Judge Aileen Cannon is leading a historic trial.
Former President Donald Trump’s classified documents case is already shaping up to be a contentious fight — and there’s one woman at the center of it all. Her name is Aileen Cannon, and she’s the U.S. Federal District Court judge who’s been assigned to preside over the legal proceedings. (This includes whether the former president will face any prison time, which could be up to 20 years behind bars).
But almost from the get-go, Judge Cannon has faced scrutiny. Just last year, she shocked legal experts across the ideological divide by suggesting that Trump get special protections as a former president and granting him a special master to review the sensitive government documents the FBI seized at his Mar-a-Lago estate. She has since remained on the case after Trump pleaded not guilty to 37 criminal counts related to the material, and Cannon even agreed to a request to delay the first pretrial conference. The hearing, which was originally scheduled for Friday, July 14, has been pushed to Tuesday, July 18, making the original Aug. 14 start date seem even more unlikely.
“This case is almost certainly not going to trial in August, but that doesn’t mean anything,” Samuell Buell, a professor at Duke Law and a former U.S. prosecutor, tells Katie Couric Media. “In federal criminal litigation, the trial date gets set as a matter of routine early, and it almost inevitably gets moved.”
Given the extraordinary and historic nature of a case involving a former sitting president, the latest development isn’t Cannon’s first test — nor will it be her last. Here’s why some are raising questions about her experience and whether she’s up for the job.
Who is Judge Aileen Cannon?
Born in Cali, Colombia, Cannon was raised in Miami, Florida, by her Cuban mother and American father. Before attending law school at the University of Michigan School of Law, she was a paralegal at the Justice Department’s civil rights division.
Then, upon graduating and passing the bar, she began her legal career as a clerk for a federal appeals judge in Iowa and went on to gain more experience at the prestigious law firm Gibson, Dunn & Crutcher, in Washington, D.C.
In 2013, she returned to the Sunshine State, where she worked as a federal prosecutor in the Southern District of Florida in the major crimes and appellate divisions. But she didn’t get much attention until seven years later, when Trump nominated her as a federal judge. At that point, the number of actual trials Cannon had presided over was quite limited (more on that in a minute), which opened the door to criticism about her experience. Though judicial confirmations like these have been traditionally divisive, she received little pushback from Democrats and was confirmed 56 to 21, with 12 Democrats joining 44 Republicans to vote in favor.
Since she was confirmed during the coronavirus pandemic, her Senate hearing took place over Zoom and it was uncharacteristically short. She revealed little about her own legal philosophy or how she would approach the job of a judge, but it’s no secret that she has long been ideologically conservative. In law school, she was part of the Federalist Society and clerked for a conservative appeals court judge. She’s also a registered Republican, according to the Times, and has previously donated to Florida Gov. Ron DeSantis’s political campaign, but we don’t know much else about her. Apparently, this points to a larger trend, according to Buell.
“There has been an overall deterioration in the resumes of people appointed to the federal bench compared to what it was 20 or 30 years ago, so not only does that make it hard to have a sense of who somebody is as a judge and what kinds of views they have, but it’s also worrying in terms of their ability to preside over the proceedings judiciously,” Buell says.
Why was she put in charge of Trump’s case?
It was the luck of the draw — or was it? During her short tenure as a federal judge in South Florida, Judge Cannon has already drawn one of the most historic cases in recent U.S. history not once, but twice.
She was first randomly assigned to Trump’s classified documents case after Special Counsel Jack Smith indicted Trump in Florida. There were likely several reasons why Smith chose to bring charges against Trump in Florida instead of Washington, D.C., where the grand jury sat. For one thing, it’s where most of the former president’s alleged crimes took place — and the decision will potentially avoid yet another legal battle over the venue of the trial.
But this gamble also ran the risk of Judge Cannon taking on the case, which is exactly what happened. Even though Buell says every district is different, the South Florida clerk’s office uses a method known as “blind random assignment” to designate presiding judges who sit in the division where the matter arose or a neighboring one. One small caveat, as Judge Cannon proved, is that they can still be randomly assigned to a case even if it relates to a previous one.
Though the chief law clerk Angela E. Noble said “normal procedures were followed,” she also acknowledged in an interview with the Times that the odds were in Judge Cannon’s favor because 50 percent of her cases fell within Florida’s West Palm Beach, which is the same district Trump’s Mar-a-Lago estate is in. Judge Cannon also happened to be just one of five eligible judges available to take on the case.
There’s still a possibility that Judge Cannon could recuse herself following her role in a previous case brought on by Trump challenging the F.B.I.’s search of Mar-a-Lago. Despite criticism that she issued rulings favorable to the former president in regards to the F.B.I.’s search of his Florida estate, Buell doesn’t think she’ll step down from the case.
“All she did previously related to this was make a judgment on a legal issue and write an opinion that ended up getting reversed,” he says. “That’s what judges are supposed to be doing. There’s nothing improper about that.”
What do we know about Judge Cannon’s record?
One of the main criticisms against Judge Cannon is her lack of experience in running criminal trials. According to a Bloomberg Law database, she was assigned 224 of these types of cases — which included drug trafficking and firearm offenses — throughout her career. But only four of those went to trial, giving her what some fear is little courtroom know-how.
Even when she doled out sentences, they were considered relatively lenient, particularly when it comes to non-violent crimes. For instance, she decided to sentence a Miami-area business owner to 32 months in prison for defrauding government agencies, which was nearly 25 percent shorter than what was recommended by prosecutors, per a CBS News review. That said, the majority of her opinions have been met without any notable controversy or disputes.
Based on what we know, some experts say Cannon’s record is far too short to indicate how she might rule in Trump’s case. While previous decisions on the case don’t indicate a clear pattern just yet, Buell says she’s demonstrated a “willingness to pursue novel legal theories” after ruling in favor of Trump’s challenge to the F.B.I.’s court-approved search of his Mar-a-Lago home.
“The vast majority of judges would’ve dismissed that case in fairly short order, but she seemed to think that because of who this was, this was wasn’t an ordinary search warrant,” he says.
Even though there’s still so much we don’t know about Judge Cannon, it’s clear all eyes will be on her in what could be the biggest case of her career. “The judges have life tenure, and judicial independence is really important,” Buell tells us. “But they’re human, and it would be unreasonable to think that she can completely insulate herself from the fact that her work will be heavily scrutinized.”
