Dearie — the only candidate for the role that both the Justice Department and former President Donald Trump’s legal team agreed on — was tapped for the position by US District Judge Aileen Cannon on Thursday.
Keep scrolling for a timeline of the investigation into Trump’s Mar-a-Lago documents
Here’s what you need to know about Dearie and the role he’ll play in the investigation.
Who is Raymond Dearie?
Dearie, a Reagan nominee, has served as a federal judge in New York since 1986. He retired in 2011 and is now a senior judge in the district.
He also served a seven-year term on the US Foreign Intelligence Surveillance Court, or FISA court.
Dearie was one of the judges who approved an FBI and DOJ request to surveil Carter Page, a Trump campaign foreign policy adviser, as part of the federal inquiry into whether Russia interfered in the 2016 election.
The process that federal investigators used to secure the FISA warrants was riddled with errors and overall sloppiness, according to a DOJ inspector general report. Two of the four surveillance warrants granted by the secretive FISA court regarding Page have since been declared invalid — including one approved by Dearie in June 2017 — because of omissions and mistakes in the FBI’s submissions to the court.
The Trump team’s nomination of Dearie is notable because Trump has repeatedly criticized the FISA surveillance and has claimed — without evidence — that it was part of a “deep state” conspiracy to undermine his campaign.
Dearie will specifically oversee the Justice Department’s review of the evidence gathered from Trump’s Florida residence and resort and filter out privileged material that may have been seized in the search.
Trump and the Justice Department, however, have disagreed on other key aspects of the special master review, including how long it should take, who is responsible for paying for it, and what type of documents are subject to review.
How long will Dearie have?
Cannon is giving Dearie a deadline of November 30 to finish his review of potentially privileged documents.
The DOJ had sought for the process to end in October, while Trump’s team said they preferred 90 days.
Cannon’s schedule means the review will end after the midterm congressional elections, essentially guaranteeing the Mar-a-Lago investigation will move slowly for the next two months, unless a higher court steps in.
She directed Dearie to prioritize sorting through potentially privileged classified records.
Why did Trump want a special master?
Trump’s legal team has broadly argued that a special master is necessary to ensure the Justice Department returns any of his private documents seized during the search of Mar-a-Lago.
The former President’s attorneys said his constitutional rights were violated, and that there may have been privileged materials seized.
But in court filings, Trump has not elaborated on what exactly he hoped a special master would filter out, besides general allusions to “privileged and potentially privileged materials.”
Beyond Dearie, Trump’s legal team had suggested lawyer Paul Huck Jr., a former partner at the Jones Day law firm, as special master — a proposal the DOJ disagreed with, noting he “does not appear to have similar experience” to Dearie and two retired federal judges the department put forth.
The DOJ’s position
Before Dearie’s selection, the Justice Department had put forward retired federal judges Barbara Jones and Thomas Griffith to potentially serve in the role.
“Each have substantial judicial experience, during which they have presided over federal criminal and civil cases, including federal cases involving national security and privilege concerns,” prosecutors wrote of Jones, Griffith and Dearie.
Dearie, however, was the only candidate both camps have agreed could serve as special master.
The Justice Department has argued that a special master shouldn’t touch any documents with classification markings and that the review shouldn’t include any executive privilege considerations.
The agency had challenged the need for a special master in court before Cannon sided with Trump. In legal filings, the DOJ said it had identified “a limited set of materials” from its search of documents taken from Mar-a-Lago that potentially contained material covered by attorney-client privilege and that it was already in the process of addressing privilege disputes.
Then-President Donald Trump left the White House for Florida ahead of President-elect Joe Biden's inauguration. According to the General Services Administration, members of Trump's transition team were responsible for packing items into boxes, putting boxes on pallets and shrink-wrapping those pallets so they could be transported.
Prior to shipping, GSA said it "required the outgoing transition team to certify in writing that the items being shipped were required to wind down the Office of the Former President and would be utilized as the Office transitioned to its new location in Florida."
GSA did not examine the contents of the boxes and "had no knowledge of the contents prior to shipping," according to an agency spokesperson. GSA was also not responsible for the former president's personal belongings, which were transported by a private moving company.
Under the Presidential Records Act, presidential records are considered federal property — not private — and are supposed to be turned over to the National Archives and Records Administration. Multiple federal laws govern the handling of classified and sensitive government documents, including statutes that make it a crime to remove such material and retain it at an unauthorized location.
After NARA realized that documents from Trump's presidency seemed to be missing from the material that it received as he left office, the agency requested the records from Trump on or about May 6, 2021, according to a heavily redacted affidavit made public Aug. 26, 2022.
The special agent in charge of NARA's Office of the Inspector General sent a referral to the Justice Department via email after a preliminary review of the boxes revealed numerous classified documents.
"Of most significant concern," they wrote, according to a heavily-redacted affidavit released last week, "was that highly classified records were unfoldered, intermixed with other records, and otherwise unproperly (sic) identified."
After an initial review of the NARA referral, the FBI opened a criminal investigation into the matter.
Trump's Save America PAC released a statement insisting the return of the documents had been as "routine" and "no big deal."
Trump insisted the "papers were given easily and without conflict and on a very friendly basis," and added, "It was a great honor to work with NARA to help formally preserve the Trump Legacy."
The Justice Department sent a letter to Trump's lawyers seeking immediate access to the material, citing "important national security interest."
"Access to the materials is not only necessary for purposes of our ongoing criminal investigation, but the Executive Branch must also conduct an assessment of the potential damage resulting from the apparent manner in which these materials were stored and transported and take any necessary remedial steps," the department wrote.
Trump's lawyers requested an additional extension.
Three FBI agents and a DOJ attorney went to Mar-a-Lago to collect additional material offered by a Trump attorney in response to the subpoena. They were given "a single Redweld envelope, double-wrapped in tape, containing the documents," according to an Aug. 30 filing.
That envelope, it was later found, contained 38 documents with classification markings, including five documents marked confidential, 16 marked secret and 17 marked top secret.
During the visit, the filing said, "Counsel for the former President offered no explanation as to why boxes of government records, including 38 documents with classification markings, remained at the Premises nearly five months after the production of the Fifteen Boxes and nearly one-and-a-half years after the end of the Administration."
Trump's lawyers also told investigators that all of the records that had come from the White House were stored in one location — a Mar-a-Lago storage room. Investigators were permitted to visit the room, but were "explicitly prohibited" from opening or looking inside any of the boxes, they reported, "giving no opportunity for the government to confirm that no documents with classification markings remained."
The Justice Department was also given a signed certification letter stating that a "diligent search" had been completed and that no documents remained.
The Justice Department filed an application for a search and seizure warrant of Mar-a-Lago, citing "probable cause" that additional presidential records and records containing classified information remained in various parts of the club.
"There is also probable cause to believe that evidence of obstruction" would be found, read the heavily-redacted copy of the affidavit laying out the FBI's rationale for the search.
The Justice Department also revealed in the Aug. 30 filing that it had found evidence "that government records were likely concealed and removed from the Storage Room and that efforts were likely taken to obstruct the government's investigation."
U.S. Magistrate Judge Bruce Reinhart in South Florida approved the application that same day.
The FBI executed the search at Mar-a-Lago, seizing 36 items of evidence, including boxes and containers holding more than 100 classified records, an order pardoning Trump ally Roger Stone and information about the "President of France."
Agents found classified documents both in the storage room as well as in the former president's office — including three classified documents found not in boxes, but in office desks.
They included items so sensitive that, "In some instances, even the FBI counterintelligence personnel and DOJ attorneys conducting the review required additional clearances before they were permitted to review certain documents."
"That the FBI, in a matter of hours, recovered twice as many documents with classification markings as the 'diligent search' that the former President's counsel and other representatives had weeks to perform calls into serious question the representations made in the June 3 certification and casts doubt on the extent of cooperation in this matter," the Justice Department wrote.
Trump and his allies, meanwhile, cast the search as a weaponization of the criminal justice system aimed at damaging him politically as he prepares for another potential White House run.
Judge Reinhart unsealed the warrant that authorized the FBI to search Mar-a-Lago, which details that federal agents were investigating potential violations of three federal laws, including the Espionage Act.
A highly redacted version of the affidavit laying out the FBI's rationale for searching Mar-a-Lago was released.
Department of Justice via AP
The Justice Department responded to Trump's request for a special master in a filing that included new details about the investigation, including an assertion that classified documents were "likely concealed and removed" from a storage room at Mar-a-Lago as part of an effort to obstruct the probe.
It included a photograph of some the material found at the club, including cover pages of paperclip-bound documents — some marked as "TOP SECRET//SCI" with bright yellow borders and one marked as "SECRET//SCI" with a rust-colored border — splayed out on a carpet at Mar-a-Lago.
"Terrible the way the FBI, during the Raid of Mar-a-Lago, threw documents haphazardly all over the floor (perhaps pretending it was me that did it!), and then started taking pictures of them for the public to see," Trump responded. "Thought they wanted them kept Secret?"
A sketch of Dearie from a court case in 2013. The Justice Department and former President Donald Trump's legal team have found rare agreement in a potential candidate to serve as the special master tasked with reviewing the documents seized from Mar-a-Lago.