The Illegal News with Sarah Longwell
The Illegal News is a podcast where law meets politics. Each week, host Sarah Longwell, publisher of The Bulwark, talks with a legal expert to break down the latest court filings, rulings, and procedural developments of the Trump era. The show aims to explain how these legal moves shape American democracy, without the jargon. It provides context for major news and highlights legal and illegal actions that may be overlooked.
Episodes
S2 Ep180: 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 defianc
S2 Ep179: 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 decis
S2 Ep178: 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 Ca
S2 Ep177: 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://u
S2 Ep176: 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
S2 Ep175: 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 th
S2 Ep174: 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 h
S2 Ep173: 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.Ready to reach your weight-loss goals? Visit https://www.forhers.com/illegalnews t
S2 Ep172: 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 bil
S2 Ep171: 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 Orga
S2 Ep170: 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.Get 15% off OneSkin w
S2 Ep169: 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.Make laundry day the best day
S2 Ep168: 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 answ
S2 Ep167: 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 challen
S2 Ep166: 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 se
S2 Ep165: 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 n
S2 Ep164: 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.Make laundry day the best day of the week! Get 20% off your entire order @LaundrySau
S2 Ep163: 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 ball
S2 Ep162: 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.Sig
S2 Ep161: 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 prose
S2 Ep160: 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 boss
S2 Ep159: 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.Get 15% off OneSkin with the code ILLEGALNEWS at https://www.oneskin.co/
S2 Ep158: 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 alrea
S2 Ep157: 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.Start your new morning ritual & g
S2 Ep156: 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 und
S2 Ep155: 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.Get 15% off OneSkin with the code
S2 Ep154: 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 s
S2 Ep153: 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 t
S2 Ep152: 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/BulwarkLiarsKingdomMake this the yea
S2 Ep151: 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 ar
S2 Ep150: 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.Get OneSkin with 15% off using code ILLEGALNE
S2 Ep149: 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 t
S2 Ep148: 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/autho
S2 Ep147: 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.Get 15% off OneSk
S2 Ep146: 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.Make laundry day the best d
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.Make laundry day the best day of the week! Get 20% off your entire order @LaundrySauce with code ILLEGALNEWS at
S2 Ep145: 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.Get 15% off OneSkin with the code ILLEGALNEWS at https://www.onesk
S2 Ep144: Trump Is Treating Elections Like Crimes (w/ Elliot Williams)
Sarah Longwell and CNN legal analyst Elliott Williams walk through a stunning week of norm-breaking: the arrest of journalists after a Minnesota protest, Trump hovering over federal law enforcement, an FBI raid on a Georgia election office, and open talk of "nationalizing" U.S. elections. They also discuss Trump’s jaw-dropping $10 billion lawsuit against the IRS and his move to take over—and pote
S2 Ep143: Secret ICE Memo Says They Can Enter Homes Without Warrants (w/ Elliot Williams)
Sarah Longwell is joined by former ICE attorney and CNN legal analyst Elliot Williams to discuss the growing clash between ICE, the Justice Department, and the courts. Williams explains why a federal judge in Minnesota is threatening contempt after ICE ignored a court order, and why DOJ’s response—appealing denied arrest warrants tied to a church protest—stunned the court. They talk about a secre
S2 Ep142: The Epstein Files Are Being Buried by DOJ (w/ Asha Rangappa)
Asha Rangappa joins Sarah to discuss the ICE raids in Minnesota, a federal court injunction limiting certain actions against protesters, DOJ retaliation, the stalled Epstein files release, and the growing use of law enforcement as a political weapon.Read the Ruling Restricting Federal Agents’ Actions in Minnesota: https://storage.courtlistener.com/recap/gov.uscourts.mnd.229758/gov.uscourts.mnd.22
S2 Ep141: Jack Smith Says He Had Trump Dead to Rights (w/ Asha Rangappa)
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.Get up to 30% off OneSkin with the code ILLEGALNEWS at https://www.oneskin.co/Make laundry
S2 Ep140: Trump’s Government is Treating Courts Like a Joke (w/ Andrew Weissmann)
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.Start your new morning ritual & get up to 43% off your @MUDWTR with code illegalnews at https://mudwtr.com/illegalnews! #mudwtrpodHead to https://FactorMea
S2 Ep139: Andrew Weissmann: Epstein Release Looks Like a DOJ Cover-Up
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.Our listeners get the Harry’s Plus Trial S
S2 Ep138: Yes, George Had to Leave. But We’re Still Here.
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.Go to https://HelloFresh.com/askgeorge10fm to get 10 free meals and a FREE Zwilling Knife (a $144.99 value) on your third box. Offer valid while supplies last. Free meals applied as discount on first
S2 Ep137: George Conway Has an Announcement
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.Get your free, personalized assessment and the best option for you at
S2 Ep136: Running the Same Dead Case Back to Another Grand Jury? That’s Desperation.
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.This holiday, give your loved ones the only gift that keeps on giving — h
S2 Ep135: Sarah and George Answer YOUR Questions!
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.Find your forever cookware @hexclad visit https://hexclad.com! #hex
S2 Ep134: George Conway: How Trump Plans to Bury the Epstein Files
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
S2 Ep133: How the DOJ Turned Its Easiest Case Into Trump’s Escape Hatch
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.Learn a new Language and get up to 55% off your subscription at https://Babbel.com/ASKGEORGE.Get 15% off One
S2 Ep132: Trump’s DOJ Lost to a Hoagie (w/ Sam Stein & Steve Vladeck)
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
S2 Ep131: Trump’s White House Fired Prosecutors for Telling the Truth!
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.Start your new morning ritual & get up to 43% off your @MUDWTR with code ASKGEORGE at https://mudwtr.com/ASKGEORGE! #mudwtrpod
S2 Ep129: Conway Explains: Trump Picked the Least Qualified Person He Could Find
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/GC21UQuxjRIGet 50% off your first order with Factor
S2 Ep128: John Bolton's Own Book Might Destroy Him
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
S2 Ep127: Is This The DUMBEST Scandal in History?
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.F*%k your khakis and get The Perfect Jean 15% off with the code ASKGEORGE15 at https://theperfectjean.nyc/ASKGEORGE15 #theperfectjeanpod
S2 Ep126: Trump’s Corruption Is as Stupid as It Gets
George Conway joins Sarah Longwell to talk the illegal news as Trump’s authoritarian playbook ramps up with attacks on free speech, politicizing the military, prosecuting enemies, and weaponizing the funding fight as Democrats refuse to bankroll Trump’s corrupt, authoritarian agenda. Plus, a revisiting of Conway’s prescient warnings from 2024 on Jimmy Kimmel Live.To get 50% off your first order fr
S2 Ep125: Trump Went Too Far? Comey & Kimmel Could Galvanize Americans (w/ Andrew Weissmann)
Donald Trump’s DOJ just indicted James Comey—but is the case already falling apart? Sarah Longwell and Andrew Weissmann (filling in for George Conway) get into why this prosecution is weak, dangerous, and could blow up in Trump’s face.
S2 Ep124: Conway DESTROYS Trump’s Pathetic “RICO for Protests”
JVL (sitting in for Sarah) is joined by George Conway to talk the administration’s “mob government” vibes, torching Todd Blanche’s RICO spin, the FCC squeeze on Kimmel, Trump’s $15B New York Times suit, and the Supreme Court’s shadow-docket green light on ICE profiling, plus why Fed independence is now on the line.Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/ASKGEORGE!
S2 Ep123: District Judges ARE Standing Up To Trump! But Will SCOTUS?
George Conway explains to Sarah Longwell the week’s most important legal news—from the Epstein files and Harvard’s lawsuit to Trump’s use of emergency powers, tariffs, and the fight for Fed independence.If you’re 21 or older, get 25% OFF your first order + free shipping @IndaCloud with code ASKGEORGE at https://inda.shop/ASKGEORGE #indacloudpodF*%k your khakis and get The Perfect Jean 15% off with
S2 Ep122: Grand Juries Are Resisting Trump’s Show Trials (w/ Andrew Weissmann)
Sarah Longwell is joined by Andrew Weissmann to break down Trump’s latest power grabs — from sending the National Guard into blue cities, to attempting to fire the Fed governor, to RFK Jr.’s anti-vax chaos at the CDC. Weissmann explains how courts, grand juries, and even officials are pushing back, what it means for democracy, and where the real dangers lie.Get 50% off your first box with Factor a
S2 Ep121: Pam Bondi’s Overreach Blows Up in Her Face
George Conway explains to JVL how Pam Bondi’s failed attempt to seize control of DC’s police exposed Trump’s push for total power — and why it’s a warning of what could come next. From the absurd “felony sandwich” case to Trump’s open threats on Truth Social, Conway lays out how the rule of law is being twisted to protect the powerful and punish the weak.Start your new morning ritual & get up
S2 Ep120: The DOJ Has Lost Their Damn Minds!
George Conway joins Sam Stein to explain the mounting legal and political chaos surrounding Trump and his allies. From the DOJ’s bizarre handling of the Epstein fallout—including Ghislaine Maxwell’s taped interview and Todd Blanche’s rumored Rogan appearance—to the escalating redistricting war in Texas—Tulsi Gabbard’s reckless document release, and Trump’s alleged meddling in the New York mayoral
S2 Ep119: Trump is Facing a MAJOR Judicial Backlash
George Conway explains to JVL what’s really going on with Trump’s obsession over Jeffrey Epstein, suspicious secret DOJ meetings, and a brewing judicial backlash against Trump’s persistent lying and disregard for the courts. Plus, George breaks down the controversial confirmation of Emil Bove and how it could reshape the courts for decades.Get a three-month unlimited wireless plan for $15/month fr
S2 Ep118: Trump’s Epstein Panic Is Loud and Clear
George Conway and JVL discuss the Epstein files—why Trump might be hiding them, whether Ghislaine Maxwell will be rebranded as a MAGA martyr, and how the conspiracy theorists demanding answers could turn on Trump himself. They also take on Trump’s surreal accusations against Obama, the legal chaos surrounding Columbia’s $200 million settlement, and why Alina Habba’s implosion as U.S. Attorney migh
S2 Ep117: Why The Supreme Court Is Broken (w/ Leah Litman)
Sarah Longwell is joined by Leah Litman, professor of law at the University of Michigan Law School and co-host of the Strict Scrutiny podcast, to discuss the Supreme Court's troubling shift toward partisanship, Justice Amy Coney Barrett’s ideological battles, and Justice Ketanji Brown Jackson’s decision to openly criticize the Court’s Trump-friendly rulings. Can anything fix the Supreme Court? Lit
S2 Ep116: Could Trump DEPORT Elon Musk?
George Conway explains to JVL why Trump’s billion-dollar settlement with Shari Redstone might be legalized bribery, the disturbing reality behind Trump’s immigration detention camps, whether Elon Musk could really face denaturalization, and how the Supreme Court’s latest moves could once again shield Trump from accountability.Bulwark+ members get exclusive access to the FULL episode! You can join
S2 Ep115: Lawless DOJ, Shadow SCOTUS, and Harvard Hate
George Conway and JVL break down a stunning whistleblower complaint accusing former Acting Deputy AG Emil Bove of telling colleagues the DOJ should ignore court orders and deport migrants anyway. They explore the Supreme Court’s unexplained decision enabling deportation to dangerous countries, the Kafkaesque Abrego Garcia case, and the GOP’s broader assault on Harvard. It’s a legal and political b
S2 Ep114: Conway Explains: Trump Is a Man With No Plan
George and Sarah dig into Donald Trump’s legal circus—his sociopathic impulses, his warped view of presidential power, and his team’s nonstop efforts to delay accountability. From a Ninth Circuit procedural win on National Guard deployment, to recycled immunity claims, to the latest twists in the E. Jean Carroll case, Conway and Longwell explain why Trump’s ego—not the law—drives it all.
S2 Ep113: Trump Keeps Lying And The Courts Know It
George Conway is joined by JVL, sitting in for Sarah Longwell, to break down the legal challenges to the federal use of the National Guard in California, how the administration is not following the laws as they are written, and how Newsom can continue to challenge the overreach. Also, they discuss the confrontation involving Senator Padilla that even shocked Corey Lewandowski, and how Trump’s sil
S2 Ep112: Trump Slams Federalist Society
George Conway and Sarah Longwell discuss Donald Trump’s investigation into Joe Biden’s presidency, Trump’s new travel ban on 12 countries, and Trump’s retaliation against Harvard and foreign exchange students. Also, another judge slams Trump’s use of the Alien Enemies Act to deport without due process, and Trump's fight with Leonard Leo and the Federalist Society.F*%k your khakis and get The Perfe
S2 Ep111: Trump’s DOJ Plays Dirty — SCOTUS Isn’t Having It
George Conway joins Sarah Longwell to explain the latest legal messes in Trump World — from Judge Ho’s cringe-worthy SCOTUS audition, to Kristi Noem’s complete ignorance of basic constitutional rights, to the potential bribery scandal involving Paramount and a bogus Trump lawsuit. Plus: why Amy Coney Barrett is suddenly the right’s new punching bag, and how the Supreme Court just exposed the admin
S2 Ep110: Trump’s SCOTUS Judges Humiliate Him
George Conway and Sarah Longwell talk the Supreme Court case on nationwide injunctions, the Trump administration’s attempts to undermine birthright citizenship, and why a $400M plane from Qatar raises serious constitutional questions.Go to https://surfshark.com/askgeorge or use code ASKGEORGE at checkout to get 4 extra months of Surfshark VPN!F*%k your khakis and get The Perfect Jean 15% off with
S2 Ep109: Judge After Judge Slaps Down Trump
George Conway and Sarah Longwell discuss Ed Martin’s nomination for US Attorney for DC being dropped, the 102 page opinion striking down the executive order targeting law firm Perkins Coie, more district courts block Trump’s use of the Alien Enemies Act while continuing to roadblock bringing Kilmar Abrego Garcia home, and Donald Trump’s refusal to uphold the constitution.For a very limited time, s
S2 Ep108: Conway Explains: The Dumbest Fight Trump Ever Picked
George and Sarah break down Trump’s latest legal circus—from the outrageous deportation overreach using the Alien Enemies Act to the shady crypto scheme no one’s talking about. They also unpack the arrest of a Milwaukee judge and Trump’s threat to strip Harvard’s tax status. This week, the stupidity is off the charts
S2 Ep107: Conway Explains: Trump Is A MENACING CLOWN!
George and Sarah unpack a week of jaw-dropping legal drama: from Trump’s middle-of-the-night deportation schemes to the Supreme Court’s surprising resistance, and Harvard’s bold legal pushback against the administration.They break down due process violations, SCOTUS maneuvering, and the growing culture of contempt in Trump’s orbit.
S2 Ep106: Reagan Judge Shuts Down Trump
A Reagan-appointed judge just delivered a powerful rebuke to Trump’s lawless deportation tactics. George Conway and Sarah Longwell break down the powerful message and what it means for the fight to save the rule of law as Trump’s deportations and attacks on institutions, including Harvard, are hitting resistance.
S2 Ep105: “The Level of Stupid is Just Tremendous”
George Conway joins Sarah Longwell to discuss the Supreme Court ruling people detained by the Alien Enemies Act are entitled to due process, the footnote in Justice Jackson’s dissent, the lawyer put on leave after telling the truth about a man sent to El Salvador, and more Trump executive orders against law firms and two for investigation into two former government employees who have spoken out ag
S2 Ep104: Conway’s FURY: “How Can You Look Yourself in the Mirror?”
Sarah Longwell and George Conway discuss a powerful letter by lawyer Paul Weiss’s granddaughters on the importance of the rule of law, the legality of recent deportations and their implications for American citizens, market reactions to “Liberation Day,” and whether Trump could legally pursue a third presidential term.
S2 Ep103: “What They’re Doing is Profoundly Evil and Wrong”
George Conway explains to JVL the backlash against Trump’s new executive order targeting law firms. They also discuss the legal implications surrounding Rumeysa Ozturk, the Tufts graduate student detained by ICE, and Columbia graduate student Mahmoud Khalil, currently being held in Louisiana, and the legality around the ICE agents being masked. Plus, the controversy over sending detained individua
S2 Ep102: The Most Disgraceful Action By A Law Firm Ever (w/ Tim Miller)
George Conway joins Tim Miller to discuss the law firm Paul Weiss bending to Donald Trump in order to have an executive order rescinded, with the exchange of pro bono lawyer support towards the administration. Read More in Morning Shots, "Big Law’s Big Capitulation"
S2 Ep101: Is Trump Declaring War on Courts?
Trump just tested the limits of executive power by deporting hundreds of Venezuelans, despite a federal court order against it. Are we headed toward a constitutional crisis? George Conway explains why Trump’s actions threaten constitutional protections, and what happens if presidents ignore judges.
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