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Trump’s Lawyers Are Already Bickering With the Special Master, Whom They Picked

Special Master Raymond Dearie asked Trump’s lawyers to explain the details over documents he’s claimed are declassified.

Former President Donald Trump looks on from the driving range at Trump National Golf Club Bedminster on July 30, 2022, in Bedminster, New Jersey.

Lawyers for former President Donald Trump are frustrated with the special master appointed in the investigation relating to classified government docs that were recently found and removed from Mar-a-Lago.

Last week, Raymond Dearie, a former chief judge for the federal court in the Eastern District of New York, was appointed special master by Florida federal Judge Aileen Cannon. Trump had sought a special master to determine whether any privilege violations had occurred when the FBI retrieved thousands of government documents from his Palm Beach, Florida, residence.

Dearie was one of two nominees picked by Trump’s team of lawyers to fill the position. While the Department of Justice (DOJ) had disagreed with the need for a special master, DOJ lawyers said they were agreeable to Dearie being chosen, prompting Cannon to appoint him to the position.

Now, it turns out, it appears Trump’s lawyers may be having regrets about their special master pick.

In a court filing on Monday night, Trump’s lawyers responded to a “draft management plan” written by Dearie. The plan asked Trump’s lawyers to provide details about documents that the former president has publicly claimed were declassified. Trump had previously claimed that the documents were his property.

In their filing, lawyers for the ex-president refused to respond to the request, explaining it could hinder a future defense for Trump should he later be indicted over the mishandling of the government documents.

“[T]he Special Master process will have forced the Plaintiff to fully and specifically disclose a defense to the merits of any subsequent indictment without such a requirement being evident in the District Court’s order,” Trump’s lawyers said in their brief.

Trump’s counsel alleged that there’s a “time and place” for disclosing “specific information regarding declassification to the Court and to the Government.”

The former president’s legal team also took issue with Dearie’s proposed timeline for completing the assessment of the documents and their privilege claims. Though he has until the end of November to complete it, Dearie’s plan suggests he could complete the process by October 7.

“We respectfully suggest that all of the deadlines can be extended to allow for a more realistic and complete assessment of the areas of disagreement,” the lawyers said.

Notably, the delay Trump’s lawyers want would push Dearie’s work past the midterm elections. The DOJ doesn’t appear to oppose most of the special master’s action plan.

On August 22, Trump demanded a special master look into claims of privilege he was making regarding 11,000 government documents — including more than 100 that were marked classified — that were taken from Mar-a-Lago last month. After Cannon appointed Dearie to the role, CNN legal analyst Paul Callan said that Trump’s lawyers decision was peculiar. Callan predicted Dearie would handle the case in a way not to Trump’s liking.

“[Dearie] is a FISA judge, [and he] has been involved in some rulings that were adverse to Trump in prior investigations,” Callan noted.

Dearie “knows a lot about executive privilege, he knows about national security issues, he’s familiar with the documents, he has the clearance required or can certainly have it updated quickly, and he has a reputation as a solid judge,” Cynthia Alksne, a former federal prosecutor, said on MSNBC on Friday.

After Trump’s lawyers filed their Monday night legal brief, Renato Mariotti, another former federal prosecutor, said it was clear that Trump regrets picking Dearie.

“I’ve seen enough: Trump’s team miscalculated by asking for Judge Dearie to serve as Special Master,” Mariotti said on Twitter.

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