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Legal Experts Question How Judge Aileen Cannon Landed Trump’s Mar-a-Lago Case

Cannon’s rulings “only make sense if you’re trying to help the former president,” said a Loyola Law School professor.

Former President Donald Trump gestures to the crowd as he arrives at the podium for a campaign rally at Legacy Sports USA on October 9, 2022, in Mesa, Arizona.

Legal experts raised questions about how Trump-appointed U.S. District Judge Aileen Cannon wound up overseeing his dispute over government documents seized from Mar-a-Lago after an investigation by The Daily Beast.

Cannon, who was confirmed days after former President Donald Trump’s election loss, has frequently raised questions from legal experts after repeatedly siding with Trump in the case. She appointed a special master in response to a request from Trump, barred the Justice Department from investigating documents marked classified and later overruled the special master she chose from Trump’s proposed list when he pressed the former president’s legal team to provide evidence of his claims that the documents may have been “planted” or “declassified.” An appeals court later overturned her order blocking the probe, agreeing with the DOJ that she abused her authority. The Supreme Court declined to intervene after an emergency request from Trump and some legal scholars now expect the entire special master order to be struck down after an appeal from the DOJ.

The Daily Beast’s Jose Pagliery notes that some “incredible coincidences” led to Cannon getting the case in the first place.

One of Trump’s lawyers took the rare step of filing the paperwork in person instead of electronically — and did so at a courthouse 44 miles from Mar-a-Lago. He ended up landing Cannon, who is both outside of West Palm Beach, where the FBI raid took place in August, and the district in which the paperwork was filed.

Trump’s lawyers blamed a “technical issue” that prevented them from filing electronically but The Daily Beast’s investigation found that the computer system was “working just fine for dozens of other lawyers making hundreds of filings that day.” Not only did Trump’s lawyers file the case in a different district than the raid but they failed to mark the case as “related” to any other litigation even though a magistrate judge in the correct jurisdiction signed off on the warrant.

“It’s clearly related. I don’t think there’s a plausible argument that it’s not related… it was related to another case in the district—in the same courthouse as a matter of fact,” Carl Tobias, a law professor at the University of Richmond, told the outlet.

“It was basically a home run to get her,” added Jessica Levinson, a professor at Loyola Law School. “They clearly made the correct calculation, because Judge Cannon’s rulings legally don’t make sense. They only make sense if you’re trying to help the former president.”

Levinson told the Daily Beast that Trump’s lawyers were clearly “judge shopping.”

“They did not want the magistrate judge to make this decision,” she said. “There was already a captain of this ship. They just didn’t like the direction this was taking.”

Trump did not take any legal action for two weeks after the raid until finally filing to request a special master to review documents even though the FBI already had a filter team screen them for potentially privileged information. Lindsey Halligan, a 33-year-old Florida insurance lawyer, went in person to file the paperwork in Fort Lauderdale. The move was so “peculiar,” Pagliery wrote, that Trump’s lawyers had to explain why they filed in person. Trump’s legal team said in a filing that a “technical issue” precluded them from filing electronically that day.

The Daily Beast reviewed the timestamps for all 1,370 court filings in the Southern District of Florida that day and interviewed attorneys who used the system that afternoon. Five attorneys said the system was working fine and showed timestamp receipts confirming their electronic filings. The district’s head clerk also confirmed that the system was working fine that day. Attorneys “responded with disbelief” at the Trump team’s claim, Pagliery wrote.

“I don’t know anybody who files in person. I didn’t even know you could do that anymore. It looks like this person was trying to select a particular judge,” one of the lawyers told the outlet, suggesting that a Trump attorney may have had “sway with a court employee.”

“I find it bizarre,” another lawyer said, adding that the only people who file in person are those that sue without the help of a lawyer.

“People don’t do this anymore. It’s extremely odd. I guess you could do this if you wanted to get a particular judge — or avoid getting a particular judge,” another attorney told the outlet.

Legal experts have questioned for weeks how Trump’s team landed the case in front of Cannon.

“If there wasn’t at least the potential to judge shop why on g_d’s green earth would Trump have gone all the way to her district to file and do so physically, when he could have electronically filed at the court in his backyard?” wondered former federal prosecutor Andrew Weissmann, who served on special counsel Bob Mueller’s team.

One of the South Florida lawyers interviewed by the Daily Beast suggested that “somebody pulled a fast one in the clerk’s office to rotate it to a friendly judge.”

But court employees told the outlet that the case was placed into the federal court system’s automatic random judge “assignment wheel.” Cannon, one of nine judges in the district, had a one-in-nine chance of landing the case but The Daily Beast found that Cannon landed nine of the 29 new complaints filed that week. The system “still appears random,” Pagliery wrote, noting that another judge also landed cases from the assignment wheel as well.

A head clerk of federal courts in a different state told Pagliery that lawyers sometimes try to time their filings as if they were players at a casino.

“If you play cards and count the cards, I suppose they could say, ‘I’ll hold this here until I see if other judges got assignments,'” she said. “But it would be very risky because it’s random.”

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