Delaying Trump’s trial until after the November election would have a momentous implication: It might mean the trial never happens at all. If Trump wins the election and the case is still pending, he’s expected to order the Justice Department to shut it down.

Even a shorter delay would be fraught: Pushing the trial into the summer or fall could run headlong into the Republican National Convention or the heart of the general election campaign.

For now, Cannon, a Trump-appointed federal district judge in Florida, is officially sticking with the May 20 trial date she announced four months ago. She even recently denied Trump’s bid to push it back. But in a series of more technical rulings, Cannon has postponed key pretrial deadlines, and she has added further slack into the schedule simply by taking her time to resolve some fairly straightforward matters.

“It could be seen as a stealth attempt to delay the ultimate trial date without actually announcing that yet,” said Brian Greer, a former Central Intelligence Agency attorney.

“There’s pretty much no chance they could go to trial on May 20 with the current schedule,” he added.

David Aaron, a former DOJ national security prosecutor, agreed, saying a May 20 trial is unlikely “unless a lot of discipline is imposed.”

Early delays in a complex case

The case would not be a simple one for any judge to manage. Trump is charged with retaining classified documents at his Florida estate after he left the White House and then impeding the government’s effort to retrieve the records. Because much of the evidence in the case is classified, a 1980 law known as the Classified Information Procedures Act, or CIPA, governs how that evidence should be handled.

Most federal judges outside the Washington area rarely encounter CIPA cases, and Cannon isn’t known to have handled one before Trump’s. She has already lamented some of the practical complications surrounding this one. A facility to store classified information near the southern Florida courthouse she has designated for the trial isn’t expected to be ready until early next year, the judge said during a Nov. 1 hearing.

Other delays are more substantive. Last month, after prosecutors in special counsel Jack Smith’s office ran into difficulties making a small amount of evidence in the case available to Trump and his lawyers due to what the government says is its extremely sensitive nature, Cannon suspended the deadlines for motions related to classified information.

She took more than five weeks to hold a hearing on Trump’s request for a new schedule and nine days more after that to issue a new one. And when she did finally set a new schedule, she put off the deadline for many pretrial motions by nearly 16 weeks.

“She’s certainly taken her time to litigate things,” Greer said.

Last week, prosecutors tried to jump-start the case by asking Cannon to give defense lawyers a Dec. 18 deadline to file most of their requests to use classified information at trial. The next day, before any of the defense attorneys had even responded, Cannon denied the request and said she doesn’t plan to set such a deadline until March 1.

“The signals are of a court that is proceeding slowly and methodically through the process,” said Brandon Van Grack, a former national security prosecutor who also was part of special counsel Robert Mueller’s team. “In order to have a trial by May, the court would just need to push the parties on a tighter deadline.”

At a hearing earlier this month, Cannon said prosecutors pressing for a faster schedule in the case were being unrealistic about the complications involved.

“I’m just having a hard time seeing how realistically this work can be accomplished in this compressed period of time, given the realities that we’re facing,” Cannon said.

A clash of legal and political calendars

Cannon’s approach stands in stark contrast with her counterpart in Washington, Judge Tanya Chutkan, who is overseeing the other federal criminal case against Trump. (Trump faces separate state-level criminal charges in Georgia and New York.)

The case in Washington, involving Trump’s efforts to interfere with the 2020 election results, is scheduled for trial in March — and Chutkan, an Obama appointee, has seemed determined to stick with that timeline. She has repeatedly insisted that she will not, and cannot, consider Trump’s political schedule as she sets deadlines for the case.

Cannon, in contrast, has so far danced around the issue of whether Trump should get any deference in scheduling because of his status as a presidential candidate. But those questions may soon become impossible to dodge.

The classified documents trial is expected to last for weeks or longer. If the May 20 start date proves infeasible, the trial could risk overlapping with the Republican convention, set to open July 15 in Milwaukee.

“Could she try to squeeze it in before that? Maybe, but I doubt she’d do that,” Greer said.

Delaying it until August, September or October would open its own can of worms, assuming Trump wins the GOP nomination. The political stakes would be white hot, as Trump would be sidelined from the campaign trail to attend a trial on charges that carry decades of potential prison time.

But pushing the trial until after the election might be the most controversial move of all. It would set up the chance for Trump to avoid the trial altogether by winning the election, because as president he could appoint an attorney general willing to fire the special counsel and drop the charges. Trump might even be able to pardon himself.

Many Trump critics are already deeply skeptical of Cannon. Before he was even indicted, she sided with Trump on issues related to the materials that investigators seized from Mar-a-Lago. A federal appeals court quickly blocked part of Cannon’s order and later overturned the rest of it.

“Judge Cannon’s bias is showing over and over again,” former Mueller deputy Andrew Weissmann wrote last week on X, formerly known as Twitter, declaring the judge to be “in the bag for Trump.”

Cannon is surely aware of the suspicion about her in some quarters. That has led some lawyers to conclude she may already know the trial is unlikely to start in May, but sees no reason at the moment to ignite the firestorm she would face if she puts it off.

Whatever Cannon’s motivations, there’s little dispute that she and prosecutors have very different views of the urgency of getting the case to trial.

“The Department of Justice is trying to do everything in its power ahead of trial to move as expeditiously as possible,” Van Grack said. “And the court is just reluctant to or resistant to any efforts to expedite the process.”

More delays on the horizon

Other significant pretrial showdowns are lurking in the case, all of which may cause further delays, attorneys warn.

One almost certain clash is over Trump’s plan to ask the judge to force prosecutors to gather more evidence that the defense thinks might be relevant to the case, like files from the National Archives and Records Administration, which manages presidential records. The Justice Department’s probe into Trump’s retention of classified records after his presidency kicked off after NARA notified the department that it was missing many records.

If any of that additional evidence is classified, the parties and the judge may have to go through multiple rounds of litigation about what portions can be used at the trial.

Another layer of complexity: Trump is not the only defendant in the case. His personal aide, Walter Nauta, and a Mar-a-Lago facilities manager, Carlos de Oliveira, are also charged for allegedly helping Trump conceal the records and other evidence from investigators.

“With three defendants all having the opportunity to make motions, it could be that at least one of the defense teams decides to move to use a lot of classified information as evidence,” Aaron said.

Prosecutors are also likely to ask Cannon to allow special procedures at the trial itself, potentially proposing a procedure called the “silent witness rule” to try to admit some evidence without it being shown or read out in court. Sometimes witnesses testifying about classified matters even appear in disguise or are obscured from the public by a divider placed in the courtroom.

Trump, his co-defendants and members of the media will likely oppose such measures, leading to more litigation. This can put the government to a choice — sometimes called graymail — between making secrets public and abandoning a prosecution or part of it.

“There are valid reasons [to object] from a press perspective and a defense perspective, but it also does provide an opportunity for mischief by the defense as part of the graymail problem that CIPA is supposed to thwart,” Aaron said. “CIPA will thwart the graymail problem, but that does sometimes take time.”