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...

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...

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

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

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...

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...

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

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...

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...

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...

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 from Santos — in one instance, the request was for a video congratulating “Beav-a-Pus” on going...

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 made possible by financial misrepresentations. It’s a big judgment — and like the judgment in the...

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...

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...

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: filing objections to No Labels’ ballot petitions, conducting opposition research on potential...

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...

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...

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...

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 SCOTUS has available to overturn their ruling, and what might happen if SCOTUS upholds the...

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...

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 and actions going all the way back to 2012; serious trouble for Alina Habba; gold bars do have...

Unfortunately we taped this episode before Elon Musk urged Disney CEO Bob Iger to go f**k 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...

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...

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...