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Not so long ago, when the FBI raided Donald Trump’s 126-room Palm Beach mansion and found scores of classified documents, the notion that the disgraced former president would return to the Oval Office seemed far-fetched to just about anyone paying attention. Just over three years later, Trump is president, and the U.S. attorney for the Southern District of Florida is investigating the raid for being part of what the president’s allies have branded a “grand conspiracy” against Trump.

From her quiet courthouse in Fort Pierce, Florida, Aileen Cannon is poised to reprise a role that gave the district-court judge an improbably influential say in national politics. Cannon is expected to preside next month over a special federal grand jury called by Jason Reding Quiñones, the U.S. attorney for the Southern District of Florida, that will probe aspects of the FBI’s raid—as well as broader allegations of a plot against Trump by Democratic politicians and other government officials. If the grand jury returns indictments, Cannon would be in a position to oversee trials of people Trump has long targeted for retaliation.

Cannon’s involvement could change the trajectory of the president’s retribution campaign. Trump’s efforts to prosecute perceived enemies have thus far rested on thin indictments brought before skeptical judges; cases against former FBI Director James Comey and New York Attorney General Letitia James, for instance, were quickly tossed out. But Trump allies insist that there is much more to come. Cases like the ones against Comey and James were a mere “appetizer,” Mike Davis, a Trump loyalist who is close with Quiñones, teased on The Charlie Kirk Show this fall. “Just wait for the main course.”

Last year, Cannon made one of the most consequential judicial decisions in decades by throwing out criminal charges against Trump related to his mishandling of classified documents. What had once seemed a rock-solid case that could end in Trump’s conviction on federal felonies had already been dramatically slowed by Cannon’s willingness to entertain even the most fantastical claims made by the former president’s lawyers. With Cannon’s dismissal of the case, the thicket of legal roadblocks impeding Trump’s return to the presidency was suddenly cleared. As liberals despaired, Cannon became a folk hero on the right, a fearless judge who would stand up to a justice system weaponized to force Trump from politics. Conservative luminaries such as former Attorney General Ed Meese, whose brief to the court heavily influenced Cannon’s 93-page decision, praised her courage and promise. Trump called her “the absolute model of what a judge should be.”

On Monday, an attorney for former CIA Director John Brennan—a frequent target of Trump’s ire who was subpoenaed by prosecutors last month—preemptively tried to persuade Cannon’s boss, Southern Florida Chief Judge Cecilia Altonaga, not to permit Cannon to hear any case brought against his client. Kenneth Wainstein’s request, first reported by The New York Times, cited “judge shopping manipulations that appear to be underway” during an already active Miami grand-jury investigation. Wainstein described the inquiry as a “politically motivated and fact-free criminal investigation.” He also questioned why it is necessary to convene an additional grand jury in Fort Pierce—where Cannon happens to be the only judge. The prosecutor, Wainstein wrote, was trying to steer the case to Cannon as part of “the President’s mandate to use the courts to punish his perceived political adversaries.” Neither Quiñones nor Cannon responded to requests for comment.

Trump frequently praises Cannon, which suggests that he’s very much aware of what she’s done for him—and continues to do. That’s why she’s emerged as a widely discussed possible nominee for an appellate seat—or even for the Supreme Court. In the five years since Trump nominated her for the district court, her record has been defined by a refusal to follow judicial norms or bend to public criticism. Her colleagues on the federal bench and others who have studied her record tell me that she is meticulous in the extreme. She insists on doing things her own way—even if that means ignoring precedents with which she finds fault or ruling in a manner that appears to give deference to the man who elevated her. When lawyers for a North Carolina man accused of trying to assassinate Trump argued that Cannon should recuse herself from the case because of perceived bias, she denied the motion and responded in October 2024 with typical precision.

“I have no control over what private citizens, members of the media, or public officials or candidates elect to say about me or my judicial rulings,” she wrote. “Nor am I concerned about the political consequences of my rulings.”

Cannon’s critics—and they are legion—find that hard to believe. To them, she is the very emblem of what happens when the law and politics collide.

The grand jury isn’t the only way in which Cannon is poised to emerge as a significant judicial figure in the new year. She has been under unusual pressure from an appeals-court panel to decide whether she will unseal the second volume of Special Counsel Jack Smith’s investigative findings, a document focused on the classified-documents case that she has kept out of public view for the past year. On Monday, she issued two rulings that made the report less likely to ever become public. She denied a motion from two advocacy groups that asked her to release the report, then issued another ruling giving Trump, the Justice Department, and other parties 60 days to file objections to unsealing the document. Trump’s personal attorney has urged her to keep the report secret, referring to Smith as a “so-called special counsel.”

Just a handful of people have seen the report. Cannon ordered it delivered to her chambers and ruled on the first full day of Trump’s second term that it would remain confidential in order to protect the rights of Trump’s co-defendants. It remained sealed long after the charges against them were dropped, which effectively negated her reasons for keeping it confidential. The report could be embarrassing for Trump. It is believed to describe his efforts to retain classified documents after leaving office, including the role allegedly played by the current FBI director, Kash Patel, who was a White House adviser during Trump’s first term. Keeping the report sealed prevented public scrutiny of Smith’s findings during Patel’s contentious Senate confirmation hearing, which critics said was the whole point. “Judge Cannon very purposely sealed the report so that it would never become public,” the former appeals-court judge J. Michael Luttig told me.

When Trump nominated Cannon in 2020, even close watchers of the judiciary barely knew her name. At 39, she would be among the youngest district-court judges in the country. Yet her nomination checked several boxes valued by Trump’s team: She was Latina, with South Florida roots, connections to the state’s Republican political circles, and a Federalist Society pedigree.

Born in Colombia, Cannon was raised in Miami in a Cuban American family shaped by anti-Castro activism and business success. She grew up hearing stories of her grandparents’ flight from Havana in 1960. Her maternal grandfather rebuilt his advertising firm into an international powerhouse serving Hispanic markets and more. Her mother, Mercedes, became an activist on Cuban issues, while her father, Michael, an Indiana native, worked in the family firm.

Cannon attended an elite private high school, graduated from Duke in 2003, and earned her law degree at the University of Michigan four years later. In Ann Arbor, she joined the campus Federalist Society, which was reshaping conservative legal strategy and building a bench of future prospects. A colleague of Cannon’s who knew her as a summer associate at the top-tier Washington, D.C.–based firm Gibson, Dunn & Crutcher told me that her conservative ideology, particularly on government power and social issues, surfaced even in casual lunch conversations. “She was very solid, very conscientious, and, frankly, at the same time, one of the most ideologically driven people I’ve ever met,” said this person, who, like some others interviewed for this story, spoke on the condition of anonymity to share candid thoughts about Cannon. “She got very animated and agitated about whatever the topic was.”

After graduation, Cannon joined the firm, where Eugene Scalia, son of the late Supreme Court Justice Antonin Scalia, was a senior partner. Cannon became a regular at George Mason University’s Scalia Forum, absorbing the principles of textualism and skepticism of federal power.

By 2013, she had traded corporate law for a prosecutor’s job in the U.S. Attorney’s Office for the Southern District of Florida. She prosecuted 41 defendants and argued four cases before juries before transferring to the appellate division, which her colleagues said was a better fit. When a slot opened in 2019 for a permanent judgeship in Fort Pierce, few ambitious lawyers stepped forward. The courthouse had a docket heavy with routine criminal cases, including more than its share of disturbing child-pornography cases developed by a federal task force in the city. Yet for Cannon, the position offered a break from the chaos of Miami. Senator Marco Rubio’s office encouraged her to apply, according to answers she gave the Senate Judiciary Committee, and by the summer of 2020, she was testifying via video.

Her confirmation hearing drew little notice. Coached by the White House counsel’s office, she fielded questions about judicial restraint with textbook answers and assured members of Congress that she would “fully and faithfully” abide by Supreme Court and Eleventh Circuit precedent. Nothing in her soft-spoken manner suggested the storm she would create.

Cannon’s inexperience—and a temperament that colleagues would later describe as exacting—surfaced almost as soon as she took the bench. She inherited some long-running civil disputes alongside the usual churn of immigration and street-crime cases. Her Fort Pierce docket includes passport fraud, drug trafficking, health-care fraud, and the occasional high-profile lawsuit. But unlike most district judges, who routinely rely on magistrates to lighten the load, Cannon tended to keep control of most matters. Inside the court, that preference produced friction—and a noticeably slower pace. A report card issued twice a year by the federal courts serves as a kind of public shaming of judges who fall behind. As one district judge explained to me, judges go to great lengths to ensure “that there is a zero beside your name” for motions pending for longer than six months. It is one of the few available tools for measuring judges’ performance.

About a year into the job, Cannon reported 40 motions pending for more than six months. Nationwide, other judges had higher backlogs, but not in the Southern District of Florida, where almost all others reported zero. She lagged behind in many later reports, frustrating plaintiffs, defendants, and their lawyers. Two of her law clerks quit, a rarity in the federal system. To explain delays, Cannon usually checked boxes citing unusually difficult cases or “heavy civil and criminal caseload.”

Fellow judges sensed that she was struggling, but they told me that she rarely reached out for advice. “She keeps to herself,” said one judge who occasionally hears cases in Fort Pierce. At one administrative meeting early in her tenure, when judges discussed COVID-era reopening plans, Cannon sharply objected to district-wide masking and vaccination protocols. Judges, she insisted, should govern their own courtrooms. To some veterans who were accustomed to newcomers showing deference to established rules and procedures, her tone landed as imperious. “This was her opening salvo: anti-mask, anti-vaccine,” one judge who was in the meeting told me. “It kind of threw us for a loop.”

Privately, lawyers grumbled about her approach, but they feared crossing her. They describe a judge who is ever-vigilant for breaches of decorum and exacting about grammar. Cannon is known to chastise even seasoned attorneys for failing to meet her detailed procedural preferences. She scolded a lawyer in a yearslong civil-rights lawsuit for being unable to immediately produce a document she wanted to review. She dismissed the case of a plaintiff who used a wheelchair and was representing himself in a lawsuit against a city over handicapped access to a pier, saying that even self-represented litigants must meet her deadlines. Long delays on routine motions were coupled with sudden decisions that blindsided lawyers and sometimes reopened cases to appeal or refiling.

Cannon has shown a willingness to place her own reading of constitutional authority above the guidance of appellate courts, which have admonished her for overreach and for misinterpreting the law in several cases unrelated to Trump. That tendency has set her apart from other district judges, who told me that they would be uncomfortable reinterpreting the limits of executive power. “When the overwhelming authority, including the Supreme Court and other courts, point in one direction, you really don’t have the right to throw all that out,” the retired federal judge Nancy Gertner told me.

Cannon’s sentencing record shows a judge not afraid to lecture defendants about family responsibility, drug abuse, and child exploitation. Although she usually followed recommendations from the U.S. Attorney’s Office, she occasionally broke away. In 2022, as threats of political violence escalated nationwide, she showed leniency to Paul Vernon Hoeffer, a Palm Beach Gardens tow-truck operator, who pleaded guilty after leaving vulgar, threatening voicemails for three female Democratic officials—including then–Speaker of the House Nancy Pelosi. A prosecutor asked Cannon to give Hoeffer 41 months in prison to reflect the severity of threats “to shoot them in the head, or cut their heads off, and that they were going to die.” Cannon gave him 18 months. “Even when political discourse is not especially eloquent or even well-informed, we cherish our constitutional freedoms as Americans,” the judge explained.

Since then, Cannon herself has been a target. An Illinois man pleaded guilty in October to federal charges of making violent threats against her, and a Texas woman received a three-year sentence last year for leaving threatening voicemails.

Judges told me that they privately worry about Cannon’s safety, particularly after she oversaw the trial of Ryan Routh, who was found guilty of attempting to assassinate Trump at a Florida golf course. Cannon allowed Routh to represent himself after reviewing his psychiatric evaluation, then cut off his incoherent opening statement in less than five minutes. The case was the third she has handled involving Trump. It likely won’t be the last.

Cannon first became entwined with Trump’s legal fate three years ago, after the FBI raided Mar-a-Lago and seized 33 boxes, including some stacked high in a gilded bathroom. Outraged, Trump brought a civil suit that landed before the judge. His attorneys asked her to appoint a special master to review more than 100 documents marked as classified. The Justice Department warned that such an intervention would be an “extraordinary judicial intrusion” that would drastically slow the case. Cannon sided with Trump. She appointed retired Judge Raymond Dearie, but the review was halted when an appeals panel—including two Trump appointees—ruled that she had overstepped her authority.

When Jack Smith, as special counsel, indicted Trump in June 2023, Cannon drew the case by random assignment. Her early rulings signaled skepticism toward the prosecution. She questioned the scope of Smith’s authority and invited outside lawyers aligned with the Federalist Society to challenge the constitutionality of his appointment.

Then, in July 2024, on the opening day of the Republican National Convention, Cannon issued her decision dismissing the case entirely. Drawing heavily from briefs submitted by Meese and others, she concluded that Smith’s appointment violated the Constitution’s separation of powers—a novel theory that had never before voided a federal prosecution. “She was careful about understanding the law and applying it,” Meese told me. Richard Swanson, the president of the New York County Lawyers Association, condemned her decision on his blog at the time and has followed Cannon’s rulings since then. “When you take a step back and look at her opinions as a whole, they’re devoid from real-world context and concealing, to some extent, her very much strong red-team agenda,” Swanson told me.

From the convention stage, Trump called Cannon “a highly respected federal judge in Florida” who had found that “the prosecutor and the fake documents case against me were totally unconstitutional.”

Trump continues to praise Cannon, calling her “brilliant” in a March speech at the Justice Department. By then, the Eleventh Circuit had invited her to sit as visiting judge, and she wrote a dense 37-page opinion on birthright citizenship that Swanson calls “a classic example of textualism run amok.” Trump’s words only fueled speculation that she might soon be elevated to join a higher court permanently.

But for now, she remains in Fort Pierce, more consequential to politics than any other district judge in recent memory.

About the AuthorMarilyn W. ThompsonMarilyn W. Thompson is an investigative reporter and editor who has held senior roles at The Washington Post and other publications. She currently works on special projects and reporter coaching for the Charleston Post and Courier.Explore More TopicsDonald Trump, Florida, Jack Smith, politics and government