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‘Very, very troubling’: Judges, lawyers flummoxed by Judge Cannon

The jurist overseeing Donald Trump’s classified documents case in Florida has raised eyebrows and alarms with her latest order

March 20, 2024 at 2:38 p.m. EDT
Aileen M. Cannon speaks remotely during a Senate Judiciary Committee hearing on her nomination to serve as a judge of the U.S. District Court for the Southern District of Florida in 2020. (U.S. Senate/AP)
8 min

Lawyers and former judges said they are baffled by an order issued this week by the federal judge overseeing Donald Trump’s pending trial on charges that he mishandled classified documents — and believe her instructions suggest the case will not go to trial anytime soon.

“In my 30 years as a trial judge, I have never seen an order like this,” said Jeremy Fogel, who served on the federal bench in California and now runs the Berkeley Judicial Institute.

On Monday evening, U.S. District Judge Aileen M. Cannon ordered the defense lawyers and the prosecutors in the case to file submissions outlining proposed jury instructions based on two scenarios, each of which badly misstates the law and facts of the case, according to legal experts.

She has given the sides two weeks to craft jury instructions around competing interpretations of the Presidential Records Act, often referred to as the PRA. While the law says presidential records belong to the public and are to be turned over to the National Archives and Records Administration at the end of a presidency, Trump’s lawyers have argued the PRA gave Trump the right to keep classified materials as his personal property.

“What she has asked the parties to do is very, very troubling,” Nancy Gertner, a former federal judge in Massachusetts, said of Cannon. “She is giving credence to arguments that are on their face absurd. She is ignoring a raft of other motions, equally absurd, that are unreasonably delaying the case.”

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Trump’s team has argued that under the PRA, he automatically designated the classified records he is accused of willfully retaining as personal documents when he removed them from the White House and took them to Mar-a-Lago, his Florida home and private club. Prosecutors and legal experts have rejected Trump’s interpretation and said the former president’s reading of the PRA is simply wrong.

Cannon is presiding over a case involving the first former U.S. president ever charged with a crime, and Fogel said it is not inappropriate for a judge in that situation to seek guidance. Still, he said, Cannon’s order is an unusual way to sequence the legal decisions and she may be putting “the cart before the horse.”

Typically, he said, judges make their rulings about the laws at the heart of the case — and then determine jury instructions closer to trial time.

“The more innocent interpretation is that she is just trying to get a sense of what the practical implications are if she decides one way or the other on the legal issues,” Fogel said. “The less charitable view is that she should decide the legal issues first and then decide how she should implement the law in the case.”

Cannon held a hearing weeks ago to discuss when to schedule the trial — one of four criminal cases Trump is facing as he again seeks the White House and has clinched enough delegates for the Republican nomination. Cannon has yet to make a decision on the trial date.

Last week’s hearing focused on two requests that Trump made to dismiss the case, one based on supposed flaws in the Espionage Act and another based on what Trump lawyers claim are the sweeping powers granted to him by the PRA.

Cannon, a Trump nominee who has been on the bench since late 2020, expressed skepticism toward both claims while also suggesting they may play a meaningful role in instructing the jury at the end of the trial. She quickly ruled against Trump’s claims about flaws in the Espionage Act and has yet to rule on the merits of the PRA request.

Her two-page order embraces at least the possibility that Trump’s PRA claims are valid, a stance that veteran national security lawyers questioned.

“The PRA is just not relevant here in any way it all; it provides no defense. To even allow it to be argued at trial would create confusion for the jury,” said Barbara McQuade, a law professor at the University of Michigan and a former U.S. attorney.

Ordinarily, a judge will take up the question of jury instructions much later in the process. McQuade called Cannon’s decision to reach for those questions ahead of a slew of other pretrial motions “premature and baffling.”

Cannon’s order suggests that she thinks the PRA is critical to the case — and that parts of the law are open to interpretation.

Jason R. Baron, former director of litigation at the National Archives and Records Administration, said that’s just not true. He said Cannon seems to continually conflate the PRA with the Espionage Act, which makes unauthorized sharing or handling of national defense information a crime. Baron said the PRA does not influence whether someone can be prosecuted under the Espionage Act.

“There is no ambiguity that the classified documents at issue in this case are presidential records,” Baron said. “He wasn’t indicted because he took newspaper clippings. He was indicted because he took documents that were marked as classified.”

Baron said the judge, who has not previously overseen a major national security trial, seems to be embracing a fantastical view of the law.

“Like the queen in ‘Alice in Wonderland,’ Judge Cannon appears to be asking the jury to believe at least two impossible things before breakfast,” Baron said. “First, that a president has unfettered discretion to decide that documents marked ‘top secret’ are his own personal records, just because he decided to keep them for himself. And second, that a president can avoid criminal prosecution under the Espionage Act because he decided that classified records were really his under the PRA. In both cases, the judge profoundly misinterprets the law.”

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Donald Trump is facing historic legal scrutiny for a former president. He has been indicted on 91 felony counts in two federal cases, in Florida and D.C., and two state cases, in Manhattan and Fulton County, Ga. He has denied all wrongdoing. Here is a list of the key probes and where they stand.
Manhattan district attorney’s investigation
Trump has been indicted on 34 felony counts following an investigation by District Attorney Alvin Bragg (D) of business matters involving Trump, including his alleged role in hush money payments to adult-film actress Stormy Daniels during the 2016 campaign. The trial is scheduled to begin March 25, with a hearing in mid-February to see if delays are needed.
Mar-a-Lago classified documents investigation
Trump has been indicted on 40 felony counts after FBI agents found more than 100 classified documents during a search of Trump’s Mar-a-Lago residence on Aug. 8, 2022, as part of a criminal probe into possible mishandling of classified information. The trial is scheduled to start in late May but could be delayed as lawyers deal with the complicated procedures surrounding classified evidence.
Justice Dept. criminal probe of Jan. 6
Trump has been indicted on four felony charges related to trying to block the results of the 2020 presidential election. Prosecutors are focusing on the Jan. 6, 2021, riot and whether Trump or his aides conspired to obstruct Congress’s certification of the election or committed fraud to block the peaceful transfer of power. Prosecutor Jack Smith is overseeing both federal investigations.
Georgia election results investigation
Former president Donald Trump and 18 others were criminally charged in Fulton County, Ga., in connection with efforts to overturn Joe Biden’s 2020 win in Georgia. The indictment follows a 2½-year investigation by Fulton County District Attorney Fani T. Willis (D). Four of Trump’s co-defendants have pleaded guilty.
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When Trump was indicted last year on dozens of counts of mishandling classified documents and obstructing government efforts to retrieve them, Cannon set a trial date of May 20. That date is no longer possible, given still-unresolved issues involving presenting the classified evidence in court.

Prosecutors have asked for the trial to start in early July; Trump’s lawyers have argued it shouldn’t begin until after the November election or, at the earliest, August.

Cannon’s recent instructions seem to entertain the notion that Trump’s legal interpretation of the PRA could be presented to the jury.

The appeals court above Cannon has already determined, on a separate matter that is also part of the Trump documents case, that the former president cannot declare classified documents his personal property.

Trump “does not have a possessory interest in the documents at issue, so he does not suffer a cognizable harm if the United States reviews documents he neither owns nor has a personal interest in,” the appeals court found in September 2022, after Trump asked the court to appoint a special master, or a neutral arbiter, to sort through the materials the FBI had seized from Mar-a-Lago.

Cannon granted Trump’s special master request, prompting an appeal from the Justice Department. An appeals court panel then resoundingly reversed her decision.

Gertner, the former federal judge, said Cannon’s latest order means it is time for special counsel Jack Smith to try to get Cannon off the high-profile case — an exceedingly rare step for any prosecutor to take. “I think that the better route is for Smith to move to recuse her now — listing all of her rulings that make little sense, the delays, rulings so far out of the mainstream that they clearly suggest bias,” Gertner said.

Other lawyers said the legal standard for recusal is so high — not just under court rules, but also in Justice Department practice — that any discussion of attempting to remove Cannon from the case is far-fetched. Typically, recusals occur when a judge has a close personal relationship with someone involved in a case or owns a significant amount of stock in a company involved.

“It’s not enough to say this judge has ruled against my case several times, therefore they must be biased. That’s not going to do it,” said McQuade, the former U.S. attorney. “I’d be surprised if an effort to remove her would be successful, and that’s a bad look for the government.”

Veteran trial lawyers say it is not unusual for a judge to make it hard for one side to try their case — and jurists are often, but not always, harder on defense lawyers than on prosecutors.

But in the Trump documents case, lawyers said, Smith may simply have to weather whatever legal storms Cannon creates, and be patient and confident that the evidence his team has amassed will ultimately convince a jury. That is what happened when a previous special counsel, Robert S. Mueller III, went to trial against former Trump campaign chairman Paul Manafort.

In that trial, U.S. District Judge T.S. Ellis III frequently made comments critical of the special counsel team and its handling of the case, questioning its judgment and limiting what evidence it could show the jury. Prosecutors pushed on, and Manafort was eventually convicted.

More on the Trump classified documents indictment

The latest: U.S. District Judge Aileen M. Cannon rejected Donald Trump’s bid to have his charges of mishandling classified documents dismissed on the grounds that a federal records law protected him from prosecution.

The case: Trump is charged with taking classified national secrets with him after he left the White House and obstructing government efforts to retrieve them. He has pleaded not guilty. Here’s what to know about the case.

The trial: Judge Cannon has not set a date for the trial. Federal prosecutors have asked her to push it back to July 8, while Trump’s lawyers are trying again to delay the trial until after the presidential election.

The charges: Trump faces 40 separate charges in the documents case. Read the full text of the superseding indictment against Trump and our top takeaways from the indictment.