Comment A federal judge’s indication that she is willing to appoint a special master to review materials seized from Mar-a-Lago by cold-blooded federal agents presents new complications and unresolved legal issues in the federal government’s high-stakes effort to wrest control of documents from former President Donald Trump. U.S. District Judge Aileen M. Cannon’s two-page order issued Saturday appeared unusual because the judge has yet to hear arguments from the Justice Department, former federal prosecutors and legal analysts said Sunday. Cannon, 41, whom Trump appointed to the Southern District of Florida bench in 2020, also gave federal officials until Tuesday to provide the court with a more detailed list of items the FBI had removed from the estate Trump in Florida on August 8. He asked the government to provide a status report on its own review of the materials and set a court hearing for Thursday in West Palm Beach, Florida. This location is about an hour from the federal courthouse in Fort Pierce, Florida, where he usually hears cases. However, her ruling left unclear how a special master would operate and who might be qualified to take on such a role in a case involving classified national security secrets. “It should be someone with expertise and experience in classified and national defense information. These 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 ex-something in government or lawyers with a lot of experience in these matters. But this will also be a moot point. Once again, we are at the border.” Legal experts said the very provisions Cannon requested from the Justice Department ahead of the hearing could make a special leader necessary by the time the parties appear before a judge. For example, federal prosecutors could indicate that the government overhaul is nearly complete. And it can provide such a specific record of the documents taken that the judge herself can assess whether they belong to the government. “There’s already been a team looking at this for almost three weeks. You don’t collect these things to let them sit there and not start. There is public pressure on them,” said Mary McCord, who served as deputy attorney general for homeland security during the Obama administration. The government could report that it has gone too far in its review, he added, making an assessment by a special master too late. “Then you can’t put the milk back in the bottle,” McCord said. “Of course he didn’t tell them to stop so they could keep looking until he made a decision.” The official list said authorities removed more than two dozen boxes of materials during the search, including 11 sets of classified documents, some of which were classified as top secret. Trump’s secret documents and the “myth” of the presidential security clearance Cannon’s hearing is being held independently of the process to approve the search warrant, which was signed by U.S. District Judge Bruce E. Reinhart. On August 22, Trump’s legal team specifically filed its request with the court to appoint a special master in a separate venue from Reinhart’s. His lawyers argued that the appointee should search through the material seized by the FBI and set aside any that should be shielded from government review because of executive privilege. Analysts pointed out that such a figure — possibly a retired judge or a lawyer with special expertise in executive privilege — would not be tasked with determining the legality of the FBI’s Aug. 8 Mar-a-Lago search or the value of the search warrant. affidavit, a redacted version of which was released Friday on Reinhart’s orders. Revised Mar-a-Lago Affidavit Released But Brand stressed that the presence of a special master could complicate the case if that person clashes with the Justice Department’s own “filter team” — also called the “nuisance team.” — officials who are not connected to the primary investigation and are tasked with ensuring that investigators do not see information they are not entitled to and that could taint the case. “The question for me is: What if the special master takes a different position than the beleaguered group? How is this resolved?’ Brad said. He also questioned how the legal battle might play out given that two judges — Reinhart and Cannon — now have jurisdiction over different aspects of the FBI investigation. Such uncertainties, Brandt said, could work to Trump’s advantage “because to the extent that this gets bogged down in a judicial entanglement, like so many things going on around him, it’s to his advantage.” The dispute over the documents has been going on for months. Trump aides turned over some documents to the National Archives and Records Administration in January. But federal authorities, after finding that 184 of them were classified, were concerned that the former president was hiding more sensitive materials that could endanger national security if they fell into the wrong hands. Trump and his advisers have defended his actions by saying he had a standing declassification order for documents moved to his residence, though there is no written record of such an order and some former Trump aides have disputed the idea. 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 for the Southern District of Florida. He clerked for Judge Steven M. Colloton, who was appointed by President George W. Bush to the US Court of Appeals for the 8th Circuit. Former Justice Department official Andrew Weissmann, who served as a senior prosecutor in special counsel Robert S. Mueller III’s investigation, said it was unclear that Cannon’s court should retain jurisdiction over the matter, given that the those documents have been returned to the National Archives in Washington and are no longer in south Florida. He said that while special civil masters have been assigned to review attorney-client privilege issues, it is almost unheard of to ask for such an amount to evaluate executive privilege claims — especially since Trump is no longer president and appears not to have no right to such a claim. “The DOJ has a lot of work to do in terms of not only defining a specific position in a special master, but also clarifying [Cannon] on issues of attorney-client privilege and executive privilege,” Weissmann said. But, he said, Trump’s team, seeking the special master in a 27-page court filing last week, opened the door for Justice Department prosecutors to publicly address not only the former president’s legal arguments, but factual inaccuracies. The Justice Department has generally declined to comment on ongoing investigations. But Attorney General Merrick Garland held a news conference after the FBI investigation to confirm that he had authorized the operation and to defend federal agents in the face of hostile criticism and physical threats from some Trump allies and supporters. “It’s not a situation where you have to worry about how much you’re going to push the envelope in a press conference,” Weissmann said. “This is a deposition, and the court is requesting a direct response to a deposition.” Maryland Gov. Larry Hogan (R) and New Hampshire Gov. Chris Sununu (R) on Aug. 28 reacted to the redactions in the affidavit to search former President Trump’s home. (Video: The Washington Post) The fight over the documents has brought another flashpoint to the nation’s political debate, with less than 75 days to go before the 2022 midterm elections. New Hampshire Gov. Chris Sununu, who has been an outspoken critic of Trump and a rumored 2024 Republican presidential candidate, suggested without evidence that the timing of the Mar-a-Lago investigation was designed to help Democrats in the midterm elections. “Former President Trump has been out of office for two years,” Sununu said on CNN’s “State of the Union.” “Do we think this is a coincidence, just a few months before the midterm elections?” 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 own party to defend the former president after some of them “passed years of shouting ‘Lock her up’ for Hillary Clinton over some emails.” On NBC’s “Meet the Press,” Kinzinger pointed out that lawmakers would never have been allowed to remove classified information from specialized, secure government facilities where it is normally viewed. “If one of us intentionally left with even one document … and our agency came to us and said you have to return that document and we refused to do it for years, we’d be in real trouble,” Kinzinger said.