WASHINGTON - Former President Donald 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, Trump's demand that an outside arbiter sift through the materials the FBI seized from his Florida estate seemed to turn in his favor. His lawsuit was assigned to a judge he had appointed, Aileen Cannon of the Southern District of Florida, who surprised legal experts by granting his request.
In naming a special master suggested by Trump's lawyers, she effectively froze the Justice Department's investigation and gave the arbiter a broad mandate. The judge, Raymond Dearie of U.S. 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 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 had filed under seal to Dearie suggest that the upsides to obtaining a special master are eroding and the disadvantages swelling.
James M. Trusty, a lawyer for Trump, did not respond to a request for comment. But late Wednesday, the Trump team refiled its complaints to Dearie - a letter dated Sunday, Sept. 25 - in unsealed form, bringing the tensions more clearly into view.
The appeals court last week freed the Justice Department to resume using about 100 documents marked as classified in its investigation, while telegraphing that the court thought Cannon likely had erred by appointing a special master.
In blocking part of 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 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 Trump's Florida compound, Mar-a-Lago. A second letter from Trusty on Wednesday said that amounts to nearly 200,000 pages of material.
Since that review is no longer delaying or diverting the criminal inquiry, it is not clear what benefits remain for Trump.
For one, a special master will cost a lot of money. Cannon rejected 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 Dearie, like an assistant who bills $500 an hour. 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 Trump, as his lawyers likely hoped in suggesting his appointment, 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 Trump to submit by Friday a declaration or affidavit verifying the inventory or listing any items on it "that plaintiff asserts were not seized" in the search.
But if Trump acknowledges that the FBI 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 Trump's lawyers to verify or object to the inventory also effectively means making them either affirm in court or disavow a claim Trump has made in public: his accusation that the FBI 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, Dearie is telling Trump's legal team "to put up or shut up," said Julie O'Sullivan, a Georgetown University professor of white-collar law.
"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," 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."
In its letter Sunday to Dearie, Trump's legal team argued that Cannon had not authorized the special master to seek a declaration verifying the inventory from Trump or his representatives. The lawyers also said they would need to see the documents marked as classified to provide any such certification.
Another tension centers on 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, Dearie said that 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 Trump's lawyers had "resisted providing any evidence that he had declassified any of these documents."
Trump, through his lawyers, is chafing at other orders from the special master, their Sunday letter shows.
For example, Dearie has said they must categorize each document Trump claims is subject to privilege. They are to say whether they mean attorney-client or executive privilege. And if they claim executive privilege, then they must also 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.
Dearie is effectively trying to force 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 in their letter, Trump's lawyers said Dearie was going beyond what Cannon had authorized him to demand of them, and said they "see no basis for segmenting" their executive privilege claims into the two different types he had identified.
For its part, the Justice Department appeared to relish Trump's growing discomfort.
"Plaintiff brought this civil, equitable proceeding," it wrote in its letter. "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 Dearie laid out.
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