WASHINGTON — Former President Donald J. Trump’s request that a judge intervene in the criminal investigation into his hoarding of government documents by appointing a special master increasingly looks like a significant blunder, legal experts say.
“Maybe from Trump’s point of view, creating delay and chaos is always a plus, but this has the feel of a giant backfire,” said Peter M. Shane, a legal scholar in residence at New York University and a specialist in separation-of-powers law.
Initially, Mr. Trump’s demand that an outside arbiter sift through the materials the F.B.I. seized from his Florida estate seemed to turn in his favor. His lawsuit was assigned to a judge he had appointed, Aileen M. Cannon of the Southern District of Florida, who surprised legal experts by granting his request.
In naming a special master suggested by Mr. Trump’s lawyers, she effectively froze the Justice Department’s investigation and gave the arbiter a broad mandate. The judge, Raymond J. Dearie of Federal District Court for the Eastern District of New York, would filter the materials not just for attorney-client privilege, which is not unusual, but also for executive privilege, which is unprecedented.
But Mr. Trump’s apparent triumph would prove short-lived. An appeals court ruling last week and a letter the Justice Department filed late Tuesday about subsequent complaints his legal team has apparently filed under seal to Judge Dearie suggest that the upsides to obtaining a special master are eroding and the disadvantages swelling.
A lawyer for Mr. Trump did not respond to a request for comment.
The appeals court freed the Justice Department to resume using about 100 documents marked as classified in its investigation, while telegraphing that the court thought Judge Cannon likely erred by appointing a special master.
In blocking part of Judge Cannon’s order, the appeals court panel, including two Trump appointees, allowed investigators to again scrutinize the material that poses by far the gravest legal threat to Mr. Trump. Potential crimes include unlawful retention of national security secrets, obstruction and defying a subpoena demanding all sensitive records that remained in his possession.
But the Justice Department acquiesced for now to the remainder of the special master process, meaning that an outside arbiter would still assess some 11,000 unclassified records and other items seized from Mr. Trump’s Florida compound, Mar-a-Lago.
Since that review is no longer delaying or diverting the criminal inquiry, it is not clear what benefits remain for Mr. Trump.
For one, a special master will cost a lot of money. Judge Cannon rejected Mr. Trump’s proposal that taxpayers should foot half the bill of the review, instead saying he would be solely responsible.
That includes the full cost of a vendor who will scan all the materials, as well as support staff for Judge Dearie, like an assistant who bills $500 an hour. Mr. Trump will also have to pay his own lawyers’ fees as they filter thousands of pages of records and then litigate disputes about which ones can be withheld as privileged.
And far from indulging Mr. Trump, as his lawyers likely hoped in suggesting his appointment, Judge Dearie appears to be organizing the document review in ways that threaten to swiftly puncture the former president’s defenses.
For example, the judge has ordered Mr. Trump to submit by Friday a declaration or affidavit that lists any items on the inventory “that plaintiff asserts were not seized” in the search.
But if Mr. Trump acknowledges that the F.B.I. took any documents marked as classified from his personal office and a storage room at Mar-a-Lago, as the inventory says, that would become evidence that could be used against him if he were later charged with defying a subpoena.
Requiring Mr. Trump’s lawyers to verify or object to the inventory also effectively means making them either affirm in court or disavow a claim Mr. Trump has made in public: his accusation that the F.B.I. planted fake evidence. While it is not a crime to lie to Fox News viewers or on social media, there are consequences to lying to a court.
Essentially, Judge Dearie is telling Mr. Trump’s legal team “to put up or shut up,” said Julie O’Sullivan, a Georgetown University professor of white-collar law.
Late Tuesday, the Justice Department indicated to Judge Dearie that Mr. Trump’s lawyers were balking at his request that their client verify the property inventory at this stage, before the documents could be categorized or reviewed for privilege. They apparently expressed such objections in a document filed under seal.
“They thought it was a win to win the first battle, but they didn’t think through what winning that battle would mean with any reputable judge who is appointed as special master,” Ms. Sullivan said. “They can’t anticipate that every judge will give them a complete pass despite the law. It was a political or a public relations strategy, not a legal one.”
Another issue centers on Mr. Trump’s public insistence that he declassified everything he took to Mar-a-Lago, a claim for which no credible evidence has emerged.
His lawyers have not repeated that claim in court. They have instead merely insinuated that he might have done so by emphasizing that a president has broad declassification powers without asserting that he actually used them on the files.
At a hearing this month, Judge Dearie said that Mr. Trump’s legal team would need to submit evidence of any declassification — like a sworn declaration or affidavit — or he would conclude that they remained classified.
“I guess my view of it is,” he said, “you can’t have your cake and eat it.”
In exempting the documents marked as classified from the special master’s review, the appeals court also focused on the disconnect. There was “no evidence that any of these records were declassified,” the three-judge panel wrote, noting that Mr. Trump’s lawyers had “resisted providing any evidence that he had declassified any of these documents.”
The Justice Department’s letter indicated that Mr. Trump, through his lawyers, is chafing at other orders from the special master.
For example, Judge Dearie has said they must categorize each document Mr. Trump claims is subject to privilege. They are to say whether they mean attorney-client or executive privilege. If they claim executive privilege, then they must distinguish between records that are merely shielded from disclosure to people outside the executive branch and those the executive branch itself supposedly cannot review. They must also explain why each document qualifies for such status.
Judge Dearie is effectively trying to force Mr. Trump’s lawyers to confront a weakness in their theory that executive privilege is relevant to the case. Many legal experts doubt a former president can invoke the privilege against the wishes of the current president, preventing the Justice Department from reviewing executive branch materials in a criminal investigation.
But for now, Mr. Trump’s legal team evidently wants to say only that various items are privileged, leaving it at that.
For its part, the Justice Department appeared to relish Mr. Trump’s growing discomfort.
“Plaintiff brought this civil, equitable proceeding,” it wrote. “He bears the burden of proof. If he wants the special master to make recommendations as to whether he is entitled to the relief he seeks, plaintiff will need to participate in the process” that Judge Dearie laid out.
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