The Illegal News with Sarah Longwell
“The Illegal News” is where law meets politics. Each week, Bulwark publisher Sarah Longwell (not a lawyer) sits down with a legal expert to unpack how the latest court filings, rulings, and procedural twists and turns of the Trump era are shaping American democracy. These are conversations about justice without the jargon, giving you context for the biggest developments and surfacing the legal (and illegal) moves not getting enough attention. If you're looking for "George Conway Explains It All to Sarah Longwell," George is off on a new adventure, but Sarah will keep you covered.
Trump Keeps Trying to Jail His Enemies. Grand Juries Keep Saying NO (w/ Andrew Weissmann) | Illegal News
Sarah Longwell and Andrew Weissmann discuss Trump’s desperate (and failing) attempts to punish his political enemies, from a grand jury’s refusal to indict Cassidy Hutchinson to a judge’s ruling against the firing of Maureen Comey. They also examine the DOJ’s election interference in California and Alaska, troubling corruption allegations involving Susan Collins, and why the Epstein files remain a problem for Trump.
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Trump’s $10 Billion BBC Lawsuit Just Backfired (w/ Andrew Weissmann) | Illegal News
Why is Trump’s own Justice Department investigating Corey Lewandowski, and is the corruption probe for real? Sarah Longwell and Andrew Weissmann examine the allegations, Trump’s attempt to challenge 20,000 California voters, Russia’s latest election interference campaign, and the surprising turn in Trump’s $10 billion lawsuit against the BBC.
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DHS Raids Ilhan Omar’s Home. Weissmann Smells a Rat. | Illegal News
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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Andrew Weissmann Sees BIG Trouble for Trump in Deportation Showdown
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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Trump’s “Grand Conspiracy” Investigation Is Falling Apart From the Inside | Illegal News
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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Andrew Weissmann: Trump’s White House Press Ban Is Going to Lose in Court
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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Alex Wagner NUKES Alito’s Defense of the Trump Election Power Grab
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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Sarah Longwell's Message for Everyone Who Thinks We’re Doomed (w/ Andrew Weissmann)
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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Whistleblower Exposes Trump’s Election Chaos Machine (w/ George Conway)
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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Trump Is Racing to Build His Ballroom Before the Courts Stop Him (w/ Andrew Weissmann)
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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Trump Just Ordered the Government to Delete the Receipts (w/ Andrew Weissmann)
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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Career Prosecutors Wanted NO PART of What Trump’s DOJ Was Doing (w/ Andrew Weissmann)
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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Trump’s Reflecting Pool Case Collapsed in SPECTACULAR Fashion (w/ Andrew Weissmann) | Illegal News
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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George Conway: Trump Showed Up to the Trial and Lost $83 Million
Sam Stein and George Conway discuss James Comey’s challenge to the “8647” prosecution, Donald Trump’s Supreme Court bid to overturn E. Jean Carroll’s $83 million defamation judgment, and the administration’s push for new restrictions on mail-in voting. They also cover the withdrawal of subpoenas targeting New York Times reporters and the delayed Paramount-Warner Bros. merger.
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<...George Conway Is Back—and Trump Gave Him PLENTY to Work With
Sarah Longwell welcomes George Conway back to The Illegal News to discuss Trump Media’s plan to sell Wall Street firms early access to Trump’s market-moving Truth Social posts. They also talk about DOJ subpoenas targeting New York Times reporters and their families, Trump’s Qatar jet, the newly activated Alien Terrorist Removal Court, and the Paramount–Warner merger.
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Senators Never Asked Blanche the Most Obvious Epstein Question
Sarah Longwell and Andrew Weissmann discuss on a week that tested both of them: Todd Blanche's confirmation hearing, and Trump's prime-time speech on election interference. Andrew walks through the cross-examination Senate Democrats didn't run—the statements that went unchallenged, the follow-ups nobody asked, and the one question about the withheld Epstein files that Blanche has still never answered. Then: why he thinks dismantling the government's election-security apparatus isn't neglect, but the point.
Also discussed: the $1.776 billion payout, the document absolving Trump of tax liability, what Blanche told the Epstein victims that simply isn't true, and why Andrew ke...
Trump's Own Judge Torched DOJ's Insane Election Subpoena (w/ Andrew Weissmann)
Andrew Weissmann joins Sarah Longwell to discuss a big week in legal news: DOJ's stunning concession in a reporter's lawsuit over the Epstein files, the questions senators must make Todd Blanche answer at his confirmation hearing, and the Trump-appointed judge who torched DOJ's demand for the names of every 2020 election worker in Fulton County. Plus: the DOJ letter that signals a plan to challenge the 2026 midterms, and the Supreme Court's surprising ruling on your phone's location data.
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https://www.contrariannews.org/p/reining-in-a-rogue-supreme-court
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MAGA is Furious at Amy Coney Barrett (w/ Steve Vladeck)
Sarah Longwell and Georgetown University Law Center's Steve Vladek discuss the Supreme Court's final day of the term—a narrow 5-4 ruling upholding birthright citizenship, the court gutting independent agency protections (while carving out a suspicious exception for the Fed), and a rapid-fire tour through rulings on mail-in ballots, trans athletes, campaign finance, TPS for Haitians, and asylum seekers at the border. Plus: why Amy Coney Barrett has become the MAGA right's newest target, and what Steve thinks Alito is waiting for before he retires.
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The Reflecting Pool is a Symbol of Trump’s Failure (w/ Andrew Weissmann)
Sarah Longwell and Andrew Weissmann talk about the Iran nuclear deal—why the "win" Trump is selling actually leaves America with less leverage, fewer allies, and zero nuclear resolution than where we started. Plus: what Jonathan Swan and Maggie Haberman's book reveals about JD Vance's behind-the-scenes opposition to the war, Trump's habit of comparing himself to history's worst tyrants, and the new DOJ legal theory that could gut Americans' right to sue polluters under environmental law.
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Stephen Miller and JD Vance Wanted to Suspend Habeas Corpus (w/ Leah Litman)
Sarah Longwell is joined by law professor and Strict Scrutiny co-host Leah Litman to discuss the White House’s plan to suspend habeas corpus, JD Vance’s push to invoke the Insurrection Act, the Gavin Newsom investigation, and the 19 Supreme Court decisions that could reshape American democracy before the midterms.
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Trump’s Pick for Attorney General Is Even WORSE Than You Think
Trump's AG nominee Todd Blanche lost Trump's own criminal trial, built an illegal slush fund, and lied on Fox News—and Republicans are confirming him anyway. Sarah Longwell and Andrew Weissmann discuss what Democrats can actually do at the hearing, why Trump is screaming election fraud while gutting the unit that investigates it, and why his DOJ now holding the only copy of the Fulton County ballots should concern you. Plus: A federal judge ruled Trump's Kennedy Center takeover illegal, his lawyers told a court they could bulldoze the Statue of Liberty, and there's now a grotesque 92-foot metal st...
Trump’s AG Pick May Not Have the Votes to Get Confirmed
Sarah Longwell and Andrew Weissmann return to disuss Todd Blanche’s growing Senate confirmation problems, Trump’s $1.7 billion “weaponization fund” scheme, why the judge isn’t letting the case die, the DOJ’s targeting of Congress members and critics, potential Ghislaine Maxwell fallout, and the reason Weissmann thinks the case against John Bolton is different than other "revenge" prosecutions.
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Judge Nukes Trump DOJ’s “Vindictive” Prosecution (w/ Mary McCord) | Illegal News
Sarah Longwell welcomes Mary McCord—former DOJ prosecutor and co-host of the Main Justice podcast—to discuss a series of jaw-dropping legal scandals surrounding Trump’s Justice Department. They include the secretive $1.776 billion “slush fund” for January 6 defendants, a federal judge exposing shocking grand jury misconduct in the Broadview Six case, the collapse of the Kilmar Abrego Garcia prosecution, growing judicial distrust of DOJ lawyers, and what happens when prosecutors start acting like political operatives instead of officers of the court.
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Andrew Weissmann: Trump's Slush Fund Isn't Just Corrupt—It's a Crime
Andrew Weissmann joins Sarah Longwell on launch day for his book 'Liar's Kingdom'—but first they discuss why Weissmann calls Trump's $1.776 billion "anti-weaponization fund" an outright fraud on taxpayers. Then: why election lies are distinct even among Trump's 30,000 lies, what Brazil and the UK do to stop them, and the publisher that vanished the day after a Trump executive order. Plus mob bosses in bathrobes.
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Trump Built a System That Pays People to Break the Law (w/ Ben Wittes)
Sarah Longwell and Ben Wittes discuss the Supreme Court mifepristone fight and why it could reshape abortion politics for years to come, then dig into Trump’s proposed $1.7 billion “weaponization” fund for Jan. 6 allies, the DOJ’s effort to protect Jeffrey Clark, and Kash Patel’s increasingly bizarre behavior as FBI director.
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Jerome Powell is Fueled by Pure Righteous Anger—And We LOVE IT (w/ Andrew Weissmann)
Sarah Longwell and Andrew Weissmann discuss the Supreme Court’s voting rights decision, the rush to redraw congressional maps before the midterms, Trump allies pushing criminal investigations against political enemies, the escalating fight over Jerome Powell and the Federal Reserve, and the growing fears around abuse of FISA surveillance powers. Plus, Weissmann explains why the SPLC case is already DOA—and why he believes these moves are straight up authoritarian.
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SCOTUS Profoundly Changed Elections—Mid-Vote! (w/ Kate Shaw)
Kate Shaw—ABC News contributor and co-host of the podcast 'Strict Scrutiny'—joins Sarah Longwell to explain a major Supreme Court ruling that American elections. Then they discuss a string of notable legal news: a DOJ filing that reads like Trump wrote it himself, Trump suing his own government for $10 billion, and the indefensible Comey “seashell” indictment.
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Check out the Strict Scrutiny podcast: https://crooked.com/podcast-series/strict-scrutiny/
Kash Patel's Lawsuit Could Backfire—BIG TIME (w/ Andrew Weissmann)
Sarah Longwell and Andrew Weissmann discuss a series of major legal developments—from a questionable DOJ indictment targeting the Southern Poverty Law Center, to Kash Patel’s high-risk lawsuit against The Atlantic, to a wave of firings inside the Justice Department that’s raising alarms.
They explain what’s actually in these cases (and what’s missing), why some of the legal theories fall apart under scrutiny, and what it all signals about the direction of the DOJ. Plus: a major ruling on Trump’s January 6 liability—and whether taxpayers could end up footing the bill.
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Judge Tosses Trump’s WSJ Lawsuit Over Epstein Birthday Card (w/ Elliot Williams)
Sarah Longwell and Elliot Williams explain why courts keep rejecting Trump's defamation claims, what “actual malice” really means, and how his wave of lawsuits is really meant to pressure the media.
Plus: the bizarre Trump-as-Jesus post, the growing use of the justice system for retribution, and why targeting witnesses like Cassidy Hutchinson should set off alarms.
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Sorry, The 25th Amendment Can't Save Us From Trump (w/ Andrew Weissmann)
Sarah Longwell and Andrew Weissmann explain the legality of Trump’s unhinged Iran threats, the legal reality behind “war crimes” warnings, and the global fallout of a strategy with no clear objective. They also discuss Trump’s push to control elections, why it’s likely unconstitutional—and why losing in court may actually be part of the plan. Plus, the Steve Bannon case and what it says about a system where accountability depends on loyalty to the president.
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Reporters Now Need ESCORTS to Do Their Jobs at the Pentagon (w/ Elliot Williams)
Sarah Longwell and Elliot Williams explain a series of legal fights that go to the core of how the country operates—from whether birthright citizenship could actually be undone, to a new immigration detention policy that could keep people locked up for years.
They also discuss the Pentagon’s escalating clash with the press and what it means for the First Amendment and the surreal push to rewrite the January 6th attack on the Capitol.
Correction (March 31, 2026, 9:20 p.m. EDT): Elliot Williams mistakenly mentioned San Antonio, Texas as the location of a court conducting legal proc...
Todd Blanche’s Jaw-Dropping Ethics Violation (w/ Andrew Weissmann)
JVL (filling in for Sarah Longwell) joins Andrew Weissmann for a wide-ranging breakdown of a system under strain. They discuss the DOJ’s $1.25M payout to Michael Flynn, a surprising leak tied to the Trump investigations, and the backlash that followed—including a top official calling prosecutor Jack Smith a “proven liar.”
Buy "Liar's Kingdom”: https://linktr.ee/BulwarkLiarsKingdom
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Trump’s Half-Baked Border Plan Collides With Legal Reality (w/ Andrew Weissmann)
Andrew Weissmann joins Sarah Longwell to explain Trump’s failed attempt to target Fed Chair Jerome Powell—and why a judge shut it down as harassment. They also discuss the Trump admin's bizarre border strategy that’s collapsing in court, as DOJ lawyers admit they’re being forced to bring cases they can’t prove. Plus: a major Supreme Court fight over immigrant protections, and new warning signs around Trump’s broader legal strategy heading into 2026.
Review of State Bar Complaints and Allegations Against Department of Justice Attorneys: https://www.federalregister.gov/documents/2026/03/05/2026-04390/review-of-state-bar-complaints-and-allegations-against-department-of-justice-attorneys
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Trump's DOJ Just Proposed a Stunning Ethics Loophole (w/ Andrew Weissmann)
Sarah Longwell and Andrew Weissmann discuss a chaotic week for the rule of law, from the DOJ bizarrely flip-flopping on defending Trump’s executive orders targeting law firms, to a Trump-appointed judge finding evidence of racial profiling in ICE stops in Minnesota, and a new DOJ proposal that could shield government lawyers from ethics investigations.
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Andrew Weissmann: This is Why America’s Institutions Are Failing
Sarah Longwell talks with former federal prosecutor Andrew Weissmann about his new book: "Liar’s Kingdom"
They discuss how Donald Trump exposed weaknesses in American institutions, why misinformation has become so central to modern politics, and what that means for the future of democracy.
Weissmann explains why simply winning elections won’t fix the problem, explores how other democracies handle threats to the rule of law, and lays out reforms that could strengthen guardrails without rewriting the Constitution.
Buy "Liar's Kingdom":
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Is This War Legal? (w/ Tess Bridgeman)
Sarah Longwell talks with Just Security’s Tess Bridgeman about whether the Iran war is legal under the Constitution, the War Powers Resolution, and international law. They discuss how presidents have stretched their authority for decades, why Congress keeps failing to act, and what it means when one man can take the country to war on his own.
Read more from Tess: https://www.justsecurity.org/author/bridgemantess/
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Trump’s Face on DOJ Is a Big Deal—Here’s Why (w/ Elliot Williams)
Sarah Longwell is joined by CNN legal analyst Elliot Williams to break down Trump’s latest legal battles—from the Supreme Court limiting his tariff plan to a judge holding ICE in contempt for ignoring court orders.
They also discuss the FCC targeting late-night shows, questions about DOJ independence after Trump put his face on the building, and new reporting on the Epstein files.
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Supreme Court Slams Door on Trump’s Tariff Power Grab (w/ Andrew Weissmann) | Illegal News
The Supreme Court struck down Trump’s sweeping tariffs in a 6–3 decision—including votes from two of his own appointees. Sarah Longwell and Andrew Weissmann explain why the Court said Congress, not the president, controls the power to tax, what the “major questions” fight was really about, and why Chief Justice Roberts appeared to take direct aim at Kavanaugh’s dissent.
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They Don’t Want Borders. They Want Your Ballot (w/ Andrew Weissmann)
Andrew Weissmann explains to Sarah Longwell the new filing from officials in Georgia’s Fulton County election office attacking the FBI's search of the county's election records last month. They also discuss the latest around ICE cases in Minnesota and get to Sarah's rapid fire questions.
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In the Epstein Releases, Victims Came LAST (w/ Andrew Weissmann)
Andrew Weissmann explains to Sarah Longwell why Pam Bondi’s bizarre hearing indicates deep problems at the Justice Department. From the DOJ’s handling of the Epstein files to the FBI’s raid on Georgia’s Fulton County election office, they discuss what’s happening behind the scenes—and whether core legal standards are being ignored.
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