• The Emerging Presumption of Irregularity
    Apr 23 2025

    This week, Ken and I have a discussion of Harvard’s lawsuit fighting the Trump Administration’s effort to punish the university for failing to submit to what amounted to a demand to place the university in a kind of federal receivership. We look at the Supreme Court's middle-of-the-night, weekend rebuke to the Trump administration, ordering a halt to Alien Enemies Act removals from the Northern District of Texas. The subtext of this order is that four of the court’s conservatives have noticed the administration’s nose-thumbing over the orders in the Abrego Garcia case and aren’t pleased about it. In other cases, Trump is trying to use his position as president to get out of paying the larger of the two judgments E. Jean Carroll won against him. The AP is learning that the relief it obtained in theory from Trump’s retribution means little in practice. And Nadine Menendez will soon be relieved of the need to take her Mercedes C-Class to the dealership for servicing.



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    43 mins
  • Please Explain What You Mean By 'Effectuate'
    Apr 12 2025

    The Supreme Court is getting increasingly involved in the sprawling litigation over Donald Trump’s many aggressive executive orders. In J.G.G. vs. Trump — the case seeking to prevent removals under the Alien Enemies Act — the high court issued an emergency ruling saying detainees are entitled to due process but they must seek it through petitions for habeas corpus in the jurisdictions where they are actually being held. Is this a rebuke to the administration, relief, or neither?

    We also discuss the Abrego Garcia case, the ACLU trying for a national injunction against AEA removals under a habeas approach, and a Trump-appointed judge prohibiting removals from his South Texas district under the AEA, for now. Plus: in the Mahmoud Khalil case, the federal government is broadly asserting its power to revoke green cards because it doesn’t like their holders’ speech — setting up a likely Supreme Court confrontation over the extent of non-citizens’ First Amendment rights.

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    41 mins
  • Venue and Jurisdiction
    Apr 4 2025
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    There has been a cat-and-mouse game about venue in several of the cases brought by people protesting the Trump administration’s efforts to remove their visas and remove them from the country. For example: if you thought your client was in New York when you filed your lawsuit, but he was really in New Jersey, and now he’s in Louisiana, should the case be transferred to New Jersey, or to Louisiana? It sounds technical but the stakes are substantial. That conversation is for all listeners this week.

    For paying subscribers: an update on the Trump administration’s war on law firms, the firms that are fighting instead of holding, how much it matters to a fancy law firm if its junior attorneys are unhappy, and whether their businesses are likely to survive the president’s assault. Plus: an analysis from law professor Steve Vladeck, who’s looked at the unusually large number of temporary restraining orders entered against the Trump Administration’s executive actions.

    If you want to hear all of that, go to www.serioustrouble.show to upgrade! Unlike Paul Weiss, we don’t cost $2,000 an hour, and we promise that we will never enter into a letter agreement with the Trump administration that contradicts our principles.

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    26 mins
  • Please Don't Hit Me
    Mar 27 2025

    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.

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    47 mins
  • Please Take Judicial Notice that Drake Is a Little Bitch
    Mar 20 2025

    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.

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    45 mins
  • At Least Everyone Knows How to Pronounce It Now
    Mar 14 2025
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    For 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.

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    30 mins
  • Short Staffing
    Mar 5 2025

    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.

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    40 mins
  • The New George Santos
    Feb 27 2025

    The Trump administration continues to ice out the Associated Press, and now the AP is suing. We discuss how the administration changed its argument (not great, from a policy perspective, but it may actually put the White House on stronger legal ground). Ed Martin — the conservative activist serving as acting US Attorney for the District of Columbia, whom Trump has named to be the permanent US Attorney for that district — continues to send out weird, threatening letters about non-criminal behavior by Democrats. Ken has instructions about what you should do if you get such a letter.

    Plus: Eric Adams now wants the charges against him dismissed with prejudice; Sam Bankman-Fried has a theory of why he, too, deserves special dispensation from the Trump administration; FIRE mounts a robust defense of pollster Ann Selzer; the Trump administration continues to face difficulty in the courts with its executive orders; and soon-to-be-long-suffering federal Judge Ana Reyes (last seen scolding the attorneys for inspectors general suing the administration) has drawn the ire of the administration itself for being too mean to them in court.

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    40 mins
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