The Illegal News with Sarah Longwell

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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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.

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Links:

Buy Sarah's book, How to Eat an Elephant: One Voter at a Time
https://us.macmillan.com/books/9781250464170/howtoeatanelephant

Giuliano da Empoli, The Hour of the Predator
https://www.penguinrandomhouse.com/books/808353/the-hour-of-the-predator-by-giuliano-da-empoli/

Julia Curlee, “The Wrong Kind of American” — The Atlantic
https://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 Atlantic
https://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.

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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.

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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.

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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.

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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.

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