S2 Ep180: Andrew Weissmann Sees BIG Trouble for Trump in Deportation Showdown

Why is Trump’s own Justice Department investigating Corey Lewandowski, and is the corruption probe for real? Sarah Longwell and Andrew Weissmann examine the allegations, Trump’s attempt to challenge 20,000 California voters, Russia’s latest election interference campaign, and the surprising turn in Trump’s $10 billion lawsuit against the BBC.Weight Loss by Hers offers access to FDA-approved GLP-1 medications, including the Wegovy® pill and pen, plus personalized support. Visit https://forhers.com/illegalnews to get started and learn more.

Sarah Longwell and Andrew Weissmann discuss the FBI raid on Ilhan Omar, Trump’s latest overtures to Putin, and the courts’ efforts to stop his taxpayer-funded campaign ads. Plus, Weissmann explains why simply ordering Trump to stop breaking the rules isn’t enough, and whether DOJ lawyers pursuing politically motivated prosecutions could eventually face disbarment.Celebrate Carbsgiving, Wildgrain’s biggest sale of the year! Get $40 off your first box of delicious sourdough breads, pastries, and more, PLUS free croissants for life. Visit https://wildgrain.com/ILLEGALNEWS40 or use code ILLEGALNEWS40 at checkout.Get 15% off OneSkin, including their new OS-01 FACE RICH CREAM, with code ILLEGALNEWS at https://www.oneskin.co/ILLEGALNEWS. #oneskinpod #adUse code ILLEGALNEWS at https://www.jonesroadbeauty.com to get a FREE full-sized mascara with your first purchase! #JonesRoadBeauty #ad

Sarah Longwell and Andrew Weissmann explain the explosive Kimberly Guilfoyle corruption allegations, including the $100,000 Amex payment, incriminating text messages, and why Trump might be reluctant to turn against her. Plus, Weissmann explains why Trump’s $5,000 election promise could constitute a crime, how a federal judge shut down a Trump DOJ prosecution, and why the administration’s defiance of court orders in its El Salvador deportations could still have serious consequences.Get 50% off Factor’s chef-crafted, ready-to-eat meals, plus one free breakfast item per box for one year! Visit  https://⁠FactorMeals.com/illegalnews50off and use code illegalnews50off. Offer valid while supplies last through October 31, 2026. See website for details.

Sarah Longwell and Andrew Weissmann discuss Jack Smith’s latest Senate testimony, including the questions Republicans didn’t ask about the actual cases against Trump and the Eric Schmitt gotcha that blew up in spectacular fashion. They also dig into the turmoil inside Trump’s DOJ, the fight over White House press access, Trump’s $1.776 billion “slush fund” case, and a Supreme Court election decision ahead of the midterms.Explore personalized weight loss care from Hers, including access to Wegovy®. Learn more at https://forhers.com/illegalnews

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.