A federal judge’s indication that she is prepared to appoint a special master to review materials seized by federal agents from Mar-a-Lago could present new complications and unresolved legal questions in the federal government’s high-stakes quest to wrest control of the documents from former president Donald Trump.

U.S. District Judge Aileen M. Cannon’s two-page order issued Saturday appeared unusual in that the judge has not yet heard arguments from the Justice Department, said former federal prosecutors and legal analysts on Sunday.

Cannon, 41, whom Trump appointed to the bench in the Southern District of Florida in 2020, has also given federal officials until Tuesday to provide the court with a more detailed list of items the FBI had removed from Trump’s Florida estate on Aug. 8.

She asked the government to give a status report of its own review of the materials and set a Thursday court hearing in West Palm Beach, Fla. That location is about an hour away from the federal courthouse in Fort Pierce, Fla., where she typically hears cases.

Yet her ruling left unclear how a special master would operate and who might qualify to take on such a role in a case involving classified national security secrets.

“It’s going to have to be somebody with expertise and experience in classified and national defense information. Those people don’t grow on trees,” said Stanley M. Brand, a defense attorney who focuses on representing clients involved in government investigations. “They are either former-somethings in the government or lawyers with a lot of experience in those issues. But that will be a contested issue as well. Once again, we’re on the frontier.”

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Legal experts said the very provisions Cannon asked of the Justice Department ahead of the hearing could render the need for a special master moot by the time the parties appear before the judge. For instance, federal prosecutors could indicate that the government review is nearly complete. And it may provide such a specified accounting of the documents taken that the judge herself could assess whether they belong to the government.

“There’s already been a team reviewing this for almost three weeks now. You don’t collect this stuff to let it sit there and not get started. There’s public pressure on them,” said Mary McCord, who served as acting assistant attorney general for national security during the Obama administration.

The government could report that it is far along in its review, she added, rendering an evaluation by a special master too late.

“Then, you can’t put the milk back in the bottle,” McCord said. “Pointedly, she did not tell them to stop, so they can keep reviewing until she makes a ruling.”

The official inventory said authorities removed more than two dozen boxes of materials during the search, including 11 sets of classified documents, some of which were marked top secret.

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Cannon’s hearing is taking place independently of the proceedings over the authorization of the search warrant, which was signed by U.S. District Judge Bruce E. Reinhart.

On Aug. 22, Trump’s legal team specifically filed its request for the court to appoint a special master in a separate venue than Reinhart’s. His lawyers argued that the appointed person should sift through the material the FBI seized and set aside any that should be shielded from government review because of executive privilege.

Analysts emphasized that such a figure – potentially a retired judge or a lawyer with specific expertise on executive privilege – would not be tasked with determining the legality of the FBI’s search of Mar-a-Lago on Aug. 8 or the merits of the search warrant affidavit, a redacted version of which was released Friday under Reinhart’s orders.

But Brand emphasized that the presence of a special master could complicate the case if that person were to clash with the Justice Department’s own “filter team” – also called a “taint team” – officials not connected to the primary investigation who are tasked with ensuring investigators don’t see information to which they are not entitled and that could taint the case.

“The question for me is: What if the special master takes a different position than the taint team? How does that get resolved?” Brand said. He also questioned how the court battle might proceed given that two judges – Reinhart and Cannon – now have jurisdiction over different aspects of the FBI search.

Such uncertainties, Brand said, could work in Trump’s favor “because to the extent this gets caught up in a litigation muddle, as do so many things that happen around him, it’s to his benefit.”

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The tussle over the documents has been underway for months. Trump aides relinquished some documents to the National Archives and Records Administration in January. But federal authorities, after determining that 184 of those were classified, grew alarmed that the former president was hiding more sensitive materials that could jeopardize national security if they fell into the wrong hands.

Trump and his advisers have defended his actions by stating that he had a standing declassification order for documents brought to his residence, though there is no written record of such a directive and some former Trump aides have disputed the notion.

Cannon, who earned her bachelor’s degree from Duke University and graduated from the University of Michigan law school, served from 2013 to 2020 as an assistant U.S. attorney in the Southern District of Florida. She clerked for Judge Steven M. Colloton, who was appointed by President George W. Bush to the U.S. Court of Appeals for the 8th Circuit.

Former Justice Department official Andrew Weissmann, who served as senior prosecutor in Robert Mueller’s special counsel investigation, said it is not clear that Cannon’s court should maintain jurisdiction in the matter given that the documents in question have been returned to the National Archives in Washington and are no longer in southern Florida.

He said that while special masters have been assigned in civil cases to review questions of attorney-client privilege, it is virtually unheard of for such a figure to be asked to assess executive privilege claims – particularly given that Trump is no longer president and appears to have no standing for such a claim.

“DOJ has a lot of work to do in terms of setting out not just a particular position on a special master but elucidating [Cannon] on issues about attorney-client privilege and executive privilege,” Weissmann said.

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Yet, he said, Trump’s team, in seeking the special master in a 27-page court filing last week, has opened the door for Justice Department prosecutors to address, in public, not only the legal arguments raised by the former president’s arguments, but also the factual inaccuracies.

The Justice Department has generally refrained from commenting on ongoing investigations. But Attorney General Merrick Garland held a news conference after the FBI search to affirm that he had authorized the operation and to defend federal agents in the face of hostile critiques and physical threats from some of Trump’s allies and supporters.

“This isn’t a situation where you have to worry about how much to push the envelope at a news conference,” Weissmann said. “This is a filing and the court directly calling for a response to a filing.”

The fight over the documents has injected another flashpoint into the nation’s political debate, with less than 75 days before the 2022 midterm elections.

New Hampshire Gov. Chris Sununu, who has been a vocal critic of Trump and a rumored 2024 Republican presidential candidate, suggested without evidence that the timing of the Mar-a-Lago search was intended to help Democrats in the midterm elections.

“Former President Trump has been out of office for going on two years now,” Sununu said on CNN’s “State of the Union.” “We think this is a coincidence, just happening a few months before the midterm elections?”

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On Sunday, Rep. Adam Kinzinger, R-Ill., who has publicly defied Trump and much of the GOP for years, said it was hypocritical for members of his party to defend the former president after some of them had “spent years chanting ‘lock her up’ about Hillary Clinton because of some emails.'”

On NBC’s “Meet the Press,” Kinzinger pointed out that lawmakers never would have been allowed to take classified information out of specialized, secure government facilities where they are typically viewed.

“If any of us walked out intentionally with even one document . . . and our organization came to us and said you have to give this document back and we refused to do it for years, we’d be in real trouble,” Kinzinger said.