The Illegal News with Sarah Longwell

Latest Episodes:

S2 Ep141: Jack Smith Says He Had Trump Dead to Rights (w/ Asha Rangappa) Jan 14, 2026

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Sarah Longwell sits down with Asha Rangappa—a lecturer at Yale Law School and co-host of the “It’s Complicated” legal podcast—to discuss Venezuela, Jack Smith's congressional testimony, the Minneapolis shooting, and the many other high-profile lawsuits and investigations that have already popped up in 2026.

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S2 Ep140: Trump’s Government is Treating Courts Like a Joke (w/ Andrew Weissmann) Jan 09, 2026

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Sarah Longwell sits down with Andrew Weissmann to break down a fatal ICE shooting in Minnesota, shocking detention conditions exposed by a federal judge, and a growing pattern of the government misleading courts and defying judicial orders.

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S2 Ep139: Andrew Weissmann: Epstein Release Looks Like a DOJ Cover-Up Jan 02, 2026

Show notes

Sarah is off this week so Andrew Weissmann joins Sam Stein to explain why the Epstein files rollout has become a legal and political disaster—from blown deadlines and redactions to the DOJ’s credibility crisis. They also discuss Supreme Court’s spotty pushback against the administration, Trump’s use of military power, and growing risks to democratic norms.
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S2 Ep138: Yes, George Had to Leave. But We’re Still Here. Dec 27, 2025

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George Conway is stepping away to run for Congress — but the show isn’t ending! Sarah Longwell explains what’s changing, what isn’t, and why The Bulwark is sharing a full episode of The Secret Podcast.
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S2 Ep137: George Conway Has an Announcement Dec 20, 2025

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George Conway and Sarah Longwell close out the year—and this chapter of the show—with a conversation on the legal chaos of the Trump era. They discuss Trump’s attacks on the media, the chilling effect of defamation suits and settlements, the collapse of the DOJ, and growing concerns about courts, contempt, and judicial authority.
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S2 Ep136: Running the Same Dead Case Back to Another Grand Jury? That’s Desperation. Dec 10, 2025

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George explains to Sarah the Supreme Court’s newest fights, Trump’s push to control independent agencies, the mess inside his DOJ, the failed effort to indict Letitia James, Alina Habba’s pitiful stint as U.S. attorney, and why the Epstein grand-jury files are finally being forced into the open under the new transparency law.
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S2 Ep135: Sarah and George Answer YOUR Questions! Dec 01, 2025

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Sarah Longwell and George Conway answer listener questions in a special mailbag episode, taking on the Supreme Court’s “shadow docket,” DOJ and court reform, post-Trump conservative rethinks, and George lists his many guitars. Plus, George explains the Lindsey Halligan ruling and what it means for the Comey and Letitia James cases.
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S2 Ep134: George Conway: How Trump Plans to Bury the Epstein Files Nov 24, 2025

Show notes

Note: This episode was recorded on Thursday, November 20.
Sarah Longwell and George Conway reflect on Dick Cheney’s funeral and contrast his final defense of democracy with Trump’s authoritarian impulses. They also discuss Trump’s attacks on Democratic veterans after video reminding service members they do not need to obey illegal orders, the continuing Epstein files fight, Texas’ gerrymander, and the Comey case unraveling.
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S2 Ep133: How the DOJ Turned Its Easiest Case Into Trump’s Escape Hatch Nov 17, 2025

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George Conway is joined by Carol Leonnig and Aaron Davis to discuss their new book ‘Injustice’, exploring how the DOJ handled Trump-related investigations from 2017 to the present, including delays, internal hesitations, and decisions that shaped the January 6 and classified documents cases.
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S2 Ep132: Trump’s DOJ Lost to a Hoagie (w/ Sam Stein & Steve Vladeck) Nov 10, 2025

Show notes

George Conway explains to Sam Stein (sitting in for Sarah Longwell) the “sandwich man” acquittal, and why tossing a wrapped hoagie at a Kevlar-clad officer wasn’t “forcible assault”, plus the collapsing Comey case built on shaky indictments, dubious authority, and a near-certain legal dead end. Then, George is joined by Steve Vladeck to discuss the Supreme Court’s review of Trump’s tariffs, where questions on limits and delegation hint the justices may strike them down.
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