Judge who sided with Trump in Mar-a-Lago case had few high-profile cases

TALLAHASSEE, Fla. — The federal judge at the center of the dispute over documents taken from former President Donald Trump’s estate is a member of a prominent conservative legal society who has had brushes with other politically-sensitive cases during her short time on the bench.

U.S. District Court Judge Aileen Cannon, who was appointed by Trump in 2020 and confirmed just days after the presidential election, had faced criticism Monday for siding with the former president and his legal team in their request for a special master to review material taken from Mar-A-Lago during the FBI’s search in early August.

The Justice Department is expected to appeal her ruling.

Some legal experts had publicly chided Cannon for her ruling, claiming that she was overly-deferential to Trump’s legal team and was generally untested. Trump’s former attorney general Bill Barr, for example, told Fox News that the ruling “was wrong” and “deeply flawed in a number of ways.”

“She is obviously very bright. Obviously very conservative. And obviously very inexperienced,” said an experienced South Florida attorney who was granted anonymity because he could have cases before Cannon in the future.

Cannon did not respond to a request for comment.

The court had randomly-assigned the Mar-a-Lago case to the 41-year-old Cannon. But in April, Trump had sought to get an unrelated racketeering lawsuit against Hillary Clinton before the Southern District of Florida, where Cannon is a judge. That case went to Clinton-appointee U.S. District Judge Donald Middlebrooks instead, and Trump asked him to recuse himself from the case.

Middlebrooks took notice of Trump’s attempt to get a judge seen as friendly in that case and specifically mentioned Cannon in court documents.

“I note that Plaintiff filed this lawsuit in the Fort Pierce division of this District, where only one federal judge sits: Judge Aileen Cannon, who Plaintiff appointed in 2020,” Middlebrooks wrote. “Despite the odds, this case landed with me instead.”

“And when Plaintiff is in litigation before a judge that he himself appointed, he does not tend to advance these same sorts of bias concerns,” he added.

While the Mar-a-Lago case is by far the most high profile case before Cannon, she also oversaw a criminal case involving Paul Hoeffer, a 60-year-old Palm Beach Gardens man who threatened to behead Speaker Nancy Pelosi and Rep. Alexandria Ocasio-Cortez (D-N.Y.), a progressive who is a regular target for conservative criticism.

Federal prosecutors sought a three-and-half-year sentence for Hoeffer but Cannon gave him 18-months in federal prison.

Cannon’s background fits the profile of many Trump judicial appointees: She is young, which means she will serve on the federal bench potentially for decades, and is a member of the Federalist Society, a conservative legal organization that has huge sway over Republican-appointed judges.

Born in Colombia, Cannon attended Duke University and graduated from the University of Michigan law school. She worked from 2009-2012 in the Washington office of law firm Gibson, Dunn & Crutcher LLP and then as an assistant U.S. attorney in the Southern District of Florida.

She was approached about a position on the federal judiciary in June 2019, when Sen. Marco Rubio’s office sent an email indicating that the Florida Republican wanted to consider her for a vacancy in the district.

Her application was submitted that month to Rubio’s Judicial Advisory Committee for the Southern District of Florida. She later interviewed with that committee and GOP Florida Sen. Rick Scott’s general counsel before traveling to Washington to interview with the White House and Justice Department legal officials.

The Senate confirmed her on Nov. 11, 2020 by a 56-21 vote. A dozen Democrats supported her nomination.

Cannon’s only political contribution was $100 to Florida Republican Gov. Ron DeSantis’ first campaign in 2018, according to campaign finance records.