Isolated and inexperienced: A portrait of the judge overseeing Trump’s documents case from veterans of her courtroom

(CNN) — Judge Aileen Cannon had been on the federal bench for little more than a year when a senior judge offered to preside over one of her first criminal trials in her isolated south Florida courthouse.

“It’s very lonely,” Senior Judge Paul C. Huck told CNN of Fort Pierce, a small fishing and citrus community on the edge of the Southern District of Florida where Cannon is the only federal judge. “It’s a pretty sleepy town with a pretty sleepy courtroom.”

Huck ultimately presided over the March 2022 criminal trial – not because Cannon needed help, he said, but because he enjoys volunteering for trials in courts across Florida.

“I thought I’d go up there and just spend some time with her and get to know her better,” Huck said of Cannon, whom he recalled as “very smart” and “very personable.”

Two years later, Cannon is now presiding over one of the most consequential and complex cases in America: the criminal prosecution of former president Donald Trump over his handling of the nation’s secrets. And she’s attracting nationwide scrutiny for how she’s approached the case.

Since Trump was first indicted a year ago, Cannon has dragged out the proceedings in ways that have flummoxed legal scholars and put a trial initially scheduled to begin last month on hold indefinitely.

Several attorneys who have practiced in front of Cannon – and who spoke to CNN for this story – pointed to her isolation as one explanation for her conduct. Cannon’s solitary post in the Fort Pierce courthouse, one that rarely sees high-profile action, deprives her of the informal, day-to-day interactions with more seasoned judges who sit at the other courthouses and could offer her advice, the lawyers told CNN.

They also said Cannon’s lack of trial experience, both as a lawyer and a judge, is apparent. In her seven years as a Justice Department attorney, Cannon participated on the trial teams of just four criminal cases.  And on the bench, she’s only presided over a handful of criminal trials – and Huck took over one of them.

For this account of Cannon’s judicial demeanor, CNN spoke to ten attorneys who have had cases – both criminal and civil – before her. The lawyers spoke to CNN on the condition of anonymity because of the professional and ethical risks of speaking to press about a sitting federal judge in front of whom they practice.

To corroborate their characterizations of Cannon’s approach, CNN reviewed the public dockets of scores of cases that have traveled through her courtroom.

The attorneys described Cannon as extremely diligent and well prepared, a tough questioner who accepts nothing at face value, and thoughtful in her rulings. But they also said that some of her habits that have raised eyebrows in Trump’s case have plagued her approach from the bench more generally.

Those tendencies include a penchant for letting irrelevant legal questions distract from core issues, a zero-tolerance approach to any technical defects in filings, and a struggle with docket management that allows the type of pretrial disputes that other judges would decide in weeks go unresolved for months.

“She is not efficient,” said one attorney who practices in south Florida. “She is very form over substance.”

Another attorney described her as “indecisive.”

A third attorney who’s had cases before Cannon said, “She just seems overwhelmed by the process.”

‘You can’t really take issue with her’

Five months after Huck visited Cannon in Fort Pierce, she was thrust into the center of back-to-back legal hurricanes. First, she oversaw the lawsuit Trump brought challenging the FBI’s search of his Mar-a-Lago residence that August, when agents found hundreds of classified documents scattered about the property. (Cannon granted Trump’s request for a third-party review of the search, only to see her rulings reversed by a conservative appeals court.)

Then, in a twist of fate last June, Cannon was assigned the criminal case in which Trump is charged with 40 felony counts of allegedly mishandling classified documents and obstructing the government’s attempts to find them.

The high-profile national security case is a dramatic departure from most of the other criminal cases playing out in Cannon’s courtroom, the bulk of which are more mundane prosecutions like gun charges or immigration infractions that are often resolved through guilty pleas, a CNN review of her case log showed.

Cannon’s assignment to the documents case was a game of odds. Though the charges were filed in West Palm Beach, the division that is home to Mar-a-Lago, Cannon was randomly chosen from a broader pool of judges in Florida’s southern district.

Her approach as a jurist – detail-obsessed to the point of tedious – appears uniquely prone to being exploited by a defense team eager to delay the case. And the complicated system Cannon has set up for redacting public filings has only exacerbated a backlog of unresolved issues.

She still has not decided foundational questions that will determine whether the Trump case will go to trial. Marginal issues clutter her docket, including a longshot motion to invalidate Jack Smith’s appointment as special counsel that she’s scheduled a hearing on later this month.

Some attorneys who have practiced before Cannon chalked up her struggle handling the practical logistics of being a trial court judge to her background of mostly appellate work for the local US Attorney’s office.  They described her as latching onto abstract, academic questions at the expense of the type of on-the-fly decision-making required by trial judges that keeps litigation moving along.

As Cannon slowly plods through the backlog of issues on her plate, special counsel prosecutors are now learning firsthand the wrath that they can incur from the judge for seemingly minor discrepancies in their filings, and they have drawn Cannon’s ire for pushing her to move more quickly to resolve the substantive pretrial issues that have slowed the pace of the case to a crawl.

“You can’t really take issue with her, otherwise it’s going to work against you,” a fourth attorney who has practiced before Cannon said.

Trump’s attorneys have also attracted heat from Cannon, though far less often than the special counsel.

Defense attorneys CNN spoke to described Cannon as a judge who gives minimal deference to defendants and as a “notoriously” tough sentencer. To that end, the long leash she’s given the Trump team in the pretrial phase of the case has struck a chord with them.

“She’s certainly not sympathetic to most defendants, and she’s certainly playing a different game with the current defendant before her,” another lawyer told CNN, in reference to Trump.

Nothing taken at face value

Not every attorney who spoke to CNN about their experience in front of Cannon was critical.  Some praised her for asking questions at hearings that showed she had done her research and said that she moved their cases along at a reasonable pace.

Veterans of her courtroom broadly agreed on one aspect of Cannon’s judicial approach: that lawyers should expect her to sharply probe any and all assertions made in her courtroom, no matter the party, with a resistance to taking anyone at their word.

“She doesn’t like any litigant to tell her what she should be doing,” one of the attorneys said.

Many recalled her rejecting joint motions – such as sentencing recommendations or requests to delay proceedings – even though there was no dispute between the two sides.

“You can’t assume that just because there’s agreement between the parties that she will go along,” one of the attorneys said, while describing her as an “incredibly hands on” judge “who wants to be the decision-maker of everything.”

Criminal defense attorneys who practice in front of Cannon appreciate that, despite being a former Justice Department attorney, she doesn’t defer automatically to the assertions of prosecutors, cutting against the stereotype of judges always erring on the side of the government.

“She doesn’t like the government to come in and play bully, steamroller,” one of the attorneys said.

In the Trump case, Cannon has repeatedly taken Smith’s attorneys to task for using broad generalizations to back up their requests – a practice that prosecutors can get away with in other courts – and demanding extreme specificity in whatever prosecutors are asking her for.

Her intense scrutiny extends to whether attorneys are following granular procedural rules about how to file submissions to her court. Last month, such deficiencies prompted Cannon to rebuff a gag order request Smith filed after Trump falsely claimed the FBI had a plan to assassinate him during the Mar-a-Lago search.

She did so because she found the prosecutors had run afoul of local rules requiring them to give the opposing side ample time to consult with them on the request. On other occasions in Trump’s case, she has rejected even routine filings for minor technicalities.

The practice is reflected in several court dockets reviewed by CNN, including at least two other examples where Cannon denied motions because she said lawyers failed to appropriately confer with one another.

One of the attorneys who spoke to CNN described Cannon’s approach to policing procedural rules as, “I decide the way it’s going to be, and if you don’t want to do it the way I tell you, that’s a problem.”

Attorneys pointed out that she is not the only judge on the federal bench who gives no leeway for even the most minor of procedural errors, but some said that her fixation on technicalities led cases to get bogged down in minutiae.

In the Trump case, it took nearly three months for several major pretrial motions to even be docketed after the cumbersome process of litigating what would be redacted in the public filings. Seven of those requests, which seek to throw out parts of the case, remain undecided, and oral arguments have been scheduled on only some so far.

And Cannon still has to handle all the other cases playing out in the Fort Pierce division while she navigates the Trump case.

Seizing on irrelevant concepts

Cannon has repeatedly hauled the lawyers in Trump’s case in for hearings on pretrial disputes in the classified documents case – several of which legal experts say appear tangential or even irrelevant.

The Florida attorneys CNN spoke to acknowledged that it’s understandable for a new judge to hold hearings on issues more experienced judges might be more comfortable in dealing with, and they did not fault her for being especially thorough in the incredibly high stakes Trump case.

Still, Cannon has asked questions in the Trump case that appear out of left field.

In March, for example, Cannon ordered attorneys to draft jury instructions that consider the Presidential Records Act, the federal law that requires an outgoing president to return government records to the National Archives at the end of their administration.

Outside experts and the special counsel’s office lambasted the request as both procedurally premature and legally unsound for how it entertained a fringe theory from the Trump team. Cannon testily defended the exercise as a “genuine attempt” to understand the parties’ positions.

Her orientation toward such legal rabbit holes is not distinct to the Trump case, veterans of her courtroom say.

“She seems to seize on concepts that for one reason or another become interesting to her whether or not they’re pertinent to the case at hand – or decide that they have importance for reasons that escape the rest of the parties in the court room,” one of the attorneys said.

Her lack of trial experience before her appointment stands out among the other judges confirmed to the south Florida federal court under the Biden, Trump and Obama administrations – all of whom had either extensive trial experience as state court judges or had tried 10 or more cases as lawyers before their nomination to the federal bench. Some attorneys say they’ve been concerned her decisions have made  it more likely their cases would be appealed.

One attorney told CNN that if he has a case that is assigned to Cannon, he asks the opposing party whether they’d consent to allowing the cases to be handled by a magistrate judge, a type of judge that does not have all the power of US district judge but can handle some kinds of proceedings.

Ultimately, nearly every attorney CNN spoke to said that Cannon, despite the criticism, is unwavering in her beliefs about how each case in her courtroom should proceed.

As one attorney put it: “She thinks what she’s doing is correct.”

CNN’s Sara Murray contributed to this report.

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