Serious Trouble

By Josh Barro and Ken White

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 Jul 6, 2022


An irreverent podcast about the law from Josh Barro and Ken White.

Episode Date
Tweeting Through It
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Sam Bankman-Fried is in serious trouble! And he has a strategy: tweet through it. We talk about the legal risks that come from tweeting through your legal risks — it’s not just that SBF risks providing evidence to help the government prove he committed crimes; he may also be committing new crimes, like wire fraud, in real time. For all listeners, we have a breakdown of the lessons in what-not-to-do from SBF. For premium subscribers, we also look at serious trouble for Elon Musk. He was in the Delaware Chancery Court this week — not to be forced to buy Twitter, but to answer a shareholder lawsuit about his compensation at Tesla. And we have updates on Donald Trump. In the Mar-a-Lago documents case, his lawyers’ arguments seem designed to try the patience of Special Master Raymond Dearie. And in one civil lawsuit, his lawyers are facing Rule 11 sanctions — you have to behave really badly for that to happen — while in another lawsuit (against Elon Musk’s Twitter!) he’s picked up a prestigious, if checkered, legal advocate: former appellate judge Alex Kozinski.

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Nov 17, 2022
'taint tortious interference, 'taint actual malice, 'taint unregistered agency

In this episode of Serious Trouble, we discuss:

- An order granting the New York Attorney General’s request for a monitor to oversee Trump Organization financial activity, and some troubles the Trumps face in this civil action that they would not face in a criminal case.

- An acquittal on all counts for Tom Barrack, a businessman and associate of Donald Trump’s who was accused of acting as an unregistered agent for the United Arab Emirates.

- The dismissal of Barstool Sports founder Dave Portnoy’s defamation case against my former employer, Insider, over Insider’s reporting on allegations regarding his sexual behavior.

- Elon Musk’s offhand allegation that people trying to pressure companies to pull their ads off Twitter are engaged in “tortious interference” with Twitter’s business.

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Nov 08, 2022
Serious Trouble in the Chess World

We answer a listener question about what’s likely to happen to InfoWars, now that Alex Jones and his companies are subject to a $965 million defamation judgment. We also talk about legal difficulties at Fox News — including one that’s overblown. And, after receiving a lot of requests from you to discuss this topic, we talk aboutd the prospects of chess prodigy Hans Niemann’s lawsuit, in which he says world chess champion Magnus Carlsen and others defamed him by accusing him of cheating. Finally, we bring you an update on Jacob Wohl and his guilty plea to a big-boy state felony — while keeping our eyes on the federal prize.

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Oct 26, 2022
Making Attorneys Get Attorneys
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Someone close to attorney Christina Bobb is making sure reporters hear it was definitely not her fault that she incorrectly told investigators in June that Trump had already handed over all the marked-classified documents remaining at Mar-a-Lago. Bobb insisted on adding a caveat to her declaration, saying it was based on information provided to her. Bobb likely did that with the intention to insulate herself from legal risk, but Ken says it could actually harm her position.

For paying subscribers, we also discussed:

- Hunter Biden’s legal predicament, why it would be leaking into the press that federal agents believe there’s enough evidence to charge him with tax and false statement crimes, and the likelihood that he might face indictment after the midterm elections

- a risible defamation suit Donald Trump has filed against CNN.

- what you do if you’re a judge or an opposing party when a litigant (such as, hypothetically, Elon Musk) promises he’s finally, really ready to perform on his commitments if you will only please, please, please delay the trial that’s about to start.

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Oct 12, 2022
Snippy Judges, Busy Courtrooms

There’s been a lot of legal news in the last ten days, and so today’s show is on the long side: nearly an hour and it’s also free for all listeners in its full length. We talked about the oddly snippy correspondence between Judge Aileen Cannon and the much more senior federal judge she’s named as special master overseeing the Mar-a-Lago documents, we answer a listener’s question about whether Trump’s position as a former president vests him with any added responsibilities, in the eyes of the courts, in addition to the ability to gain special dispensation, which “Real Housewives” franchise best embodies the spirit of Donald Trump’s fractious legal team, an update on prosecutions related to the January 6 riot, and a look at dueling appellate decisions in the 5th and 11th Circuits, reaching different conclusions about whether state governments can tell social media platforms what content to host on their sites.

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Oct 05, 2022
11th Circuit Smackdown
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Whew, it’s been a big news week! Big enough that we had to record this episode one and a half times: on Wednesday, following the first conference with Special Master Raymond Dearie; and again on Thursday, after the 11th Circuit Court of Appeals made Dearie’s job much easier by saying the DOJ is free to use approximately 100 marked-classified documents seized from Mar-a-Lago and that Dearie need not review them. This episode covers the 11th Circuit order, what's left for Judge Dearie to review, New York Attorney General Letitia James’s new civil lawsuit against the Trumps — and for paid subscribers: the wind-down of Special Counsel John Durham’s probe into the FBI investigators who investigated Donald Trump, angry judges presiding over the Parkland shooter’s sentencing and Alex Jones’s latest defamation trial, and a civil lawsuit and a criminal investigation relating to the Venezuelan migrants who were talked — apparently under false pretenses — into boarding a plane to Martha’s Vineyard.

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Sep 22, 2022
'Sir, this is a Hardee's, and you are served.'
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If you are a lawyer, it is important to make sure you get paid for your work, especially if your client is someone like Donald Trump, who has very complex legal needs and a history of trying not to pay his vendors. So we weren’t surprised that attorney Chris Kise, one of the big shots on Trump’s legal team, has collected a $3 million fee deposit in preparation for what could be very extensive legal billings. Plus: we discussed how it works when multiple lawyers from different firms team up on the same criminal defense — “badly,” is the short answer — and what you should do if the FBI tries to question you at a Hardee’s.

For paying subscribers only, we have a discussion of Judge Aileen Cannon’s latest puzzling order in the lawsuit Trump brought over the search of Mar-a-Lago. She’s named a well-respected senior federal judge — Raymond Dearie — as special master, and given him a deadline of November 30 to complete his review of seized documents.

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Sep 19, 2022
We Can Have a Little of the Warrant Application, As a Treat
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Dear listeners,

It’s another week of serious trouble!

This week, Ken and I talk about the unsealed application for the Mar-a-Lago warrant, such as it is — most of the juicy bits are blacked out, but we did learn some things about what the government is investigating and who does not seem to be a target.

The government says its “privilege review team” — an alternative, loser terminology for the taint team — is already done reviewing the documents from Trump’s boxes. As such, Trump’s demand for a special master to oversee that review may be moot, but we’ll know more after Judge Aileen Cannon holds a hearing about it on Thursday.

Plus, for paying subscribers: the speed with which Judge Cannon has acted on Trump’s requests has alarmed and annoyed some Trump critics. But if Trump’s objective with his motions is (as it is so often) to delay the proceedings, then her speedy responses — and her choice not to enjoin the government’s investigative activities — aren’t serving his interests so far.

And we talk about Ben Shapiro, who says he was defamed. Shapiro is on better grounds than many who cry defamation — provably false statements of fact were made about his alleged receipt of PPP loans, possibly with reckless disregard for the truth — but he stumbles at the key last step: showing he suffered quantifiable harm due to the statements.

Finally, at the very end of the paid version of the show, we have an outtake for fans of taint team talk.

You know you want to hear it.

Enjoy the show!


Aug 30, 2022
The taint team is tainted, Trump alleges

It’s another action-packed week for Serious Trouble! On today’s episode, we talk about former Trump Organization CFO Allen Weisselberg’s plea deal that will send him to Rikers Island for about three months for tax crimes — and won’t involve testifying against Donald Trump personally. We look at the legal fight over the sealing of the application for the Mar-a-Lago search warrant, and at Trump’s… filing, of sorts, demanding the return of “his” documents and the appointment of a special master to weed out any potentially privileged materials, instead of a taint team that he considers to be tainted. Plus, we talk about Trump’s difficulties in retaining A-list legal counsel, and we apologize to a listener for doubting that he’s served on 15 juries in his lifetime. Thank you for your service, Tim!

This week’s episode is free for all listeners, so if you like it, we’d encourage you to help us get the word out — share it with a friend, or post it on social media. If you’re a paid subscriber, thank you; if you’d like to become one and get every single episode, you can do that by going to

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Aug 23, 2022
The Mar-a-Lago Warrant
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Now we’ve seen the warrant! On this week’s show, we talk about the search of Mar-a-Lago, and what it tells us about why the FBI wanted to poke around there. We discuss how Merrick Garland avoided pulling a Comey, when we might see the affidavit supporting the search warrant, we answer a question from a listener about how the government handles public trials involving classified documents it can’t share publicly, and how we might be able to assess whether a prosecution related to the offenses at issue here is worth the trouble. For a transcript of this episode and to become a subscriber and join the Serious Trouble community, go to

Aug 16, 2022
They Even Broke Into My Safe!
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Well, there’s been some serious trouble this week. The FBI executed a search warrant, looking for documents at Mar-a-Lago. According to former president Donald Trump, they even broke into his safe! What had to happen for such a warrant to be approved, and why federal prosecutors would have sought it — can it really be just about the Presidential Records Act? Who is entitled to what information, and when? Trump has been complaining a lot about the raid, but he hasn’t shown us the search warrant detailing exactly what the Feds were supposed to be looking for and what potential offenses they were related to. Plus: Alex Jones. Will he actually have to pay close to $50 million to Sandy Hook families? And how come his lawyers failed to claw back the private documents they accidentally produced to the plaintiffs? Well, maybe they didn’t have a lot of better options. Visit to subscribe, and to access discussion threads, links and episode transcripts.

Aug 09, 2022
Alex Jones and the Very Good, Totally Brutal Cross Examination

In this episode, Ken and Josh discuss the cross examination of Alex Jones in the trial that will determine the damages for the defamation claim on which he already lost to parents of a child killed in the Sandy Hook massacre. After Jones repeatedly failed to comply with orders to turn over records and documents (to the point that he lost by default because he was so uncooperative), Jones’ lawyer accidentally shared the entire contents of Jones’s phone — including texts about Sandy Hook — with the plaintiffs’ attorney and then failed to take the necessary steps to assert privilege over any of the contents and retract them. Ken and Josh also discuss the questions jurors had for Jones.

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Aug 04, 2022
Consider This a Target Letter

On this episode of Serious Trouble, we talk about developments in Fulton County DA Fani Willis’s investigation of efforts to steal Georgia’s electoral votes in the 2020 election. Willis sent “target letters” telling all 16 members of the fake Trump slate they might be prosecuted. When do DAs send letters like that, and what should you do if you get one? Plus, we discuss a memo from Attorney General Merrick Garland, which lays out the cautions US Attorneys should take before bringing politically sensitive indictments. And, Indiana’s Attorney General called the doctor who performed an abortion for a 10-year-old girl from Ohio “an abortion activist posing as a doctor, with a history of failing to report,” on national television, and he suggested she might have committed a crime. What’s her recourse in Indiana?

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Jul 21, 2022
Elon Musk, Chancery Courts, Specific Performance, and the Pride of Delaware

Elon Musk agreed to buy Twitter. He doesn’t want to buy it anymore. Twitter wants to enforce the contract that requires him to buy the company, and so they’re arguing in the chancery court in Delaware about what will happen next.

What is a chancery court? What is “specific performance”? Will a Delaware court actually force this company — an entity with employees, customers, and significant societal influence — into the hands of a buyer who doesn’t want to own and operate it?

Listen to this episode where we discussed all those matters. For a transcript of this episode visit

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Jul 15, 2022
The Return of Patsy Baloney

Ken and Josh discuss an apparent agreement for Pat Cippolone (or “Patsy Baloney,” if you ask an auto-transcription system) to talk with the January 6 committee, and why his interview will be a little complicated because of privilege issues — both attorney-client privilege and executive privilege. We look at how that might matter, and what he might say that’s of interest. Plus: grand jury subpoenas in the Atlanta DA’s investigation, what happens when an interested third party is paying your legal expenses, and a Washington Post op-ed claims it’s easier than people say to show Donald Trump had the requisite intent to commit certain crimes. Is that true? We don’t think so, and we’ll address why.

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Jul 07, 2022
SPECIAL EXTRA EPISODE: 'They're Not Here to Hurt Me'

Surprise! This is an extra, unscheduled episode of Serious Trouble, about some breaking news in investigations related to the January 6 riot — a federal search of attorney John Eastman’s electronic devices, and a unexpectedly scheduled hearing with testimony from Cassidy Hutchinson, a former aide to Trump’s White House chief of staff, Mark Meadows. (We said we’d do at least 40 episodes a year, but that’s a floor, not a ceiling!)

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Jun 29, 2022
Serious Trouble, Episode 2: Why Is It So Hard To Hold Police Accountable For Failures Like Uvalde?

To find episode notes, transcripts, a discussion thread and to become a subscriber (so that you receive all Serious Trouble episodes), visit us at

This week's episode is all about the Uvalde massacre, the botched police response, and what legal rights you have to expect the police to perform their jobs. You may be surprised to learn they’re pretty limited. Ken and Josh also talk about where the idea of qualified immunity comes from, and when it does (and doesn’t) protect police from liability for their actions. And they discuss why Texas law may put the various government agencies involved in this debacle on pretty solid ground when they refuse to disclose embarrassing documents, such as body camera footage.

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Jun 23, 2022
Serious Trouble, Episode 1: The Show, The January 6 Committee Hearings, And The Depp/Heard Trial

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Dear readers,

Serious Trouble is not a Trump show — it’s a show about law. But the top legal story this week is about Trump, so that’s how we’re starting: with a discussion of the theory of Trump’s criminality advanced by the January 6 investigating committee.

What would it entail to prove in court that Donald Trump criminally sought to interfere with an official proceeding, and should the Justice Department try? What sort of criminal defense would Trump mount if it got to trial? Would Sidney Powell and Rudy Giuliani end up on the witness stand?

We also talked about how some of the witnesses in deposition videos presented by the committee seemed to be almost enjoying themselves, especially former Attorney General Bill Barr. Can a deposition be fun? Ken has some thoughts on why it can be a good strategy for lawyers to try to keep things feeling fun and light even when the matters at hand are deadly serious.

And we talked about our ambivalence at having missed the defamation lawsuit between Johnny Depp and Amber Heard — arguably the most prominent defamation case in decades and also a huge, embarrassing mess. We’ve talked a lot over the years about how hard it is to prove defamation, especially against a public figure — so how did they both prevail on at least some of their claims? And what does the verdict mean for future defamation litigants?

We hope you enjoy the episode. If you have questions or responses, please share them in the comments section below, or you can email us at

And here are some links to documents and statutes we discussed on today’s show — you might find these useful as you listen. We’ll prepare a list like this for you to accompany every episode we release.

* Here’s a transcript of the episode.

* Title 18, United States Code, Section 1512(c)(2) is the statute prohibiting obstruction of an official federal proceeding — did Trump violate it?

* Title 18, United States Code, Section 371 contains both the plain-vanilla federal law prohibiting conspiracy to violate federal statutes and the prohibition on defrauding the federal government — did Trump violate that?

* What does “defraud the United States” mean? Well, we know what the Department of Justice thinks that it means — take a look at the relevant section of the United States Attorney’s Manual, which includes the case Ken quotes in the episode.

* What law governed the Johnny Depp v. Amber Heard trial, and what issues were actually before the jury? Read the jury instructions and find out:

* Here’s the SNL cold open about the Depp/Heard trial being “for fun”:

We’ll be back with another episode for you next week.

Very seriously,

Ken White, Josh Barro & Sara Fay

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Jun 16, 2022