An Untested Judge in the Trump Documents Case

Judge Aileen M. Cannon, a previously obscure Trump judicial appointee, has been viewed with incredulity by much of the legal establishment ever since she issued a ruling temporarily halting the federal investigation into the former president’s handling of classified documents. After a conservative appeals court slapped her down, Democrats said she was either incompetent or some kind of black-robed Trojan horse for the MAGA movement.

On Friday morning, that view began to change.

In a ruling that set a start date for the documents trial on May 20, 2024 — splitting the difference between prosecutors who wanted the trial to begin in December and a Trump team that pushed for a date after next year’s election — Judge Cannon showed, for now, that she is the jurist her defenders have described: a level-headed and mostly ordinary conservative judge not beholden to the man who appointed her.

“The notion that she’s inexperienced is misplaced and ignores her exceptional résumé before taking the bench,” said Jesse Panuccio, a prominent Florida defense lawyer who served in the Trump administration as acting associate attorney general. “It also penalizes her for being a mild-mannered woman. They wouldn’t be saying this if she was a big-personality male.”

There were hints of that jurist earlier in the week when Judge Cannon conducted a brisk pretrial conference at the federal courthouse in Fort Pierce, Fla., to hear arguments about the timing of the trial. Over two hours, she left little doubt as to whose courtroom it was.

“That’s not my question,” she snapped at one of the lawyers for former President Donald J. Trump for offering a rambling rejoinder to one of her queries. Attentive to the point of reminding each side what the other had said earlier, she frequently pushed for more specifics, asking the Trump team at one point, “Can you put more meat on the bones to that?” At another moment she asked the Trump side to “articulate precisely” the “novel questions” they had said should delay the trial.

Judge Cannon appeared sympathetic to the Trump team’s argument that the classified documents presented complex issues that might require more preparation time, but she also nodded when prosecutors argued that Mr. Trump should not be treated differently from any other citizen.

Most of all, Judge Cannon made clear her preference that the trial be put on the docket sooner rather than later. “I don’t want to have delays,” she warned the defense team, then concluded by promising to issue a ruling “promptly.” Less than 72 hours later, she set the May trial date, which falls two months before the Republican National Convention, when Mr. Trump, the current Republican front-runner, could be at the start of a general election campaign.

The scrutiny is hardly over for Judge Cannon’s conduct overseeing the most consequential trial in at least a generation, one in which prosecutors have charged a former president with federal crimes related to the illegal retention of classified documents. But at this point some veterans of the federal bar say that the Democratic hand-wringing over Judge Cannon’s initial ruling, soundly rejected by the U.S. Court of Appeals for the 11th Circuit, in Atlanta, will prove to be unwarranted.

“Especially given that Judge Cannon is relatively new to the federal bench, I fully expect that she was chastened by the 11th Circuit’s reversal,” said J. Michael Luttig, a former judge for the U.S. Court of Appeals for the Fourth Circuit.

Several in the Florida legal community who know Judge Cannon have taken exception to assertions that she is a dunce, a Trump stealth warrior or both.

One of them, a veteran federal prosecutor, suggested that Judge Cannon was merely being “hyper-cautious” in appointing a special master to review the documents at issue in the Trump case. Another, a longtime defense attorney in the state, insisted that Judge Cannon would have issued the same ruling had the former president been a Democrat.

A close inspection of Judge Cannon’s trajectory, including interviews with friends, former classmates and colleagues, reveals a diligent conservative achiever who seemed destined for success but perhaps ill-equipped for the notoriety that has now overtaken her.

“There are some judges who might see the Trump case as a way to make their name,” Mr. Panuccio said. “Knowing her, I can’t imagine her saying, ‘I hope the assignment wheel turns it to me.’”

High school in Coconut Grove

In an advertisement that ran in her high school senior class yearbook, the parents of the future judge proudly declared, “Look out world. Here comes Aileen!” For most of her professional life, however, Aileen Mercedes Cannon seemed laboratory-designed to attract as little attention as possible.

At the time of her nomination in May 2020, Ms. Cannon, then 39, was one of hundreds of assistant U.S. attorneys working in Florida’s Southern District. She had published no legal essays, given no speeches, worked for no elected officials. Like many federal prosecutors working cases involving drug traffickers and violent criminals, Ms. Cannon avoided social media.

A registered Republican who had contributed $100 to the 2018 campaign of Gov. Ron DeSantis, she had otherwise engaged in no known political activity. Apart from a few fanciful essays she had written during her college years for El Nuevo Herald, the independent Spanish-language sister paper to The Miami Herald, Ms. Cannon’s interactions with the media had consisted of a single interview she and her husband had given to a wedding website in 2009, when they disclosed that his proposal to her was briefly interrupted by the sighting of a turtle.

During her opening statement to the Senate Judiciary Committee in an otherwise perfunctory nomination hearing on July 29, 2020, Ms. Cannon volunteered information about a motivating force in her life. She spoke of her mother, Mercedes Cubas, “who at the age of 7 had to flee the oppressive Castro regime in search of freedom and security,” and also her mother’s parents, who “were forced to leave everything they had worked so hard to build in Cuba to build a life here in the United States.”

Those who know Judge Cannon say that her Cuban-exile heritage undergirds her patriotism and conservative values. Still, that origin tale falls somewhat short of hardscrabble.

Judge Cannon’s mother arrived in Miami from Havana in 1960, according to Florida records, on a Pan American flight and listed as her new place of residence the stately Miami Colonial Hotel. Her father, Judge Cannon’s grandfather, Jose Manuel Cubas, had co-owned with his brother a successful Havana-based advertising firm, Siboney, that they soon re-established in Puerto Rico, with offices to follow throughout Latin America and the U.S. Its client list would include Colgate-Palmolive, Kellogg and Red Lobster.

To the extent that there was tragedy in Ms. Cannon’s life, it occurred on the side of her father, Michael Cannon, an Indiana-bred advertising executive who worked at Siboney and married Ms. Cubas in 1978, three years before Ms. Cannon was born in Colombia, where her father was working for Siboney at the time. In 1984, Mr. Cannon’s father and Judge Cannon’s grandfather, William P. Cannon, a U.S. Navy veteran, was shot and killed in his home by his son-in-law. (Aileen Cannon was 3 at the time.)

Ms. Cannon’s parents divorced in 1997, her junior year at Ransom Everglades Upper School, a private college preparatory institution located in the lush Miami suburb of Coconut Grove. On a campus that did not disqualify high achievers from cool-kid status, classmates remember Ms. Cannon as being part of the in crowd: studious and prone to taking a seat at the front of the classroom in the manner of a teacher’s pet, while also regularly cavorting with the flashiest girls on campus. Still, she was not among the two voted by her graduating class of about 130 as “most likely to succeed,” and three classmates told The New York Times in recent weeks they never expected her to be in national headlines.

In 1999, Ms. Cannon enrolled at Duke University, where she pledged the Delta Delta Delta sorority while maintaining the reputation of a workhorse. From there, she entered the University of Michigan Law School, graduated magna cum laude in 2007, and had a clerkship a year later in Des Moines with Steven M. Colloton, a conservative judge on the U.S. Court of Appeals for the Eighth Circuit. In 2009, she moved to Washington and spent three years as a litigation associate in the demanding law firm of Gibson, Dunn & Crutcher.

At Ransom Everglades, Ms. Cannon extolled a Reagan-esque faith in the free market, just as she did at Duke, according to classmates at both schools. She joined the conservative Federalist Society at Michigan Law, a decision that reflected a desire to find community on an otherwise liberal campus rather than a careerist calculation, two people who knew her said. She secured the clerkship with Judge Colloton based on her productivity rather than her conservative bona fides, according to Ryan Koopmans, a lawyer who clerked for the judge the year before Judge Cannon.

“He wants clerks like her who would do the work and do it well,” Mr. Koopmans said. “I met with her the day she interviewed with Judge Colloton, and I don’t recall even knowing her politics.”

By the time she returned to Florida in 2013 to work as an assistant U.S. attorney in the state’s Southern District, Ms. Cannon was widely viewed as a solid if unspectacular litigant. First in the major crimes division and later in the appellate division, colleagues remember her as “bookish,” “thorough” and “courteous,” capable of handling complicated cases while not attempting to hog credit for the outcome. Ms. Cannon was now married to a restaurant executive, Josh Lorence, a mother to two young children and not regarded as an ambitious climber in South Florida’s legal circles.

Still, after a seat became vacant on the U.S. District Court for Florida’s Southern District in the summer of 2017, word eventually reached both the office of Senator Marco Rubio, Republican of Florida, and the Trump White House Counsel’s Office — exactly how, no one seems to remember — that a certain prospective replacement checked a number of boxes. The lawyer in question was female. She was young. She was of Cuban heritage. She was conservative. She had a top-tier law school pedigree. She possessed unimpeachable legal credentials and no skeletons in her closet, nor even the remotest paper trail.

There was an additional benefit to Ms. Cannon, according to two people familiar with the judicial nominations process during the Trump era: She and her husband lived in Vero Beach, a short commute to the mausoleum-like courthouse in Fort Pierce that had recently been vacated by Judge Robin L. Rosenberg. It was a somewhat scruffy outpost that other potential nominees were reluctant to relocate to.

In June 2019, Mr. Rubio’s staff contacted Ms. Cannon and urged her to apply for the vacant seat. She did so that month. On Nov. 12, 2020, five days after The Associated Press declared that Mr. Trump had been defeated by Joseph R. Biden Jr., Judge Cannon was confirmed by a vote of 56 to 21. Fittingly, her ascent received almost no notice.

Her history on the bench

Judge Cannon’s ruling in September — when she decreed that a special master would decide which, if any, of the government documents seized at Mr. Trump’s private club could be perused by Justice Department officials — has prompted the parsing of her history on the bench for portents.

But as is the case with most jurists, her rulings offer a mixed narrative. Last year, she sentenced Paul Hoeffer, who had pleaded guilty after placing threatening phone calls to prominent Democrats to 18 months in prison, less than half of what federal prosecutors had recommended. Mr. Hoeffer’s calls had included one to former Speaker Nancy Pelosi, whom he vowed to behead.

That same year, Judge Cannon also awarded a lighter sentence than requested by prosecutors to a three-time felon who had thrown a chair at a federal officer during a trial while threatening to kill him. In April, Judge Cannon denied a motion by a former Florida Republican congressman, David Rivera, to vacate a $456,000 fine he was ordered to pay for violating Federal Election Commission guidelines. Mr. Rivera has appealed her decision to the 11th Circuit.

In interviews, three Florida lawyers who have tried cases before Judge Cannon described her as even-handed, soft-spoken but firm, and well prepared. A different question, they acknowledged, is whether she is up to officiating a first-of-its-kind criminal case that could very well make the O.J. Simpson murder trial resemble a bird-watching convention.

One of the Florida lawyers, Jeffrey Garland, who is based in Fort Pierce, noted that the area’s conservative jury pool gives Mr. Trump a decided advantage but that Judge Cannon would still be accorded the leeway to steer them. “In federal court, the judge is going to give them the laws to follow,” Mr. Garland said. “And what she gives them is very likely going to strongly influence the outcome of the jury’s fact-finding.”

To those who have long known her, such as Alejandro Miyar, a Miami-based lawyer and former Obama administration official who graduated with Judge Cannon from Ransom Everglades, being up to the task does not mean that she is likely to relish her moment as the center of attention.

“I can’t think of any world in which she would want to make this case about her,” he said.

Kitty Bennett contributed research.