The Illegal News with Sarah Longwell

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.
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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.
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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.
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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.
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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/
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