A federal judge has appointed Raymond J. Dearie, a former chief federal judge in New York, to sort through the more than 11,000 documents — including classified materials — that FBI agents seized from former president Donald Trump’s Florida residence last month, to see if any should be shielded from criminal investigators because of attorney-client or executive privileges.
The decision could significantly slow a high-profile investigation of the former president, one that prosecutors say has already been paused at a key juncture by the judge’s skepticism that the Justice Department has treated Trump fairly.
Trump’s legal team proposed Dearie as a candidate to be the special master in the high-profile case, and the Justice Department agreed with the selection last week. But the two sides still disagree on whether searching through the highly sensitive classified documents taken by the FBI should be part of the special master’s responsibilities.
Ultimately, U.S. District Judge Aileen Cannon ruled in Trump’s favor and said the special master should examine about 100 documents with classified markings, and said Dearie should prioritize those materials over the more than 11,000 nonclassified documents that were taken in the Aug. 8 search. She denied a bid by prosecutors to allow them to use the seized material in their ongoing criminal investigation before Dearie conducts his review.
In her Thursday night ruling, Cannon rejected Justice Department arguments that her decision will cause serious harm to the national security investigation. Evenhanded application of legal rules “does not demand unquestioning trust in the determinations of the Department of Justice,” the judge wrote in a decision that is almost certain to be appealed by the government.
Cannon, a Trump appointee confirmed by the U.S. Senate just days after Trump lost his bid for reelection, added that she still “firmly” believes that the appointment of a special master, and a temporary injunction against the Justice Department using the documents, is in keeping “with the need to ensure at least the appearance of fairness and integrity under unprecedented circumstances.”
Prosecutors signaled last week that if Cannon did not amend her restrictions on the criminal investigation of Trump and his aides for possibly mishandling national defense information, or hiding or destroying government records, they would file an appeal to the U.S. Court of Appeals for the 11th Circuit in Atlanta.
At the same time, prosecutors asked that any special master review not include the classified documents the FBI found among the confiscated materials when it executed the court-approved search warrant. The government said that delaying investigators’ access to those documents could pose national security risks. The Washington Post reported on Sept. 6 that the seized material included information on a foreign nation’s nuclear capabilities and other sensitive documents so closely held that only a small circle of top government officials are permitted to access them.
In asking the judge to back off at least part of her special master ruling, prosecutors had argued that Trump could not possibly have an attorney-client or executive privilege claim over classified documents, which by definition are the property of the federal government.
Cannon roundly rejected those arguments in her filing, saying that whether the documents marked classified were actually classified is a matter of dispute. Trump’s lawyers have suggested the documents may not be classified, but have not asserted in their court appearances or court filings that Trump declassified them.
The judge nevertheless said she did not necessarily believe the prosecutors, writing, “The Court does not find it appropriate to accept the Government’s conclusions on these important and disputed issues without further review by a neutral third party in an expedited and orderly fashion.”
While Cannon ordered the Justice Department not to use any of the seized material while awaiting the special master review, she did allow the Office of the Director of National Intelligence to conduct an assessment of any risks to national security. Prosecutors had claimed the two inquiries were “inextricably intertwined,” because the FBI is an intelligence agency, and some of the tasks necessary to conduct a risk assessment would have to be done by the FBI.
Cannon’s 10-page ruling rejects that argument, saying FBI agents can do what is needed for the risk assessment, even though they cannot proceed with the criminal investigation. She ordered the assessment to proceed. The judge said prosecutors were relying heavily “on hypothetical scenarios and generalized explanations that do not establish irreparable injury.”
Her ruling did not directly address a different argument by prosecutors, which said that keeping the classified documents off-limits to investigators could make it harder for them to determine whether any more classified material appears to be missing.
In appointing the special master, Cannon appeared to leave most details of the review up to Dearie, including what type of material might be covered by executive privilege, a loosely defined legal concept that has historically been applied to material about a sitting president’s deliberations, to shield them from another branch of government or the public. In this case, Trump’s lawyers have raised the possibility that Trump, as a former president, could claim such a privilege over material sought by the executive branch. Cannon’s rulings in the case have not made clear how she would define such a privilege.
Cannon’s order Thursday night also seems to imply that it will be in some measure up to Dearie to decide whether the 100 or so documents marked classified are, in fact, classified, and whether Trump can make any privilege claim over them.
Dearie, 78, was nominated to the federal bench in Brooklyn by President Ronald Reagan after serving as U.S. attorney in the same district. Fellow lawyers and colleagues describe him as an exemplary jurist who is well suited to the job of special master, having previously served on the Foreign Intelligence Surveillance Court, which oversees sensitive national security cases.
Patrick Cotter, who served as a federal prosecutor in Brooklyn, said he was surprised Trump’s team suggested such a smart, low-key judge.
“There wasn’t much personality, and I mean that as a compliment. Ray wasn’t chummy, and he wasn’t a good ol’ Brooklyn boy or highfalutin’ guy trying to impress you,” Cotter said. “He was a very matter-of-fact, down to earth judge with a minimum of pomposity. He will do a credible job, and will do it quickly.”
Paul Bergman, a former federal prosecutor and a friend of Dearie’s for decades, called him “a perfect choice for this kind of thing, in terms of his rock-bottom judicial integrity.”
Bergman said Dearie “has been called upon to perform something that is a vital task, and I don’t know that there’s anybody, frankly, out there better qualified to do this than him.”
In 2015, Dearie took the unusual step of reducing the prison sentences of three convicted Canadian terrorists, saying he had been “haunted” by the case and his growing sense that their sentences were unfair.
Under federal law, Dearie had been required to sentence the men to 25-year terms for conspiring to acquire missiles on behalf of the Tamil Tigers, a rebel group fighting the government of Sri Lanka. He later cut those sentences to 15 years.