S2 Ep151: Trump’s Half-Baked Border Plan Collides With Legal Reality (w/ Andrew Weissmann)

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 #ad Use 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 #laundrysaucepod Weight 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/illegalnews Show 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/447368 Paramount 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. #ad Get 15% off OneSkin with the code ILLEGALNEWS at https://www.oneskin.co/ILLEGALNEWS #oneskinpod #ad Ready 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.