Serious Trouble

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 h...

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 prurien...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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 mad...

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. Ke...

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 himse...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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:...

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, ov...

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 i...

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 th...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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 SC...

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 Trum...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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 an...

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...

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 ele...

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 “bur...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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...

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...

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 co...

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 th...

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 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.serioustrouble.show/subscribe

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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.

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 strang...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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 tria...

This is a free preview of a paid episode. To hear more, visit www.serioustrouble.show 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 defen...