For many judicial nominees, a Senate confirmation hearing is one of life’s most grueling experiences—an hours-long job interview led by lawmakers who are trying to get them to face-plant on national television.
Not for Aileen Cannon. When the federal judge who will oversee former President Donald Trump’s criminal trial testified in 2020, the Senate Judiciary Committee didn’t go easy on her so much as they ignored her.
Cannon, then a 39-year-old prosecutor, appeared on Zoom alongside four other nominees, her face framed by a wall of diplomas on one side and an American flag on the other. Her opening statement lasted all of three minutes and sounded like an Oscar winner’s speech—lots of thank-yous and little else. She didn’t say a word about her legal philosophy or how she would approach the job of a judge. The senators didn’t seem to mind: None of them addressed a question specifically to Cannon for the rest of the hearing. The committee’s chair at the time, Senator Lindsey Graham of South Carolina, skipped the proceeding entirely, as did each of the five most senior Republicans on the panel. The hearing was over after barely an hour. Three months later, while Trump was beginning his effort to overturn his defeat in the presidential election, a bipartisan Senate majority (including a dozen Democrats) voted to confirm Cannon’s nomination as a federal judge in the Southern District of Florida.
For low-profile nominations like Cannon’s, perfunctory hearings aren’t unusual. But the scrutiny she was spared in the Senate is coming her way now. After just two and a half years as a judge, Cannon will soon preside over a trial with no precedent in American history. The defendant is the former president who appointed her, and her rulings during the investigation that led to Trump’s indictment have already prompted many legal experts to fear that she will tilt the trial in his favor.
But some of the Democratic lawyers who have appeared in Cannon’s courtroom don’t share those worries. They say that she is a smarter, more deliberate, and more even-handed judge than the early criticism of her would suggest. “I think the government should be very happy that they have Judge Cannon,” says Richard Klugh, a longtime defense attorney in Miami who has dealt with Cannon both as a judge and when she served as a federal prosecutor there. Klugh, a lifelong Democrat, told me that aside from her “narrow” rulings on Trump’s case last summer, he had heard no complaints about Cannon from either prosecutors or defense attorneys. “She’s very confident, very honest … and very thorough,” he told me. “She’s confident enough to go through things independently.”
[Read: Will Trump get a speedy trial?]
That may be, but she’s extremely inexperienced. Since taking her seat on the bench, Cannon has worked mostly out of a courthouse in Fort Pierce, a two-hour drive from Miami and a town that one local lawyer described to me as “a backwater.” She has presided over just four trials as a judge, none of which covered crimes remotely similar to the willful retention of classified documents that the government has accused Trump of committing. (She is set to oversee a far more complex trial involving alleged Medicare fraud in the coming months.)
Cannon was born in Colombia and is the daughter of Cuban refugees. In her brief statement to the Judiciary Committee, she described how her mother, at the age of 7, “had to flee the repressive Castro regime in search of freedom and security.” Cannon graduated from Duke University, and by the time she earned her law degree from the University of Michigan, she had already joined the conservative Federalist Society. After law school, she embarked on a fairly conventional legal career: She clerked for an appellate judge, spent several years at a large law firm, and then became an assistant U.S. attorney in Miami. In written responses to the Judiciary Committee, Cannon wrote that she considered herself both an “originalist” and a “textualist”—two approaches long identified with conservative judges—but that she would follow all precedents set by the Supreme Court and other appellate rulings.
Two South Florida lawyers told me that they were struck by Cannon’s overt religiosity, which has seeped into her pronouncements in court. She routinely tells defendants “God bless you” after they enter guilty pleas, said Valentin Rodriguez, a lawyer who has appeared before Cannon. “In my entire 30-year career I’ve never had a judge mention God to a client ever,” Rodriguez told me. “She does that as a matter of course.”
Although presidents formally nominate all federal judges, they frequently appoint district-court judges at the recommendation of home-state senators. Cannon told the Judiciary Committee that she was first approached about filling a judicial vacancy by the office of Senator Marco Rubio in 2019, nearly a year before Trump sent her nomination to the Senate. Her appointment came at a moment when Trump and then–Senate Majority Leader Mitch McConnell were trying to reshape the federal courts by filling as many open judgeships as possible with young conservatives in their 30s and 40s. Three previous nominations for judgeships in Florida’s Southern District had gone to men in their 40s. “It made sense that Trump would select a woman with good credentials who also happens to be Hispanic,” a South Florida defense lawyer who knows Cannon told me. (The lawyer requested anonymity to speak candidly about a judge in their jurisdiction.)
At the time of her nomination, Cannon had virtually no public profile outside of the courtroom. On her Senate questionnaire, she said she had never given a speech, served on a panel discussion, or testified before a legislative body. She had never held public office and told the Senate she had never participated in a political campaign, although she and her husband each contributed $100 to Ron DeSantis’s bid for governor in 2018. The only interview Cannon said she had ever given for publication was for a photo feature on TheKnot.com about her wedding. Her relative anonymity has caused headaches for publications that have searched in vain for a public photo of Cannon that hasn’t already been used repeatedly; almost every story features the same Zoom screenshot from her Senate testimony in 2020.
Like most Republican-appointed judges in Florida’s Southern District, Cannon is known as a tough sentencer. But there have been notable exceptions when she has handed down a shorter prison term than she could have, Rodriguez told me. He mentioned a case in which a 21-year-old defendant, Artavis Spivey, who had been incarcerated on and off since he was 11, pleaded guilty to armed carjacking. He and another defendant committed the crime just 18 days after Spivey had been released from prison. Cannon sentenced Spivey to 15 years, but Rodriguez said she could have added many more years to his term. “She could have thrown the book at him, and I think she saw redeeming qualities in the young man,” Rodriguez said. Spivey had grown up in a troubled home without a father, “kind of given up by his parents,” Rodriguez added. “That experience tended to make me appreciate the fact that she could look beyond just the retribution and vengeance of a sentence and look at the person.”
[Andrew Weissmann: A ruling untethered to the law]
Cannon also handed down a lighter-than-expected sentence to a 34-year-old man, Christopher Wilkins, who threw a chair at and threatened to kill a federal prosecutor after receiving a 17.5-year sentence on gun and witness-tampering charges. Cannon added six and a half years to his prison term, which was less than the sentencing guidelines called for. “I’ve heard stuff about tough sentencing. I can’t report that. I can report fair sentencing,” Wilkins’s lawyer, Jeffrey Garland, a Republican, told me.
Yet none of the decisions that Cannon has made in her young judicial career have stirred as much controversy as her rulings in the lawsuit that Trump filed after the FBI searched his Mar-a-Lago estate for unreturned classified documents last summer. Cannon initially appointed a special master to review the documents that federal investigators had collected, and barred the government from accessing some of them. The rulings were a gift to Trump at the time and delayed the FBI’s investigation. But in a sharp rebuke of Cannon, the conservative Eleventh Circuit Court of Appeals overruled her decisions and said she should not have even heard the case.
Some legal experts have cited those rulings and the fact that Trump appointed Cannon as reasons for her to recuse herself or be taken off the case. A few of the Florida defense lawyers I interviewed—who, it should be noted, routinely argue against the government’s position—characterized Cannon’s orders as understandable considering how unprecedented the case was. The defense lawyer who spoke on the condition of anonymity, however, was more critical. “That ruling was totally out of bounds,” the lawyer told me.
One of the most significant decisions Cannon now faces is whether to attempt to hold the trial in advance of the 2024 presidential election. Should Trump win the White House, he could quash the government’s prosecution of him. South Florida lawyers were dubious that Cannon could try the case before the election, noting the complexities surrounding classified documents that frequently slow down prosecutions at the federal level. Howard Srebnick, a Democratic defense lawyer on the Medicare-fraud case before Cannon, also praised her early performance on the bench. But he said that it still took 18 months for the Medicare case to get to trial even though it does not involve government secrets. “The notion that this case could go quickly? That’s absurd,” Klugh told me.
Still, Cannon has already issued her first order—one that could indicate she wants to move swiftly. On Thursday, she instructed lawyers who want to take part in the case to get security clearances by next week. That was the first of many decisions Cannon will make that, in ways big and small, will shape the first-ever federal criminal prosecution of a former president. They will change Cannon’s life, creating a reputation for favoritism or fairness where none existed. A young judge whose photograph had never appeared in a newspaper until last year is set to become a household name. As Rodriguez observed with a slightly nervous laugh: “She’s going to be famous for a long time.”
