S2 Ep170: George Conway: Trump Showed Up to the Trial and Lost $83 Million

Sarah Longwell and Andrew Weissmann cover Trump’s escalating war with the press, from his White House ban on CNN, MS NOW, and Politico to the growing consolidation of major media companies. They also debate Zohran Mamdani’s approach to Trump, unpack the dubious “national security” rationale for Trump’s giant arch, and discuss Weissmann’s victory in the defamation lawsuit brought against him by Cassidy Hutchinson’s former lawyer.Find the fall pieces you’ll reach for most at Quince. Download the Quince app for app-exclusive offers, or go to https://www.quince.com/illegalnews for free shipping on your order and 365-day returns. Now available in Canada and the UK, too.#ad Make laundry day the best day of the week! Get 20% off your entire order @LaundrySauce with code ILLEGALNEWS at https://laundrysauce.com/ILLEGALNEWS #laundrysaucepodWeight Loss by Hers offers access to affordable FDA-approved GLP-1 medications, including the Wegovy® pill and Wegovy® pen, with personalized treatment plans and 100% online access to licensed providers. Get started at https://forhers.com/illegalnewsShow Links:CNN, MS NOW & Politico sue over Trump’s White House press ban:https://www.reuters.com/legal/government/news-outlets-will-ask-judge-end-trumps-white-house-ban-hearing-2026-09-23/Trump & Zohran Mamdani press conference:https://www.c-span.org/event/news-conference/nyc-mayor-zohran-mamdani-holds-press-conference-following-meeting-with-pres-trump/447368Paramount settles states’ lawsuit over Warner Bros. takeover:https://www.reuters.com/legal/litigation/paramount-settles-with-california-other-states-clearing-major-hurdle-warner-bros-2026-09-21/Trump says planned arch will house drones, snipers & ammunition:https://www.washingtonpost.com/politics/2026/09/20/trump-says-planned-arch-will-be-military-complex-drones-snipers/Passantino v. Weissmann — court ruling:https://law.justia.com/cases/federal/district-courts/district-of-columbia/dcdce/1%3A2023cv02780/260017/53/

JVL is joined by Alex Wagner to trace how four conservative power brokers built the legal machine that would reshape the Supreme Court decades later, and how that project helped create the politics we’re living with today. Plus, they break down Samuel Alito’s dissent in the Supreme Court’s mail-ballot ruling and Trump’s escalating fight over the Kennedy Center.Alex Wagner’s “The Steal”: https://us.macmillan.com/books/9781250901637/thesteal/Start your free trial of Perplexity Computer today at https://pplx.ai/illegalnews and experience the next phase of AI. #adGet 15% off OneSkin with the code ILLEGALNEWS at https://www.oneskin.co/ILLEGALNEWS #oneskinpod #adReady to reach your goals? Visit https://www.forhers.com/illegalnews to get personalized, affordable care that gets you. Weight Loss by Hers is not available in all 50 states. Wegovy® is the registered trademark of Novo Nordisk A/S. To get started and learn more, including important safety information, Wegovy® clinical study information, and restrictions, visit https://www.forhers.com/illegalnews.

Andrew Weissmann turns the tables on Sarah Longwell for a conversation about her new book, How to Eat an Elephant: One Voter at a Time—and what a post-Trump political future could look like. They get into Trump’s unusual hold on his voters, the right-wing media ecosystem, why Democrats too often let polls dictate what they believe, and what years of listening to voters have taught Sarah about how to build a pro-democracy coalition that can actually win.Factor makes chef-crafted, dietitian-designed meals that are ready to eat in just two minutes, with no prep or cleanup. Choose from more than 100 menu items each week, including meals, snacks, and add-ons. Head to https://factormeals.com/illegalnews50off and use code illegalnews50off to get 50% off and 1 free breakfast item per box for 1 year, while supplies last until 10/31/2026.Weight Loss by Hers offers access to affordable, FDA-approved GLP-1 medications, including the Wegovy® pill and Wegovy® pen, with treatment handled 100% online. Connect with a licensed provider to see if treatment is right for you, and if prescribed, medication is delivered directly to your door. Visit https://forhers.com/illegalnews to get personalized, affordable care that gets you. Weight Loss by Hers is not available in all 50 states. Wegovy® is the registered trademark of Novo Nordisk A/S. To get started and learn more, including important safety information, Wegovy® clinical study information, and restrictions, visit https://forhers.com/illegalnews.Links:Buy Sarah's book, How to Eat an Elephant: One Voter at a Timehttps://us.macmillan.com/books/9781250464170/howtoeatanelephantGiuliano da Empoli, The Hour of the Predatorhttps://www.penguinrandomhouse.com/books/808353/the-hour-of-the-predator-by-giuliano-da-empoli/Julia Curlee, “The Wrong Kind of American” — The Atlantichttps://www.theatlantic.com/magazine/2026/10/trump-white-house-transgender-mike-pence/688284/Julia Curlee interview, “The Trump Administration Wanted Her Expertise, Just Not Her” — The Atlantichttps://www.theatlantic.com/podcasts/2026/08/ra-trans-cia/688289/

Sarah Longwell and George Conway discuss Trump’s attempt to overhaul mail-in voting before the midterms—and why Conway thinks the administration’s chaotic new USPS system is likely to lose when it gets back to the Supreme Court. They also cover SCOTUS letting Trump continue construction on his ballroom, the possibility that Democrats could stop the project in January, and the Epstein questions that still aren’t getting enough attention.Ready to reach your weight loss goals? Weight Loss by Hers offers access to personalized, affordable care, including FDA-approved GLP-1 medications such as the Wegovy® pill and Wegovy® pen. Visit https://www.forhers.com/illegalnews to get started and learn more, including important safety information, clinical study information, and restrictions. Weight Loss by Hers is not available in all 50 states. Wegovy® is the registered trademark of Novo Nordisk A/S.Factor makes chef-crafted, dietitian-designed meals that are ready in two minutes, with no prep or cleanup. Head to https://FactorMeals.com/illegalnews50off and use code illegalnews50off to get 50% off and 1 free breakfast item per box for 1 year, while supplies last until 10/31/2026.

Sarah Longwell and Andrew Weissmann discuss a pair of Supreme Court moves benefiting Trump, including John Roberts allowing construction on the White House ballroom to continue and a ruling affecting Trump’s plans for mail-in voting. They also examine Greg Abbott’s refusal to extradite an ICE officer accused of shooting a man and lying about it, a provocative case involving a traveler who wiped his phone rather than let border agents search it, and the unanswered questions surrounding Natalie Harp’s lack of a security clearance despite her extraordinary access to Trump.Ready to reach your goals? Visit https://forhers.com/illegalnews to get personalized, affordable care that gets you.Sleep cooler this summer with Boll & Branch. Get 15% off your first order plus free shipping at https://BollandBranch.com/illegalnews with code illegalnews. Exclusions apply.Use code ILLEGALNEWS at https://jonesroadbeauty.com to get a Free Gift with your first purchase! #JonesRoadBeauty #adSave 20% Off Honeylove by going to https://honeylove.com/ILLEGALNEWS! #honeylovepod

Andrew Weissmann joins Sarah Longwell to discuss the Trump administration’s move to erase corporate ownership records, the latest developments in the Fauci investigation, how a bizarre election controversy in Alaska led to a DOJ investigation, and what Democrats still need to learn about persuasion in the Trump era.Ready to reach your weight-loss goals? Visit https://www.forhers.com/illegalnews to get personalized, affordable care that gets you.Upgrade your everyday with Quince and get free shipping on your order and 365-day returns at https://www.quince.com/IILEGALNEWS.Make laundry day the best day of the week! Get 20% off your entire order with code ILLEGALNEWS at https://laundrysauce.com/ILLEGALNEWS #laundrysaucepod #adBulwark LIVE: GOOD FIGHT TOUR with Tim, Sarah, Sam and JVL is coming to the Southeast in October. Tickets go on sale August 21. Paid members of the Bulwark members get early access via our presale NOW. Head to https://www.thebulwark.com/Events for details and to get your tickets.

Sarah Longwell and Andrew Weissmann discuss the escalating campaign against Anthony Fauci, why his lawyers may see the congressional investigation as a perjury trap, and what happens now that his contempt referral is headed to Trump’s DOJ. They also take on Bill Cassidy’s vote to confirm Todd Blanche, Trump and RFK Jr.’s attacks on vaccines, and a stunning foreign bribery case involving a $10 billion investment offer, career DOJ prosecutors who wanted no part of the dismissal, and a federal judge questioning the administration’s reasons for trying to make the case disappear.Ready to reach your goals? Visit https://forhers.com/illegalnews to get personalized, affordable care that gets you.

Sam Stein and Andrew Weissmann discuss the Justice Department’s dismissal of charges over damage to the Lincoln Memorial Reflecting Pool, potential recourse for Olympian David Hearn, and Trump’s response. They also examine Todd Blanche’s Senate confirmation prospects, the proposed “anti-weaponization” fund and tax-immunity agreement, Capital One’s anti-money-laundering claims involving Trump Organization accounts, and Anthony Fauci’s decision to invoke the Fifth Amendment before Congress.Head to https://FactorMeals.com/illegalnews50off and use code illegalnews50off to get 50 percent off and 1 free breakfast item per box for 1 year, while supplies last until 10/31/2026.

Sam Stein and George Conway discuss James Comey’s challenge to the “8647” prosecution, Donald Trump’s Supreme Court bid to overturn E. Jean Carroll’s $83 million defamation judgment, and the administration’s push for new restrictions on mail-in voting. They also cover the withdrawal of subpoenas targeting New York Times reporters and the delayed Paramount-Warner Bros. merger.Get 15% off OneSkin with the code ILLEGALNEWS at https://www.oneskin.co/ILLEGALNEWS#oneskinpodGo to https://Dupe.com for their 100% Free Research for Me comparison shopping tool. Finally feel good about what you’re buying with Dupe.com.Ready to reach your goals? Visit https://forhers.com/illegalnews to get personalized, affordable care that gets you.

Sarah Longwell welcomes George Conway back to The Illegal News to discuss Trump Media’s plan to sell Wall Street firms early access to Trump’s market-moving Truth Social posts. They also talk about DOJ subpoenas targeting New York Times reporters and their families, Trump’s Qatar jet, the newly activated Alien Terrorist Removal Court, and the Paramount–Warner merger.Make laundry day the best day of the week! Get 20% off your entire order @LaundrySauce with code ILLEGALNEWS at https://laundrysauce.com/ILLEGALNEWS #laundrysaucepod