Serious Trouble

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Venue and Jurisdiction Apr 04, 2025

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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.

Please Don't Hit Me Mar 27, 2025

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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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Please Take Judicial Notice that Drake Is a Little Bitch Mar 20, 2025

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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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At Least Everyone Knows How to Pronounce It Now Mar 14, 2025

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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.

Short Staffing Mar 05, 2025

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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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The New George Santos Feb 27, 2025

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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.

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

Not Like U.S. Attorneys Feb 19, 2025

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Emil Bove's weaponization of the Justice Department is leading to resignations, including of a former protégé; Pam Bondi's bark is worse than her bite; Alex Spiro is a good lawyer.

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

Everyone Is Fired Feb 05, 2025

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This week: more firings — dozens of DOJ line prosecutors who worked on January 6 cases. Trump’s flurry of executive actions has drawn a flurry of litigation, much of it related to the Administrative Procedure Act. States and grantees are suing to stop the OMB funding pause, and finding success so far. Unions representing government workers are suing Elon Musk’s access to their information. Several anonymous FBI agents are even suing to stop disclosure to Trump officials of which cases they worked on, and a lawsuit fighting Trump’s executive order defunding grants related to DEI. The actions of the DOGE team seem like they might be illegal on several dimensions, and we discuss threats from acting US Attorney Ed Martin to bring bogus investigations against people who commit offenses like disclosing the names of people who work for Elon Musk.

Finally, we take a look at the assist the FCC is giving Trump as he seeks to shake down Paramount, and we recognize another recipient of the Senate Twink Memorial Award for Belatedly Good Judgment. Head over to serioustrouble.show to find an episode transcript and 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

Settlements and Separations Jan 31, 2025

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Just a week and a half back into the presidency, Donald Trump has seen to it that various federal prosecutors who were involved in prosecuting him have been fired. Can he do that? Also: the DOJ continues to drop cases against defendants who enjoy Trump’s political favor, so other defendants and convicts are trying to curry Trump's favor, including former Sen. Bob Menendez, who was just sentenced for a bribery scheme that didn’t even involve a Mercedes E-Class. And Meta has paid a large settlement to Trump — mostly going to his presidential library foundation — in what looks like a strategic payment to get back in the president’s good graces, since Trump’s underlying lawsuit against the company was quite bogus. Finally, we look at Devin Nunes (remember him?) losing in court again, and at the question of whether there is even a federal payment freeze for the federal courts to stay anymore.

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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

Thank You For Suing, Drake Jan 24, 2025

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This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

It's the first Serious Trouble of the new Trump administration. We start with a discussion of pardons: the ones Joe Biden gave on his way out of office and the ones Donald Trump gave on his way in.

For premium subscribers: the Jack Smith reports (the one about the January 6 prosecution which was released publicly, and the one about the documents prosecution, which Judge Aileen Cannon has blocked from being released to Congress), New York Mayor Eric Adams’ overt campaign for a pardon, a defamation lawsuit that CNN lost (and apparently deserved to lose, says Ken), and finally, we express our thanks to Drake for filing consistently entertaining legal actions that we get to cover — in this case, a defamation lawsuit against his own music label.

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