When Donald Trump’s beloved federal judge issued yet another head-turning order this week to throw the upcoming Mar-a-Lago classified documents trial into limbo, she actually did him an even bigger favor—she created chaos that can spill over into his other legal battles ahead of the 2024 election.
U.S. District Judge Aileen Cannon has pushed back what might have been a one- or two-day meeting with prosecutors to review classified documents until February. On Thursday, she also refused to even schedule a court hearing to hear what sensitive national security documents Trump’s lawyers want to use at trial—until sometime after March 1. It’s a one-two punch that will potentially delay the trial by up to four months.
But by keeping her scheduled May 2024 trial date in Florida, she actually made it worse for judges overseeing Trump cases in Atlanta, New York City, and Washington—a feat that’s akin to booking a restaurant reservation one doesn’t intend to keep.
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“The tricky thing is, it puts them in limbo. Another judge could schedule something for May but may not want to, because it’s possible trial will still go in May. If you’re a cynic—and I’m not—you might say she deliberately did this,” said Brian Greer, a former CIA lawyer who spent years working on cases involving classified records.
Criminal trials are sophisticated spectacles that involve laborious logistics. And the stakes are even higher when they involve novel legal issues that need to get sorted out ahead of time—or face the risk of repeating the entire affair due to a mistrial or a sweeping appeal.
That’s particularly true with Trump, given that he’s the first former president to face criminal charges, as well as the first to waive expired credentials in an attempt to avoid them. Meanwhile, he’s also the first to launch a presidential campaign that, if successful, threatens to halt or overturn the very trials he’s trying to avoid.
Trump’s first bout is set for the week of the Super Tuesday primary elections in March, the scheduled start of his federal trial in Washington, D.C., for his failed attempt to remain in power after losing the 2020 election. Any delay in that trial is sure to conflict with his next trial, set just three weeks later. That’s when the Manhattan District Attorney will seek to convict him for faking business records to cover up his 2016 hush money payment to the porn star Stormy Daniels. Sometime after that, Trump will likely face his massive mob trial against a Fulton County district attorney who’s accused him and 18 others of running a racketeering scheme to steal the election in Georgia.
So while these three other judges figure out how to keep their cases chugging along toward trial, they’re competing with a nebulous case in South Florida—one that could claim a huge block of time to figure out unprecedented constitutional issues. That’s especially true because the case is being overseen by a judge with less experience presiding over trials than the average municipal traffic court administrator. (As of June, Cannon had only overseen roughly 14 courtroom days of trials since her appointment by Trump in 2020, according to The New York Times.)
For now, Cannon is keeping her May 2024 trial date penciled in, even as she erases deadlines she set in July. Her latest decision has lawyers and political scholars once again scratching their heads and wondering whether to blame her inexperience—or what’s suspected to be an allegiance to MAGA.
“She is a full fledged member of the Trump defense team. Aileen Cannon is utterly unfit for the bench. Someone should introduce an impeachment resolution against her. It will go nowhere but will highlight her outrageous conduct,” tweeted Norman J. Ornstein, a senior fellow emeritus at the American Enterprise Institute, a conservative think tank.
The way she refused the DOJ’s request to somehow speed things along by resetting some deadlines in December invited commentary that credited her for helping Trump as best she can.
“This is how Trump has beat the legal system for five decades,” tweeted crime fiction writer Don Winslow.
However, some have noted that Judge Cannon appears to be operating with plausible deniability in mind. The legal journalist Liz Dye, who now runs the Law and Chaos blog, pointed out that Cannon earlier this month formally denied Trump’s request to delay his Mar-a-Lago trial—allowing her to appear fair, even though her subsequent deadline shuffle does the very same thing.
Cannon has consistently rewarded the former president who gifted her a lifetime appointment. She stopped the FBI from sorting through the Top Secret records special agents recovered at his Florida mansion—until an appellate court reversed her at breakneck speed. She feigned an invasion-of-privacy crisis that never really posed any harm to the ex-president—and got caught. Then, in August, she questioned the Justice Department’s continued use of a secret grand jury far outside her district—perfectly positioning Trump’s lawyers to decry “abuse” over what appeared to be a parallel investigation in Washington.
Her bizarre rulings continue to shock legal scholars. But according to a source with direct knowledge of internal discussions on Trump’s legal team, they also justified the congratulatory celebrations his lawyers had when they—against the odds—landed this rookie judge on one of the most historic criminal cases in American history.
She keeps giving Department of Justice Special Counsel Jack Smith a hard time. And she’s doing it again.
Her latest calendar-juggling trick is more revealing than it would seem at first glance, particularly for the few attorneys who have extensive expertise in a relatively obscure corner of national security law. That’s because she’s delaying some pretty basic, perfunctory legal steps in these types of criminal cases involving government secrets. Understanding how she’s doing that requires a deeper dive into the unique elements of a case like this one. After leaving the White House in shame three years ago, Trump hoarded boxes full of classified documents all over his oceanside estate at Mar-a-Lago. The Mediterranean-style villa naturally became the GOP version of a Venetian-veneered event venue, with regularly scheduled political fundraisers and dinners fetching up to $100,000 per plate.
But the mansion is also a private club that’s become a destination for MAGA fans from around the world—racking up an endless stream of cameos geolocated on Instagram from the likes of aspiring social media influencers, rising rightwing podcasters, and wannabe politicians. This is why the FBI was so concerned that hundreds of classified documents were lying around in Trump’s bathroom, tucked into his desk drawer, and shoved into clumsily stacked boxes.
Now that the DOJ has seized them back, prosecutors have no intent to display them at a public trial that’ll be closely watched by the entire world. Instead, this has become the best possible example of a 1980 law—ironically, crafted by then-Senator Joe Biden (D-DE)—called the Classified Information Procedures Act.
CIPA allows the government to pare down the evidence before it’s shared with the very person it accuses of a crime, then limits that collection even further before trial. It’s intended to give prosecutors the ability to turn over any exculpatory evidence and present a criminal case against someone in court, only without spilling national secrets in broad daylight.
Greer, who handled these types of cases as a former CIA lawyer, created a handy diagram that captures the very complicated legal process by portraying it as an upside-down triangle—something he calls the “CIPA funnel.” At the top is the wide universe of all potential evidence that can be shared in a court case, while the bottom is a much smaller and very pointy shape that represents the little bit that makes it to trial.
“It’s all about narrowing the scope of classified information at issue in the case,” he said.
It’s a thorough filtering process. Prosecutors, seized evidence in hand, meet with intelligence agencies. Spy officials approve wholesale redactions and rephrase entire segments to pluck out details. A lot happens behind the scenes before prosecutors even show up for pretrial hearings. Sometimes, the DOJ ditches incriminating evidence because it’s just too sensitive to show at trial, he said.
“The information subject to a Section 4 motion could be inculpatory rather than exculpatory. Let’s say a foreign government sends a cable to CIA saying, ‘We had to pull a source from the field and now they’re under 24-hour security.’ This information would be technically discoverable but it’s inculpatory, and it’s an example of the type of thing that DOJ might try to remove in Section 4. There are less extreme examples of that,” he said.
And established case law dictates that prosecutors are only compelled to turn over some version of classified information if they plan to use it at trial—or if the judge would find it “helpful,” “essential,” or “relevant to the determination of the guilt or innocence” of a person.
Greer paints the picture using another hypothetical. If the British government sends a cable to the CIA saying it doesn’t think a particular secret agent was “burned” by the fact that Trump kept a certain classified document lying around Mar-a-Lago, the U.S. government would summarize that before turning it over to Trump’s lawyers—and disguise it even further before it’s merely discussed in a vague way at trial. In this example, the 23rd classified page seized by FBI agents would never make it to a public courtroom.
“We’d say, ‘In March of 2022, a foreign government told CIA a source in charged document 23 was assessed to be not at risk.’ We wouldn’t name the source, the codename of the source, and we’d fuzz up the dates of data collection. The identity of the government isn't relevant, neither is the source… nor naming the station that received the cable. We’d surgically remove the discoverable information in the document, produce it in a new Word document, and sanitize the most sensitive aspect of it,” he said.
And that’s where Judge Cannon comes in.
In the run-up to Trump’s trial in Fort Pierce, Florida, Cannon must decide whether she agrees with the DOJ’s paring down of the most sensitive evidence. To do that, at this point, she needs to get a memo from prosecutors and hold what’s called a CIPA Section 4 hearing. Cannon has delayed the DOJ memo deadline from October until December. And while she could likely spend a day or two flipping through the really sensitive evidence—which is believed to be a tiny slice of the classified records in question—Cannon instead recently set aside Feb. 15 and 16.
“The hearing is much different from what you’d expect. It’d just be the judge getting into a secure room with prosecutors and going through the documents. She’d say, ‘Let me see the full document you’re substituting. Let me see what you’re withholding. Some judges don’t do that at all and just rule from the papers. Others want to review everything,” Greer said.
“I think she could do that a week after DOJ files a Section 4 motion. Instead, she’s doing it 74 days after they file their motion,” he added.
What’s worse is that Cannon is also postponing the very next step: CIPA Section 5, in which Trump’s lawyers will identify what they want to use at trial. While that could theoretically get started now with the 5,500 classified documents the feds have already turned over to the defense, Cannon has instead pushed off the mere discussion of those things until after March 1, thus ensuring that the DOJ and Trump duke it out for weeks or months starting in the spring.
As time goes on, a May 2024 Mar-a-Lago trial looks less and less likely. Legal observers think August is more realistic—conveniently for Trump, one month after the Republican National Convention in Milwaukee, Wisconsin.
