"Cannon is a bad judge": Legal experts say Trump taking advantage of judge's "rookie problem"

As the pre-trial proceedings in Donald Trump's Florida criminal case drag on, some legal experts are increasingly skeptical that the case will go to trial this year. Others worry it won't see a trial at all. 

U.S. District Judge Aileen Cannon, the Trump-appointee overseeing the case, in which the former president is accused of willfully retaining national security secrets after leaving office and attempting to thwart government efforts to retrieve them, has yet to confirm a trial date despite holding two separate hourslong hearings expected to address the matter earlier this month. 

She also has yet to rule on multiple defense motions to dismiss the case while disputes over classified evidence have stretched across months and a contentious request from Trump's legal team to release the names of the government's witnesses sits unresolved, according to the Associated Press. Legal experts expressed concerns over her recent order requesting end-of-trial jury instructions that suggests Cannon is still considering a Trump claim about his authority to possess the documents that days earlier she had seemed openly skeptical of. 

The delays can, in part, be attributed to the presumptive GOP nominee's frequent legal tactic to delay his four criminal cases as he carries out his 2024 presidential campaign. But his Florida case has entered unique territory because of how few substantive decisions the judge has made to progress toward a trial, raising the chance that the case won't go to trial before the November election. 

"Judge Cannon is a bad judge and has made bad rulings and has favored Trump at every possible turn, number one," former federal prosecutor Neama Rahmani told Salon. 

Since her assignment to Trump's case last year, Cannon, a former federal prosecutor who was appointed to the bench in 2020, has faced intense scrutiny for her relative inexperience as a judge.

That factor presents a "bigger problem" than Trump's frequent delay tactics because she appears to have "lost control of the trial," David Schultz, a Hamline University legal studies and political science professor, told Salon.  

"The fact that she's [held] a bunch of hearings, she doesn't have clear orders, she's all over the map — I think it's a rookie problem, or relative rookie problem, that she just does not have control over the courtroom, and Trump's taking advantage of it," Schultz said, contrasting Cannon's handling of Trump's lawyers with that of New York Judge Juan Merchan, who sternly set a trial date in the former president's Manhattan criminal case on Monday and scolded Trump's legal team for their latest delay attempt.  

"Every frivolous argument that Trump has raised, [Cannon has] entertained, going back to the search warrants that were executed at Mar-a-Lago," Rahmani added, referencing Cannon's appointment of an independent arbiter in response to a Trump lawsuit to parse the records the FBI seized from the property. A federal appeals court panel of judges unanimously reversed that appointment, stating that Cannon overstepped her authority. 

But the pre-trial discovery portion of the proceedings revolving around the Classified Information Procedures Act also contribute to the case's lag, Rahmani explained. The CIPA Act sets "specific guidelines" for the disclosure of classified material and their admission into evidence, requiring all parties in a case to have clearance to review the documents and to only access some sensitive materials in a designated, secure facility. 

The need to keep the document's intelligence information classified so it's not revealed to the public during trial has also led prosecutors to seek "redacted versions" or summaries of the exhibits for jurors, he added.

"There's this whole procedural back-and-forth in these types of cases that just delays things already," Rahmani said, noting that much of the responsibility in resolving those procedural matters falls on Cannon.

Special counsel Jack Smith and his team have continuously urged the judge to push the case forward, the AP noted. Though they've avoided mentioning the upcoming election, they frequently emphasize the public's interest in a quick resolution to the case and highlighted what they say is overwhelming evidence — from surveillance video and a defense lawyer's notes to close Trump associates' testimony — establishing the former president's guilt.

Trump and co-defendant Walt Nauta were arraigned in Miami last June, both pleading not guilty to all charges. Co-defendant Carlos De Oliveira, who was charged in July's superseding indictment, pleaded not guilty in mid-August following his first court appearance in late July.

For a case like this, the timeline from the defendants' arraignment or initial court appearance to a trial should last no longer than a year, maybe even less, Schultz said, noting a defendant's Constitutional right to a fair and speedy trial.

Even then, Cannon has been moving so slowly in deciding key matters in the case that she's fallen out of step with her proposed timeline and ushered in a level of uncertainty among legal experts about the ultimate fate of the case.

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With Cannon's handling of the case thus far, Rahmani doesn't expect the case to go to trial until 2025 if Trump loses in November. But if Trump wins the former federal prosecutor predicts the case will be dismissed because of the Department of Justice's "long-standing policy" against prosecuting sitting presidents. 

Though Schultz thinks the case could go to trial before the end of the year, he also still believes it's possible for Cannon to get it on track for an October trial date, just ahead of the election.

To do so, Cannon would need to "pretty quickly" take "more control" of the case and "do a better job" with scheduling, convening in the next "three to four weeks" with the parties to set a timeline for discovery and affidavits, Schultz explained.

Whether she will do that, however, is a different question.

"I'm a little skeptical of it at this point," Schultz said through a chuckle. "Sounds like what she needs to do is to talk to one of the senior judges to get some advice ... or some mentoring in terms of what to do."