A federal judge on Tuesday expressed skepticism about an attempt by former President Donald J. Trump’s lawyers to once again skirt the issue of whether Mr. Trump had declassified some of the highly sensitive records seized from his Florida estate by the F.B.I. last month.
The statements by the judge, Raymond J. Dearie, who is acting as a special master reviewing the seized materials, were an early indication that he may not be entirely sympathetic to the former president’s attempts to bog down his evaluation with time-consuming questions over the classification status of some of the documents.
Days after the extraordinary search of Mr. Trump’s estate, Mar-a-Lago, the former president made public statements claiming that he had in fact declassified some of the seized records, suggesting that the Justice Department had no case against him for illegally retaining sensitive government material. But neither he nor his lawyers have ever made those same assertions in court — or in court papers — where they could face penalties for lying.
Instead, they have danced a fine line between suggesting that, as president, Mr. Trump had the authority to declassify the documents, while remaining silent on the issue of what he actually did — or did not do. At the same time, Mr. Trump’s lawyers have pursued another line of argument, telling Judge Dearie that he should not simply take the Justice Department’s word that some of the seized records are classified, as prosecutors claim.
At his first hearing as special master, Judge Dearie seemed to cut through this confusing web, telling Mr. Trump’s lawyers in direct terms that he was likely to deem the documents classified — unless they offered evidence to the contrary.
That prompted one of the lawyers, James Trusty, to say that Mr. Trump’s legal team might in the future offer that sort of evidence — in witness statements, for example — but that to do so now would telegraph its legal strategy to the government.
While Judge Dearie was open to the notion that Mr. Trump’s lawyers might at some point mount a declassification defense, he seemed displeased that they were casting doubt on the government’s assertions about the classification status of the documents without backing up their claims with evidence.
“My view is, you can’t have your cake and eat it too,” Judge Dearie said.
In addition to the documents case, Mr. Trump is facing several civil and criminal investigations into his business dealings and political activities.
Judge Dearie was appointed as a special master last week by a federal judge in Florida, Aileen M. Cannon, who ordered him to perform by Nov. 30 a series of tasks related to the documents. He is responsible for settling the classification status of about 100 of the records seized from Mar-a-Lago. He has also been given the job of reviewing a larger trove of about 11,000 documents and determining if any are protected by either attorney-client or executive privilege.
Almost everything about Judge Dearie’s appointment is unusual — including the fact that he held the hearing on Tuesday in his own courtroom in Federal District Court in Brooklyn even though the lawyers arguing before him were based in Washington and Florida, where Mr. Trump initially requested a special master.
“I realize that I’ve dragged you all to Brooklyn, New York,” the judge said as the hearing began, adding that he hoped to keep such inconveniences at a minimum.
It was also somewhat unusual that Judge Dearie’s work was moving forward even as the Justice Department waited to get a ruling from an appeals court that could directly affect the case. On Friday, prosecutors asked the U.S. Court of Appeals for the 11th Circuit in Atlanta to allow them to resume using the 100 classified documents in their investigation of whether Mr. Trump had illegally kept national defense information at Mar-a-Lago or obstructed repeated efforts by the government to retrieve the records.
On Tuesday, Mr. Trump’s lawyers filed their own papers to the same appeals court, making some of the same arguments they had made before Judge Dearie. They claimed, for example, that the Justice Department had not proved that the documents it had deemed as classified continued to be classified and hinted that Mr. Trump might in fact have declassified them.
“The government again presupposes that the documents it claims are classified are, in fact, classified and their segregation is inviolable,” the lawyers wrote. “However, the government has not yet proven this critical fact. The president has broad authority governing classification of, and access to, classified documents.”
But apparently undercutting that argument, Mr. Trusty told Judge Dearie at the hearing that he wanted some of his legal partners to get expedited top secret security clearances so that they, too, could view the documents. Mr. Trusty said he already had a top-secret clearance from another case.
Complicating the matter even further, Julie Edelstein, a lawyer for the Justice Department, told Judge Dearie that a handful of the documents at issue were so secret that even Mr. Trusty’s clearance might not be enough.
Mr. Trusty responded that “it was kind of astounding” that the government would seek to keep Mr. Trump’s legal team from seeing some of the classified material in the case. They needed to see it all, he said, to determine whether the government had acted properly by removing it during the search of Mar-a-Lago.
Much of the hearing was devoted to more mundane matters of scheduling, as Judge Dearie sought to move the document review along at a brisk pace. He told the parties that they needed to agree by Friday on a vendor that would handle the task of digitizing the large trove of material so that the government can share it with Mr. Trump’s lawyers.
In a letter to Judge Dearie submitted on Monday, Mr. Trusty said that the schedule set forth for the review was a bit aggressive. Judge Dearie had ordered both sides in the case to inspect the records and offer their thoughts about whether the documents were privileged or unprivileged, or belonged to the government or Mr. Trump, by Oct. 7.
“We respectfully suggest that all of the deadlines can be extended to allow for a more realistic and complete assessment of the areas of disagreement,” Mr. Trusty wrote.
In court on Tuesday, Judge Dearie acknowledged Mr. Trusty’s concerns but said he would push the case forward.
“We are going to proceed,” he said, “with what I call responsible dispatch.”
