Federal judge now at center of Trump's Mar-a-Lago search a 'stickler for procedure'
A federal judge who is at the center of the latest legal tempest that surrounds last month’s search of former president Donald Trump’s Mar-a-Lago estate in Palm Beach is known as a stickler for procedure who is tough on lawyers and regularly ignores recommendations from prosecutors.
Since she was appointed by Trump in May 2020, U.S. District Judge Aileen Cannon has become known as what one criminal defense attorney jokingly called “a loose cannon.”
While most of the half-dozen attorneys interviewed by The Palm Beach Post did not want their names to be used for fear it could hurt clients with pending cases before her, all agreed she rules her Fort Pierce courtroom with an unconventional, but decidedly iron, fist.
“The little bit I’ve seen of her it’s clear that she controls her courtroom,” said Donnie Murrell, a West Palm Beach criminal defense attorney who agreed to speak on the record. “She lets attorneys know what she expects of them and expects attorneys to respond in kind.”
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Working largely in obscurity first as a federal prosecutor and now as a judge in the small northernmost outpost of the sprawling South Florida district, Cannon on Thursday will be catapulted into the national limelight.
During a hearing in West Palm Beach that is expected to attract news reporters from across the nation, Cannon will decide whether to grant Trump’s request to appoint a special master to review roughly 30 boxes of material that FBI agents carried out of the 58-bedroom estate on Aug. 8.
In court filings this week, prosecutors blasted the request, saying it would cause a needless delay in an ongoing espionage investigation. A special team has already screened the materials that included more than 100 classified documents, including some that contain highly sensitive top secret information, they said.
“Appointment of a special master is unnecessary and would significantly harm important governmental interests, including national security interests,” wrote South Florida U.S. Attorney Juan Antonio Gonzalez and Jay Bratt, chief of counterintelligence and export control for the U.S. Department of Justice.
Colombian-born judge dabbled in journalism before law school
Attorneys who have appeared before Cannon said the 41-year-old Colombian-born jurist who dabbled in journalism before going to law school at the University of Michigan is unquestionably smart and meticulously prepared.
Recognizing she was a Trump appointee, West Palm Beach attorney Scott Skier said he was worried when he went before Cannon to request leniency for a client who pleaded guilty to a charge of entering the country illegally for a second time after being deported.
But, he said, his fears were largely unfounded.
“She reviewed my pleadings. She challenged my arguments,” Skier said. “She wasn’t like a puppet federal judge. I found her to be thoughtful.”
While she didn’t give his client the break he sought, she didn’t exceed recommended sentencing guidelines to unfairly punish him because he was part of a group that Trump repeatedly demonized.
“Clearly, she’s going to be tough on defendants,” Skier said. “But that doesn’t disqualify you from being a good federal judge.”
Other attorneys said Cannon regularly ignores federal sentencing guidelines, throwing uncertainty into a process that is designed to be reliable and equitable. Prosecutors warn that their recommendations, typically accepted by federal judges, could be rejected, defense attorneys said.
Cannon issues elaborate orders of how legal briefs should be filed and rejects those that aren’t to her liking, attorneys said. “She’s bizarrely strict with form,” one attorney said. “She’ll bounce filings for crazy, ridiculous reasons. It’s form over substance.”
Cannon’s ascent to the judiciary was quick. When she was recommended by Florida Republican U.S. Sens. Marco Rubio and Rick Scott she had been a lawyer for just 12 years. That is the threshold the American Bar Association uses to give nominees a “qualified” rating.
In her application to the federal bench, she said that after graduation from law school in 2007 she worked for a year as a clerk for Eighth District U.S. Court of Appeals Judge Steven Colloton in Iowa. Colloton was among 25 judges Trump said he would consider for openings on the U.S. Supreme Court.
Cannon left the clerkship to join a Washington-based law firm that specializes in defending people and companies accused of regulatory or security violations. After three years, she joined the U.S. Attorney’s Office in Fort Pierce.
Initially hired in the major crimes division, she later moved to its appellate section. Before that move, she said she participated in four jury trials and successfully prosecuted another roughly 35 people on various charges, including fraud and immigration, firearms and drug offenses, she wrote.
Like many of Trump’s judicial picks, Cannon is a member of the Federalist Society. She joined in 2005 when she was in law school. The national conservative group was formed in 1982 with the goal of “checking federal power, protecting individual liberty and interpreting the Constitution according to its original meaning."
The case that pits the U.S. Justice Department against the former president is undoubtedly the most legally complex and momentous of Cannon’s brief judicial career that was further constrained because her appointment came at the height of the COVID-19 pandemic when court systems were largely shut down.
In addition to dealing with the request to appoint a special master to review the seized documents, the news media will ask her to release a detailed description of what was taken from Mar-a-Lago — a request Trump has made. Given the “extraordinary circumstances,” prosecutors said they don’t object to the request.
Cannon was briefly a member of the media. In the summer of 2002, when she was an undergraduate at Duke University, Cannon wrote feature stories for El Nuevo Herald, the Miami Herald’s Spanish language newspaper. Topics included flamenco dancing, Latina artists, festivals and the benefits of yoga for pregnant women.
Should a special master be allowed? Local attorneys are mixed
Defense attorneys were split on what decision should be made. After receiving Trump's request to appoint a special master, Cannon said she was inclined to approve it. But, that was before the government explained what it believes is at stake.
Murrell, the West Palm Beach criminal defense attorney, said the defense bar has long criticized the government’s claims that its so-called “filter teams” or “taint teams” work independently.
“Isn’t that like the fox guarding the hen house?” he said of claims made by many defense attorneys, not just those representing Trump.
However, at the same time, the documents are highly classified. Prosecutors said that some of the FBI counterintelligence agents and DOJ attorneys had to get additional clearances before they could review some of the documents. A special master would also need that high-level clearance, an investigation that could be protracted.
Further, Murrell said, the prosecutors have said that the documents have already been reviewed. Those that are off-limits because they involve attorney-client privilege have been removed, prosecutors said.
“The Justice Department has already been through them,” Murrell said. “It seems Trump’s attorneys were fairly tardy in making their request.”
But, attorney Michael Salnick said, the extra review would help quell concerns that the search was nothing but a fishing expedition, as part of ongoing efforts by Democrats to vilify Trump and derail any plans he has to retake the Oval Office. He blames the left, particularly the media for creating "a circus" around the court proceedings.
Trump's request simply makes sense, he said. "If it's done right, it's kind of like a double check and I don't think there's anything wrong with that," Salnick said.
Jane Musgrave covers federal and civil courts and occasionally ventures into criminal trials in state court. Contact her at jmusgrave@pbpost.com.