• Hell No Bill
    Feb 13 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    This 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.

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    20 mins
  • Court Therapy
    Feb 7 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    This 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.

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    24 mins
  • Lemon Law
    Jan 31 2026

    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.

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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
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    44 mins
  • 120 Days
    Jan 23 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    This week, Ken and Josh discuss the end of Lindsey Halligan's purported reign in the Eastern District of Virginia, and news reports that ICE is relying on a secret legal memorandum asserting that it can enter homes to search for aliens subject to final orders of removal, even if there’s no warrant from an Article III judge authorizing them to do so. That's for all subscribers. Paying subscribers also get:

    * A look at the order enjoining ICE from certain enforcement tactics in Minnesota, but it’s subject to an administrative stay, for now — and, since this is Fourth Amendment Fun week, we have another opportunity to discuss how you might have a Fourth Amendment right, but that doesn’t mean you’ll get to use it.

    * The case of Geraldo Lunas Campos, a Cuban national who died in ICE custody earlier this month. ICE says his death was a suicide, but his family disputes that, citing other detainees who claim he was choked by guards. (A county medical examiner’s report also deemed his death a homicide — a determination of manner of death, not a finding of legal culpability.) Alas, it’s up to DOJ to keep those witnesses available to testify, and if DOJ doesn’t want to, they’ll likely be deported.

    * The federal charges for anti-ICE activists who are accused of disrupting a Twin Cities church service this past weekend — they were charged under the so-called Klan Act, and the charges were obtained via criminal complaint to a magistrate judge, which means prosecutors will still need to get a grand jury to agree to indict — and prosecutors’ failure so far to charge journalist Don Lemon.

    * The Supreme Court’s ongoing effort to carve out the Federal Reserve from its plans to neuter independent boards and commissions (special unique historical tradition etc etc).

    * And a weird one: former Sen. Kyrsten Sinema has been sued for alienation of affection — still an available tort in North Carolina and five other states! — by the estranged wife of one of her former staffers, who says Sinema stole her man.

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    19 mins
  • You Are Not Jay Powell
    Jan 16 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    Fed Chair Jerome Powell dropped a bombshell on Sunday: a video disclosing the Fed had been subpoenaed in a criminal investigation related to his congressional testimony about cost overruns in the Fed’s headquarters renovation. Powell said bluntly that the investigation is an effort to use the DOJ to assert control over the Fed and its interest-rate setting apparatus. Did this make Ken scream "shut up!!!!" at Powell's video? Meanwhile, Minnesota and some of its municipalities have sued the federal government, arguing that the ICE surge in the state is illegal and unconstitutional. Those discussions are for all listeners. Paying subscribers also get:

    * A look at intensifying turnover in US Attorneys’ offices, including the resignation of top prosecutors who had been leading the investigations into welfare fraud in Minnesota that was concentrated in the state’s Somali-American community.

    * DOJ’s argument for why Lindsey Halligan can keep calling herself a US Attorney after a judge ruled she isn’t one.

    * Senator Mark Kelly’s many arguments for why Pete Hegseth can’t reduce his rank and pension.

    * Some “shut up” news: prosecutors want to admit several incriminating statements from defendant Thomas Goldstein’s pre-trial New York Times profile.

    * And a look at a bizarre situation where Bruce Fein insists he somehow became Nicolas Maduro’s lawyer even though Maduro says he never hired him.

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    27 mins
  • Cartel De Los Soles
    Jan 9 2026
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    This week’s episode starts with the arrest and indictment of Nicolas Maduro, and the fatal shooting of Renee Nicole Good at the hands of an ICE agent in Minneapolis. That’s for free subscribers.

    Paying subscribers also get a look at a shadow docket ruling from the Supreme Court that curtailed Trump’s ability to deploy the national guard, and the surprising statutory reading that got a majority of the court there. We look at a dismissal of criminal charges from another scrap with ICE in Los Angeles, we discuss Mark Kelly’s legal options for fighting the reduction of his pension (and why he might choose not to use them), we consider why Lindsey Halligan keeps insisting she’s the US Attorney for the Eastern District of Virginia, we look at the bizarre upcoming criminal trial of Scotusblog co-founder Thomas Goldstein, and we have an update on the saga of the still-held-in-contempt Charles C. Johnson.

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    25 mins
  • ⬛⬛⬛⬛⬛⬛⬛⬛⬛⬛
    Dec 23 2025

    Some of the Epstein files have been released, but there's a lot of blacked-out text and pictures. The Justice Department is supposed to redact certain information but of course there’s the ever-present question of whether all redaction “errors” are errors, or whether this administration has its thumb on the scale for the president.

    Also in this episode: the Pulitzer Board requests President Trump's medical, financial and tax records, an LA man who towed an ICE vehicle around the block during a raid was acquitted of stealing government property, Milwaukee Judge Hannah Dugan was convicted in federal court of obstructing an effort by federal immigration agents to detain someone she had called to her courtroom. And Caroline Ellison, former partner to Sam Bankman-Fried in multiple senses of the term, has been sprung from Club Fed in Danbury, Connecticut. Speaking of SBF: apparently he’s transformed himself into something of a jailhouse lawyer but he seems to be about as good at jailhouse lawyering as he was at crypto investing.

    Finally, we look at a maybe-not-so-fearsome terrorism indictment and we discuss the ongoing contempt saga that has caused Ken to feel a surprising emotion regarding Charles C. Johnson: pity.



    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
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    37 mins
  • What Part of 'No Bill' Don't You Understand?
    Dec 16 2025
    This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

    A grand jury has refused to indict Letitia James — no, this isn’t a repeat of last week’s email; it just happened again since we last recorded. This time, it’s a different grand jury, and we discuss further impediments to the resurrection of the cases against her and James Comey. That, plus a discussion of the unlikely-to-matter pardon of former Colorado election official Tina Peters, is for free subscribers this week. Paid subscribers also get:

    * A look at a lawsuit from the National Trust for Historic Preservation which aims to stop the construction of Trump’s new White House ballroom.

    * Another trial court win for Gavin Newsom as he tries to end Trump’s activation of the California National Guard (though the outlook in the appeals courts is more dubious).

    * Costco’s lawsuit seeking return of its tariff payments under IEEPA, and why Costco would sue now, long after a few plaintiffs stood up to bring a test case but before the Supreme Court rules on it.

    * And the order that has, for now, freed Kilmar Abrego Garcia to return to Maryland.

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    22 mins