• Humphrey's Executioner
    Jul 9 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    Humphrey’s Executor, which has been obviously dead for some time, is now officially overturned. Except! The Federal Reserve is special and unique and in a historical tradition. Also this week: John Bolton has pleaded guilty to mishandling national defense information and might even get jail time. In Florida, federal prosecutors mistakenly disclosed Jack Smith’s report on the documents investigation to Carmen Mercedes Lineberger, as part of their prosecution of Lineberger for stealing a copy of the report (which she labeled as a “bundt cake recipe,” oops).

    For paying subscribers: In Chicago, US Attorney Andrew Boutros is in more trouble. And in Minnesota, more subpoenas have been quashed as politically motivated. Alleged pipe bomber Brian Cole hasn’t been pardoned. Todd Blanche doesn’t want to release more Epstein documents. A prosecution relating to Trump’s reflecting pool is likely to face problems. Florida’s “Stop WOKE Act” has been thrown out. And the ACLU of Maine wants the Secret Service to let the “Cats on a Couch” lady troll JD Vance in person.

    Upgrade your subscription now at serioustrouble.show.

    Show More Show Less
    21 mins
  • At Least the Fancy Lawyers Are Still Getting Rich
    Jun 26 2026

    David Lat joins Josh Barro for a conversation about the state of the legal industry under Donald Trump — how Big Law and the legal industry are faring after those executive orders and settlements — and they talk about how AI is changing the work of law firms, from staffing to billing rates. Plus: a look at the unusual breakdown in Thursday’s Supreme Court decision in the Monsanto case.

    We hope you enjoy the episode and the holiday, and Ken and Josh will be back with more after July 4. To find a transcript of this episode and sign up for updates from us, got to www.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
    Show More Show Less
    46 mins
  • America's Next Top Tort
    Jun 19 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    The U.S. Attorney’s office in Chicago has dismissed another high-profile case — this one a COVID fraud case — that had been led by AUSA Sheri Mecklenburg. We discuss that and more developments in the Broadview Six case. Meanwhile, in Minnesota, federal prosecutors have obtained a conspiracy indictment against self-proclaimed “Antifa” activists who sought to interfere with ICE operations in the Twin Cities. And the slush fund drama continues even as Todd Blanche seeks approval to become for real-for real Attorney General. And soon-to-be-congressman Brad Lander is acquitted in his own misdemeanor case about ICE obstruction.

    Plus, for paying subscribers:

    * A look at Sam Bankman-Fried’s prison life, his aspirations to return to changing the world (something Judge Lewis Kaplan would really like him not to try to do again), and how Michael Avenatti thinks he’s too full of himself,

    * A loss in Trump’s fight to eliminate “woke” signage from national parks,

    * Tyra Banks’s stronger-than-expected defamation claim against Netflix, in which she is invoking the Earl Milford doctrine (with representation from Clare Locke!), and

    * A look at some guys who are arguably even dumber than Jacob Wohl.

    Show More Show Less
    28 mins
  • This Shrek Film Was Not In Theaters
    Jun 5 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    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. We discuss challenges to his “anti-weaponization fund," and 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.

    * A gadfly blogger in Ohio is arrested for texting an image to a state senator that apparently depicts Shrek masturbating. Is that a crime?

    Show More Show Less
    24 mins
  • Court Officers Behaving Badly
    May 29 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    The ‘Broadview Six’ case was one of the Trump administration’s prominent prosecutions of anti-ICE protesters. 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 the judge, who is not amused.

    For all subscribers, we discuss that and US Attorney Andrew Boutros, who issued a weird memo promising reform, and the news that his office is apparently running a criminal investigation into E. Jean Carroll, examining whether she lied in a deposition hundreds of miles from Chicago.

    For paying subscribers (upgrade your subscription now at serioustrouble.show) 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.

    * 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.

    Show More Show Less
    23 mins
  • The No-Judgment Fund
    May 22 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    Donald Trump has announced a new $1.776 billion “anti-weaponization fund” to be doled out as he sees fit to “victims” of the “weaponization” of the Justice Department. It's financed from the Judgment Fund, a strange legal creature — 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? Also: 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."

    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.”

    * 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.

    Show More Show Less
    30 mins
  • 'Advice of Counsel' Does Not Apply to Advice from Licensed Airboat Captains
    May 15 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    The lurid JP Morgan sex case has gotten more interesting: apparently, the bank offered a $1 million settlement to the banker who wanted an eight-figure settlement related to the lurid sex-harassment allegations he has made against a senior colleague. Something is weird here. Also this week:

    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, the DOJ is also suing the DC Bar to stop professional discipline for Jeffrey ‘Oil Spill’ Clark, and 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.

    That’s for all listeners this week. Upgrade 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.

    Show More Show Less
    17 mins