U.S. District Judge Aileen Cannon has been on the federal bench for less than four years, and yet is likely already in the midst of the most consequential case of her legal career. Yet Cannon consistently has shown little urgency to match the import of special counsel Jack Smith’s classified documents case against former President Donald Trump. On Tuesday, Cannon announced that the trial for the man who appointed her will be postponed indefinitely due to the large number of pretrial issues that have yet to be resolved.
To say that Cannon finds herself in an entirely avoidable situation is an understatement. The primary speed bump preventing a swift speedy resolution of the issues she cites in explaining her delay is none other than Cannon herself. It’s impossible at this juncture to definitively apportion the blame for this cascading failure on inexperience, partisan malice and simply being dealt a bum hand. What is clear though is that Cannon has made what should have been one of the most straightforward cases against Trump into a quagmire of her own creation.
What is clear though is that Cannon has made what should have been one of the most straightforward cases against Trump into a quagmire of her own creation.
On paper, Cannon largely blames the slow-moving process on the Classified Information Procedures Act, a 1980 law that lays out rules for the use of classified documents in criminal trials. “Finalization of a trial date at this juncture — before resolution of the myriad and interconnected pre-trial and CIPA issues remaining and forthcoming — would be imprudent and inconsistent with the Court’s duty to fully and fairly consider the various pending pre-trial motions before the Court, critical CIPA issues, and additional pretrial and trial preparations necessary to present this case to a jury,” she wrote in Tuesday’s order.
It’s true that cases covered by CIPA do tend to be more difficult to handle than those with less potentially sensitive charges, as judges balance the accused’s ability to mount a viable defense without revealing government secrets. Cannon is clearly aware of charges that she is intentionally slow-rolling the case: In a footnote to Tuesday’s order, she says that since March she has heard and resolved five motions from the defense, including Trump and co-defendants, as well as multiple CIPA-related motions. She adds that she’s ruled upon other matters as well in the weeks since March, including redaction and sealing requests and “other miscellaneous motions.” It’s an impressive list — but not exactly one that inspires sympathy when you consider some of the reasons why she may be struggling to handle the workload.
Cannon’s name first became widely known soon after the FBI searched Mar-a-Lago in August 2022 and seized boxes of documents that Trump had refused to return to the federal government, which were found to include hundreds of pages of classified documents. When Trump’s lawyers demanded a “special master” to slow down the Justice Department’s examination of the seized material, citing “executive privilege,” Cannon obliged. Her ruling was smacked down in the usually very conservative 11th Circuit Court of Appeals, but not before it drew a lot of scrutiny on Cannon and the fact that she was a Trump appointee.
Lawyer and legal commentator David Lat wrote last month that in the special master case, “Judge Cannon thought like a pointy-headed appellate judge, not a commonsensical trial judge,” seizing on the novel legal issues at play rather than the matter directly at hand. This led to her “grossly overthinking the matter” and issuing an opinion that “was too clever by half — and just plain wrong — which is why the Eleventh Circuit made short work of it,” he continued in his Substack newsletter. Since then, Lat reported, Cannon’s office has struggled with the heavy workload, higher than normal turnover in her chambers, the required clearances her clerks need to handle classified material, and a new propensity for micromanaging given the increased scrutiny on her after the special master ruling. It’s entirely possible that a more experienced judge than Cannon would be facing similar problems. It’s entirely possible that a more experienced judge would be facing similar problems. But that Cannon is even in a position to make these decisions is due to an almost literary twist of fate. There are more than two dozen federal district judges in the southern district of Florida. Cases are assigned at random among them. It is only through the luck of the draw that Trump would see his classified documents case fall before Cannon. With the shadow of the special master case looming over her, she’s opted to take her time to get things right. Yet that has opened her up to an entirely different set of criticisms. That includes her frankly bizarre decision to have the prosecution and defense spend time on crafting potential jury instructions and arguments regarding the Presidential Records Act rather than deal with the more pressing issues on her plate. Unfortunately for everyone who isn’t a co-defendant in this case, Cannon’s careful treading fits perfectly with Trump’s preferred strategy of delaying his court appearances for as long as possible. The trial had originally been scheduled to begin on May 20 — though given that Trump is in the middle of a separate criminal trial in New York, that was clearly not going to happen. Both Smith, who brought the charges against Trump last year, and the former president’s lawyers agreed that a delay would be necessary. Smith’s team argued that a summer trial was still possible, while Trump naturally pushed for a trial date after Election Day. Since a hearing on the matter in March, Cannon had only given hints at when a rescheduled trial would take place, the last of which was Monday when she bumped back a key CIPA-related filing deadline. Again, the evidentiary role of classified material would likely slow down any criminal trial, let alone one involving a former president. But given the clear evidence that Trump was in possession of the documents seized despite a subpoena to return them and attempted to foil the government’s efforts to recover them, this should be an open and shut case once it gets before a jury. Instead, Cannon has only painted herself into a corner, overcorrecting from her past mistakes in a way that has only exacerbated her subsequent follies.
Hayes Brown is a writer and editor for MS NOW Daily. 
