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Aileen Cannon: The judge with Trump’s fate in her hands was appointed by him

A Florida district judge assigned to oversee Donald Trump’s classified documents case is attracting criticism given that it was Mr Trump himself who elevated her to the bench.

Aileen Cannon is the federal judge with the US District Court for the Southern District of Florida overseeing the Espionage Act and obstruction of justice case against Mr Trump, who’s charged with the illegal possession of classified documents at his Florida estate after leaving the White House in January 2021 and for impeding efforts by the US government to reclaim them.

According to the indictment, Mr Trump allegedly attempted to hide boxes of classified documents following a grand jury subpoena that ordered their return.

Mr Trump’s aide Walt Nauta and Mar-a-Lago property manager Carlos de Oliveira were also indicted and have also moved to dismiss the charges against them. All men have pleaded not guilty.

If the former president is convicted, Judge Cannon will be tasked with handing down a sentence to the very man who nominated her to that position.

Mr Trump was charged with 37 felony counts related to the mishandling of presidential records, including highly sensitive national defence information, since his departure from the White House in January 2021.

On 1 August 2023, Mr Trump was indicted on four counts in the federal probe led by Mr Smith into Mr Trump’s efforts to overturn the 2020 election.

He has insisted that he is “an innocent man” in angry statements and postings to Truth Social, alleging that he is the victim of “rabid wolves” and the “weaponisation” of the justice system by the “corrupt” Joe Biden administration, even as the indictment revealed photos of boxes of files stacked high in the glitzy ballrooms and bathrooms of his Mar-a-Lago estate in Palm Beach.

Angela Noble, the court’s chief clerk, insisted that “normal procedures were followed” in assigning Judge Cannon to the case.

However, Judge Cannon came under fire for delivering rulings widely considered favourable to Mr Trump throughout the investigation into the classified documents.

After the FBI executed a search warrant in August 2022 to enter Mar-a-Lago and search for classified documents, lawyers for Mr Trump filed a complaint arguing that the search had been illegitimate and unconstitutional.

Judge Cannon subsequently issued an order prohibiting the US government from “further review and use of any of the materials” seized from Mar-a-Lago “for criminal investigative purposes”.

The ruling attracted concern in legal circles as an unprecedented instance of a federal judge assuming the authority to halt a pre-indictment criminal investigation into a suspect. Her ruling was later reversed by the US Court of Appeals for the 11th Circuit.

In 2022, Judge Cannon also sided with Mr Trump’s request that an independent special master be appointed to review the documents before they could be examined by the Justice Department, a decision that was branded “deeply flawed” by Mr Trump’s own former attorney general Bill Barr.

After appointing special master Raymond Dearie, Judge Cannon then overruled a number of his procedural proposals and sided with Mr Trump’s attorneys on several key points.

The appeals court ruled that Judge Cannon had “improperly exercised equitable jurisdiction” and directed her to stand down from the case.

Aileen Cannon is a federal judge with the US District Court for the Southern District of Florida (Southern District of Florida/Wikimedia Commons)
Aileen Cannon is a federal judge with the US District Court for the Southern District of Florida (Southern District of Florida/Wikimedia Commons)

Slate legal analyst Mark Joseph Stern called that decision “one of the most humiliating appellate smackdowns in recent history, a total demolition of literally every action that Cannon had taken from the outset of the case”, also labelling the judge “a venal mediocrity”. He also suggested that the “total lack of principle” and “evident incapacity to experience shame” was likely to prove beneficial to Mr Trump.

On 14 March 2024, Mr Trump joined his attorneys inside a federal courthouse in Florida for a hearing on his attempts to throw out criminal charges stemming from his retention of classified documents stashed at his Mar-a-Lago property.

In two of their motions to dismiss the case, lawyers for the former president argued that his charges under the Espionage Age are unconstitutionally “vague” and that the Presidential Records Act protects him from prosecution.

The motions to dismiss the case add to his growing list of attempts to evade the 91 criminal charges against him in four separate criminal cases in four jurisdictions.

Mr Trump’s attorneys have argued in court filings that Mr Trump had “virtually unreviewable” authority to designate presidential records as personal ones, and that the National Archives and US Department of Justice were unauthorised to retrieve records that Mr Trump was given “unreviewable discretion” to label “personal” before he left the White House.

On 14 March, Judge Cannon suggested those arguments are “premature”.

The former president “never” deemed those records as his personal ones, prosecutor Jay Bratt told the judge.

“Not only is it premature, it never happened,” Mr Bratt said. “He doesn’t say there, ‘I can show you this because it’s personal.’ ... In fact, he’s saying the opposite.”

Prosecutors with the office of special counsel Jack Smith previously argued in court filings that the documents recovered from Mar-a-Lago are “indisputably presidential”, and that the Presidential Records Act (PRA) would still apply to any classified information discovered at his residence. The former president is not charged with violating the PRA.

“Nothing in the PRA leaves it to a president to make unilateral, unreviewable, and perpetually binding decisions to remove presidential records from the White House in a manner that thwarts the operation of the PRA – a statute designed to ensure that presidential records are the property of the United States and that they are preserved for the people,” prosecutors wrote.

Mr Smith has proposed a trial should start on 8 July, while Mr Trump’s attorneys have suggested that a trial should start on 12 August, if at all.

Judge Cannon is of American-Cuban descent and was born in Cali, Colombia, in 1981. She was raised in Miami where she attended the Ransom Everglades School, then Duke University in Durham, North Carolina, and then the University of Michigan Law School.

She clerked for an appellate judge in Iowa for one year after graduating, then worked for the corporate law firm Gibson Dunn in Washington, DC, from 2009 to 2012, and then as a federal prosecutor in the Southern District of Florida, based out of Fort Pierce, from 2013 to 2020.

Following her nomination by Mr Trump, she was confirmed as a federal judge by the US Senate in November 2020 in the dying days of his one-term administration.

Her appointment to the bench came just 12 years after she first qualified to practice law, the minimum experience the American Bar Association requires nominees to have.

Judge Cannon is a registered Republican, has been a member of the conservative Federalist Society since 2005 and reportedly donated $100 to Florida governor Ron DeSantis’s gubernatorial election campaign in 2018.