Aileen Cannon Is Heading for Legal Trouble

The judge overseeing the Mar-a-Lago classified documents case has set special hearings for Donald Trump's two co-defendants—but could now be facing an appeal over the lack of written reasons for holding the hearings.

The hearings come one year after Judge Aileen Cannon, a Trump appointee, was sharply criticized by an appeal court for her handling of a major part of the case against the former president.

Several legal experts told Newsweek that Cannon was out of her depth in the Trump case, with one New York University professor comparing her to a contestant on a cooking show who has previously only ever baked a pop tart.

Cannon, who sits on Southern Florida federal court, has agreed to a Justice Department request to set so-called "Garcia hearings" for Trump's butler, Waltine Nauta, 41, and Trump's property manager, Carlos de Oliveira, 56.

Trump Lawyers Leaving Aileen Cannon's Court House
Attorneys for former President Donald Trump Todd Blanche (C) and Chris Kise (3nd R) leave The Alto Lee Adams Sr. United States Courthouse on July 18, 2023 in Fort Pierce, Florida. The lawyers attended the...

In the upcoming hearing, set for October 12, Cannon will explain to the two defendants that there is a potential conflict in the case as their lawyers also represent people that the government wants to call as witnesses.

Nauta is represented by attorneys Sasha Dadan and Stanley E. Woodward, while De Oliveira is represented by Larry Donald Murrell, Jr., and John S. Irving.

Trump faces 40 counts in the classified documents case, including 32 counts of unlawful retention of national defense information; one count of conspiracy to obstruct justice; one count of withholding a document or record and one count of corruptly concealing a document or record. He has pleaded not guilty to all charges.

Nauta has pleaded not guilty to charges he helped Trump hide secret documents, while De Oliveira has pleaded not guilty to four counts related to an alleged attempt to delete surveillance footage at Mar-a-Lago.

Woodward previously or currently represents three people the government intends to call as witnesses in the upcoming trial, and Irving represents three people the government intends to call as witnesses, according to legal submissions by Department of Justice special counsel, Jack Smith.

However, despite the complexity and importance of the case, Cannon has not stated her reasons for calling the special hearing—a year after she was upbraided by the appeal court for not giving sufficient reasoning for her rulings on a vital piece of evidence in the Trump case.

In that decision, the 11th Circuit Court of Appeals strongly criticized Cannon when she granted Trump's request that the government be blocked from using the evidence it obtained from Trump's Mar-a-Lago estate search warrant to advance its investigation.

The appeal court said Trump had failed to provide adequate information upon which she could base a decision, yet "[T]he district court [Cannon] was undeterred by this lack of information."

Cannon, who is originally from Colombia, is a registered Republican who was appointed to her federal judgeship by the Trump administration.

In a biting analysis on the online creative writing site, Substack, lecturer and former federal prosecutor Joyce Vance said that Cannon could be facing similar criticism for her lack of reasoning in the conflict of interest case.

"She hasn't even bothered to draft a written opinion to clarify her thinking, at least so far. She may face a similar fate with the Court of Appeals this year if prosecutors take another appeal to Atlanta," Vance wrote.

Peter M. Shane, adjunct professor of law at New York University, told Newsweek that Cannon does not have enough trial experience to handle a case of this magnitude.

"Cannon's initial rulings were so egregiously wrong that they raised some reasonable doubts as to her impartiality. But I am equally troubled that one of the most potentially consequential criminal trials in U.S. history is in the hands of a federal judge with just a handful of criminal trials under her belt, so to speak, none of them especially complex,' he said.

"I wouldn't want to enter the final rounds of the Great British Baking Show if my experience was limited to successfully toasting Pop Tarts. But the statute on disqualification does not mention inexperience as a basis for removal," Shane added.

He said he doubts "another Eleventh Circuit scolding" will prompt Cannon to recuse herself from the Trump case.

New York University law professor Stephen Gillers said that another appeal of a ruling by Cannon could open grounds for her to be removed from the case.

"I can't say whether she should be removed but if one of her rulings goes to the circuit [appeal court], that gives the prosecution an opening to ask the circuit [to] remand to another judge."

"Here, recusal would be based on perception of partiality. Self-recusals for that reason are almost unheard of. There has to be a motion," he said.

Newsweek has contacted the Justice Department and the federal courts in southern Florida for comment.

Uncommon Knowledge

Newsweek is committed to challenging conventional wisdom and finding connections in the search for common ground.

Newsweek is committed to challenging conventional wisdom and finding connections in the search for common ground.

About the writer


Sean O'Driscoll is a Newsweek Senior Crime and Courts Reporter based in Ireland. His focus is reporting on U.S. law. ... Read more

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