Serious Trouble

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week Ken and Josh discuss Anthropic's big win, the injunction on Trump's ballroom construction, and what to make of the block on Trump's executive order defunding PBS and NPR since Congress has rescinded their funding.That's for all subscribers. Paying subscribers will also hear our conversations about:* 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.Upgrade your subscription to receive all of our episodes at serioustrouble.show.

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week Ken and Josh discuss Judge Lewis Kaplan 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 subscribers. Paying subscribers will also hear our conversations about:* 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.Upgrade your subscription to receive all of our episodes at serioustrouble.show.

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week Ken and Josh discuss 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.That’s for all subscribers. Paying subscribers will also hear our conversations about:* 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.Upgrade your subscription to receive all of our episodes at serioustrouble.show.

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week Ken and Josh discuss the Customs Service saying its computers won't let it refund IEEPA tariffs, more situations where courts are telling the Trump Administration it can’t just ignore the need to get officials confirmed by the Senate, and another decision about ICE.That's for all subscribers. Paying subscribers will also hear our conversations about 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 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 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.Upgrade your subscription to receive all of our episodes at serioustrouble.show.

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week Ken and Josh discuss how The Trump Administration surprised 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.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.Upgrade your subscription to receive all of our episodes at serioustrouble.show.

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week Ken and Josh discuss more on tariffs — 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 all 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.Upgrade your subscription to receive all of our episodes at www.serioustrouble.show.

This week Ken and Josh discuss the Supreme Court's 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. Also this week, we look at a contempt order from Judge Laura Provenzino, putting a Special Assistant U.S. Attorney in contempt over the government’s failure to return identification documents to a non-citizen released from immigration custody on her orders. 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.Upgrade your subscription to receive all of our episodes at serioustrouble.show. 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

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week Ken and Josh discuss a D.C. grand jury declining to indict Democrats in Congress, Don Lemon's new high-profile lawyer, and Trump's lawsuit against the IRS.That’s for all 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.Upgrade your subscription to receive all of our episodes at serioustrouble.show.

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.showThis week, Ken and Josh discuss Julie Le, the DOJ lawyer who vented in court that it "sucks" to represent this government. They cover 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.That’s for all subscribers. Paying subscribers will also 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.Upgrade your subscription to receive all of our episodes at serioustrouble.show.

This week Ken and Josh discuss how the Feds got an arrest warrant for Don Lemon after all. 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.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.Upgrade your subscription to receive all of our episodes at serioustrouble.show. 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