On this week’s show, we delve into the grand jury transcripts from the Broadview Six case, which show an array of embarrassing misconduct by AUSAs from the office of the US Attorney for the Northern District of Illinois. As Ken describes, these are things that AUSAs are very clearly taught not to do. And yet.

Also this week: a couple of new flavors of AI hallucination trouble in the courts. In one case, both sides used error-prone AI to write their motions, leading the judge to disqualify both sides’ attorneys from the case. In three other cases highlighted by Eugene Volokh, judges have admonished attorneys for failing to notice the opposing party’s AI hallucinations. As Ken notes, it is a lawyer’s job to check the other side’s work — and AI is making it easier to find errors at the same time that it’s making it easier to make errors.

Speaking of sloppy lawyering, Donald Trump’s legal team that’s suing the BBC for him isn’t doing such a good job. He’s having APA trouble with his effort to impose high fees on H-1B visas, and the Trump-Kennedy Center lost a lawsuit against a performer who canceled a scheduled performance (the performer had never signed a contract, oops). And Judge Richard! Leon! says there’s no Trump slush fund to enjoin, for now! But he will keep watching! So don’t try any funny business!

Also, Matt Taibbi filed another dumb lawsuit and lost.

Plus: Ken Paxton’s old lawyer endorses against him, and does so in a such a way that he’s careful to avoid breaching rules of professional responsibility — though another lawyer might decide it’s most prudent to keep negative opinions about ex-clients to himself. And we look at ways that being a mess can help you in court: Brallan Perez Alarcon successfully argued that he lacked the requisite intent to threaten ICE agents because he was too drunk. And George Santos is probably too silly to have his threats taken as true, either.

No paywall in this episode; it is available to all subscribers. We hope you enjoy it,

Josh

Click here for a transcript of this episode.

This week’s Serious Trouble comes to you live from a perch overlooking the soon-to-be-built Trump National Championship Golf Links at East Potomac Park by Donald J. Trump. Or, maybe — as I looked over the federally administered national parkland along the Potomac River, I was looking at a suite of projects where the president’s “just do things” approach has faced intermittent trouble in court.

For example: Trump’s name has been ordered down off the Kennedy Center, which is once again just the Kennedy Center. Trump’s closure of the center has also been enjoined, though he probably will ultimately be able to close and renovate it, though it would take an act of Congress to put his name on the building.

In less concrete terms, his “anti-weaponization fund” is also facing challenges — that motion from 35 retired federal judges is getting more traction than Ken expected; though it’s still unlikely to mean the fund will be blocked, though perhaps some attorneys involved in the Trump-IRS litigation that preceded it will be sanctioned. We also discuss the status of various lawsuits aimed at stopping the fund and the ripeness and standing challenges they face. And we look at the “you fucking dingus” doctrine — the extent to which Trump’s most cartoonish actions cause judges to hunt for ways to respond to them.

That’s for free subscribers. Paying subscribers also get:

• Alexis Wilkins vs. MS NOW, and the George Costanza theory of actual malice.

• The junior lawyer leading the James Comey seashell prosecution steps down (as lawyers flee the government more broadly) while a judge in another case rules that “8647” is not a true threat.

• Trump really doesn’t want to pay tariff refunds, and Ilya Somin argues the tariff cases show how CASA has created a mess.

• A CIA official gets indicted for lying on his resume, but really for stealing tens of millions of dollars worth of gold that he was somehow able to order to his office.

• George Santos appears to be under investigation for insider trading in a prediction market about George Santos. Remember, Santos wasn’t pardoned, his sentence was commuted, so he’s still a felon and should be careful about situations that might lead to him getting sentenced as a repeat offender.

• A gadfly blogger in Ohio is arrested for texting an image to a state senator that apparently depicts Shrek masturbating. Is that a crime? Ken assesses whether you have a First Amendment right to send Shrek smut to your lawmakers.

We hope you enjoy the show,

Josh

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The ‘Broadview Six’ case was one of the Trump administration’s prominent prosecutions of anti-ICE protesters, including politically prominent figures like Kat Abughazaleh. Federal prosecutors in Chicago brought felony charges to fanfare, then curiously dropped them, keeping only misdemeanor counts. Now we know why: They engaged in egregious misconduct to obtain the felony indictments, which they then sought to conceal from Judge April Perry, who is not amused.

Now, the charges are all dismissed with prejudice, Perry is considering sanctions, and US Attorney Andrew Boutros has issued a weird memo promising reform — his tone is less combative than usual for the Trump DOJ, and instead by turns conciliatory and self-congratulatory for having decided that misconduct is bad and must be stopped. Boutros, a former AUSA and white-collar criminal defense partner at Dechert, surely knew better than to handle this the way his office did. Alas. Oh, and Boutros is also in the news because his office is apparently running a criminal investigation into E. Jean Carroll, examining whether she lied in a deposition hundreds of miles from Chicago.

We discuss that for all subscribers. For paying subscribers this week, there’s also:

• Kilmar Abrego Garcia’s big and unusual win on vindictive prosecution, which is already inspiring the Southern Poverty Law Center.

• A sordid case involving an Eleventh Circuit judge whose sofa cushion required forensic testing after clerks asserted she was noisily carrying on an affair in chambers. Gross!

• A free speech win for West Point faculty.

• An interesting new insider trading case involving Polymarket.

• A probably-too-clever motion attacking the “anti-weaponization fund,” and

• More bad news for ex-JP Morgan banker Chirayu Rana.

We hope you enjoy the episode,

Josh

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Donald Trump has announced the creation of a $1.776 billion “anti-weaponization fund” to be doled out as he sees fit to “victims” of the “weaponization” of the Justice Department. To be financed how, you might ask? From the Judgment Fund, a strange legal creature we’ve talked about a few times before — it’s a permanent, unlimited appropriation the federal government can use to pay judgments and settlements. But like… doesn’t that have to be for real lawsuits with plausible claims that could win in court? If the fund is a blank check like the president claims, is it even constitutional? We discuss. We also look at the troublesome issue of who would have standing to enforce the law against what the president is trying to do — probably not these guys, unfortunately.

Also this week: an ex-AUSA has been criminally charged for sending herself electronic copies of confidential reports about the findings from Jack Smith’s documents investigation into the president. She gave the files names like “bundt cake recipe,” which is a bad fact, indicating consciousness of guilt. But the statutes she’s been charged under were designed to deal with situations where employees steal physical, valuable things from the government and thus deprive the government of their use — it’s not clear they apply to emails of copies. Note, these documents were not classified.

That’s for free subscribers. Paying subscribers get our discussions about:

• An ICE agent facing state criminal charges in Minnesota.

• Elon Musk losing in his civil trial against Sam Altman, and the complex set of circumstances that led the presiding judge to seek an advisory verdict from the jury before disposing of the case herself.

• A counterclaim from Lorna Hajdini in the JP Morgan saga.

• Chud the Builder, unfortunately (in part because of his whiny lawyer).

• Trouble for timeshare billionaire Stephen Cloobeck — Eric Swalwell’s onetime benefactor — and Cloobeck’s ex-Penthouse Pet fiancée, Adva Lavie, a.k.a. “Mia Ventura.” Lavie faces criminal charges for stealing from rich, old men (not Cloobeck) (yet); she’s out on bail but wore her ankle monitor on a trip to the Israeli consulate to get a new passport, which is a no-no. Cloobeck’s been charged with trying to intimidate witnesses against Lavie and making “annoying” phone calls.

• Rep. Max Miller, who apparently has the worst luck with women, is suing his ex-wife for defamation, saying she’s making up lies about him being abusive, just like his ex-girlfriend before her, whom he also sued for defamation when she called him abusive.

• And Clavicular pleads no-contest to shooting a dead alligator, is sentenced to non-livestreamed community service — and gets brutally mogged by Judge Marcus Bach-Armas, a total chad who used to be in-house counsel for the Miami Dolphins.

We hope you enjoy the episode,

Josh

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The lurid JP Morgan sex case has gotten more interesting: according to reports, the bank offered a $1 million settlement to Chirayu Rana, the banker who wanted an eight-figure settlement related to the lurid sex-harassment allegations he has made against a senior colleague. That’s more than you’d expect a firm to offer to settle a mere nuisance suit. Something is weird here, but as Ken notes, two things can be true at once: A plaintiff can be exaggerating and sort of nuts, and there can be some kind of underlying misconduct that motivates a defendant to settle.

The Justice Department wants to stand in as the defendant in the case where E. Jean Carroll won a large judgment for comments Donald Trump made about her during his first presidential term, which would defeat her claim, since the government cannot be liable for defamation. Trump and the government didn’t propose this in a timely manner, however, so we probably won’t get to develop more case law on whether “she’s not my type” can be work-related speech from the president. The DOJ is also suing the DC Bar, trying to stop professional discipline for Jeffrey ‘Oil Spill’ Clark. And Ken says, no, U.S. Attorney Jeanine Pirro does not need to recuse herself from Cole Allen’s case merely because she was present at the White House Correspondents’ Dinner, despite what some ex-AUSAs might say on television.

That’s for all listeners this week. Upgrade to paid to hear about much more:

• Another Trump tariff effort gets struck down because the Court of International Trade decided to actually form a view on what constitutes a balance-of-payments crisis.

• ABC fighting back against the Federal Communications Commission, urged on by the commission’s lone Democratic member (and Ken explains why they’re even bothering to fight at the agency level before going to court.)

• The fight over the Lincoln Memorial reflecting pool, or “more aesthetic standing bullshit,” as Ken’s notes describe it.

• Richard Murdaugh’s remarkable win in court (for now).

• A silly lawsuit against Matt Damon, and

• A misdo charge for Clav, who says he was merely following the guidance of a licensed airboat captain when he shot a (possibly already dead) alligator.

We hope you enjoy the episode,

Josh

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We have a lot of really stupid litigation to cover this week, starting with the JP Morgan lawsuit so many of you asked us about. This is the case of Chirayu Rana, an ex-banker who has made salacious allegations against a former JP Morgan colleague, saying she forced him into a sexual relationship, spiked his drink with Viagra, threatened his career, and racially belittled his wife. It’s great tabloid fodder, but the emerging consensus is that Rana is making it up.

Among other blows to Rana’s credibility, the New York Post reports he obtained bereavement leave from JP Morgan for his father’s death, but the Post found his father in Virginia, very much alive and insisting that his son is a “good guy.” Also, Rana apparently discussed very similar allegations with a public online lawyer chatbot — and in the version he apparently gave the chatbot, the abuse happened when he worked at Morgan Stanley and the abuser was a man.

What can you do if you are a bank or a banker and someone makes preposterous allegations against you in a legal filing, which is privileged against defamation claims? Well, you could sue for malicious prosecution or abuse of process, but typically, the lunatic you’re up against isn’t a deep pocket, and your best course of action is to seek dismissal and draw as little attention as possible.

Speaking of dumb litigation, Blake Lively and Justin Baldoni have settled, with no exchange of funds between the two sides. The Post cites “sources” who say legal bills for the two sides totaled $60 million — the sourcing on that number is a little thin, but Ken considers it a plausible magnitude for an 18-month litigation involving dozens of fancy lawyers.

Also this week:

• Matt Taibbi lost his dumb lawsuit against Eoin Higgins.

• A Michigan defendant who made way more threatening-sounding comments than James Comey ever did nonetheless enjoys First Amendment protection (but will have to seek relief in state court if prosecutors go after him again).

• Does Cole Allen belong on suicide watch?

• DOJ apologizes to a federal judge for not telling her a detained migrant in her court was wanted for murder (she released the migrant and then DHS attacked her for releasing an accused murderer).

• The FTC surrenders in its fight against Media Matters.

• The DOJ seeks to memory-hole the Jerome Powell subpoenas (which would perhaps make it easier to reissue them later).

• Gavin Newsom is getting further than we expected with a kinda dumb defamation lawsuit against Fox News.

• And preservationists try to stop Donald Trump from tearing up the East Potomac Park golf course to build a championship-style course.

We hope you enjoy the episode,

Josh

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The president really wants James Comey on trial, and Todd Blanche really wants to be the official Attorney General, and so Comey has been indicted again — this time, purportedly for threatening the president with seashells. As with the last indictment, Comey will seek dismissal on the grounds of selective and vindictive prosecution. He may also be able to challenge the facial validity of the indictment — usually, there’s not much opportunity do to this in a criminal case, but Ken says the government got too specific in the indictment for its own good, giving a judge the opportunity to assess before trial whether the seashell statement at issue could plausibly amount to a threat. Indeed, even Jonathan Turley can’t bring himself to argue that this indictment makes sense.

Speaking of threats to the president, Cole Tomas Allen was tackled and arrested when he tried to charge the ballroom at the Washington Hilton with a shotgun. The criminal complaint is vague on whether Allen got a shot off or not, but it doesn’t really matter either way — bringing the gun to the ballroom is enough to count as an attempt at assassination, and Allen’s unnervingly-normie writings will undermine any attempt at an insanity defense.

Plus, we look at Maurene Comey’s lawsuit over her firing for being James Comey’s daughter.

That’s this week’s free show. Paying subscribers also get:

• Jeanine Pirro’s screw-up that has resulted in Trump getting less influence at the Federal Reserve than he’d probably have if she’d just played it cool.

• A wrench in Trump’s plan to have the IRS pay him a big settlement.

• Roy Moore and Diddy have something additional in common — they both are failures at defamation litigation.

• A well-deserved spanking for Sam Bankman-Fried.

• The SPLC, fighting back.

• An apology to Elon Musk from the busybodies at the California Coastal Commission, and

• An apology from Sullivan & Cromwell for AI hallucinations in a filing.

We hope you enjoy the episode,

Josh

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The Atlantic has reported that Kash Patel is often drunk and derelict in his duties as FBI Director. But Patel says he’s only guilty of working really hard, and he’s suing the Atlantic. He’s got a theory he says is a “slam dunk” — The Atlantic defamed him with actual malice because he denied the accusations against him but they printed him anyway. That theory didn’t work for Trump against The Wall Street Journal and it didn’t work for Patel against Frank Figliuzzi Jr., who accused him of being a nightclub rat on Morning Joe, but maybe it will work this time? (It won’t).

Also, his lawyer did something incompetent — shocker.

And more formidably, former Capitol Police officer Shauni Kerkhoff is suing The Blaze and two of its “journalists” for accusing her of being the Capitol Hill pipe bomber, on the basis of a shoddy “gait analysis” alleging that her limp — due to a college soccer in jury — matched the way the bomber walked on surveillance video. Proving actual malice is hard — as a police officer, Kerkhoff is treated as a public figure in the coverage of her work — but the journalists’ persistence with their accusations even after Brian Cole was arrested for the bombings strengthens her case. She also has very real defamation lawyers: Clare Locke, the firm that got the huge settlement out of Fox for Dominion Voting Systems.

That defamation coverage is for all listeners this week. In the full premium episode, there’s also:

• Even more defamation coverage, with Laura Loomer losing at summary judgment in her lawsuit against Bill Maher, and Megan Thee Stallion failing to obtain a court order instructing Milagro Cooper to stop talking about her.

• A preliminary injunction telling Apple and Facebook to restore anti-ICE resources they took off the internet at the government’s behest.

• The SPLC indictment.

• A settlement for Carter Page.

• A Sam Bankman-Fried update.

• And a court ruling that says it’s legal to be a huge dick in Alabama.

We hope you enjoy the episode,

Josh

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Eric Swalwell’s campaign for California governor flamed out spectacularly over the weekend, and now prosecutors in Manhattan and Los Angeles are looking into sexual assault allegations against the now-former congressman. Meanwhile, US Attorney Jeanine Pirro — who oversees local felony prosecutions in the District of Columbia — has set up a hotline for victims who may have been assaulted by Swalwell there. And, a succession of lawyers for Swalwell have gone on the offensive, sending out cease-and-desist letters and attacking his accusers as politically motivated and dishonest.

Besides looking into Swalwell, Pirro sent a couple of her henchpersons to the under-construction Federal Reserve headquarters looking for … something. An “I personally ordered the cost overruns” note from Jay Powell? We’re not sure, and probably neither were they — going to the crime scene is not something AUSAs do, as Ken notes from his own rueful experience of being denied an all-expenses paid trip to the Inland Empire, and the stunt seems only to have strengthened the resolve of Sen. Thom Tillis to block any confirmations of Trump Fed nominees.

That’s on this week’s show plus, for paying subscribers:

• Trump moves to vacate convictions of Oath Keeper and Proud Boy January 6 defendants whose convictions he’d previously chosen not to pardon;

• A panel of the DC Circuit Court of Appeals again frustrates James Boasberg’s investigation into non-compliance with his orders about deportations;

• Trump’s defamation lawsuit against the Wall Street Journal is dismissed for failure to plead actual malice;

• The Pentagon continues to try to avoid complying with an order to reinstate reporters’ access;

• Bill Essayli loses yet another case against immigration protesters; and

• A lesson on aesthetic standing (and how not to use AI!) from the Tiger King.

We hope you enjoy the episode,

Josh

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Michael Avenatti, sentenced to over 11 years in prison for stealing money from his clients, has gotten out after a little over 4 years behind bars. He’s still not a free man — he’s living in a halfway house in the Los Angeles area, where he’ll be expected to find work, perhaps as a podcaster. And in part he owes thanks to his former nemesis, Donald Trump, for signing the First Step Act, which allows for earlier release of certain first-time offenders.

Meanwhile, Pam Bondi has been released from her own version of federal custody, and the Justice Department says this means she doesn’t have to comply with a subpoena to testify before congress about her handling of the release of the Epstein Files. Members of the House Oversight Committee, including some Republicans, are crying foul, saying their subpoena remains in force. Ken says, if Bondi were his client (lol), he’d advise her to comply. But if DOJ doesn’t care to make her talk, Congress will have limited ability in practice to force her to do so.

Meanwhile, Ed Martin wants his DC bar disciplinary proceedings removed to federal court. How can you remove something that’s not a lawsuit to federal court? That’s an excellent question, Ken says — one that Jeffrey Clark helped us find the answer to.

This week’s full show has all that plus:

• Trump’s emergency motion to lift the stay on construction of the “desperately needed” White House ballroom, and a discussion of why the plaintiffs’ claims to standing are stronger than we gave them credit for last week.

• A Clavicular-alligator update.

• If you’re going to talk about how you want to do terrorism, don’t do it in front of your dash cam.

• Long-suffering federal judge Lewis Liman’s 152-page order dismissing most, but not all, of Blake Lively’s claims against the producers of It Ends With Us (and their publicists), and Ken’s discussion of why you shouldn’t sexually harass your independent contractors, even if it might technically not be illegal.

• Elon Musk’s antitrust loss.

We hope you enjoy the episode,

Josh

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Last week, we talked about a court hearing that seemed to have gone well for Anthropic, and indeed, the hearing was swiftly followed by a preliminary injunction from Judge Rita Lin, barring various Pentagon actions against the AI company, including a supply-chain risk designation that threatened much of the company’s private business.

And there’s another big injunction, this one from Judge Richard Leon, who loves to use exclamation points in his orders! Judge Leon says Trump must stop work immediately on his ballroom! If he wants it built, Congress is going to have to pass a law authorizing it! But why does the National Trust for Historic Preservation even have standing to challenge the ballroom project? Their members don’t appear to suffer an especially particularized injury, beyond having to look at a building they think is ugly! Ken says standing is a doctrine judges just make up as they go along!

Plus, Donald Trump’s executive order defunding PBS and NPR is blocked, but since Congress subsequently acted to rescind their funding, the effect of enjoining the order is limited.

Free subscribers hear about those cases. For paying subscribers, there’s much more! Including:

• Covington & Burling warned its client, ActBlue, that some statements ActBlue made in a 2023 letter to congressional leaders may have been misleading, and that ActBlue’s CEO probably needs her own lawyer to deal with her legal exposure around that fact. ActBlue responded by firing Covington & Burling. It’s a big old mess, and Ken describes how this kind of thing can happen when you represent an entity, and the entity’s legal needs don’t always line up with the legal needs of its executives.

• A Colorado appeals court threw out Tina Peters’ nine-year sentence for voting machine tampering, saying the judge raised her sentence in response to her constitutionally-protected speech.

• After his car accident, Tiger Woods issued a statement saying he will step away and “seek treatment.” It’s an implicit admission of DUI, but as Ken notes, he’s very unlikely to beat the rap on DUI anyway, and this is a situation where his PR need to speak up and take responsibility may actually outweigh his legal prerogative to shut up.

• FBI agents are suing Kash Patel for wrongful termination, and taking the opportunity to tell embarrassing stories about Patel that may not be strictly germane to their litigation.

• Some people who went to the Capitol for January 6 have filed a new class action lawsuit, apparently hoping to join in on the Trump settlement gravy train.

• Be careful what buttons you click on LinkedIn.

• And, by popular demand, Ken analyzes Clavicular’s predicaments.

We hope you enjoy this episode,

Josh

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Judge Lewis Kaplan is losing some patience with Sam Bankman-Fried, and not just because Bankman-Fried’s mom tried to communicate with him ex parte. SBF has been making purportedly pro se filings, at least one of which appears to have been dictated to and FedExed by his mother, and he simultaneously has an appeal proceeding in the appeals court with real lawyers. Kaplan says he has to choose — are you pro se or not? And he wants to know — have any lawyers besides mom been helping with these filings he’s supposedly personally responsible for?

Meanwhile, the “Department of War” has been having a rough time in court. The Pentagon’s anti-reporting press policy has been thrown out as a First Amendment violation, so now the Pentagon says no reporters at all can work out of the Pentagon press room. Meanwhile, Anthropic won a preliminary injunction blocking the Pentagon’s declaration that the company is a “Supply Chain Risk.” (The Anthropic order came down after we taped — we’ll have a further update on next week’s show.)

That’s for all listeners. For paying subscribers, we also cover:

• DOJ’s admission that it had no evidence of a crime related to Jay Powell’s testimony about Federal Reserve headquarters renovation cost overruns (and the surprisingly low bar for issuing a subpoena that the government nevertheless failed to clear).

• A surprisingly practical choice by DOJ in New Jersey.

• Minnesota’s effort to force the federal government to disclose investigative material related to the shooting deaths of Alex Pretti and Renée Good.

• Mike Lindell in contempt of court.

• Mike Flynn getting a settlement from Trump for his alleged persecution by Trump’s own DOJ.

• No protective order for those DOGE henchman depositions.

• And the Oklahoma Supreme Court telling attorneys to go ahead and use AI, if they dare.

We hope you enjoy the episode,

Josh

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Afroman has won his legal battle with the sheriff’s deputies who raided his house in 2022 and then became unwitting stars of his music videos mocking them. Several of the deputies, including “Officer Poundcake,” sued for misappropriation of their likenesses, defamation, and other torts. But a jury sided with Afroman, agreeing that his songs about the officers were social commentary and that his statements about them, however juvenile, were insults rather than literal factual claims of having, for example, slept with one of their wives.

This week, for all listeners, we recap the Afroman trial and also look at a rough hearing for AUSAs in New Jersey, as the Trump administration decides it will hire candidates straight out of law school to work in US Attorneys’ offices.

For paying subscribers, there’s much more:

• Judge James Boasberg’s order quashing subpoenas to the Federal Reserve, U.S. Attorney Jeanine Pirro’s choice to appeal that order, and Boasberg’s other order requiring the disclosure of grand jury no-bills.

• Capitol pipe bomber defendant Brian Cole, who has made his anticipated claim that the president’s pardon of January 6 rioters also applies to him (even though this seems to go against the plain language of the pardon, which applies only to those “convicted” of offenses related to January 6.)

• Sam Bankman-Fried’s mom, who got slapped down for trying to have ex-parte communications with the judge overseeing his case; Judge Lewis Kaplan reminded Prof. Barbara Fried that she might be a lawyer, but she’s not her son’s lawyer, at least not in this case.

• Defendants convicted of terrorism-related offenses in Texas over an anti-ICE action where they set off fireworks and one defendant shot a law enforcement officer in the neck; as Ken notes, despite the rhetoric on both sides, this trial was never really about whether ‘Antifa’ constitutes a terror organization.

• More hot hot administrative procedure action, with Judge Brian Murphy issuing a preliminary injunction against the new, laxer child vaccination guidelines from Robert F. Kennedy Jr’.s Department of Health and Human Services.

• And dog-fashion magazine Dogue, which is being sued by Condé Nast for infringing the Vogue trademark.

If you want to get all that, go ahead and hit the button below:

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We hope you enjoy the episode,

Josh

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As we discussed last week, Judge Richard Eaton of the U.S. Court of International Trade rather impatiently told the Trump Administration to stop charging IEEPA tariffs already, since the Supreme Court has deemed them illegal. The Customs Service responded, claiming that’s literally impossible — too many importers have already made estimated tariff payments, and their computers aren’t programmed to separate out IEEPA from non-IEEPA tariffs when finalizing the bills due. Give us 45 days to reprogram our computers, they ask, and then we’ll refund all the money. As Ken notes, you might want to lead with “we can fix this in seven weeks” rather than sticking it at the end of your brief explaining why you won’t do what a judge has already ordered you to do.

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Free subscribers this week get our conversation about that, plus more situations where courts are telling the Trump Administration it can’t just ignore the need to get officials confirmed by the Senate — including at Voice of America, where Kari Lake has now been robbed not just of two statewide offices but also her role as CEO.

For paying subscribers, we cover a number of additional lawsuits, including some especially weird ones:

• Voting machine maker Smartmatic’s parent company under indictment over bribes its former executives are alleged to have paid in the Philippines, alleges that it is being selectively and vindictively prosecuted.

• Anthropic is suing over the Pentagon’s “supply chain risk” designation that threatens the company’s business. The company makes First Amendment claims, but Ken thinks its less glamorous arguments — like that the designation violated everyone’s favorite law, the Administrative Procedure Act — are more persuasive.

• Nippon Life Insurance Company of America is suing OpenAI, the makers of the ChatGPT AI engine. Nippon says it has been dogged by a vexatious litigant — she decided she didn’t like the settlement she’d signed with the company, and when her human lawyer advised her that settlements are a no-backsies kind of situation, she fired him in favor of the AI engine that gave her the advice she wanted to hear: sue, sue, sue. Nippon says this is tortious interference with the valid settlement contract they’d entered with their aggrieved former policyholder. Because tortious interference requires knowledge of the contract you’re interfering with, this lawsuit turns an interesting philosophical question into an interesting legal one — did OpenAI “know” that Nippon had a settlement, simply because their former policyholder told ChatGPT about it?

• And Ed Martin appears to be the Justice Department official with some especially stupid bar trouble.

This is an especially meaty show (oh, and we also look at another decision about ICE) so we hope you all get the full thing so you can hear all of it. If you’re not a subscriber and you want to be, hit the button below.

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We hope you enjoy the episode,

Josh

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The Trump Administration surprised many observers by withdrawing its efforts to appeal its losses against all four law firms that challenged its legal orders against them. Then, it surprised observers again by changing its mind and asking to appeal the cases after all. We discuss why, whether you’re allowed to do that, and what happens to the nine firms that didn’t fight when the other firms win.

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We also look at a strange letter from the Department of Justice to state bar associations, telling them they’ll have to pause investigations into DOJ lawyers, or else. It’s unclear what authority DOJ thinks it has here, but they may be upset about a Florida Bar investigation into Lindsey Halligan. And we talk about news that DOJ tried to come up with a way to do a criminal prosecution related to President Biden’s autopen, but didn’t.

That’s for all listeners. Paying subscribers get a whole lot more this week:

• You’d think, now that the IEEPA tariffs have been thrown out, customs would stop charging them to importers. You’d be wrong! The customs bureau keeps finalizing tariff payments including the now-barred IEEPA charges — in a filing issued after we taped, they argued their computers won’t let them stop — but Judge Richard Eaton from the U.S. Court of International Trade has told them to cut the crap and refund taxpayers’ money. Ken and I discuss how this episode might affect the next round of tariff litigation over the new legal authorities the administration is leaning on to replace IEEPA.

• There’s Administrative Procedure Act news! Judge Lewis Liman says the Trump Department of Transportation can’t end New York’s congestion pricing program, in an order that Ken calls “149 pages of pain.” One of the issues? As often happens with APA cases, the DOT said New York couldn’t challenge its move because they hadn’t actually imposed a “final” agency action. Unfortunately for DOT, President Trump last February tweeted a picture of himself wearing a crown and declaring “CONGESTION PRICING IS DEAD,” which sounded pretty final to Liman.

• We have an update on West Virginia judges resisting the Trump administration on ICE.

• We look at why Tom Goldstein couldn’t save his own ass in court, discuss the superseding indictment with a whopping 39 defendants in the St. Paul ICE Church protest case, and we discuss the prosecution in Alabama of a woman who dressed up as a giant penis for a No Kings protest. Local prosecutors argue, among other claims, that she sought to mislead officers as to her identity by saying her name was “Antifa,” and that her huge penis costume was so distracting that it constituted a criminal traffic hazard.

To hear all that, hit the button below and join us. Join us! One of us!

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We hope you enjoy the episode,

Josh

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This week’s Serious Trouble opens with more tariff talk — what awaits litigants like FedEx who seek refunds of payments they made under President Trump’s now-invalidated tariffs, and what courts might do with his efforts to reconstruct the tariffs under non-IEEPA legal authorities that come with their own difficulties. We discuss news that Jeanine Pirro has given up on indicting the Democrats who made the “you must refuse illegal orders” video, and we have an update on Matthew Isihara, the SAUSA who was held in contempt of court in Minneapolis. (At least the detainee who got dumped in El Paso without his documents will get his plane ticket paid for.)

That’s for free subscribers. Paying subscribers (thank you for your support!) also get our looks at:

• The magistrate judge who authorized a search of a Washington Post reporter’s home but is now angry that the government failed to alert him to a law that appears to make their search illegal. (Isn’t it his job to know the law?)

• Aileen Cannon’s efforts to block the release of Jack Smith’s report on the Mar-a-Lago documents investigation.

• A ruling from a federal judge in West Virginia with a novel Fourth Amendment theory prohibiting certain ICE tactics (this is likely to get a lot of appellate action).

• A ruling that it’s not misleading for Buffalo Wild Wings to market its “boneless wings” which aren’t actually made from wing meat.

If you want to hear all that, hit the button below and join our club, we’d love to have you.

We hope you enjoy the episode,

Josh

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Just as we were sitting down to tape, the Supreme Court dropped its ruling in Learning Resources v. Trump, throwing out the massive country-specific tariffs the president purported to impose under the Nixon-era International Emergency Economic Powers Act. The opinion was messy: 6-3, but with the six-justice majority not agreeing on exactly why the tariffs were illegal. Justice Gorsuch, in particular, issued a concurrence describing his bones to pick with almost everyone: the court’s liberals, who said this decision could be reached without recourse to the “major questions” doctrine; the dissenting conservatives, who he saw as concocting an ad-hoc exception to the doctrine; and Justice Barrett, with whom he has a somewhat inscrutable disagreement over how to think about the doctrine, despite both of them voting the same way. He does think Roberts is cool, at least.

Also this week, we look at a contempt order from Judge Laura Provenzino, putting a Special Assistant U.S. Attorney (a J.A.G. attorney on loan from the Department of Defense) in contempt over the government’s failure to return identification documents to a non-citizen released from immigration custody on her orders. He was fined $500 per day — a fine the government will reimburse — and as such, the order is more symbolic than effectively coercive. We discuss how an order like this matters, and how judges could further escalate in the face of widespread noncompliance by the federal government in these immigration cases.

Plus, we discuss a mistrial over a defense attorney’s t-shirt, Judge Paula Xinis’s rejection of yet another effort to detain Kilmar Abrego Garcia, Sen. Mark Kelly’s exclamation-mark-laden preliminary win against efforts to reduce his military rank and pension, and a Minnesota judge’s order directing the government to let ICE detainees talk with their lawyers. And we look at an all-timer performance from billionaire Les Wexner’s attorney, who whispered in his ear during a congressional deposition, threatening to kill him if he says any more answers longer than five words.

We hope you enjoy the episode,

Josh

Click here for a transcript of this episode.

When we’ve previously talked about the ways the Trump Administration might retaliate against six Democrats in Congress who made a video reminding servicemembers to refuse illegal orders, we didn’t even discuss the possibility of a civilian prosecution, because it was so preposterous — but US Attorney Jeanine Pirro’s office tried, preposterously, and they got no billed very hard, with zero grand jurors voting to indict the officials, according to NBC News. Perhaps Steven Vandervelden, a former underling of Pirro’s from the Westchester DA’s office who retired from his legal career to pursue dance photography, but rejoined government to help Pirro prosecute cases like this one, should get back to his other job.

Meanwhile, Don Lemon has a new, high-profile lawyer: Joseph H. Thompson, who until just a few weeks ago was a senior attorney in the US Attorney’s Office in Minnesota, leading those welfare fraud cases that caused President Trump to take so much interest in the state in the first place. Now, having quit the office in disgust, he’s a defense lawyer.

Trump is suing the IRS for ten billion dollars — can he do that? — and his Justice Department is trying to dismiss the Contempt of Congress case for which Steve Bannon served a few months in custody — Bannon is still appealing, so DOJ still may be able to make it go away.

That’s all for free subscribers this week. Paying subscribers get more conversation:

• A look at a highly consequential ruling from the Fifth Circuit, upholding the Trump Administration’s novel and very aggressive views on what aliens it may detain pending deportation. Most other courts have rejected these theories — including a majority of Trump’s own trial court appointees who have heard relevant cases — and there’s some skepticism that the Supreme Court will go along.

• The DOJ seized 2020 election ballots from Fulton County, with a fairly batshit search warrant that Ken is surprised got approval from a magistrate judge. Fulton wants its ballots back; we discuss whether they’ll get them and what might happen if Trump tries to get a warrant for ballots in an election where a count is ongoing rather than complete.

• We look at an alleged jewel thief who had the option of going to prison or Ecuador and unsurprisingly chose Ecuador — reflecting a serious failure of coordination between prosecutors and immigration authorities.

• And finally, is murder a crime of violence? The answer might surprise you.

To get all of that, hit the button below.

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We hope you enjoy the episode,

Josh

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Until recently, attorney Julie Le had been detailed from the Department of Homeland Security to represent the government in various immigration-related cases in court in Minnesota. She wasn’t enjoying it. “This job sucks,” she told Judge Jerry Blackwell, in a hearing where she explained that she was trying to get her client to comply with court orders, but that it was very hard, due to a combination of this administration being both overwhelmed and uninterested in complying with certain laws. She also noted that, as a non-white person, she shared concerns about the government’s actions in the Minneapolis area.

You can see a full transcript here — it’s remarkable.

Ken and I discuss what you should do if you’re a lawyer whose client is frustratingly non-compliant and taking actions that bother you; venting to the judge is the wrong course of action, but there are other options available. We talk about how judges can handle the Trump Administration’s learned helplessness, and what escalating remedies they are increasingly looking towards. And we look at the DOJ’s efforts to manage the fact that lawyers are fleeing its offices.

That’s for all listeners. Paying subscribers get our takes on other topics, including:

• Judge Kate Menendez’s ruling that denied Minnesota the preliminary injunction it sought against Operation Metro Surge. As we expected, the state’s novel theory that federal government’s actions are a 10th Amendment violation was a bridge too far, even for a judge who seemed to be looking for some avenue to rein in the operation.

• Judge Ana Reyes’s grant of a temporary restraining order on the grounds that the Trump Administration may have violated the Administrative Procedure Act by revoking Temporary Protected Status for hundreds of thousands of Haitians, and the limits of using the APA to litigate substantive questions about immigration policy.

• Bill and Hillary Clinton’s emerging deal to testify before the House Oversight Committee and avoid the otherwise-likely prospect of contempt of congress prosecutions.

• Former Minnesota Vikings offensive tackle Matt Kalil’s lawsuit against his ex-wife Haley, over her disclosure on a podcast that his incredibly large penis made their sex life impractical and was a major driver of their divorce. He says this was an invasion of privacy; she argues in a motion to dismiss that the story is about her sex life too and she’s free to tell whoever she wants. Is this the first case of a reverse Streisand Effect, where you litigate because you want to draw more attention to an allegation that’s been made about you? What even are the damages at issue here? Would Matt Kalil like to visit Fire Island this summer? Ken and I discuss.

We hope you enjoy the episode,

Josh

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Just before we taped on Friday morning, we got word that Don Lemon had been arrested in Los Angeles on a grand jury indictment related to an anti-ICE protest two weeks ago at Cities Church in St. Paul, Minnesota. After taping, we obtained the indictment, which already gives us some material for next week. The indictment charges Lemon, along with his producer and several activists, with one count of conspiracy under USC 18 § 241 (the “Klan Act”) to violate USC 18 § 248 (the Freedom of Access to Clinic Entrances Act, which criminalizes certain activities interfering with the use of places of worship), and a further count of direct violation of USC 18 § 248. Section 248 only criminalizes certain modes of interference with a religious service, introducing additional fact hurdles for prosecutors which we’ll discuss next week. Meanwhile, Lemon has been released without bond, as we expected, pending a future court appearance in Minneapolis.

Before prosecutors got the grand jury indictment, they tried through some really irregular channels to get Lemon arrested more quickly. When a magistrate judge rejected an arrest warrant application for Lemon last week, rather than applying again or proceeding to the grand jury, prosecutors asked Judge Patrick Schiltz to overrule the magistrate, then asked an appellate panel to force Schiltz to rule on their motion right away, fearing that if Lemon wasn’t arrested immediately, there would be an epidemic of illegal church invasions. Schiltz took exception to this, and the appeals panel backed him up, though one of the appellate judges remarked that he thought all the arrest warrants were sufficiently supported but the government just didn’t need the weird emergency relief it was seeking.

Also this week: we look at federal judges (including Schiltz) who are incensed that ICE isn’t promptly complying with their habeas corpus orders, and how this mess is downstream of rules that prohibit nationwide injunctions and are clogging some courts with individual lawsuits seeking relief from immigration detentions. We have an update on Minnesota’s 10th Amendment case — Judge Kate Menendez appears skeptical that she is in a position to provide the sweeping relief the state wants, though she does want more briefing on the threat letter from Attorney General Pam Bondi to the state. And in another case, an order from Menendez restricting ICE tactics has been stayed — another case where we’re seeing the limited authority of courts to provide prospective relief from potential victims of illegal policing tactics.

In non-ICE news, it appears likely that Jeffrey Toobin will have to testify at Tom Goldstein’s criminal trial, though he has a good argument for limiting his testimony to fairly boring topics. Candace Owens says Turning Point USA has sent her a letter threatening to enforce a non-disparagement agreement they say she has violated by spreading conspiracy theories about Charlie Kirk’s death. And a defendant in Northern California called up a local news station during her trial to protest that she only threw parties where she gave alcohol to minors because of COVID.

We hope you enjoy the episode,

Josh

Click here for a transcript of this episode.