CNN
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A criminal case that was once viewed as the most open-and-shut prosecution against former President Donald Trump has been mired in delay, unresolved logistical questions and fringe legal arguments that appear to have hijacked the judge’s attention.

US District Judge Aileen Cannon, who was appointed to the federal bench by Trump in 2020, has drawn out the case with an unusual, eyebrow-raising approach in her nearly 10-month oversight of the case, delaying rulings on what experts say are routine legal questions that must be resolved before the case can go to trial.

The longer it takes for Cannon to decide these issues, the more likely a trial would need to wait until after the November presidential election.

Prosecutors’ impatience was evident in fiery filings late Tuesday night, where special counsel Jack Smith said Cannon had asked for briefs that were premised on a “fundamentally flawed” understanding of the case that had “no basis in law or fact.”

Smith’s team previewed their desire to potentially appeal the dispute around how Cannon apparently views the case – which would further slowdown the timeline.

Regardless of whether they go that route, Smith has almost no options for speeding her up, as judges have nearly carte blanche authority to manage their dockets as they see fit.

“If the judge wants to drag it out, she can kind of drag it out,” said Alan Rozenshtein, a University of Minnesota Law School professor and former Justice Department attorney. “We invest enormous discretion in trial judges to run their cases, for better or for worse, and this case is – in that sense – like any other case.”

Frustration with how slowly a case is plodding along is nothing new in the criminal justice system, and slow-moving pretrial proceedings over the classified documents at the heart of the case were always expected. But Cannon’s critics view the pace of the Trump prosecution with added suspicion because of how she handled a separate, 2022 lawsuit Trump brought attacking the FBI’s documents investigation.

In that lawsuit, Cannon granted an extraordinary Trump request for a third-party review of the FBI’s 2022 search of his Mar-a-Lago resort for the classified documents. A conservative appeals court repeatedly reversed her rulings in the lawsuit, scolding her for giving Trump special treatment no other private citizen would receive, and shut down the review.

Now, critics accuse Cannon of – purposely or not – playing into Trump’s strategy of delaying the trial until after the election. If Trump wins the White House, he will presumably make the case go away.

Cannon’s rulings in the 2022 lawsuit were so “outside the bounds” that “people rightly became suspicious of her motives,” said Barbara McQuade, a former US attorney in the Obama administration.

“It is equally plausible,” McQuade said, while stressing she does not know what’s going on behind the scenes, “that she is very inexperienced and unsure of herself and is going as slowly as possible in the hopes that she won’t be first” among the Trump criminal cases to go to trial.

Ty Cobb, a former lawyer for the Trump White House, told CNN’s Erin Burnett Wednesday he also thinks the delays have cast an air of suspicion around Cannon: “I think the evidence is just too overwhelming.”

“Yes, she may be incompetent, but at this stage of the game, you know, her incompetence is so gross that I think it clearly creates the perception … of partiality and her attempt to put her thumb on the scale,” he said on “OutFront.”

Legal experts have said that prosecutors have put forward strong evidence that Trump violated the law by keeping sensitive national security documents at his Mar-a-Lago club and by then allegedly obstructing the investigation into the documents’ whereabouts. Trump and his two co-defendants, who work for him, have pleaded not guilty.

But no matter how cut and dry the case may seem to outsiders, prosecutors won’t get a chance to put that evidence in front of a jury until Cannon works through a deep backlog of outstanding legal issues.

Cannon has yet to decide more than a dozen motions that have significant – and potentially fatal – implications for the criminal case, and legal experts are flummoxed by the massive amount of work she has left to do.

The case is about to truck past the May trial date she scheduled for it last year and Trump has eyed using the other criminal cases against him as an excuse to postpone this trial even longer.

Nevertheless, Cannon has rebuffed nudges from the prosecutors that the pace could be picked up.

“I can assure you that in the background there is a great deal of judicial work going on,” she said at a March hearing for considering a new trial date. “So while it may not appear on the surface that anything is happening, there is a ton of work being done in the background.”

After a flurry of hearings in the fall, proceedings in the case all but disappeared from the public eye as Cannon and the attorneys slogged through sealed proceedings that discussed classified information. The only hearings that have played out in public in the past several months are two proceedings in March discussing the trial schedule, Trump’s efforts to dismiss the case and his attempts to access additional information from the government.

Among the motions on the table are at least nine efforts by Trump and his two co-defendants to dismiss the charges against them.

That includes claims that Trump should have immunity in the case because he was still president when he first took the documents, that the Justice Department is selectively and vindictively prosecuting them, and that the special counsel doesn’t have the authority to bring charges.

Cannon has not yet ruled on any of those assertions. She also hasn’t ruled on a Trump request for information from a range of government entities including the Biden White House, nor has she decided a government plea that certain witness information be shielded from public view in court filings.

“There’s just so much to be done,” Cobb said, adding, “she seems to stumble on the most fundamental things.”

Perhaps most notably, the judge has yet to formally reschedule the trial, despite holding a hearing more than a month ago on the matter. Jury selection is ostensibly scheduled to begin in May, but Cannon has signaled that even a summer trial start date is now out of reach. It is unclear whether she is trying to wrap up some of the pending pretrial disputes, including the several bids by the defendants to get the charges tossed, before resetting the trial date.

“The delay seems unusual and, in light of her track record, it’s hard to give her the benefit of the doubt,” said McQuade, who now teaches at University of Michigan Law School.

“Her delays here are extraordinary,” Cobb added. “She hasn’t even set a trial date, that’s remarkable.”

Cannon has created a tedious process for attorneys to get permission to file redacted versions of their filings. That protocol has led to its own tangle of disputes over what information should be shielded from public release that appear to be preventing multiple major motions from even being docketed.

But some of the slow-moving proceedings are typical, experts say, specifically around how classified materials would be handled in the case.

“If you think about how an ordinary 21st century office works in terms of being able to print wirelessly to a printer, to work from home, to have your cell phone in your office – all of these are things you can’t do when you’re processing classified information,” David Aaron, a former Justice Department national security prosecutor, said in an interview with CNN.

“You have to be in a special room with limited equipment. You can’t bring your cell phone. You might not have internet access. You can’t file anything electronically,” Aaron said. “That adds friction to the way that you practice law.”

Debates over how classified information can be used are conducted almost entirely in secret, and often in hearings where only one side of the case is in the room at a time, known as an “ex parte” hearing. The unusual nature of how the hearings are conducted, Aaron said, can also slow down the process, which is governed by a law called the Classified Information Procedures Act, or CIPA.

“A lot of judges are seeing CIPA for the first time, and they’re often not initially comfortable with the idea of ex parte, or non-public, proceedings because that’s just not how American criminal cases usually go,” he said.

Cannon, appointed to the bench less than four years ago, has had limited trial experience both as a judge and in her previous role as a DOJ attorney.

According to what is on the public docket, Cannon has cleared key steps in that process. But in the non-classified legal fights playing out in public, particularly over Trump’s efforts to have the case thrown out, Cannon seems to have let tangential legal issues distract her from resolving the central questions, experts say.

“She is getting lost in arguments that any other judge would have dismissed right away,” said Mark Schnapp, a defense attorney in south Florida, where the case is proceeding.

While Cannon has hinted that she views Trump’s far-fetched legal arguments with more sympathy than legal experts say is warranted, she has given little indication about how she’ll rule on Trump’s challenges, aside from one hearing in March when she heard arguments on two Trump claims for why the charges against him should be dismissed.

But court observers were shocked when Cannon summoned the parties to Florida to present their theories on the validity of the charges.

Hours after the hearing, Cannon rejected Trump’s first claim, that the national defense law he is charged under was too vague. She suggested, however, she could consider his arguments again when the case was closer to trial.

Rozenshtein, who is an alum of the DOJ National Security division during the Obama administration, said the order was an example of Cannon “kicking the can down the road.”

“This is in line with Judge Cannon’s approach to legal issues, where she is just overcomplicating things enormously,” he said.

She has yet to decide the second Trump claim from the hearing – his argument that a law known as Presidential Records Act gave him the power to take the sensitive government documents with him when he left the presidency. Trump’s arguments have been rebuffed by legal experts across the ideological spectrum, who note that the Presidential Records Act was passed to ensure that government records were being kept in government hands at the end of the presidency.

Even the National Archives itself said that Trump was misstating the significance of the law in an unusual rebuke on their website last year.

In the meantime, Cannon asked the attorneys in the case to engage in a thought exercise – what a trial jury would be instructed on reaching a verdict if Trump is allowed to argue that he had full authority to keep any documents he chose – leaving even experienced legal watchers questioning why she is pushing the attorneys into uncharted territory at the boundaries of the case.

“It’s such a clearly wrong legal argument,” said McQuade. “It’s hard to make sense of what she’s doing here.”

Prosecutors told Cannon Tuesday night that if she was going accept Trump’s arguments that he had the authority under the PRA to take at least some of the classified documents with him from the White House, that she should issue that ruling soon so Smith’s office could ask an appeal court to review it while the case continued to move towards trial.

“The real question is not any particular action that Judge Cannon makes,” said Rozenshtein. “It’s when you stack them all up on top of each other, you get a sense of someone who, in the best case, does not have her arms around this case, and in the worst case, could lead people to question her motives.”

This story has been updated with additional information.

CNN’s Jack Forrest contributed to this report.