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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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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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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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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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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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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George Conway explains to Sarah Longwell Trump’s Orwellian purge of DOJ prosecutors over January 6th, and the legal contortions fueling his push for authoritarianism, from National Guard moves to third-term loop holes.

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George Conway explains to Sarah another week of legal chaos, with prosecutor Lindsey Halligan’s bizarre texts, the illegal U.S. boat strikes in the Caribbean, Trump’s $230 million claim against his own government, and the ACLU defending a man arrested for playing the Darth Vader theme.

Show Notes:

Tim’s conversation with Anna Bower https://youtu.be/GC21UQuxjRI

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George Conway explains to Sarah Longwell how the indictment of John Bolton fits into Donald Trump’s broader pattern of targeting critics — but also why Bolton’s case may have more substance than Trump’s other so-called “revenge prosecutions.” They discuss what makes the Bolton charges different, the double standard around classified information, and how Trump’s effort to label peaceful protests as “rebellion” reveals his authoritarian instincts.

Sarah Longwell and George Conway discuss Trump’s fake prosecutions of Comey and Letitia James, the “Truth Social DM” fiasco, and his escalating use of the National Guard to provoke chaos — plus why Americans aren’t taking the bait.

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