explain why Trump’s economic illiteracy and its consequences may prove to be what saves American democracy. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by Maya Wiley, president and CEO of the Leadership Conference on Civil and Human Rights, to discuss the case of Kilmar Abrego Garcia and its implications for the rule of law in America. Wiley argues that the case -- and Donald Trump's open defiance of the Supreme Court's unanimous order that the administration facilitate Garcia's repatriation from a notorious penal colony in El Salvador -- is about more than Garcia's fate, immigration or foreign policy, the Trump administration's deportation agenda, or even the constitutional principle of due process. It's about Trump's yen for unchecked power, and how, if he gets it, the next Kilmar Abrego Garcia could be you. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by longtime Wall Street eminence and former “car czar” Steve Rattner to discuss the impact of Donald Trump’s tariff jihad on global financial markets and the American economy. Rattner explains why the theory of the case animating Trump’s protectionist agenda is “disjointed,” “illogical,” and “incoherent,” and its execution has been even worse; why the reputational damage the U.S. is suffering as a result among its allies around the world will be difficult to undo; why the claims by Trump’s advisers that last week’s abrupt policy shifts were all part of some master plan are ludicrous on their face; and why the endgame of the full-scale trade war now underway with China is impossible to foresee. Rattner also assesses the degree of fiscal irresponsibility Republican budget plan making its way through Congress—and whether the chickens may finally be about to come home to roost when it comes to America's unprecedented debt and deficits. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by former U.S. Cybersecurity and Infrastructure Security Agency director Chris Krebs to discuss the Trump 2.0 rollback of the nation’s cyberdefenses—an interview taped just an hour before Trump ordered the Justice Department to investigate Krebs, who earned the president’s enmity four years ago by declaring the 2020 election “the most secure in American history.” Krebs details the rapidly escalating and dramatically expanding threats posed by Chinese and Russian hackers to America's corporations, public and private infrastructure, and voting systems; how and why the administration is dismantling the agencies and programs designed to stave off those threats; and the potential risks to the security of our elections as a result of gutting CISA, the organization Krebs once led … and Trump himself signed into law. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by Marc Elias, the attorney whom Donaled Trump has cast as his bete noire in the legal profession, to discuss the president’s war on the judiciary, the bar, and the rule of law itself. Elias explains why the executive order titled “Preserving and Protecting the Integrity of American Elections” is designed to do just the opposite, making it the most dangerous of Trump's myriad power grabs; why we aren’t yet in a constitutional crisis but soon could be; and why Trump’s threats have caused so many prestigious law firms to bend the knee. Marc also tells John why he hasn’t done the same despite being plenty worried by Trump’s singling him out as a “very bad" person and a “thug". To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

John is joined by former AP Washington Bureau Chief Ron Fournier and current Wisconsin Democratic Party chair Ben Wikler to discuss a week in which America’s de facto co-presidents seemed trying to outdo each other in terms of wreaking havoc and stoking panic. Fournier assesses the motives behind Donald Trump’s market-crashing tariffs and their potential political implications; explains why the results of Tuesday’s special elections in Florida and Wisconsin are so ominous for Republicans; and issues a partial mea culpa for being dismissive about Cory Booker’s 25-hour Senate filibuster. Then Wikler takes listeners inside the Wisconsin Supreme Court race, detailing the ways in which Musk was the gift that kept on giving and laying out how Badger State Democrats plan to build on their big win in the country’s swingiest swing state. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices