
Serious Trouble
An irreverent podcast about the law from Josh Barro and Ken White. www.serioustrouble.show
Latest episodes

May 7, 2025 • 47min
Voir Diddy
This week on the show: Jury selection for Sean Combs' eight-week RICO trial, which is moving along very quickly for for a complex federal criminal case.Plus: a ruling in the Alien Enemies Act cases, a ruling that gets at the heart of the policy question: whether there is an “invasion” or “predatory incursion” that triggers presidential powers under the law in the first place. It's a strange one.Another long-running case where ICE contends it doesn’t matter that it violated a court order about how to remove a person due for deportation, since he’d still be removable even if they did everything right.Long-Suffering Federal Judge Beryl Howell takes a shot at the many firms that chose to settle with the Trump administration instead of fighting. Meanwhile, the firms that settled have been insisting that they agreed to very little, and we may be about to get some information about how true that is.Visit serioustrouble.show to sign up for our newsletter and find a transcript of this episode. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.serioustrouble.show/subscribe

May 2, 2025 • 29min
Please Forget My Oopsie
Dive into the complex world of immigration law where a judge's arrest and controversial gang membership designations spark intense debate. Discover the legal obstacles faced during the Trump administration, revealing flaws in evidence and civil liberty concerns. The mishaps of filing internal deliberations publicly serve as a cautionary tale. Get insights on George Santos's potential prison time and the reasons behind Sarah Palin's legal setbacks against The New York Times. Prepare for a rollercoaster of legal intrigue and unexpected twists!

Apr 23, 2025 • 43min
The Emerging Presumption of Irregularity
Harvard is pushing back against the Trump administration's attempts to impose federal control, raising questions about academic freedom. The Supreme Court recently challenged the government on deportation orders linked to the Alien Enemies Act. Tensions between the press and administration are highlighted as the Associated Press faces exclusion from press pools. Additionally, legal battles around high-profile defamation and bribery cases reveal complexities in accountability and the justice process, painting a vivid picture of today’s legal landscape.

Apr 12, 2025 • 41min
Please Explain What You Mean By 'Effectuate'
The Supreme Court's involvement in Trump’s executive orders is heating up. Detainees are entitled to due process, but must navigate habeas corpus petitions. The complexities of the Alien Enemies Act expose tensions between deportation rights and government enforcement. A case raises alarms about free speech, as the federal government tries to revoke green cards based on political expression. Additionally, the podcast dives into media access issues and high-stakes mediation dynamics, revealing the intricate dance between law, politics, and individual rights.

Apr 4, 2025 • 26min
Venue and Jurisdiction
Dive into the cat-and-mouse game of legal venue and jurisdiction, where a misstep can cost you dearly. Discover how the Trump administration's policies complicate immigration cases and challenge law firms. Hear insights on political corruption in law, including a high-profile case dismissal that casts doubt on judicial integrity. Explore how shifting political landscapes affect legal strategies and the survival of firms. This thought-provoking discussion reveals the intricate web of law, power, and justice.

Mar 27, 2025 • 47min
Please Don't Hit Me
Paul Weiss is the third law firm to come under attack from the Trump administration and the first one to cut a deal, agreeing to certain terms about its practices in exchange for Trump withdrawing an executive order that effectively aimed to bankrupt the firm. The firm had different things to say about the agreement than Trump did — and we discuss what a capitulation like this might do for its business, staffing and more at Paul Weiss and throughout Big Law.Plus: Columbia University has similarly given in to demands from the administration, an appeals court panel has backed up Judge James Boasberg, declining to disturb his temporary restraining order that bars the administration from more renditions under the Alien Enemies Act, for now. And the Houthi war planning Signal chat is now the subject of a lawsuit — also before Judge Boasberg, lol — alleging that the administration is disobeying the Federal Records Act by setting those messages to auto-delete.Visit serioustrouble.show to sign up for our newsletter and find episode transcripts. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.serioustrouble.show/subscribe

Mar 20, 2025 • 45min
Please Take Judicial Notice that Drake Is a Little Bitch
The latest, most brutal entry in the rap battle between Kendrick Lamar and Drake comes in the form of a motion to dismiss. Drake, you will remember, sued Lamar’s record label (which is also Drake’s record label) for defamation, alleging that Lamar’s hit single “Not Like Us” defames him by calling him a pedophile. But as UMG’s attorney Rollin Ransom points out, rap battles are well known to feature hyperbolic accusations and insults that are not necessarily factual, which means they are unlikely to be defamatory. Plus, Drake explicitly dared Lamar to call him a pedophile — or, more specifically, Drake released a track in which he used an AI-generated Tupac Shakur voice to urge Lamar to “talk about [Drake] likin’ young girls.” It’s all very embarrassing, but as Ken notes, while UMG has a strong argument that it did not assist in defaming its own client, their argument is one a judge might not agree to consider in its entirety at this stage in the case.Plus: Trump tries to give Paul Weiss the Perkins Coie treatment, several of Trump’s major executive actions are facing new roadblocks in the courts, Nancy Mace faces a defamation lawsuit where the speech or debate clause is likely to provide her an important shield, and Ed Martin continues to Ed Martin.Visit serioustrouble.show to find a transcript of this episode, relevant links and to sign up for our newsletter. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.serioustrouble.show/subscribe

Mar 14, 2025 • 30min
At Least Everyone Knows How to Pronounce It Now
This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showFor all subscribers: we have a discussion of President Trump’s jihad against Perkins Coie, and Long-Suffering Federal Judge Beryl Howell’s lack of patience for it. And we talk about the arrest of green card-holder Mahmoud Khalil at Columbia University — and the efforts of the Trump Administration to expel him using little-used but very broad powers for the Secretary of State to expel aliens on the grounds that their presence would have “potentially serious adverse foreign policy consequences for the United States.”For paying subscribers:* The Trump administration’s effort to revoke hundreds of millions of dollars in grants to Columbia, on the grounds that the university has violated Title VI.* Ed Martin’s vague-yet-menacing letter to Georgetown Law School, saying he is conducting an “inquiry” into the school’s alleged teaching of DEI. * Updates on multiple cases where government lawyers say something in court and Trump administration officials say something else online that undermines their case.* The advice Paul Clement gave Dale Ho about Eric Adams, how Sam Bankman-Fried got himself thrown into solitary confinement by giving a jailhouse interview to Tucker Carlson, and some tips on best practices for distributing a podcast from federal prison, whether or not you are George Santos.

Mar 5, 2025 • 40min
Short Staffing
Acting US Attorney for the District of Columbia Ed Martin continues to make bizarre and political use of the DOJ for Trump’s political purposes — this time, he's trying to impanel a grand jury to hear evidence about heated political remarks Sen. Chuck Schumer made in 2020 about Supreme Court justices. It hasn't worked, and neither has his effort to get a magistrate judge to approve a warrant to freeze the bank account of an environmental organization. Plus: why lawyers working on EO litigation may be showing up unprepared, Tina Peters, George Norcross III, and where to sue if you have a Brazilian business dispute.Visit serioustrouble.show to sign up for our newsletter and find a transcript of this episode. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.serioustrouble.show/subscribe

Feb 27, 2025 • 40min
The New George Santos
The podcast dives into the legal showdown between the Associated Press and the Trump administration over press access. It explores Ed Martin’s politically charged letters targeting Democrats and the implications for due process. Discussions also touch on Sam Bankman-Fried’s self-victimization strategies from prison and the complexities of pardon applications linked to January 6th. Additionally, the episode scrutinizes a controversial Iowa poll and the ensuing lawsuit by Donald Trump, highlighting the intersection of polling accuracy and First Amendment rights.
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