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Tweet Share Share Comment When I called up Lee Kovarsky, who teaches law at the University of Texas, I was looking for a translator. I’d been seeing one headline after another about the classified documents case against Donald Trump in Florida, where special prosecutor Jack Smith is accusing Trump of storing boxes of classified information at Mar-a-Lago. It’s being heard by a Trump judge, Aileen Cannon. And if you read the headlines, this case is not going well. He said it’s gotten to be a little bit like The Jerry Springer Show.
But these are lawyers, so in reality no one is throwing chairs at each other. Instead, they’re arguing through exhaustive paragraphs and late-night filings. Judge Cannon has called motions from Jack Smith “unprecedented and unjust.” Smith has openly worried Cannon’s understanding of the case could be based on a “fundamentally flawed legal premise” that would “distort the trial.”
On Thursday’s episode of What Next, we dug into the very technical, very legal catfights throwing the special counsel’s case against Donald Trump in Florida into chaos. Our conversation has been condensed and edited for clarity.
Mary Harris: So, Judge Aileen Cannon has been involved in this classified documents case since before it was even a case, right?
Lee Kovarsky: Law enforcement is reviewing all the stuff seized from Mar-A-Lago, and the Trump people go in and try to file a separate lawsuit to stop the DOJ from reviewing the stuff that was seized. The case gets assigned to Judge Cannon, and the Trump people are jubilant. Everybody knows that if Trump perceives a judge as being at all out of alignment with him, he just attacks, and he wasn’t attacking.
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It was a big win for them to get that case assigned to her because that case was crazy. You don’t get to go into a separate court and try to ask that court to stop the government from reviewing stuff it seized in a criminal investigation against you. There is an extraordinarily limited set of circumstances in which that sort of request should ever be indulged.
What did she do to try to sort out what had gone on at Mar-a-Lago?
The first thing she did was exercise power over the case at all. The second thing that she did was use that power to appoint the special master. And the reason she appointed the special master was because the Trump people were making various claims of privilege—attorney-client privilege, executive privilege. They were asserting all of these reasons why law enforcement shouldn’t be able to look at the documents.
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A special master is basically an objective third party, someone not affiliated with either side who would review all these documents. Almost immediately, Cannon’s decision to appoint one made everyone—except for Trump’s legal team—mad. Federal law enforcement was outraged because it would have stopped their investigation. Lawyers were outraged because the legal theories underlying this decision didn’t seem to be sound. And so, the DOJ appealed.
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Jack Smith won an extremely decisive judgment in the 11th Circuit shutting that whole thing down.
This is Southern judges. This is a conservative circuit, right?
Yeah, it’s a conservative circuit. And that panel did include Judge William Pryor, who is the most revered conservative on the 11th circuit. He’s extraordinarily close with Justice Clarence Thomas, and he joins this unsigned opinion that really claps back at Justice Cannon.
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When Jack Smith does charge Donald Trump, my memory is that it was kind of a wild card who the judge would be when this went to trial. How did this get back to Judge Aileen Cannon again?
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The warrant litigation happened there because that’s where the search was. Jack Smith felt like he had to file in that judicial district, and given the way divisional assignment works, there was a nontrivial shot it got assigned to Judge Cannon. And he lost the lottery. They were stuck with the worst conceivable judge for this litigation.
Judge Cannon has been presiding over this case for 10 months now. Is that a long time to be in this kind of beginning stage?
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Stuff that she’s doing is generating very unusual reasons for delay. For example, these ancillary procedural issues that should be easily resolvable are taking a really long time. There’s still a lot of pending motions in front of Judge Cannon that she should have resolved already.
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Let’s talk about this argument that the Trump team is making that the Presidential Records Act nullifies Jack Smith’s case against Trump, because this is one of these issues that’s tying things up.
The PRA is a statute they passed after Nixon tried to take a bunch of stuff that belonged to the American people. Outgoing presidents, under the PRA, are supposed to give all records in their possession to the National Archives, with the exception of purely personal records. The personal records category is really small. For example, diaries about personal lives, new puppies, disobedient grandchildren. The process of retrieving presidential records with Trump was chaos, because of course it was. And in the process of retrieving the material, the archives figured out that Trump had taken national defense information.
OK, that does not sound like a puppy.
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It is not a puppy. There is no charge for violating the PRA because the PRA is not a criminal statute, and it doesn’t have anything to do with retention of national defense information. So, the PRA comes in this way: In February 2024, Trump’s lawyers make a slightly different argument, which is what exploded last week. Trump’s lawyers make this wild two-step argument. First, that possession of NDI becomes authorized if the president designates a document containing it—literally any document he wants—as a personal record within the meaning of the PRA. The second step of the argument is even more ridiculous. They say that the very act of physically removing the records from the White House operated as a decision to classify the records as personal. It’s like an Escher painting of insipid legal argumentation, except written in purple crayon.
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It’s this wild, crazy argument. So, Trump says it should be dismissed. And then, Cannon issues this wacky order seeking input on PRA instructions for the jury, which, of course, sends the signal that she’s indulging this Escher-painting-purple-crayon argument. The special counsel responds, clearly pretty annoyed. He files a response to the order, saying that the PRA doesn’t have anything to do with the case.
Jack Smith also asked for Judge Cannon to announce her intentions with respect to the PRA instruction before trial. The reason he wants her to declare her intentions now is because if she says that she’s going to indulge that theory now, he can take it to the 11th Circuit.
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But if Cannon doesn’t declare her intentions with respect to the PRA before the jury is sworn, and if she instructs the jury on a PRA defense and a jury acquits on that basis, there’s nothing that Jack Smith can do. Trump skates, because there’s no appeal, because you can’t try him again after he’s been acquitted—even if the acquittal is based on a legal error.
What do you think is motivating Judge Cannon here? I can’t figure out what the goal is.
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There’s this debate online and in the media generally about whether this is bias or incompetence. And for whatever reason, people treat those as mutually exclusive categories. I actually think it’s both. And you can’t really understand what’s happening unless you attribute her pattern of behavior in part to each of those things.
Why do you think it’s both?
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She consistently is making gigantic legal mistakes, but she’s always making them in the same direction. She did it with the special master. She’s now doing it with the Presidential Records Act. It’s also a major asymmetry in her rhetorical swipes, which are fast and furious and consistently at the special counsel office’s expense. I don’t think she understood this PRA stuff at the outset, but she surely understands now that she’s indulging an absurd argument, and she’s doing it in a way that seems to suggest that she’s trying to evade appellate review—before she can facilitate an acquittal in a posture that’s not reviewable. And that’s very transparent to people who know what they’re looking at.
If you’re Jack Smith, what are your options?
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Surely Jack Smith is considering whether to force a more definitive ruling about the PRA from Cannon so they can force the 11th Circuit to reverse it.
How would he do that?
That would require something called a motion in limine, which is basically an order asking the judge to bar the introduction of evidence on a particular issue at trial, on the ground that it would be unduly prejudicial or confusing or inappropriate for some other reason.
So he tells the judge, like, “OK we’re going to not have evidence on the Presidential Records Act, because that does not apply here.”
Right. So, Judge Cannon would deny that motion, presumably. And Jack Smith could take the order denying that motion up to the 11th Circuit. If he gets that motion up there, he has a decent shot of winning.
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But then the case would go right back down to Judge Cannon.
Then the wisdom of that option depends on what you think Judge Cannon’s likely to do after that, which leads me to my second option. If you’re really, really, really skeptical about Judge Cannon and her receptivity to your arguments in this case, then you’re probably thinking about recusal. And that’s a Hail Mary. It’s unlikely to succeed. It’s deeply antagonistic because it basically accuses the judge of bias or appearance of bias. And it often fails. So, people who are sophisticated litigators often don’t do that because it so often fails, and all you’re left with is an angered and antagonized judge who you’ve just called biased.
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But in this case, what’s the alternative? If you think Cannon’s already exercising all conceivable discretion against you, then maybe an incremental step that runs the risk of even more discretion exercised against you isn’t quite as costly as it might be in other circumstances.
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View Transcript I wonder if we could envision the future for this case a little bit—if Donald Trump wins the election in November or if he loses. Because it seems like those are potentially different futures.
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The case is going to go away one way or another if Trump wins. Either a Justice Department that he will have staffed with extreme loyalists will find a way to dismiss the case or, if worse comes to worse, Trump will pardon himself. What happens to Aileen Cannon? It is quite likely that she gets a promotion, at least to the 11th circuit. It’s only rational for Trump to do that. Trump wants to signal to other officials that if they are aligned with him, if they are on board with him, if they protect him, then there will be a bounty; there will be a reward. And what better way to send that signal than by promoting Judge Cannon for her part in deferring the criminal prosecution? It’s hard for me to see a world where she doesn’t get some payoff.
If Trump loses the election, what happens?
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There’s some disagreement about what happens next. I actually think if the case hasn’t gone to trial and Trump loses the election, then Jack Smith will start to have an easier time. Why? Because this potential payoff, whether consciously or subconsciously, if Trump loses the election, the specter of her being promoted and celebrated goes away.
If I’m Judge Cannon, it seems like I have every incentive to delay this trial as long as possible, because there’s basically no risk to doing that, and there’s potentially a very high reward if Donald Trump gets reelected.
Yeah, there’s a high reward if Trump gets reelected. And as for the downside, her professional reputation, which judges care about, is not in a great place. She’s going to have some work to do to leave some legacy. So if you’re her and you just wait, the payoff is higher and the downside is lower. I don’t see why you wouldn’t do what you can to stall, which explains what’s happening.
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