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Dive into the complete episode list for Serious Trouble. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.

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Pub. DateTitleDuration
01 Feb 2023STFU SBF00:19:30
This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

This week, we talk about how not to stay out on bail (yes, once again, it's Sam Bankman-Fried), and how the judge is likely to respond to him contacting FTX employees. We also talk about David DePape, who seems pretty nuts — but not nuts enough to have an effective insanity defense for his attack on Paul Pelosi. That’s the end of the free episode. For paying subscribers, we continue on with answers to your questions about Alec Baldwin, who has officially been charged with involuntary manslaughter. And we have more Trump litigation to discuss — he’s suing Bob Woodward, saying Woodward wasn’t supposed to release the audio recordings of Trump’s interviews with him. And Manhattan DA Alvin Bragg appears to be investigating another angle on possible criminal wrongdoing — but not a very promising one.

Visit serioustrouble.show to become a paying subscribe and to find relevant links and episode transcripts.

08 Feb 2023Elon, Being Elon, Gets A Win00:25:06
This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

Elon Musk got a big win in the civil trial over whether his “funding secured” statements defrauded shareholders. We talked about how “that’s Elon being Elon” can be an effective defense. We also talked about Sam Bankman-Fried and the ever-sprawling pool of potentially-cooperating witnesses who might tell prosecutors about his and FTX’s wrongdoing. For paying subscribers, there’s more: the California State Bar might disbar attorney John Eastman, Mark Pomerantz has written a book about how he thinks the Manhattan DA's investigation of Donald Trump could have been different (he quit the investigation), and the feds are investigating George Santos about the GoFundMe for that poor service dog's care.

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17 Feb 2023A Jury So Special and Grand00:32:09

Dear listeners,

We’re back with more serious trouble!

On this week’s show, we take a look at the (partial) report of a Georgia special grand jury that had been investigating efforts to interfere in that state’s reporting of its 2020 presidential election results. The report says the grand jurors think they heard some perjury. And its unreleased portions may contain recommendations about criminal charges — recommendations that Fulton County District Attorney Fani Willis could bring to a regular grand jury for indictment.

We talk about Mike Pence’s effort to avoid a subpoena from Special Counsel Jack Smith. Pence says he’s can’t be forced to testify about January 6 because of the “speech or debate” clause of the US Constitution, which protects senators and representatives from being questioned about their official duties. Except… he wasn’t a senator or a representative, he was the Vice President. The VP has an odd place in our constitutional structure — mostly executive, but also the presiding officer of one house of our legislature — and we talk about the possibility that Pence could assert testimonial protections assigned to either branch.

We talk about federal prosecutors’ efforts to pierce attorney-client privilege and force one of former president Trump’s attorneys to testify about his interactions with his client — which gives us an opportunity to talk once again about the crime-fraud exception to attorney-client privilege.

We talk about Alec Baldwin. As we discussed a couple of weeks ago, he has a good argument that the firearms enhancement prosecutors want to use to extend his sentence can’t be applied to him. His expensive, talented and aggressive lawyers are on that question — after a Variety reporter asked them about the issue, after hearing about it on our podcast — and they’re also looking to disqualify the currently-assigned special prosecutor on his case. Meanwhile, Baldwin is preparing to restart production on Rust… so Ken talks about why it might not be the best idea to literally act out the events that led up to your criminal charges while you face trial.



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22 Feb 2023Bad News for Fox News00:35:29

Defamation litigation tends to be unavailing. Many offending statements don’t meet the definition of defamation — they may be opinions, or insults, or false statements against a public figure made without actual malice, or even true factual statements you just didn’t like hearing. This week’s episode is mostly a deep dive into defamation lawsuits brought against Fox News (and related parties) by two voting technology companies, Dominion Voting Systems and Smartmatic. This litigation looks different from most defamation litigation. Smartmatic and Dominion are large companies whose business has likely been impaired by the lies told about them. Those lies were broadcast extremely widely — no need to worry about the Streisand effect. One of the entities that shared many of the lies, Fox News, is a very deep pocket. And Fox has good reason to worry it could end up facing some very large judgments. Ken and Josh discuss the favorable rulings and power moves in both of these cases, plus an update on Rust shooting. (Appellate public defender Caitlin Smith, who wrote into us several weeks ago about why the enhancement was invalid, has been proved right.) And we talked about how Sam Bankman-Fried got into a position where the judge presiding over his case seems to like him less than the prosecutors do.

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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
08 Mar 2023The Anti-Privilege of Being Donald Trump's Attorney00:34:47

First: Yet another of SBF's top lieutenants has pleaded guilty to crimes including wire fraud and commodities fraud, and in the plea documents we learned more about SBF’s ill-advised campaign finance schemes. Plus, prosecutors and his own lawyers are proposing an agreement to further restrict SBF’s access to technology — including taking away his smartphone. Then Josh and Ken catch up on Donald Trump’s legal affairs. There are signs that special counsel Jack Smith is trying to move swiftly toward charging decisions — though “swiftly” means something different to a federal prosecutor than to most people, and legal wrangling over efforts to pierce Trump’s attorney-client privilege could delay matters. We talked about why some of Trump’s conversations with lawyers might not be privileged, and what it means for the investigation that prosecutors are so interested in his dealings with his lawyers. And then we talked about different kinds of privilege, relating to Trump’s former role as president. Trump says he can’t be sued for inciting violence on January 6 because remarks he made on the White House lawn were given in his official capacity. The Department of Justice narrowly disagrees (which is surprising). Finally, we looked at Trump’s assertion that executive privilege bars Mike Pence from testifying before a grand jury regarding events related to January 6. In doing so, he faces a legal problem we’ve discussed before: How can you assert executive privilege against the executive branch?

Visit serioustrouble.show to find a transcript of this episode and to subscribe.



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
15 Mar 2023The Week Of Unintended Consequences00:33:47

It appears that E. Jean Carroll’s defamation lawsuit against Donald Trump might actually go to trial pretty soon — the court is behaving like it does when a trial is about to begin. This week, we talked about evidence of Trump’s prior behavior — two other accusations from women who say he committed sexual crimes against them, decades apart — that Judge Lewis Kaplan has decided may be admitted in court. Usually, testimony about prior bad acts isn’t allowed in evidence because it’s prejudicial, but there’s a special, legislated exception for evidence about sexual assaults. Even the Access Hollywood tape will be admitted under this exception.

We also talked about moves by Manhattan DA Alvin Bragg, who may be preparing to indict Donald Trump for falsifying business records related to his hush-money payment to porn actress Stormy Daniels. And we talked about Peter Strzok and Lisa Page, the former FBI staffers who were involved in both an extramarital affair and the FBI’s investigation into the Trump campaign’s links to Russia. He’s suing for wrongful termination and she’s suing over the release of her embarrassing text messages; long-suffering federal judge Amy Berman Jackson is presiding over their case, and she’s decided they may depose both Trump and FBI Director Christopher Wray, but only about specific topics and only for two hours each. We discussed what you have to show in order to get the right to depose a president (or former president) himself when you sue the US government.

Visit serioustrouble.show to find a transcript of this episode and to support our 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
30 Mar 2023Because I Got Sued00:15:54
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Ken is back from his vacation, and there were no Trump indictments while he was gone. Isn’t that nice? We discuss the evidence that led many people, including Trump himself, to declare an indictment was imminent; and we discuss what we might infer about whether there will even be an indictment. Plus, updates on other Trump-related legal proceedings: anonymity for the jury in E. Jean Carroll’s defamation lawsuit, and a not-yet-released ruling that requires Mike Pence to testify about some topics for a grand jury in Washington D.C.

But none of those is the big story of the week. BY OVERWHELMING REQUEST: we discuss the police raid on Afroman's house, how he turned footage of that raid into new songs and music videos and merch (including footage of a cop apparently getting a little distracted from his official duties by a lemon pound cake that was on Afroman's kitchen counter), and how he's being sued by the cops for doing so.

That Afroman conversation is for paying subscribers only, as is our update on Sam Bankman-Fried, who has been indicted yet again for serious financial crimes. (Sam! Enough already.)

Visit serioustrouble.show to become a paying subscriber and you'll receive all of our full episodes from now on.

06 Apr 2023The Indictment00:11:34
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Well, this one’s a doozy. There’s a reason this week’s episode for paid subscribers is more than an hour long. After years of hearing that “the walls are closing in on Donald Trump,” after two impeachments, and after Ken and Sara and I produced hundreds of podcast episodes regarding his legal travails, Donald Trump has finally been charged with a felony — 34 of them, actually. It’s quite complicated and interesting, and we have a lot of analysis of how we got here and what’s likely to happen next. And yet. The charges that Manhattan DA Alvin Bragg have brought… well, they’re a real stretch. Still, even though this looks like a weak prosecution, it’s going to be a complicated and interesting one.

Become a paying subscriber to hear the entire episode and all future episodes. Sign up for $6/month or $60/year at serioustrouble.show. This is a 100% listener-funded podcast, and we are proud of it.

13 Apr 2023Goat's Dominion00:25:30
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This week, Ken and Josh discuss major developments in Dominion Voting Systems’ lawsuit against Fox News, which will imminently go to trial in Delaware. So far, pre-trial rulings have been in Dominion's favor, but as we saw a few months ago in the Tesla shareholder lawsuit against Elon Musk, it’s possible to win big on the pre-trial motions and still lose at trial. We discussed that outlook as the parties proceed into jury selection. We also talked about a goat — you have probably read about Cedar, the goat that the Shasta County Fair Board had seized and killed after the young girl who was raising him decided she didn’t want to give him up for slaughter. Ken describes why they’re going to have a tough time getting relief in court.

And for paying subscribers, we have more conversation about Manhattan DA Alvin Bragg’s indictment of former president Donald Trump. Many of you pointed out the case looks stronger than commentators (including us) have given it credit for, and we discuss those specifics.

Visit serioustrouble.show to become a free or paying subscriber of our podcast. Thank you for your support!

19 Apr 2023Wow, That's a Lot of Cash00:31:07
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Well, holy crap. As you’ve likely heard, Dominion v. Fox will not be going to trial. We recorded this episode on Tuesday morning, and then when the settlement came out, we recorded again — so this is some fresh, fresh content, looking at what forces would have driven the parties to get to ‘yes,’ and how the settlement came to be so large — likely the largest settlement ever paid in a defamation case in the US.

Read more from Josh and Ken, support our show, and find other links (including Josh's lemon pound cake recipe) at serioustrouble.show.

27 Apr 2023Tucker Said It00:24:36
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*This episode contains un-bleeped profanity, as usual, but the swear jar is used once.

Tucker Carlson has been dismissed from Fox News. Media accounts on why he was fired differ, but the departure looks like it was, in one way or another, downstream of the lies Fox broadcast about Dominion Voting Systems and the legal proceedings that ensued. Ken and I talked this week about the stresses that litigation can impose on any organization, and about what you can do when you want to fire an employee who’s also a key witness in a lawsuit you face. Meanwhile, the civil trial over E. Jean Carroll’s rape allegation against Donald Trump has begun in New York. We talk about the opening statements, which reflect quality representation on both sides of the case, and about when a defendant should and should not show up to court.

That’s the show for free subscribers. Paying subscribers also hear about Mike Lindell, who offered up a $5 million reward to anyone who could “Prove Mike Wrong” and an arbitration panel has ordered him to pay up, which he didn’t want to do, even though he was proved wrong. Paying subscribers also get an update on Hunter Biden, who’s made some dumb choices in a custody proceeding that could hurt his position vis-a-vis the ongoing criminal investigation into his finances. And you hear an expert listener’s answer to our question about Afroman, “Under the Boardwalk,” and intellectual property. We knew the RICO Hotline would come through on that one.

Visit serioustrouble.show to find a transcript of this episode and to support our show.

05 May 2023A Detailed Explanation of the Rule Against Perpetuities00:46:45

This episode of Serious Trouble, live and in person with Ken and Sara! This week, Ken and I talked about the Walt Disney Company’s lawsuit against Florida Gov. Ron DeSantis, which raises an interesting legal question: When is an otherwise-constitutional government action made unconstitutional by the motive that elected officials had for acting? The Disney case also gave me an opportunity to make Ken talk about the rule against perpetuities, which was almost as enjoyable as when I make him read out the RICO Hotline email address.

There’s more in this episode. We also talked about developments in E. Jean Carroll’s civil lawsuit against former president Donald Trump over the rape she says he committed against her in the 1990s. And we talked about developments in other proceedings — Trump’s loss in the suit he brought against his niece and The New York Times, Mike Pence’s appearance before special counsel Jack Smith’s grand jury in Washington DC, and the dismissal of the involuntary manslaughter charge against Alec Baldwin.

This episode is free for all listeners. It also includes questions and feedback from a few of you — we appreciate all your emails and comments. Of course, if you want to join those comments, you have to be a paying subscriber… so if you’re not, maybe consider an upgrade? We’d love to have you on board. 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
11 May 2023At Least George Was Working00:35:50

This week, Ken and I discussed the verdict — and the $5 million judgment — in the Carroll v. Trump case, and whether Donald Trump erred, in retrospect, by not showing up for trial. We also talked about his prospects for appeal (slim) and when E. Jean Carroll can expect to get her money. We talked about Rep. George Santos, who has been indicted for crimes including unemployment insurance fraud. (How pedestrian!) We talked about his best strategy going forward from this point, and the major bargaining chip he holds — his ability to resign from the office he olds (for now) as part of any plea deal.

Visit serioustrouble.show to become a support of the show — you'll find a transcript of this episode and the rest of the Serious Trouble episodes there too.



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
17 May 2023Preclusion00:38:45

Ken and I started this week talking about the CNN town hall with Donald Trump. On CNN’s air, Trump repeated his denials of his assault of E. Jean Carroll — denials for which he was ordered (the day before the town hall) to pay a defamation judgment. Carroll has mused about suing him again, and she could, though her main challenge in court would be showing that his fresh denials further harmed her, beyond the damages she’s already been awarded compensation for. We also talked about the legal considerations facing CNN or any other network that might interview a person who is likely to make defamatory statements. We talked about George Santos, who appears to be quite enjoying his role as a federal defendant, and about whether you should give a hyped-up press conference explaining why it was okay for you to take the unemployment benefits the government has charged you over (no). And we talked about Nina Jankowicz, former head of the short-lived Disinformation Governance Board at the Department of Homeland Security. That board was dissolved after extensive attacks on Jankowicz in conservative media, and now she’s suing Fox News for defamation. Ken and I discussed her uphill legal battle.

Visit serioustrouble.show to find a transcript of this episode and to support our work.



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
24 May 2023Shopping With Rudy00:42:05

Is Rudy Giuliani in serious trouble? He’s facing two lawsuits. One is for getting a supermarket employee arrested. The other is… well, it’s for a lot of stuff. Ken and Josh discuss the prospects for ShopRite employee Daniel Gill’s lawsuit over Rudy crying “assault” over a tap on the shoulder. s for Noelle Dunphy, she has some pretty shocking claims about several areas of alleged misconduct, and we want to see what does (or doesn’t) come out in discovery to support them. We also talk about Mark Pomerantz — the former Manhattan prosecutor who somehow took the Fifth when House Republicans tried to question him about the investigation into Donald Trump — and John Durham, whose own prosecutorial endeavors have wound down with a fairly underwhelming report. We talk about signs of activity in the Trump documents case that are maybe being over-read in the press, and about new infighting in Trump’s legal team. And we talk about E. Jean Carroll’s other lawsuit — the one that’s still tied up in questions about whether Trump can be sued personally for statements he made about her while he was president — and what significance that lawsuit holds now that she’s already won a multimillion dollar judgment on closely related claims.

Visit serioustrouble.show to find a transcript of this episode, relevant links and to support our work.



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
06 Jun 2023The Legal Brief: Beyond the Machine00:22:55

In this eye-opening episode of "The Legal Brief: Beyond the Machine," renowned attorneys Ken White and Josh Barro explore the potential risks and limitations of using AI, specifically ChatGPT, for drafting legal briefs. Joined by esteemed legal professionals and experts, they delve into the allure of technology, the nuances AI may overlook, and the potential ethical dilemmas and risks of inaccurate information. Discover why relying solely on ChatGPT for your legal briefs may not be as foolproof as it seems. Tune in to gain valuable insights that challenge conventional perceptions and reshape the way you approach legal writing in the digital era.



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15 Jun 2023Luck Of The Draw00:21:25
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We got a lot of listener feedback about last week’s episode, especially about Kenny Raincloud’s take on how Judge Aileen Cannon could tank the government’s case against Donald Trump if she cares to. This week, for paying subscribers, Ken responds to a lot of that feedback — getting especially specific about the attorney-client privilege issues that are likeliest to trip up the government, and how the government could (maybe) get an appeals court to remove Cannon from the case. We also talked (for all subscribers) about Trump’s arraignment, and the especially lenient conditions of release that were offered to the former president.

Plus, for paying subscribers: drama between the large law firm Lewis Brisbois and a pretty large new firm founded by 140 (!) attorneys who simultaneously left Louis Brisbois. No one looks good. And we have an update on the ChatGPT case, where attorneys Steven A. Schwartz and Peter LoDuca have been in the unfortunate position of pleading stupidity to a federal judge.

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10 Jun 2023Big-Boy Federal Felonies00:31:04
This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show

There is no such thing as an emergency podcast. But… this is as close as we get. Serious Trouble is back for a second time this week because Donald Trump has been indicted. Again. But this time in federal court — and on a set of charges that can’t (easily) be dismissed as chickenshit. The 49-page indictment has remarkable and hilarious detail, including Trump making the sorts of statements prosecutors can only dream of when trying to prove a crime with a challenging intent requirement. As Ken says in this episode, it’s a set of facts a prosecutor could reasonably feel cocky going into court with against a normal defendant. But Trump isn’t a normal defendant, and it won’t be a normal case.

This week’s show is more than an hour — for paying subscribers. Everyone gets the first half hour. Visit serioustrouble.show to become a paying subscriber and get access to the full episode and all the other episodes we make too.

03 Jul 2023Special Episode: How To Be A Smarter Consumer Of Legal News00:53:08

Happy Fourth of July Week! Josh and Sara and I will be back to breaking news next week. For now, enjoy this deep dive special episode about how to be a critical consumer of legal news, and hear a useful explainer of the U.S. Sentencing Guidelines — helpful for anyone who has ever read the words "they face a maximum of __ years in prison."

Visit serioustrouble.show to see notes about this epsiode, including a transcript, and we welcome you to support our podcast for $6/month or $60/year there.



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
22 Jun 2023Don't Admit Your Crimes in Televised Interviews or Soul-Baring Autobiographies00:47:38

We’re back with another episode of Serious Trouble. And this week, Ken feels compelled to summon the scream of a goat to express his feelings as we add two more items to the list of contexts in which one should just shut up if under criminal investigation. One of those contexts is a televised interview with Fox News Channel’s Bret Baier. We look at the admissions Donald Trump made about which documents he retained and why, and how those could help the government, particularly if Judge Aileen Cannon were to throw out other evidence of Trump’s knowledge and intent that is needed to prove the charges against him.

Another such context is Hunter Biden’s 2021 tell-all autobiography, in which he made admissions related to a gun purchase for which he has not yet been charged with a crime. The issue is that Hunter falsely claimed not to be addicted to any illegal substances when he purchased a gun in 2018. As Ken notes, this is a crime that’s rarely prosecuted, and one that prosecutors might never have thought of if he hadn’t written the book. Also this week, we look at news reports about internal disagreement within the Department of Justice about whether the January 6 investigation should have turned sooner to the question of criminal liability on the part of Donald Trump, we also look at initial orders from Judge Aileen Cannon in the documents case — boilerplate so far — and at the complicating role that the Classified Information Procedures Act could play in the case’s early days.

Visit serioustrouble.show to find a transcript of this episode and to support our work.



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
29 Jun 2023I'm a Legitimate Person00:46:45

The goat is back. You can thank Rudy Giuliani, who — for some unknown reason — sat for a voluntary interview with federal investigators. This week, we talked about The Tape — the recording of Trump bragging about his possession of a classified Iran war plan he now says he didn’t possess at all. Trump says it’s a misunderstanding: he’s a “legitimate person,” and if he was talking about having “plans,” they were probably for buildings or golf courses. But what the documents were or weren't about is, as far as his legal case goes, unimportant. The key legal thing about the recording is what it shows about his knowledge about classification. After all, the government never found the war plan document, and it never charged him for possessing it. Speaking of never finding that document — maybe it’s at Bedminster, right? Ken and I talk this week about news about Bedminster, and why the government never executed a search warrant there like they did at Mar-a-Lago. We also talk about early orders coming down from Judge Aileen Cannon — so far, they seem pretty sensible and appropriate. Finally, we talk about Hunter Biden and the IRS whistleblower who says prosecutors protected him from the felony charges he should have faced.

Visit serioustrouble.show to find a transcript of this episode and other relevant links, and you can also become a member and support the show there.



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
18 Jul 2023Not-So-Speedy Trials00:46:04

This week, we talk about the arguments before Judge Aileen Cannon about when she should schedule the federal criminal trial of Donald Trump. The Trump team has made arguments for a long delay, some of them very splashy and aggressive — most prominently, their insistence that he should not be tried until he is no longer a prominent political candidate. But there are lots of other reasons a trial like this would take a long time to start and it seems likely that Trump’s side will succeed, one way or another, at pushing back the trial’s start well into next year or beyond.

We talk about Rudy Giuliani and Lin Wood — the former may lose his law license because of his 2020 election-related shenanigans, and the latter has given his license up so he can stop going to so many hearings. We talk about E. Jean Carroll, who is still trying to sue Donald Trump for statements he made while in office — and who no longer faces opposition from the Department of Justice in her effort to do so. And we talk about Elon Musk, who is suing Wachtell Lipton, the law firm that represented Twitter in its successful effort to force Musk to close the acquisition deal he’d agreed to.

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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
28 Jul 2023This Episode Has Been Superseded00:59:57

When Sara, Ken and I discussed when to record this week’s episode, we were concerned about when a new federal indictment of Donald Trump might drop. Naturally, one dropped literally minutes after we finished our recording session — but not the one we’d been preparing for. A federal grand jury in south Florida has issued a superseding indictment in the documents case, which adds new charges, some new amusing color about security cameras, and a new defendant.

So, we re-started the recording to produce a superseding opening segment to this week’s podcast (while preserving our original episode opening, for transparency and for your amusement). Meanwhile, in indictments that didn’t happen: Trump hasn’t been indicted in the January 6-related case for which he received a target letter over the weekend, but an imminent indictment is likely, quite possibly next week. And Hunter Biden didn’t get indicted on Wednesday even though he wanted to be, because his attorneys and the government didn’t agree on the meaning of the convoluted plea and diversion agreements they had negotiated. Oh! And Sam Bankman-Fried. He’s in trouble again. Would a gag order from the judge be more effective than a de facto gag order from....his parents? Support our show and find a transcript of this episode 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
02 Aug 2023Trump Is Indicted for Trying to Steal the Election00:26:46
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Donald Trump got indicted again. (And this time, we hadn’t started recording the week’s episode. So we set about doing so, on an urgent but non-emergency basis.) This new federal indictment, issued in Washington DC, is for trying to steal the 2020 election. This was a grave abuse of his office, for which he was impeached though not convicted. Special prosecutor Jack Smith says it was also a crime — actually, several crimes. On this week’s episode, Ken and I discuss Trump’s likely defenses. Free subscribers will hear all of that.

Paying subscribers get a lot more, including: a discussion of Trump’s six alleged co-conspirators, some of whom are likely to be indicted later; the indirect role of the January 6 riot in the government’s case, what we know about Judge Tanya Chutkan, who is likely to preside, when we can expect this trial to start (and how long it will take), and what sort of sentence Trump might face if he’s ultimately convicted.

If you are a paying subscriber to Serious Trouble, we appreciate you and we’re glad for your support, which makes this show possible. If you’re not a paying subscriber and you’d like to hear all the topics I list above, join our community and unlock this full length episode (and all of our future episodes) for $6/month or $60/year at serioustrouble.show.

09 Aug 2023Penal Colada00:46:46
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Another serious week on Serious Trouble! In Washington DC, Trump's attorneys are fighting with prosecutors about what Trump can say in public about his case and what's obtained in discovery. It's not a gag order, and Ken says what Trump's already saying about Mike Pence and others on social media aren't true threats either. Speaking of dumb things to post online, Ken’s been writing/complaining about bad, misleading coverage of the Trump cases: clickbait-y stories about potential sentences and whether or not Jack Smith’s charges in D.C. violate established law. That's the episode for free subscribers. Paying subscribers get our discussion of Judge Aileen Cannon's first sort of spicy order in the Trump documents case, and also, by request, a discussion of an academic scandal at Harvard with a litigation angle. It's an accusation of research dishonesty in a study about honesty — and now the professor is suing both Harvard Business School and the authors of a research integrity blog that pointed the issues out to Harvard. Juicy.

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15 Aug 2023This Episode Is Not RICO01:01:30
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The big Georgia indictment came out late Monday night, conveniently released around 11pm eastern, with many counts and many defendants, including Donald Trump. We will soon have an episode for you about it — but that's not what this is. This show, taped on Monday morning, covers developments in Trump's federal criminal case in DC, Twitter's unsuccessful effort to get the right to warn Trump about a search warrant, Sam Bankman-Fried's return to jail over his improper dealings with witnesses (and why Trump gets more leeway), more legal bumbling from Rudy Giuliani, and a fancy hotel's defamation lawsuit against a very unlikable rich kid who nonetheless has constitutional rights that a court has been trampling on. We hope you enjoy the show and we'll be back with more on Georgia later this week.

15 Aug 2023Unfortunately, This Episode Is RICO00:21:55
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Okay, now it’s RICO. Donald Trump and 18 alleged co-conspirators have been indicted on 41 counts in Fulton County, Georgia, and the headline count is RICO: District Attorney Fani Willis alleges this group constituted an enterprise trying to steal Georgia’s electoral votes (and those of other states) in violation of Georgia’s version the Racketeer Influenced and Corrupt Organizations Act. We’re skeptical of Willis’s plan to take this thing to trial within six months. In fact, we think the whole thing is overcomplicated and excessively vulnerable to constitutional challenge. Georgia defense lawyer Andrew Fleischman joins us to discuss the overreach and excessive creativity in this indictment, and the likelihood that any Georgia RICO prosecution will drag on for years, with Trump's own trial very possibly moved into Federal court. Not great.

23 Aug 2023Removal00:52:31

The big action this week was again in Georgia, where 3 of the 19 defendants in Fulton County DA Fani Willis’s RICO case sought to remove their cases to federal court. Removal of criminal cases is unusual — it’s much more common in civil court — so the law on when a federal officer must be tried in federal court is less well developed than you might hope. Ken and Josh talked about the varying strength and creativity of the removal arguments from Jeffrey Clark, Mark Meadows and David Shafer. And we’re still waiting for the removal notice from Trump himself. The whole situation is a bit of a mess — expect Fani Willis to keep moving straight ahead — it could take years to resolve.

In other news, we’ve learned more about the demise of Hunter Biden’s proposed plea agreement, including some signs that Republican political pressure was an important factor in the deal falling apart. And we talked about a remarkable and bold threat from Hunter’s lawyer — that they would seek to put Joe Biden on the stand if Hunter went on trial. Yikes. And we talked about further signs of the financial strain legal troubles are putting on Rudy Giuliani — and about the former president’s limited willingness to help him out with that.

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31 Aug 2023No! Bad Lawyer! Bad!00:31:54
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Rudy Giuliani and Michael Avenatti both used to be good lawyers — or, they at least used to seem to be good lawyers — but those days are long past. This week, Ken and Josh discuss Giuliani and Avenatti — a two-fer — and how Giuliani’s drinking actually poses multiple problems for Donald Trump’s likely legal defenses in Jack Smith’s January 6-related case. We also talk about the trial date that’s been set in that case — March 4 — and the mess that could ensue if Trump tries to skip his own trial, which could result in Chutkan deciding whether it’s worth the drama of having him arrested for violating his bail terms. And we talk about the expanding complications in the prosecution Fulton County District Attorney Fani Willis has brought against Trump and 18 alleged co-conspirators, all of whom she hopes to try in one single trial. Some of the defendants want to delay the trial, while others want to go to trial quickly.

Free subscribers get our conversations about Georgia and Giuliani. Paid subscribers also get the conversation about the DC case and the March 4 trial date, and Michael Avenatti. Visit serioustrouble.show to become a paying subscriber.

08 Sep 2023Severance Pays00:44:17
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Here’s what’s on tap in this week’s episode of Serious Trouble.

- The sentences that have been coming down for some of the prime movers behind the January 6 riot at the Capitol

- Fulton County DA Fani Willis says it will take her four months and 150 witnesses to try her big election RICO case — and that each trial will take that long, whether it involves one defendant or all 19. Really?

- Sidney Powell and Ken Chesebro want to be tried separately, but the judge said no. And Trump wants to sever his case from the other 18 defendants.

Plus: an even bigger Georgia RICO case, Trump takes another loss in E. Jean Carroll's other civil case against him, Elon Musk threatens to sue the ADL, and prosecutors say they might soon indict Hunter Biden on gun charges, which seems odd.

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12 Sep 2023What About All the People I Didn't Indict?00:25:57

This episode starts in Georgia and with Mark Meadows, who lost harder than we expected in his efforts to keep his RICO trial in federal court. And we discuss the report of the investigative special grand jury, which recommended charges against 39 individuals — way more sweeping than the already-cumbersome 19-person indictment that DA Fani Willis got from the regular grand jury. Plus: a very strange open letter from some criminal defense attorneys to Ken Chesebro, urging him to protect his interests by pleading guilty. A reminder: You shouldn’t take unsolicited legal advice offered over the internet, and you shouldn’t really offer it either — though as Ken notes, this isn’t professional misconduct, it’s just stupid. And speaking of stupid, we talk about Peter Navarro, who walked himself into a federal criminal conviction through a set of actions even the Wall Street Journal editorial page couldn’t defend.

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21 Sep 2023The Lawsuit Matryoshka00:18:49
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Rudy Giuliani's ex-lawyer is suing him for non-payment; Hunter Biden is suing the IRS for airing his dirty laundry; the FTX bankruptcy estate is suing SBF's parents for being morons; Ray Epps, still not a Fed, is pleading guilty; Jack Smith wants a gag order on Donald Trump.

30 Sep 2023Bribery Is Still Illegal00:45:31

The McDonnell line of Supreme Court cases isn't likely to save Bob Menendez; Hunter Biden sues Rudy Giuliani and Robert Costello, who is suing Rudy Giuliani; Judge Tanya Chutkan isn't going anywhere



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09 Oct 2023Donald Trump's First Gag Order00:41:10

Donald Trump withdrew his lawsuit against Michael Cohen so he wouldn’t have to sit for a deposition on the holiday, but Columbus Day didn’t stop us from bringing you a new episode of Serious Trouble. This week, we look at Trump’s first gag order: The former president’s gratuitous social media attacks against Judge Arthur Engoron’s law clerk enraged the judge and led him to order Trump (and also the other parties in the New York AG’s civil fraud lawsuit) not to publicly criticize his staff. We also talk about scheduling. Trump has asked Judge Aileen Cannon to delay his criminal trial in the documents case, which is currently set for May. We talk about defamation litigation — Rudy Giuliani is suing Joe Biden for calling him a Russian pawn, a California college student is suing Elon Musk for accusing him of being a fake white nationalist, and a Georgia voter is suing Dinesh D’Souza for calling him a ballot mule. And we look briefly at the Georgia RICO case, where one minor defendant is pleading guilty and cooperating — though it remains to be seen how that will effect the cases DA Fani Willis can present against more prominent defendants.

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17 Oct 2023Donald Trump's Second Gag Order00:47:04

When it rains, it pours: Donald Trump is now subject to not one but two gag orders, and the new one is more expansive than the first. Judge Tanya Chutkan's order isn’t as broad as the government requested — Trump is still free to criticize Judge Chutkan herself, as well as the US government and the Justice Department, though not the individual prosecuting attorneys — but it’s broad enough to be constitutionally questionable. Trump will appeal the gag order — and Ken is pleased that this case will present an opportunity to develop law in this area, since it’s currently unclear what the Constitution demands when balancing defendants’ speech rights and the courts’ needs. Of course, there’s also the open question of what Judge Chutkan will actually do if and when Trump violates her order.

Also on this episode: two superseding indictments for members of Congress — Senator Bob Menendez and Representative George Santos. We take a look at Sam Bankman-Fried’s ongoing trial and at how being in federal custody might affect your access to Adderall. We talk about DA Fani Willis’s apparent intention to call Alex Jones to testify in the upcoming “cheese and crackers” RICO trial of Kenneth Chesebro and Sidney Powell.

And we have an update on the case of Prof. Francesca Gino, who sued Harvard (and several of her fellow behavioral scientists) after Harvard suspended her without pay following concerns those scientists raised about data fraud in her papers.

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25 Oct 2023You Wouldn't Like Me When I'm Angry00:43:20

It’s been a heated week at Donald Trump’s civil fraud trial in New York. Judge Arthur Engoron was enraged at Trump’s failure to fully comply with an order to take down a web post attacking his law clerk and he imposed a $5,000 sanction. Trump attorney Christopher Kise also drew the judge’s ire for his rude and dismissive comments to that same law clerk and to one of the attorneys from the New York Attorney General’s office. Not great.

Plus: we're up to four guilty pleas in DA Fani Willis' RICO prosecution, Judge Tanya Chutkan issued a written version of the gag order she’d already announced in court, but then issued a stay pending appeal. That stay means Trump remains free to run his mouth as he likes (except about Arthur Engoron’s court staff) and he has been. In New Mexico, prosecutors plan to take Alec Baldwin’s manslaughter charge to a grand jury again — we discuss what could be going on here. And Ken and I talked some about whether it might be a good idea to put Sam Bankman-Fried on the stand to defend himself, and after recording, we learned his defense team intends to do just that.

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01 Nov 2023Serious Trouble Episode 6900:18:50
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Donald Trump may be in serious trouble, but Michael Cohen’s testimony isn’t the reason. On this week’s episode, Ken and I talk about the thud with which Cohen’s testimony landed at the civil trial over alleged fraud at various Trump businesses. Judge Arthur Engoron called a little impromptu hearing in which Trump took the witness stand, testifying about who exactly he was referring to when he told reporters a person sitting “alongside” the judge was even more partisan than him. In DC, Judge Tanya Chutkan has un-stayed her broader gag order, so Trump is again permitted from “targeting” court staff, the prosecution team, and likely potential witnesses.

Plus: in Colorado, there’s a trial to decide whether Trump can even be on the state’s presidential ballot, or whether part of the 14th Amendment bars him from serving as president again on the grounds that he participated in an insurrection or rebellion in violation of his oath of office. And: an update on Sam Bankman-Fried, who has testified in his defense — we talk about how that went. Finally, from Long Island, an update on George Santos.

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08 Nov 2023A Whole Lot Of Finding Out00:41:00

Welcome to this week’s episode of Serious Trouble, in which Josh attempts to troll Ken about maximum sentences. Sam Bankman-Fried was speedily convicted by a jury that took only several hours — one of them spent at dinner — to deliberate. Will the government bother to try him on the remaining charges? Meanwhile, also in New York, Trump and his lawyers continued on a strategy best described as “burn everything down and see what emerges from the ashes.” Plus: former White House Chief of Staff Mark Meadows’ publisher sues him because he’s allegedly made statements to Special Counsel Jack Smith that contradict the 2020 election narrative in his book. But Josh and I want to know — what exactly did the publisher think they were paying for? Finally: John Eastman. And Lizzo.

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17 Nov 2023Incitement00:52:35

Donald Trump “re-truthed” a post calling for a “citizens’ arrest” of Judge Arthur Engoron and New York Attorney General Letitia James. Normally, when people ask Ken whether a statement is illegal incitement, the answer is a quick “no,” but this case is closer. Also in New York, Mayor Eric Adams looks to be in somewhat serious trouble. The FBI raided the home of his chief fundraiser and his own electronic devices were seized. Hunter Biden wants to subpoena documents about his prosecution from Trump administration officials, going all the way up to the president himself, as part of an effort to make a defense of selective prosecution. There’s one big problem — he isn’t being prosecuted by the Trump administration.

In Georgia, District Attorney Fani Willis says Trump’s RICO prosecution is likely to stretch into 2025 — no surprise to you if you listen to this podcast — and some of the minor defendants have been making trouble. And in Washington, something seems to be in the water at the Capitol building. Congressman Tim Burchett says former speaker Kevin McCarthy intentionally elbowed him in the kidney — which would be assault, but not the kind of assault that ever gets prosecuted. And the House Ethics Committee says George Santos spent campaign funds on botox, OnlyFans, and a modest shopping spree at Hermès — not only illegal, but behavior he’s already under indictment for. Not smart.

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30 Nov 2023Officers of the United States00:39:03

Unfortunately we taped this episode before Elon Musk urged Disney CEO Bob Iger to go fuck himself. If we had waited, we would have been able to discuss how Musk had reinforced one of Ken’s points about Twitter’s lawsuit against Media Matters for America over its report showing that Twitter served up ads for major brands next to neo-Nazi content. That discussion is at the end of this episode. We also talked about Judge Tanya Chutkan’s gag order against former president Donald Trump that looks likely to produce some judicial clarity on the under-litigated question of how courts must balance the free speech rights of defendants with the prerogative of judges to oversee orderly trials. Plus: more statees debate Trump's eligibility for the ballot, Hunter Biden dares House Republicans to invite him to testify in an open hearing, and if you're a RICO defendant, is it wrong to tag witnesses on social media?

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07 Dec 2023Absolute Immunity00:18:26
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One of Donald Trump’s favorite arguments is that the presidency shields him from legal proceedings. He’s made that argument in criminal cases and in civil ones, but this week, we talk about rejections of those arguments from two different judges. Plus: Jack Smith wants to introduce Trump's political statements and actions going all the way back to 2012; serious trouble for Alina Habba; gold bars do have serial numbers, you know; Rudy doesn't show up in court; and was that wrong — taking a phone call while on the witness stand?

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19 Dec 2023Justice Delayed00:46:24

We have two episodes coming for you this week, one right now and one near the end of the week. On the second episode, we’ll be taking your end-of-year questions — if you have a burning question for Ken, please send it to the RICO hotline by Wednesday morning so we can consider it for inclusion.

On today’s show, we talk about a couple of significant matters that stand to delay former President Trump’s federal trial for actions related to the aftermath of the 2020 election. One is his appeal of Judge Tanya Chutkan’s ruling that he is not presidentially immune from trial. It seems likely an appeals court will rule as soon as mid-January, and it’s not clear the Supreme Court will have any interest in taking the case up after that. We'll see. The potentially thornier matter is a separate case the Supreme Court is considering, in which the court could reject the expansive theory of “obstruction of an official proceeding” that federal prosecutors have used in charging many cases related to January 6. Plus: the state of the gag orders on Trump and Hunter Biden. Hoo boy. He already faced a kind of weak-ass gun charge in Delaware, and his lawyers have some pretty good arguments about why that case should be dismissed. But now he’s also been indicted in Los Angeles for felony tax evasion, and the complaint in that case is brutal.

There’s lots more to talk about this week, including the huge defamation award against Rudy Giuliani — we’ll be taking that and some other juicy stories up in the next episode in just a few days.



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21 Dec 2023Uncivil Procedure00:23:09
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Thank you for all the questions you sent in this week! On a related note: take our “explicit” content warning extra seriously this week. All subscribers get our discussion about the Colorado Supreme Court deciding Donald Trump may not appear on that state’s presidential primary ballot, the multiple routes that SCOTUS has available to overturn their ruling, and what might happen if SCOTUS upholds the decision.

If you've been thinking about becoming a paying subscriber to the show, this is the week to do it. serioustrouble.show/christmas gets you a discount, and you'll get to hear about:

Rudy Giuliani's $148 million judgment for his lies about two election workers Ruby Freeman and Shaye Moss; another instance of citing fake cases in a brief submitted to the judge (and this time it involves Michael Cohen); the Senate sex video and the potential criminal implications of it; and the presidents of three elite universities who appeared on the Hill, seemingly more prepared for a deposition than for an argument with Elise Stefanik on national television.

Finally, we have a little time to talk about George Santos, and how the justice system might interfere with the launch of his reality TV career. And we talk about what Ken hopes not to talk about in 2024. We'll be back in January! Thanks for listening.

04 Jan 2024The First Amendment Rights of Vegans00:41:38

It’s a new year and we’re back with more Serious Trouble. This week: the ongoing appeal in the DC Circuit Court of Appeals, where Donald Trump argues he is presidentially immune from trial over his actions that led up to the January 6 riot. This appeal has paused the clock on the criminal case, but probably not for much longer — the appeals court is moving the appeal very fast, and it’s unclear the Supreme Court will have any interest in reviewing their decision. The case may be back in Judge Tanya Chutkan’s hands by the beginning of February.

Plus: can Trump turn this trial into a circus? Why were charges dropped against SBF? Why isn't Michael Cohen going to get out of supervised release early? And was getting fired for making vegan porn a violation of a (now former) state university chancellor's First Amendment Rights? Let's find out.

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11 Jan 2024Estop! or My SEAL Will Shoot00:39:11

It’s a big week for Donald Trump being literally, physically in court — on Thursday, he'll be in court for closing arguments in the New York AG's civil case against him, and he attended Tuesday’s appellate hearing over his claim that presidential immunity shields him from Jack Smith’s prosecution related to January 6. Ken and I talked about how those arguments went — the judges had some interest in procedural issues, like whether they should even be hearing an appeal before the case is decided, and whether Trump is judicially estopped from saying he can’t be tried since Alan Dershowitz argued during his second impeachment that he was susceptible to trial and that was a reason for the Senate not to convict. But the judges also gave signs they might get to the meat of the question, and that they were unimpressed by the argument that, even if a president ordered SEAL Team Six to assassinate a political opponent, he couldn’t be criminally tried unless he were first impeached and convicted by Congress.

Plus: the pending civil case against Trump from E. Jean Carroll, Roger Stone apparently venting about killing two members of the House, Bob Menendez running his mouth on the Senate floor, and then there's Fani Willis, who just might be in very serious trouble. Visit serioustrouble.show to sign up for our newsletter and find a transcript of this episode.



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16 Jan 2024Sweetie, Please File This Lawsuit00:34:41

Donald Trump wasn’t supposed to give a closing statement at the New York AG’s civil trial, but he gave a brief one anyway — and why not? There’s no jury to influence and, let’s be honest, Judge Engoron seems to have made his mind up. Plus: Rudy Giuliani is bankrupt and faces the creditors’ committee of his nightmares. Michael Flynn has a performative defamation lawsuit against Andrew Weissmann, over the allegation that he was actually guilty of the crime he pleaded guilty to. And Bill Ackman says he’ll sue Business Insider for reporting that his wife, former MIT professor Neri Oxman, committed plagiarism — though really, Oxman would have to sue, and an unwinnable lawsuit (as it looks to be) is likelier to serve his PR goals rather than hers.

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24 Jan 2024RICO Is When People Are Mean to Me00:20:46
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The centrist political group No Labels sent a letter to the Justice Department last week, and it’s really something. No Labels plans to run a third-party presidential ticket on dozens of state ballots later this year and mainstream Democrats really don’t like the idea. So they’ve been playing political hardball: filing objections to No Labels’ ballot petitions, conducting opposition research on potential candidates, telling operatives aligned with No Labels that they’ll never work in this town again, etcetera. That’s politics. Right? Well, No Labels says it’s actually a criminal RICO conspiracy to deprive them, their donors, and their potential voters of their civil rights, and they would like DOJ to prosecute some people over it.

Free subscribers will hear that conversation. Paying subscribers get much more — new developments in the divorce debacle that threatens to engulf Fani Willis’s prosecution of Trump and many of his associates under the Georgia RICO statute (it's messy), an update on the second E. Jean Carroll civil trial against Donald Trump in Manhattan, which has been going less than smoothly in Long-Suffering Federal Judge Lewis Kaplan’s courtroom, and Alec Baldwin’s latest indictment for involuntary manslaughter in New Mexico, and the evidentiary issue that is going to give the government a lot of trouble securing a conviction.

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31 Jan 2024More Than Incremental Damages00:35:50

The verdict has come down in the latest E. Jean Carroll defamation case against Donald Trump and the award is enormous: $83.3 million, or more than 16 times the $5 million she was awarded in the first defamation trial. Trump’s bizarre trial strategy is a likely culprit behind the huge judgment: his choice of a combative-yet-incompetent lawyer, his tactic of making as obnoxious a spectacle of himself as possible, and his insistence on relitigating questions that were supposed to have been settled in the first case, all failed to combine to send the jury any message like “this man has already been ordered to pay enough money.”

Huge damage awards often get reduced — will this one?

Also in this episode: Peter Navarro is sentenced to jail time, a judge is sick of hearing that the January 6 defendants are getting a raw deal, another judge does not think it is cool that an IRS contractor illegally leaked Donald Trump’s tax returns, and many listeners correctly identified the first federal judge we deemed "long suffering."

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07 Feb 2024Immune Response00:40:42

A little less than a month after hearing oral arguments, the DC Circuit Court of Appeals has rejected Donald Trump’s argument that he is immune from being prosecuted for acts within the “outer perimeter” of his presidential duties. That should clear the way for Judge Tanya Chutkan to again move toward the start of a criminal trial, unless the Supreme Court decides it wants to consider the case. Ken and Josh talk about the judges’ reasoning, reasons the Supreme Court might decide to sit this one out, and when Chutkan could realistically proceed toward trial under various scenarios.

Plus: Fani Willis' responds to a Georgia RICO defendant regarding her personal relationship with the special prosecutor she hired to oversee the case, Taylor Swift's lawyers send a nastygram to a college student tracking her private plane, Jack Burkman's giving up his law license, and it turns out that the Senate employee who filmed a sex tape in the Hart Building had the good sense to exercise his Fifth Amendment right not to talk to Capitol Police, which means he has better judgment than about half the people we talk about on this show.

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17 Feb 2024Big Judgment00:24:30
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Late Friday, Judge Arthur Engoron issued his long-awaited verdict in the civil fraud lawsuit brought by New York Attorney General Letitia James, and it orders Trump and his affiliated entities to disgorge nearly $400 million to the state of New York for what he says are ill-gotten profits and interest savings made possible by financial misrepresentations. It’s a big judgment — and like the judgment in the E. Jean Carroll case, one he’ll have to put cash up for pretty soon, even if there will be years of appeals. Ken and I discuss what this means for Trump and his businesses, and whether (again, like in the Carroll case) he ended up with a worse legal outcome because he was so obnoxious during the trial process.

Plus: in Washington D.C., the Supreme Court is considering whether to overturn Colorado’s decision blocking Donald Trump from that state’s presidential ballot on 14th Amendment grounds. It can be hazardous to read into oral arguments, but the judges’ questions did not seem auspicious for Colorado. Meanwhile, the court must now decide (and will, probably any day now) whether to involve itself in Trump’s January 6-related federal criminal case. Special Counsel Robert Hur decided not to recommend any criminal charges against President Joe Biden related to his handling of classified documents, but the White House was less than thrilled about Hur’s report explaining why. A Biden accuser faces his own indictment — from Special Counsel David Weiss, who’s also prosecuting Hunter Biden — for making up allegations about the Bidens, Burisma and bribes. And finally, we talk about Georgia. What a mess. District Attorney Fani Willis took the stand in a hearing about whether she should be disqualified from the RICO prosecution she brought against Donald Trump on conflict-of-interest grounds related to a romantic relationship she had with Nathan Wade, the special prosecutor she hired to lead the case. The two-day hearing was salacious.

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23 Feb 2024Fursona Non Grata00:24:53
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George Santos is back, and Ken couldn’t be happier about it. This time, George is on the left side of the v., for once: he’s suing Jimmy Kimmel over copyright infringement. The most shocking part is he may have a good case. Santos says Kimmel committed various torts when he ordered many embarrassing Cameo videos from Santos — in one instance, the request was for a video congratulating “Beav-a-Pus” on going to work at Arby’s in his “fursona” — paying only for personal-use licenses, but then broadcasting the videos for commercial purposes on ABC and across various social media platforms.

Alexander Smirnov, Hunter Biden’s now-indicted accuser, says he had contacts with Russian intelligence. And Hunter himself remains combative with federal prosecutors — pointing out that one of their pieces of “evidence” that Hunter had a cocaine problem is a photo of sawdust that was sent to Hunter as part of a message urging him not to use drugs.

For paying subscribers: in Georgia, we’re all waiting for Judge Scott McAfee to decide whether to disqualify District Attorney Fani Willis from the RICO prosecution of Donald Trump and others. And we took a number of the questions you sent in about the large judgment Trump now owes to New York State for business fraud — including about why this money even goes to the state, and about what will happen if he is unable or unwilling to post an appeal bond covering the amount he will owe if his appeal loses, and bankruptcy. Thank you to everyone who sent in questions — we plan to take more of them next week.

29 Feb 2024G.A. Law00:40:10

The mess in Georgia continues. As a reminder, this all bears on the question of whether Fani Willis and her office will be disqualified from conducting the RICO prosecution of Donald Trump and his various co-defendants over his efforts to steal Georgia’s electoral votes. This week, Ken and I invited Georgia attorney Andrew Fleischman back on the show to talk about just how this case got so prurient and stupid, what might happen with it next, and whether this is just what happens when prosecutors have to defend and defense attorneys have to prosecute.

Meanwhile, in New York, District Attorney Alvin Bragg wants Donald Trump under another gag order — raising some questions that courts have gotten better at answering over the last few months. And out west, Biden accuser Alexander Smirnov got sprung from jail and almost immediately re-arrested, as Los Angeles-based Judge Otis Wright sought to ensure that he could not flee the country. And another SoCal federal judge, Cormac Carney, is in a spat with the Ninth Circuit over his unusually expansive view of when a defendant can get off on the grounds of selective prosecution.

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06 Mar 20249-0, but also 5-400:44:09

The Supreme Court is asserting itself in matters related to Donald Trump. The justices held unanimously that states may not block Donald Trump from their election ballots on the grounds of 14th Amendment disqualification, though the justices did have a sharp disagreement about the court’s choice to foreclose other non-congressional federal paths to disqualifying Trump or other candidates who may have engaged in insurrection. Meanwhile, the court will consider Trump’s claims about presidential immunity, and on an expedited basis — oral arguments will be next month, with a decision expected by late June. That sets up the awkward possibility that Trump’s criminal trial related to January 6 will begin in the fall and be ongoing on Election Day, if Judge Tanya Chutkan is serious about her stated intention not to let a defendant’s busy schedule get in the way of a trial.

Trump’s deadlines to post his appeal bonds approach, with courts so far unimpressed with his requests for delays and discounts. What happens if he fails to post sufficient bonds? And where could hundreds of millions of dollars come from? Allen Weisselberg is getting a little more prison time — this time for lying about the lies about the size of Trump’s penthouse — and Ken and I discuss why we feel… well, we don’t exactly feel sorry for him, but we do find something a little odd about how it’s Allen who keeps getting sentenced to custody when he’s not exactly the primest mover behind Trump-entity misdeeds. And Hunter Biden talked to a congressional committee, and when he did so he really talked.

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13 Mar 2024DON'T LIE TO YOUR LAWYER00:28:23

It’s a hat trick for Sen. Robert Menendez: his superseding indictment has been superseded once again, this time with charges that he and his wife obstructed justice, including by directing their lawyers to lie to the government about a Mercedes C-300 convertible she received as a bribe. Ken says this sort of thing — lying so your lawyer will lie for you — is not a good idea, but just because it’s a bad idea doesn’t mean it doesn't happen...a lot. Plus: Trump posted a bond of nearly $92 million in the second case E. Jean Carroll won against him. The bond is good news for Carroll — it means she’ll get paid, sooner or later, and without the need to chase Trump through the courts hunting for his assets. But Trump still faces a looming deadline to post a much larger bond in the New York Attorney General’s case, and if he is unable to (or chooses not to) we’ll still see what it looks like to pursue him with debtor’s exams and liens and the like. Visit serioustrouble.show to find a transcript of this episode and our newsletter sign-up.



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20 Mar 2024Belatedly Good Judgment00:23:55
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Donald Trump’s criminal trial in Manhattan was slated to start next week, but it will be delayed due to the late production of a large volume of documents from the US Attorney’s office. And Trump has said he can’t find a bond for the New York Attorney General’s civil judgment against him, so you can expect to see Attorney General Letitia James starting to collect on that judgment by other means quite soon.

In Georgia, Judge Scott McAfee has decided not to disqualify Fani Willis or her office from the RICO prosecution of Trump and his associates. But McAfee’s decision is otherwise scathing. Nathan Wade wins our Senate Twink Memorial Award for Belatedly Good Judgment for changing his mind about an interview on “Meet the Press." Good call, Nathan! In Florida, Judge Aileen Cannon has issued some more bizarre orders in the documents case. What she's doing is not exactly what you would do if you were trying to tank the case, but “incompetent” and “malevolent” are not mutually exclusive theories of what Judge Cannon is up to. And finally, we answer an excellent listener question sent in by Ben Dreyfuss about what lawyers in movies sometimes do when their clients to lie to them.

Free subscribers get the conversations about New York and a bit of the goings on in Georgia. Paid subscribers get the whole shebang, including a conversation about why some of the charges in the Georgia case have been dismissed, and Ken’s explanation of why he’s less like those movie lawyers and more like Alan Dershowitz. Visit serioustrouble.show to upgrade and you'll hear the whole thing.

28 Mar 2024The Low, Low Price of $175 Million00:36:46

A panel of New York appellate judges has reduced Donald Trump’s bond in the New York Attorney General’s civil case to $175 million, an amount he can probably afford. Ken and I discuss possible reasons the court took this surprise action — as is typical for this kind of decision in New York, the judges didn’t really explain their reasoning — and the likely course of Trump’s appeal to come later this year. Meanwhile, in New York Supreme Court (which is the trial court), Trump’s criminal trial over falsification of business records starts next month — we have pretrial updates, including on the gag order for the former president modeled on another recent gag order.

Plus: why are law clerks quitting Judge Aileen Cannon's chambers? And Rod Blogojevich is told to "just go."

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05 Apr 2024Sam Bankman Unfreed00:39:50

Sam Bankman-Fried has been sentenced. And at his sentencing, we saw a not-too-uncommon pattern for sentencings in major white-collar cases: Judge Lewis Kaplan read him the riot act, ruled against him on all the key issues driving the sentence guideline calculation; accused him of lying on the stand; and then sentenced him to far less than the guideline sentence.

Speaking of BS of interest to investors, Trump Media & Technology Group is worth billions of dollars, at least for now. Donald Trump has to wait six months for his share lockup to expire before he can start passing his shares off to new bagholders. So in the meantime, he’s suing his co-founders, saying they were bad at their jobs and therefore shouldn’t get to keep their shares. Is that how it works? Plus, Trump faces an expanded gag order in his Manhattan trial — one whose limits he appears intent to continue to push. And in Florida, after we recorded, Judge Aileen Cannon ruled (sort of) about issues related to the Presidential Records Act.

Plus: updates on Hunter Biden and John Eastman

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16 Apr 2024Blasts From the Past00:35:15
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Donald Trump’s criminal trial in New York has begun, with jury selection underway. Ken and I discuss Trump’s last-ditch efforts to get this trial delayed, and public support he has gotten from a surprising advocate: imprisoned ex-attorney Michael Avenatti, who phoned into MSNBC from his oceanfront Los Angeles home to say he thinks the case is seriously flawed. Meanwhile, in Florida, Judge Aileen Cannon did something we said she might: She declined to make any decisions about those jury instructions she asked attorneys a bunch of weird questions about. Smith is in a bind. We discuss why.

Plus: Incompetent ratfucker Jacob Wohl and his sidekick Jack Burkman are in trouble again. And actress Gina Carano (from Disney's "The Mandalorian") is a character on Serious Trouble for the first time this week.

23 Apr 2024If You Voir Something, Dire Something00:38:29

The trial has begun! Judge Juan Merchan seated 12 jurors and 6 alternates in three days of voir dire. We discuss the pace of jury selection and complicating factors (that strong opinions about this defendant are common and often expressed on social media), plus: Ken discusses his philosophy of choosing a jury as a defense lawyer, why it’s more of an art than a science, and how it will matter that this Manhattan jury is unusually highly educated.

We also discuss a question that, as we sent out this episode, remains before Judge Merchan — should Trump be held in contempt for his repeated public statements about witnesses and the jury, in spite of the gag order on him? And we talk about the theories of the case laid out in opening statements from the prosecution and the defense.

And amid all this, George Santos has clawed his way back into the news in a small way. Yay! Visit serioustrouble.show to sign up for our newsletter and find a transcript of this episode.



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01 May 2024Contempt00:22:20
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Judge Juan Merchan has found Trump in contempt of court and fined him $9,000 — $1,000 per violation of the terms of his gag order, the maximum authorized by New York law. He also noted those fines might not be large enough to influence Trump's behavior, and he threatened to jail him if he violates the order again. Is that threat credible? Ken says so.

Plus: witness testimony in Merchan's courtroom, another New York judge declines to reduce E. Jean Carroll's award, the Supreme Court hears oral argument about presidential immunity, Arizona announces a fake electors indictment, and Harvey Weinstein's New York convictions have been overturned.

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09 May 2024Yo Momma So Dumb She Thought These Trials Were Happening Before The Election00:37:51

Josh thoughtfully attempted to wreck Ken right out of the gate by using the terms “missionary position” and “Donald Trump” in the same sentence of the cold open, live, in person, in Ken's office. He’s referring, of course, to Stormy Daniels’ frankly disturbing testimony about a sexual encounter with Trump, an encounter that sounded not particularly consensual. The rest of the proceedings were more substantive than salacious, with the prosecution steadily building a case through notes, Michael Cohen’s secretly recorded conversations with Trump, and witness observations. But can they convince the jury this was all in service of a different crime, as required for a felony?

Meanwhile, Judge Merchan found Trump in contempt over a whiny social media post about jurors but rejected the DA’s motion as to three other posts. In Florida and Georgia, the prosecutions of Trump are lagging. Who's surprised?

Plus: Nathan Wade thinks workplace romance is as American as apple pie, Rep. Henry Cuellar is in trouble, and the beef between Kendrick Lamar and Drake.



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14 May 2024Is Michael Cohen a Good Witness?00:33:53

New York prosecutors have been using Michael Cohen not just as a vehicle to introduce documents, but to offer his own recollections and assessments of Donald Trump’s state of mind, including why he chose to pay for Stormy Daniels’ silence. Meanwhile, Trump has had friends visiting him at court — Republican politicians, some of them vice presidential hopefuls, who have made statements to the press that Trump himself is gagged from making. Indicted Rep. Henry Cuellar looks to be in even more serious trouble than he was last week, and Sen. Bob Menendez's trial has begun, with jury selection aided by a high-priced jury consultant. Steve Bannon has lost his appeal and will likely to have to serve out his (short) sentence for contempt of Congress before Trump has a chance to pardon him. And Rudy Giuliani is being sued again, this time in pursuit of a court order to bar him from lying — good luck with that.



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21 May 2024Rudy Got Served!00:21:09
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Happy Birthday to America’s Mayor, now 80 years old! Rudy had a big bash to celebrate his 80th birthday last Friday, down in Palm Beach. He posted a photo from the party on social media, taunting Arizona Attorney General Kris Mayes for her failure to serve a summons on him for his indictment for trying to steal that state’s presidential election. And then, around 11pm, agents from Mayes’s office approached him to serve his summons on person.

Plus: the cross-examination of Michael Cohen, Trump reportedly edits the statements of the given by his surrogates who say what he’s not allowed to under the gag order, Paul Pelosi's attacker is sentenced but there's a hitch, and Hunter Biden is in serious trouble.

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29 May 2024G.L.O.A.T.00:40:30

It’s Wednesday, and the jury in Donald Trump’s Manhattan criminal trial has had his case for about half a day. On Wednesday morning, Judge Juan Merchan instructed the jury on the law — a long and boring process that Ken says jurors often basically ignore — and sent them out to deliberate. And now we wait.

Ken and Josh discuss closing arguments in which prosecutors dryly laid out the facts of the case they had presented, while Trump’s attorney Todd Blanche employed the “cockroach in the spaghetti” strategy, arguing the government’s case relied on claims and observations from Michael Cohen, whom a reasonable person would not trust. Indeed, Blanche deemed Cohen the G.L.O.A.T. — the “Greatest Liar of All Time” — a phrase that may overstate how great Cohen is at lying.

Plus: updates from the documents case in Florida, Rudy agrees to stop lying, Jenna Ellis gives up her law license and the Menendez case hits a speedbump.

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01 Jun 2024The Verdict00:17:35
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The verdict is in! Ken and Josh discuss the jury's relatively quick decision, the path to sentencing, whether Trump is likely to face a custodial sentence or community service or what, and (for paying subscribers) the arguments Trump will raise on appeal, which courts he can raise them in, and what prospects he has for getting his conviction overturned.

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13 Jun 2024YSLRICO00:40:50

Hunter Biden has been convicted on three federal felony gun charges. In this case, Hunter has the same misfortune as Donald Trump in the Manhattan DA’s case: were he less famous, he’d likely never have ended up in court over these charges.

Plus: updates on Trump's probation interview, an update from FLorida and election-related charges in Wisconsin, and then there's Georgia.

In Georgia, Fani Willis’s RICO case against Trump and company remains on hold indefinitely while an appeals court considers whether Willis should have been required to recuse herself. It’s not like this case was going to trial anytime soon, but now it is surely going to be years. Shouldn’t have slept with the special counsel! And another one of Willis’s RICO cases — the one against rapper Young Thug and alleged members of (what prosecutors allege was) his street gang, Young Slime Life — has gone completely off the rails, with Judge Ural Glanville holding an ex-parte meeting with prosecutors and a key witness, getting very angry when defense attorney Brian Steel found out about the meeting, and then ordering Steel to jail for contempt of court. Steel is supposed to serve ten weekends in jail; Judge Glanville granted his request to be jailed alongside Young Thug so they can keep preparing for trial. Steel has also appealed the contempt order; this case, too, is likely to be getting appellate review before it’s even over.



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21 Jun 2024Nathan Wade Speaks (Please Stop Speaking, Nathan Wade)00:29:18

Nathan Wade went on CNN, and had to be stopped by his handlers mid-interview because he was about to answer a question about when he and DA Fani Willis started having sex. Then, he went on The Daily Show and said he wasn’t sleeping with his boss because Willis was never his boss, but was more like his client. Shut up, Nathan Wade! Why does he do this?

This week, besides that debacle: the Supreme Court’s 8-1 decision in U.S. v. Rahimi, which doesn't bode well for Hunter Biden; Steve Bannon reports to prison; continuing chaos in the YSL trial; and a news report that Judge Aileen Cannon turned down some colleagues’ polite suggestions that she might want to let a different, better judge handle the Trump documents case.

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27 Jun 2024This Is Going to Ruin the Tour00:32:03

We have a real parade of idiots on tap for you this week. Jacob Wohl, Alex Jones, Robert Menendez, Nathan Wade, Justin Timberlake…oh, and Donald Trump too. Strap in, because they’re all doing shit that’s pretty stupid. Visit serioustrouble.show to sign up for our newsletter and find a transcript of this episode.



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02 Jul 2024Donald Trump Wins The Immunity Idol00:20:52
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Remember when most people thought that the Supreme Court would find a way to help Donald Trump without making crazy new law? Well. About that. Ken explains why the Supreme Court’s decision on Donald Trump's appeal in the January 6 prosecution is the worst of all possible worlds. Josh and Ken discuss how this snarls all of the criminal cases against Trump. Plus: more SCOTUS opinions that involve serious trouble, including the end of Chevron deference.

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11 Jul 2024He'll Be An Old Thug By The Time This Trial Is Over00:31:23

We’ve had some time to digest the Supreme Court decision on immunity, so this week Ken and I talked through the various criminal proceedings involving Donald Trump to discuss how they’ll be impacted. The short answer is: a lot.

Also in this episode: Missouri has sued New York, saying the Manhattan DA’s prosecution and associated gag order have deprived Missouri voters of their First Amendment right to hear from political candidates. Alec Baldwin’s trial is starting in New Mexico; the Young Thug case continues to be stalled and it's even messier now; and in Louisiana, a federal judge will review rapper Baby Gangster’s lyrics, as BG tries to return to work while on supervised release.

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17 Jul 2024Bad Week for Prosecutors00:31:45

Well, it’s been a more eventful week than usual. President Trump was shot in the ear at a rally — a shocking security failure by the Secret Service, and now the subject of an FBI investigation; there is much to look at even though there is no shooter to pursue. Ken and Josh discuss why “stochastic terrorism” isn't a useful concept when talking about law or policy, and how admonishments that people should be careful about what they say lest they inspire violence are now being thrown back at liberals.

In addition to still being alive, Trump is also no longer a federal defendant in the documents case, for now — Judge Aileen Cannon dismissed that case, saying the appointment of a special counsel to prosecute him was never authorized by law. Rudy Giuliani’s bankruptcy case has been dismissed — a mixed blessing. Judge Ural Glanville has been removed from the Young Thug RICO trial, which is likely to lead to a mistrial. And Alec Baldwin’s manslaughter case is dismissed with prejudice due to extreme incompetence on the part of prosecutors in New Mexico.

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29 Jul 2024Defamation Claims00:36:02

On this week's episode, Josh and Ken delve into two defamation cases where Trump has survived motions to dismiss, and the close legal questions that allowed those cases to proceed. They also look at a civil lawsuit where Hunter Biden is making headway, and at Hunter's effort to rely on Aileen Cannon's favorable ruling toward Donald Trump to fight his own criminal cases. They discuss settlements for Lisa Page and Peter Strzok, and they look at the latest headache facing New York judge Arthur Engoron.



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08 Aug 2024Hot Hot Scheduling Action00:47:27

As we’ve discussed, the Supreme Court threw a major wrench into the various prosecutions of Donald Trump with their ruling on presidential immunity. The RICO prosecution in Atlanta was already so hopelessly fucked that they probably won’t need to think about it for a couple of years, and the documents case in Florida is, for now, dismissed. But in New York, Judge Juan Merchan is proceeding toward sentencing, notwithstanding immunity being one of Trump’s several issues for appeal, and in Washington, DC, Judge Tanya Chutkan is trying to figure it out, though the issue probably won’t even be fully briefed until after the election.

Plus: Judge Chutkan has ruled that Trump was not a victim of selective or vindictive prosecution. A committee of the District of Columbia Bar Association has recommended that Jeffrey Clark’s law license be suspended. Sen. Bob Menendez has been convicted — showing that bribery is still illegal. The Washington Post has a somewhat odd story about an investigation in a possible Egyptian effort to bribe Donald Trump that did not amount to much. And the QAnon Shaman has won a court order instructing the government to return his headdress.



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15 Aug 2024Hacks00:47:12

Elon Musk has produced some new legal issues for us this week. He has sued a coalition of advertisers for colluding to boycott the Twitter platform, saying this is an antitrust violation, and Musk is also the subject, along with Donald Trump, of a labor law complaint before the National Labor Relations Board, filed by the United Auto Workers.

Plus: Trump may sue the federal government over the Mar-a-Lago raid, Missouri will not get the Supreme Court to consider whether its voters were harmed by the gag order in Trump’s New York criminal case. Saying that JD Vance fucked a couch isn’t defamatory (it’s satire) and saying Trump wasn’t almost in a helicopter crash with Willie Brown isn’t defamatory either (it’s true). And Trump’s campaign was hacked. And oh my god, the Young Thug Georgia RICO trial, it’s an even bigger mess than the Trump Georgia RICO trial.

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22 Aug 2024Oh, You!00:41:06

George Santos has pleaded guilty and will likely be sentenced next February to several years in federal prison. Santos also lost his copyright claim against Disney over his Cameo videos that were broadcast on Jimmy Kimmel Live. Disney had less luck trying to argue that a customer whose wife died of an allergic reaction would have to arbitrate any wrongful death claim because of an obscure clause in the service contract for Disney+. Several associates of Matthew Perry were indicted for their roles in getting him the ketamine that killed him, and DC Councilmember Trayon White, last seen saying dumb things about the Rothschilds, is now a defendant in a very dumb bribery case.



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30 Aug 2024Take Two00:25:20
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Jack Smith is attempting to salvage his two federal prosecutions of Donald Trump with a superseding indictment that removes evidence about Trump’s presidential acts from the document backing his charges over Trump’s effort to steal the 2020 election. The new indictment removes the allegations that are closest to the core of presidential powers — for example, Trump’s efforts to get the Department of Justice to open a bogus investigation — while retaining other acts Smith believes he can successfully argue were unofficial. Plus: Jack Smith counters Judge Cannon's dismissal of the documents case; Arizona defendants in the case about the state’s fake-elector scheme are using the state’s very odd anti-SLAPP statute to argue their charges should be dismissed; onetime-superlawyer Tom Girardi was convicted of stealing huge sums from his clients; the Ketamine Queen now has a prominent defense lawyer; LiveNation’s CEO may have to be deposed in a lawsuit over the Astroworld music festival disaster, despite the apex witness doctrine and Texas’s efforts to position itself as the pro-business court state.

Finally, we have a correction from last week. When we talked about a motion Disney made in a wrongful death case arguing a litigant would have to arbitrate because he entered into an arbitration agreement as part of his Disney+ service contract, we misidentified the prestigious law firm that surprised us by making the argument. It was White & Case, not O’Melveny & Myers. We regret the error.

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06 Sep 2024One Weird Trick00:41:34

You probably saw the moronic TikTok trend in which check fraud became trendy and was rebranded as a “glitch” that allowed you to get large amounts of money out of any Chase ATM, even if you had little cash in your account. It’s federally illegal, it’s illegal in every state, and “I saw it on TikTok” isn’t a defense. Still, that doesn’t necessarily mean every one of these cases will be interesting to prosecutors.

Speaking of stupid criminals: Jacob Wohl and his sidekick Jack Burkman are back in the news; Russians are indicted over a scheme to pay right-wing influencers; Trump tries (again) to get his hush money prosecution removed to federal court, but is still unlikely to succeed.

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13 Sep 2024Reversible Error00:23:49
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Josh and Ken discuss developments in the Data Colada-Francesca Gino-Harvard case, Sarah Palin's defamation case against the New York Times (for free subscribers), and (for paying subscribers) the different philosophies the judges have about how the presidential election should affect the scheduling of the Trump criminal cases they preside over.

Plus: Hunter Biden's Alford plea, the Tenet Media FARA case and whether it’s okay to be an unregistered foreign agent if you’re the agent of a Belgian, and a pre-indictment preview of the serious trouble that awaits New York Mayor Eric Adams and many of his aides.

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20 Sep 2024RICO Freak-Off (feat. Sean 'Puffy' Combs)00:33:41

We were kind of expecting Sean Combs to get indicted sooner or later, but we weren’t expecting the indictment to be for RICO. Federal prosecutors allege that Combs, as the leader of the “Combs Enterprise,” led a criminal organization for purposes including coercing female victims to have sex with male prostitutes at drug-fueled orgies known as “freak-offs.” Is that really RICO?

Plus: just gun charges (for now) for the man caught laying in wait for Donald Trump at his Florida golf course with a rifle, and a lot of hot, hot defamation action. Visit serioustrouble.show to sign up for the newsletter and to support the show.



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26 Sep 2024Superseding Indictment00:23:40
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Ryan Wesley Routh has been charged with attempting to assassinate a major presidential candidate. Ken and Josh discuss how proving Routh’s intent to kill the former president might be challenging (had he not left a note expressing his intent), and we talk about what “attempt” is — Routh never pulled the trigger, but there are a number of “substantial steps” he took toward killing Trump that should still make this case not that hard for prosecutors to prove.

Plus: a light sentence for Caroline Ellison for her role in the FTX implosion, Judge Chutkan OK's a long brief from the special counsel on presidential immunity, an advocacy group tries to get criminal charges for Trump and Vance for their comments about Haitian immigrants in Ohio, Brett Favre can't sue Shannon Sharpe, and Matt Gaetz updates. Sign up at serioustrouble.show to listen to the whole episode.

30 Sep 2024To Be On Safe Side, Please Delete All Messages You Send Me00:38:20

Federal prosecutors allege that New York mayor Eric Adams accepted tens of thousands of dollars of free business-class upgrade on Turkish Airlines as part of a broader scheme to receive illegal support from foreign nationals (including concealed political donations from Turks) in exchange for official favors, including from the Fire Department of New York. This is a long, fun “speaking indictment” with juicy details.

Plus, there’s other news: Three Iranian hackers indicted for the breach of Trump campaign documents; a hot bench in an appellate hearing over the $450 million Trump civil judgment that may or may not amount to anything; and a settlement in Smartmatic v. Newsmax that everyone is pretending to be happy about.

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10 Oct 2024XL Brief00:19:14
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The long memo Jack Smith promised is here: a 185-page document laying out evidence he’d like to present in his January 6-related case against Donald Trump. The memo has to be so long because the Supreme Court decision on presidential immunity was so complex and vague: Smith must show, act by act, that he’s offering evidence either of Trump’s unofficial actions, or of official acts where he can overcome the presumption of immunity. Ken and I discuss how Smith argues that most of the acts he wants to present are unofficial, his case that Trump’s official efforts to coerce Pence are fair game, and how long it’s going to take courts to adjudicate all these questions before a trial can start (years). For paying subscribers, we also discuss:

* One of the bitchiest motions Ken has ever seen

* Clare Locke surviving a motion to dismiss in their nine-year-old-fan-of-Kansas-City-Chiefs client’s defamation case against Deadspin, for having accused him of wearing blackface and hating black people and Native Americans

* Garth Brooks (a.k.a. the anonymous celebrity “John Doe”) facing an anonymous lawsuit from his former hairstylist, who he also tried to sue anonymously to stop her from suing him anonymously

* Professor Joe Gow, who will sue the University of Wisconsin for dismissing him over his vegan porn side project;

* Former Mesa County Clerk Tina Peters getting nine years in prison for her “Stop the Steal” efforts

* Updates on the Eric Adams scandal

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18 Oct 2024Twelve Busybody Idiots00:42:20

SpaceX is suing the California Coastal Commission for objecting to a plan to increase the frequency of SpaceX launches from Vandenberg Space Force Base. The commissioners did raise some concerns that actually relate to the Pacific coastline, but they also mouthed off about how they dislike SpaceX CEO Elon Musk’s general political activities. And Judge Tanya Chutkan considers how the Supreme Court decision in Fischer affects the criminal charge against Donald Trump for obstructing an official proceeding, and considers a motion from Trump to delay the release of an appendix to Jack Smith’s long memo on the evidence he wishes to present in the case.

Plus: Mark Robinson (the Republican nominee for governor of North Carolina) is suing CNN, Ruby Freeman and Shaye Moss continue to seek to collect the $146 million judgment they won against Rudy Giuliani, and Fani Willis replies all. Yikes.



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24 Oct 2024Michael Avenatti Is Still a Bad Lawyer00:23:37
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For all listeners, we have updates this week on Michael Avenatti, Aileen Cannon, Laura Loomer and Bill Maher. Our valued paying subscribers (thank you for your support!) will also hear about: the Central Park Five lawsuit against Donald Trump, Rudy Giuliani being ordered to hand over assets to the election workers he defamed, FTX defendant Ryan Salame, who alleges (dubiously) that federal prosecutors double-crossed him and his girlfriend, and Ron DeSantis ordering Florida television stations to stop airing commercials for a pro-choice ballot measure.

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05 Nov 2024Young Thug Pleads Out00:40:39

For your Election Day listening pleasure, we have an episode for you covering the news that has arisen in the lead-up to the election:

* Updates on Eric Adams, Arizona Attorney General Kris Mayes says her office is looking into whether Donald Trump illegally threatened Liz Cheney at a rally in Arizona.

* Young Thug, the Atlanta rapper who has stood accused of running a street gang, pleaded guilty in the long-running, very messy RICO case where he has stood trial alongside several of his associates.

Plus: MyPillow founder Mike Lindell is saying a lender did the RICO, Rudy Giuliani is having a rough time defending himself in litigation brought by his (alleged) ex-employee, Noelle Dunphy; can Elon Musk give million-dollar prizes to PA voters who sign his organization's petition? And Trump is trying to use the law against the media in various ways that are likely to prove unavailing.

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13 Nov 2024The Aftermath00:28:46
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Last week’s presidential election, which has made Donald Trump once again the president-elect, will obviously have profound effects on the various criminal cases against him. On this show, we cover the Department of Justice winding down the two federal prosecutions and why they're doing it now, and the prospects for the prosecutions in Georgia and New York.

For paying subscribers: a deeper conversation on what should have been done differently in the handling of all these prosecutions. How could this have played out differently? Would it have been different, after all? Plus: an update on the search for Rudy Giuliani’s assets — he showed up to vote in the very same Mercedes convertible his creditors have been having trouble locating — and one FTX-related story we missed last month.

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22 Nov 2024Matt Gaetz Pulls Out00:16:42
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Wouldn’t you know we recorded this show Thursday at 11am Eastern, just in time for Matt Gaetz to withdraw his candidacy for Attorney General a bit after noon? Don’t worry — we went back and recorded a new beginning of the episode, tossing out the now moot (probably?) conversation we had about the ethics report everyone in Washington wants to see. Ken and I still took the opportunity to talk about how a DOJ under someone (probably?) more competent will look different than one that Gaetz would have run. And we look at another cabinet nominee — Pete Hegseth, slated to run the Department of Defense — who also stands accused of sexual misconduct that also never resulted in criminal charges.

Paying subscribers (thank you for your support!) get a bunch more, including:

* Drama over The Onion’s attempt to buy Infowars at a bankruptcy auction

* Donald Trump’s new anti-SLAPP motion, and an update from Ken on a defamation case he successfully defended on anti-SLAPP grounds.

* The raid on Diddy’s prison cell

* Another lawsuit from a celebrity John Doe! Plus, more Rudy Giuliani nonsense.

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27 Nov 2024Diss Isn't RICO00:45:56

Did you know Ken is a huge Kendrick Lamar fan? Well, not really. But he is psyched that Lamar and Drake have produced some truly hilarious litigation to discuss. Their beef goes back years, and they have traded diss tracks — in Kendrick's latest, he calls Drake a “certified pedophile” who’s “tryna strike a chord and it’s probably A Minor.” Is that defamation? If you’re a regular listener to this show, you know it very likely isn’t — and even Drake isn’t quite ready to sue for defamation. But he has filed — in two different states — petitions for pre-litigation discovery, to explore the possibility that Lamar and their shared label, Universal Music Group, may have committed various torts against him. What torts? Well, in the Texas petition, he wants to look at defamation. In New York, he wants to explore the possibility that Lamar and UMG competed against him unfairly, by nefariously over-promoting the song, or something. He also suggests this could be the RICO!

Plus: Jack Smith has moved to dismiss the January 6-related case against Donald Trump on the grounds that the Office of Legal Counsel has long prohibited prosecutions of sitting presidents. DOJ is also dropping its appeal of Judge Aileen Cannon’s decision throwing out the documents against Trump — but the department is not yet dropping the appeal with regard to his co-defendants, meaning there will be at least a part of this prosecution left for Trump’s DOJ to cancel. Jussie Smollett’s conviction got tossed by the Illinois Supreme Court, and Ken answers several of the questions you sent in.

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06 Dec 2024Pardon Me For All That I Have Done00:24:04
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Joe Biden has committed the ultimate act of snowplow parenting: a presidential pardon for his son, and not just for the specific acts he faced charges over, but for anything he did between 2014 and five days ago. This week, Ken and I discuss exactly how unusual this pardon was and exactly what kinds of norms about pardons even remain to enforce, and rumors that Biden might hand out a lot more preemptive pardons for figures who could be targeted by an FBI led by Kash Patel — and what it would mean for the rule of law if he did.

That’s for free subscribers. For paid subscribers, we have Atlanta criminal defense attorney Andrew Fleischman back with us this week, to talk about the ignominious end to the Young Thug RICO trial, plus a look at Chancellor Kathaleen St. Jude McCormack’s repeat rejection of Elon Musk’s $50+ billion pay package, a discussion of Judge Arun Subramanian’s repeat rejection of Sean Combs’s request for bail, and answers to listener questions about Drake’s legal beef with Kendrick Lamar.

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13 Dec 2024Six-Pack Abs Can't Save You Now, Luigi00:41:17

People get really weird when a murder suspect is hot, huh? Luigi Mangione needs to be extradited to New York, and he’s resisting that — we discuss why it can make sense for a defendant to delay the inevitable. Also in New York, Daniel Penny has been acquitted of criminally negligent homicide in the killing of Jordan Neely. Juries can get weird. Plus: InfoWars may not be sold to The Onion after all, an expert witness in AI used AI to write his testimony and it hallucinated some fake cases (oops!), we have learned that John Doe is Jay-Z, and some Trump associates are now facing charges in Wisconsin related to defrauding the fake electors.

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18 Dec 2024An Expensive Settlement00:48:35

This is our last episode of 2024! We'll be back right after the new year to discuss new messes. Today, we look at the substantial settlement that Disney-owned ABC has agreed to pay over George Stephanopoulos’s repeated assertions that Donald Trump had been found “liable for rape” by a jury or juries. And Trump sues CBS, Ann Selzer and the Des Moines Register. Plus: Judge Juan Merchan has ruled that the Supreme Court decision establishing a sphere of presidential immunity does not compromise the guilty verdicts Trump faced in his court — we discuss the reasons. Meanwhile, Mike Flynn has lost an incompetently-litigated defamation case against Rick Wilson; a Blue Cross customer faces criminal charges for telling a call center worker “you people are next” in an argument over a claim denial; and Ingrid Lewis-Martin, Eric Adams’ longtime right-hand woman, continues to find ways to annoy Ken by not shutting up about her impending criminal charges.

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03 Jan 2025Petite Policy00:27:45
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Welcome to the first Serious Trouble episode of 2025! For all subscribers this week, Ken and Josh discuss Luigi Mangione’s indictments in both Pennsylvania and New York, and he’s also the subject of a federal criminal complaint. Both New York and the Feds look eager to prosecute him, and there’s going to be wrangling over who gets to go first, with an important difference in the stakes — he’s facing a capital federal charge, while New York does not have the death penalty. New York’s top count — murder as an act of terrorism — poses some challenges for the state to prove.

For paying subscribers: The dueling lawsuits brought by the actors Blake Lively and Justin Baldoni, each accusing the other of wrongdoing during and after the making of their hit film “It Ends With Us;” a discussion of the appellate ruling that upheld one of the judgments E. Jean Carroll won against Donald Trump; a look at why Matt Gaetz, even after resigning from Congress, couldn’t block the release of the ethics committee report that alleges he had sex with a 17-year-old in violation of Florida law; and an update on the civil lawsuit against Jay-Z, who will continue to defend himself against a rape allegation from an anonymous plaintiff — and about how his hyperaggressive lawyer, Alex Spiro, is pissing off Judge Analisa Torres.

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10 Jan 2025I Am Not In Serious Trouble00:39:43

It’s already a busy 2025 for some of our favorite characters. On this episode: Rudy Giuliani has been held in contempt in proceedings in Judge Lewis Liman’s courtroom, where he has stalled the liquidation of his assets for the benefit of two women he defamed. Donald Trump gets an "unconditional discharge" penalty from Judge Juan Merchan and is trying to stop the release of Jack Smith's report. George Santos asks a judge to delay his sentencing so he can develop and monetize his podcast (!), Eric Adams wants to know who's accusing him of what, and finally: did Josh defame Luigi Mangione?

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14 Jan 2025Unconditional Discharge00:30:19

The Supreme Court declined to save Donald Trump from being sentenced in his New York criminal case, but the justices said that decision was in part because there wasn’t much to save him from: Judge Juan Merchan had indicated that he would sentence Trump to an unconditional discharge, i.e. no punishment. In other Trump-criminal-case-wind-down news, Judge Aileen Cannon has continued to make trouble for DOJ officials seeking to release parts of a report about Trump’s two federal criminal prosecutions. Plus: Smartmatic’s defamation case against Fox News (and Fox Corporation) moves closer to trial; an FBI informant lied to the government about Joe and Hunter Biden receiving $10 million in bribes from Ukrainian sources and he was also evading taxes, and so he ended up being prosecuted by the same prosecutor who was prosecuting Hunter Biden for evading taxes, and he pleaded guilty, and now he's been sentenced; and Rudy Giuliani is now in double contempt, in federal courts in New York and Washington.

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24 Jan 2025Thank You For Suing, Drake00:21:22
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It's the first Serious Trouble of the new Trump administration. We start with a discussion of pardons: the ones Joe Biden gave on his way out of office and the ones Donald Trump gave on his way in.

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

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31 Jan 2025Settlements and Separations00:34:42

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

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05 Feb 2025Everyone Is Fired00:42:42

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

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



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19 Feb 2025Not Like U.S. Attorneys00:38:13

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



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27 Feb 2025The New George Santos00:39:50

The Trump administration continues to ice out the Associated Press, and now the AP is suing. We discuss how the administration changed its argument (not great, from a policy perspective, but it may actually put the White House on stronger legal ground). Ed Martin — the conservative activist serving as acting US Attorney for the District of Columbia, whom Trump has named to be the permanent US Attorney for that district — continues to send out weird, threatening letters about non-criminal behavior by Democrats. Ken has instructions about what you should do if you get such a letter.

Plus: Eric Adams now wants the charges against him dismissed with prejudice; Sam Bankman-Fried has a theory of why he, too, deserves special dispensation from the Trump administration; FIRE mounts a robust defense of pollster Ann Selzer; the Trump administration continues to face difficulty in the courts with its executive orders; and soon-to-be-long-suffering federal Judge Ana Reyes (last seen scolding the attorneys for inspectors general suing the administration) has drawn the ire of the administration itself for being too mean to them in court.

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05 Mar 2025Short Staffing00:40:29

Acting US Attorney for the District of Columbia Ed Martin continues to make bizarre and political use of the DOJ for Trump’s political purposes — this time, he's trying to impanel a grand jury to hear evidence about heated political remarks Sen. Chuck Schumer made in 2020 about Supreme Court justices. It hasn't worked, and neither has his effort to get a magistrate judge to approve a warrant to freeze the bank account of an environmental organization. Plus: why lawyers working on EO litigation may be showing up unprepared, Tina Peters, George Norcross III, and where to sue if you have a Brazilian business dispute.

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