US District Judge Raymond Dearie in a courtroom sketch from 2013.
Jane Rosenberg—Reuters
Updated: September 20, 2022 9:15 AM EDT | Originally published: September 15, 2022 8:49 PM EDT

On Thursday night, Judge Raymond J. Dearie of the Federal District Court in Brooklyn was appointed the special master to evaluate the over 11,000 documents seized by federal officials during an August search of former President Donald Trump’s Mar-a-Lago residence and determine if any should be kept from criminal investigators due to privilege.

Judge Aileen M. Cannon of the Southern District of Florida, a Trump appointee, approved Dearie for the position after extensive back and forth between Trump’s team and the Justice Department (DOJ) over the scope of the special master’s review. Trump’s team argued that the special master should be able review the roughly 100 documents with classification markings, stating the Trump should have the right to assert executive privilege over any potentially classified materials that might be presidential records. Cannon not only approved that request but also barred the FBI from working with those classified materials until the special master’s work is complete. DOJ appealed her decision on September 8, arguing it could risk “irreparable harm” to national security and intelligence interests. (The appeal is currently pending before the 11th Circuit Court of Appeals.)

In her Sept. 15 ruling appointing Dearie, Cannon reaffirmed that the special master’s search will include classified documents, but directed Dearie to prioritize those documents “as a matter of timing.” She also reaffirmed that the FBI cannot access those classified materials until Dearie’s work is complete.

Dearie will now be tasked with reviewing the thousands of documents taken by the FBI during the unprecedented search of the former President’s home to make recommendations on whether any should be shielded from federal officials due to attorney-client or executive privilege. Trump’s team and DOJ have also sparred over Dearie’s timeline. DOJ has requested the review to end by Oct. 17, while Trump’s team has proposed mid-December, after the midterm elections.

Cannon said that Dearie will need to complete his review of materials by November 30—a timeline more similar to what Trump’s legal counsel had suggested. But she also stated that Dearie will need to propose his own timeline, and both legal teams are set to meet on Sept. 20 to discuss the matter. Cannon also said that Dearie must submit interim reports and recommendations throughout his work, meaning he could make recommendations on key documents before his entire review is complete. Trump’s team has said they oppose having to immediately disclose information about the “declassification” of certain documents, as DOJ has requested.

Read More: The Major Ongoing Investigations Into Donald Trump

Dearie’s chambers declined to comment. President Trump’s legal counsel and DOJ did not respond to TIME’s request for comment.

Here’s what to know about the investigation’s new special master, Judge Dearie.

Who is Raymond Dearie?

Judge Raymond Dearie, 78, was nominated to the U.S. District Court of the Eastern District of New York by then-President Ronald Reagan in 1986. He served in the role for decades and assumed senior status in 2011, meaning he semi-retired but still hears a reduced number of cases.

Those who know Dearie say his years on the bench will have prepared him well for his new role. Steve Gold, a professor of law at Rutgers who clerked for Dearie after law school, explains that federal judges regularly decide disputes about evidence and questions of privilege. Thus Dearie is coming into the role of special master with “lots and lots of experience assessing whether or not a particular document was subject to a privilege, and therefore not available to the other side,” Gold says.

In 2012, Dearie was appointed by Supreme Court Chief Justice John Roberts to serve a seven-year term on the United States Foreign Intelligence Surveillance Court, also known as the FISA court. The 11 body court—which the Foreign Intelligence Surveillance Act established in 1978—reviews requests for warrants by the U.S. government to conduct electronic surveillance, physical searches, or other investigative actions related to foreign intelligence.

That too, former colleagues say, will be valuable experience for Dearie. “The most important part of [the FISA Court] is dealing with the classified material and observing all the precautions that you have to take,” says C. Roger Vinson, a senior U.S. District Court Judge in the Northern District of Florida who served with Dearie on the FISA Court. “Most judges, and anyone else without having experience in that area, are not fully aware of all the special things that you have to observe.”

In 2017, Dearie was among the FISA court judges who approved the FBI and Justice Department’s request to surveil then-Trump campaign foreign policy advisor Carter Page as part of its inquiry into potential Russian interference in the 2016 election. Two of four of those warrants were later declared invalid after a 2019 review by the Inspector General found errors and omissions in the applications to surveil Page.

Some Trump critics have argued his request for a special master was a delay tactic meant to stall the investigation until after the midterms, when Republicans are expected to take control of the House of Representatives. A former colleague of Dearie’s, who requested anonymity to speak candidly, says that while Dearie is a “straight shooter” and not an ideologue, he might “not be the fastest reviewer that they could have picked.” Given the top secret nature of some of the documents he’s tasked with evaluating, Dearie might also be limited to working with aides that have high levels of security clearance, which could slow down the process even further.

This image contained in a court filing by the Department of Justice on Aug. 30, 2022, and redacted by in part by the FBI, shows a photo of documents seized during the Aug. 8 search by the FBI of former President Donald Trump's Mar-a-Lago estate in Florida. (Department of Justice/AP)
This image contained in a court filing by the Department of Justice on Aug. 30, 2022, and redacted by in part by the FBI, shows a photo of documents seized during the Aug. 8 search by the FBI of former President Donald Trump's Mar-a-Lago estate in Florida.
Department of Justice/AP

What’s happening with the classified documents investigation?

Cannon’s appointment of Dearie is the latest step in an ongoing battle between Trump’s team and federal officials over whether a special master should be allowed to review the documents seized from Trump’s Mar-a-Lago residence.

According to an unsealed affidavit, the Justice Department first launched its criminal investigation over the winter after the U.S. National Archives and Records Administration (NARA) told officials it had received 15 boxes of records from Mar-a-Lago—some of which allegedly contained “highly classified documents.” Federal officials then opened a probe into how such materials came to be held at Mar-a-Lago, and during an Aug. 8 search of the private beach club found 11 more sets of classified documents, including some marked top secret, per an unsealed search warrant. (Trump’s legal team did not respond to TIME’s request for comment on the investigation. He has denied all wrongdoing.)

On September 5, Cannon approved Trump’s request to appoint a special master to evaluate the materials seized from Mar-a-Lago and block federal prosecutors from reviewing the materials until the special master had finished their review. The unusually sweeping ruling stated that the special master could evaluate documents that are not only subject to attorney-client privilege, but also could be shielded under executive privilege. Cannon reaffirmed that ruling on Thursday, and said Dearie would be required to “submit interim reports and recommendations as appropriate”—meaning he will likely make some of his recommendations about privilege before his entire review is done.

Still, legal experts tell TIME such a search could delay the Justice Department’s investigation by some weeks if not months. In addition to the classified materials taken from residences, over 10,000 documents with classification markings were also taken, according to unsealed court documents.

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Write to Madeleine Carlisle at madeleine.carlisle@time.com.

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