A portrait of the judge overseeing Trump’s documents case from veterans of her courtroom

CNN

In her seven years as a Justice Department attorney, Cannon participated on the trial teams of just four criminal cases.
She still has not decided foundational questions that will determine whether the Trump case will go to trial.
Defense attorneys CNN spoke to described Cannon as a judge who gives minimal deference to defendants and as a “notoriously” tough sentencer.
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.
And Cannon still has to handle all the other cases playing out in the Fort Pierce division while she navigates the Trump case.
Still, Cannon has asked questions in the Trump case that appear out of left field.
Her orientation toward such legal rabbit holes is not distinct to the Trump case, veterans of her courtroom say.
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.

POSITIVE

After serving for little over a year on the federal bench, Judge Aileen Cannon accepted an offer from a more experienced judge to oversee one of her first criminal trials in her remote south Florida courthouse.

Paul C. Senior Judge said, “It’s very lonely.”. Huck described Fort Pierce to CNN as a tiny fishing and citrus community located on the Southern District of Florida’s periphery, where Cannon serves as the lone federal judge. The town and the courtroom are both rather shady. “.

The criminal trial in March 2022 was finally presided over by Huck, who claimed that he enjoyed volunteering for trials in various Florida courts and that Cannon didn’t need his assistance.

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

The criminal prosecution of former President Donald Trump for his handling of the country’s secrets is currently under Cannon’s purview, two years after it began. She’s also coming under fire across the country for the way she’s handled the case.

Cannon has drawn out the legal proceedings in ways that have baffled legal experts since Trump was first charged a year ago. As a result, a trial that was originally set to start last month has been postponed indefinitely.

As one explanation for her behavior, a number of lawyers who have worked with Cannon and who spoke with CNN for this story suggested that she may have been isolated. The lawyers told CNN that Cannon is deprived of the casual, daily encounters with more experienced judges who sit at the other courthouses and could provide her with advice due to her lone position in the Fort Pierce courthouse, which seldom sees high-profile action.

They added that it is clear that Cannon has never tried a case in his capacity as a judge or attorney. Only four of the seven years Cannon worked as an attorney for the Justice Department’s trial teams involved criminal cases. Huck took charge of one of the few criminal trials that she has presided over while on the bench.

Ten lawyers who have represented Cannon in both criminal and civil cases were interviewed by CNN to provide an overview of her judicial style. Due to the ethical and professional ramifications of discussing a sitting federal judge with the media, the attorneys only spoke to CNN under the condition of maintaining their anonymity.

CNN looked through the public dockets of numerous cases that have passed through Cannon’s courtroom to support their descriptions of her judicial style.

Cannon’s tough questioning style, which demands that nothing be taken at face value, meticulous preparation, and thoughtful rulings were all praised by the attorneys. However, they added that some of her behaviors that have drawn criticism in Trump’s case have affected her approach to the bench in general.

These behaviors include a propensity to allow extraneous legal questions to divert attention from important matters, a strict stance against technical errors in filings, and a difficulty managing the docket that results in the months-long pending status of pretrial disputes that other judges would settle in a matter of weeks.

An attorney from south Florida claimed, “She is not efficient.”. She prioritizes form over substance. “.

“Indecisive” was how one lawyer put her. “.

She simply appears overwhelmed by the process, according to a third lawyer who has represented clients before Cannon. “.

“It is really impossible to take offense at her.”.

Huck was thrown into the thick of two legal hurricanes five months after seeing Cannon in Fort Pierce. First, she was in charge of Trump’s lawsuit contesting the FBI’s August search of his Mar-a-Lago home, during which time they discovered hundreds of classified documents strewn all over the grounds. (After granting Trump’s request for an outside review of the search, Cannon saw her decisions overturned by a conservative appeals court. ).

In June of last year, by a strange turn of events, Cannon was then given the criminal case where Trump faces 40 felony counts of allegedly mishandling classified documents and impeding the government’s search for them.

A CNN analysis of Cannon’s case log revealed that the high-profile national security case is a stark contrast to the majority of the other criminal cases pending in her courtroom, which are primarily more routine prosecutions like gun charges or immigration violations that are frequently settled through guilty pleas.

It was a coin toss as to Cannon’s assignment in the documents case. Despite the fact that Mar-a-Lago is located in the West Palm Beach division, Cannon was selected at random from a larger group of judges in Florida’s southern district.

Her meticulous and laborious approach as a jurist seems particularly vulnerable to being manipulated by a defense team hoping to drag out the proceedings. Furthermore, the convoluted procedure Cannon put in place for redacting public filings has only made the backlog of unsolved problems worse.

She remains undecided on fundamental issues that will decide whether or not the Trump case proceeds to trial. She has a longshot motion to nullify Jack Smith’s appointment as special counsel that she plans to hear later this month among other marginal issues that clog her docket.

Some former colleagues of Cannon attributed her difficulty managing the day-to-day operations of presiding over a trial court to her experience primarily handling appeals for the US Attorney’s office in the area. They said she tended to focus on scholarly, abstract questions rather than the kind of quick decisions trial judges need to make to keep cases moving forward.

Special counsel prosecutors are now experiencing firsthand the wrath of the judge for even seemingly insignificant inconsistencies in their filings, and they have angered Cannon by pressuring her to move faster to resolve the substantive pretrial issues that have caused the case to drag to a standstill. This is all while Cannon slowly works through the backlog of issues on her plate.

One of Cannon’s former colleagues, a fourth lawyer, warned against taking issues with her since it would only serve to hurt your case.

Though not nearly as frequently as the special counsel, Cannon has also taken shots at Trump’s legal team.

According to defense lawyers that CNN spoke with, Cannon is a “notoriously” harsh sentencer who shows little respect for defendants. This is why the Trump team has taken a strong objection to the long leash she has given them during the pretrial phase of the case.

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

Not accepting anything at face value.

Not every lawyer who discussed their experience appearing before Cannon with CNN was unfavorable. She moved their cases along at a reasonable pace, according to some who applauded her for posing research-based questions during hearings.

Lawyers should anticipate Cannon to closely examine any and all claims made in her courtroom, regardless of the party, and to not believe anything that she says. This is one aspect of Cannon’s judicial style that many of her former colleagues agreed upon.

One of the lawyers remarked, “She doesn’t like any litigant to tell her what she should be doing.”.

There was no disagreement between the two sides, but many remembered her rejecting joint motions (like recommendations for sentencing or requests to postpone proceedings).

One of the lawyers said, “You can’t assume that just because there’s agreement between the parties that she will go along,” characterizing the woman as a “very hands on” judge who “wants to be the decision-maker of everything. “.

Criminal defense lawyers that work with Cannon recognize that, in contrast to the common belief that judges always side with the government, she doesn’t automatically acquiesce to the claims of prosecutors despite her background as an attorney with the Justice Department.

According to one of the lawyers, “she doesn’t like the government to come in and play bully, steamroller.”.

Prosecutors can get away with using broad generalizations to support their requests in other courts, but Cannon has repeatedly called Smith’s attorneys’ requests in the Trump case into question for not being specific enough and for expecting prosecutors to provide extreme specificity.

If lawyers are adhering to specific procedural guidelines regarding the submission of materials to her court, she is closely monitoring this. Due to these shortcomings, Cannon last month rejected a request from Smith for a gag order, which was made after Trump made up the accusation that the FBI was planning to kill him during the Mar-a-Lago search.

She took this action because she discovered the prosecutors had violated local laws requiring them to provide the other side with enough time to consult with them regarding the request. In other instances involving Trump, she has denied even standard filings due to insignificant technicalities.

Several court dockets that CNN examined show evidence of the practice, including at least two additional instances in which Cannon denied motions on the grounds that attorneys had not properly conferred with one another.

Cannon’s method of enforcing procedural rules is defined by one of the lawyers who spoke with CNN as follows: “I decide how it’s going to be, and if you don’t want to do it the way I tell you, that’s a problem.”. “.

There are other federal judges who do not allow even minor procedural errors to go unpunished, as noted by the attorneys. However, some claimed that the judge’s obsession with details caused cases to become mired in detail.

The lengthy process of arguing over what would be redacted in the public filings in the Trump case meant that several significant pretrial motions were not even docketed for almost three months. Only a few of those requests—seven of which aim to have certain portions of the case thrown out—have oral arguments scheduled as of yet.

As Cannon manages the Trump case, she also has to deal with every other case that is pending in the Fort Pierce division.

grabbing onto unrelated ideas.

Several of the pretrial issues in the case involving the classified documents, which some legal experts claim are irrelevant or tangential, have been brought up by Cannon on multiple occasions when the attorneys representing Trump have been called in for hearings.

The Florida lawyers CNN spoke with agreed that it makes sense for a novice judge to hold hearings on cases that more seasoned judges might feel more at ease handling, and they did not criticize her for being particularly thorough in the extraordinarily consequential Trump case.

In the Trump case, Cannon has nevertheless raised some seemingly unexpected questions.

During March, for instance, Cannon gave lawyers instructions to write jury instructions that take into account the Presidential Records Act, a federal statute that mandates that a departing president return official government records to the National Archives at the conclusion of their term.

The request was chastised by outside experts and the special counsel’s office for being both procedurally premature and legally unsound due to its consideration of a fringe theory put forth by the Trump team. Cannon angrily justified the exercise as a “genuine attempt” to comprehend the viewpoints of the parties.

Experts from her courtroom say that her approach to these kinds of legal detours is not unique to the Trump case.

“She seems to latch onto ideas that, whether or not they are relevant to the case at hand, catch her attention for some reason, or she decides that they are important for reasons that the other lawyers in the room fail to see,” one of the attorneys remarked.

Compared to the other judges confirmed to the South Florida federal court under the Biden, Trump, and Obama administrations—all of whom had either tried ten or more cases as attorneys prior to their nomination to the federal bench, or had substantial trial experience as state court judges—her lack of trial experience prior to her appointment stands out. Certain lawyers express their apprehension that her rulings have increased the possibility of their cases being challenged in court.

According to an attorney who spoke with CNN, if he has a case assigned to Cannon, he asks the other party if they would agree to have the cases handled by a magistrate judge, a judge with some of the authority of a US district judge but not as much.

In the end, almost every lawyer CNN spoke with stated that Cannon is steadfast in her opinions about how every case in her courtroom ought to go forward, in spite of the criticism.

“She thinks what she’s doing is correct,” one lawyer stated.

CNN’s Sara Murray contributed to this report. “.

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