Who Is Raymond Dearie? Mar-a-Lago Special Master

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 at 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 Thursday 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. She also said that Dearie must propose his timeline. However, he could alter the November deadline depending on what he suggests. Cannon stated that Dearie should submit interim reports, recommendations and other information throughout the course of his review. This means that he can make key recommendations before his complete review is completed.

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

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

Raymond Dearie: Who are you?

In 1986, President Ronald Reagan nominated Judge Raymond Dearie to the U.S. District Court for the Eastern District. After serving in this role for many decades, he was elevated to senior status in 2011. He is semi-retired and still receives cases.

People who have known Dearie know that his experience on the bench has prepared him for this new position. Steve Gold, Rutgers’ professor of Law, explained that federal judges are regularly called upon to resolve disputes over evidence or questions about 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.

Supreme Court Chief Judge John Roberts appointed Dearie in 2012 to serve a seven year term on the United States Foreign Intelligence Surveillance Court. This court is also known by 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.

Former colleagues agree that this will also be a valuable learning 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. After a review in 2019 by Inspector General, two of the four warrants were declared invalid.

Trump opponents have suggested that Trump requested a special master to hold off the investigation. He did this to prevent the probe from being completed until the next midterms when Republicans are likely to control 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)

The following image is from a court file filed by Department of Justice on August 30, 2022. It shows an image of documents that were seized by FBI during their Aug. 8 search of Donald Trump’s Mar-a-Lago Florida estate.

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. Trump has denied any 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. This unusually expansive ruling provided that the special Master could assess documents not only protected by attorney-client privileges, but also 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. Unsealed court documents reveal that more than 10,000 documents with markings on them were also taken.

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Send an email to Madeleine Carlisle at

Read More From Time

Send an email to Madeleine Carlisle at


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