Federal prosecutors overseeing the investigation into former President Donald J. Trump’s handling of classified documents are seeking to pierce assertions of attorney-client privilege and compel one of his lawyers to answer more questions before a grand jury, according to two people familiar with the matter, adding an aggressive new dimension to the inquiry and underscoring the legal peril facing Mr. Trump.
The prosecutors have sought approval from a federal judge to invoke what is known as the crime-fraud exception, which allows them to work around attorney-client privilege when they have reason to believe that legal advice or legal services have been used in furthering a crime. The fact that prosecutors invoked the exception in a sealed motion to compel the testimony of the lawyer, M. Evan Corcoran, suggests that they believe Mr. Trump or his allies might have used Mr. Corcoran’s services in that way.
Among the questions that the Justice Department has been examining since last year is whether Mr. Trump or his associates obstructed justice in failing to comply with demands to return a trove of government material he took with him from the White House upon leaving office, including hundreds of documents with classified markings.
Last May, the Justice Department issued a subpoena for any classified documents still in Mr. Trump’s possession, after he had voluntarily turned over an initial batch of material to the National Archives that turned out to include almost 200 classified documents. In June, Mr. Corcoran met with investigators and handed over more than 30 documents in response to the subpoena.
Another lawyer for Mr. Trump, Christina Bobb, then signed a statement asserting that a “diligent search” had been conducted at Mar-a-Lago, Mr. Trump’s residence and private club in Palm Beach, Fla., and that there were no additional documents bearing classification markings. Ms. Bobb has told investigators and others that Mr. Corcoran drafted the statement, and that she added some caveats to it, seeking to make it sound less ironclad.
But when the F.B.I. searched Mar-a-Lago, agents found more than 100 additional classified documents. The affidavit submitted by the Justice Department to obtain the search warrant said that there was “probable cause to believe that evidence of obstruction” would be found in the search.
Mr. Corcoran recently appeared before a grand jury in Federal District Court in Washington and is believed to have asserted attorney-client privilege on behalf of Mr. Trump in refusing to answer certain questions related to his representation in the documents investigation, according to three people familiar with the matter.
It remains unclear what questions Mr. Corcoran sought to avoid answering by asserting attorney-client privilege or what crime the Justice Department cited in invoking the crime-fraud exception in its motion to Judge Beryl A. Howell, the chief judge in the Washington federal courthouse, who oversees all grand jury matters.
But after his appearance in front of the grand jury, Mr. Corcoran received notice that the Justice Department was seeking to use the exception to break through his assertions of privilege. Judge Howell, who has consistently decided in the government’s favor on privilege issues surrounding Mr. Trump, will ultimately rule on the department’s request about Mr. Corcoran. She will be stepping down from the position of chief judge next month.
The push for Mr. Corcoran’s testimony is another sign of the aggressive efforts being made by Jack Smith, the special counsel overseeing the investigations into Mr. Trump, to secure testimony. Mr. Smith is guiding both the investigation into Mr. Trump’s handling of the classified documents and the inquiry into Mr. Trump’s efforts to remain in office after his election defeat in 2020 and how they led to the Jan. 6, 2021, assault on the Capitol.
It remained unclear if the crime-fraud arguments in the Justice Department’s motion to compel Mr. Corcoran’s testimony included evidence beyond what was initially contained in the search warrant affidavit.
It was also not immediately clear whether the Justice Department suspects misconduct by Mr. Corcoran and Mr. Trump, by Mr. Trump and others or by Mr. Trump alone. The crime-fraud exception is generally used to get around attorney-client privilege if a client uses legal services in the furtherance of a crime. Occasionally, the crime-fraud exception is used if lawyers and their clients conspire together to commit some offense.
A spokesman for the special counsel’s office declined to comment. A spokesman for Mr. Trump did not respond to messages seeking comment.
Prosecutors overseeing the documents investigation have also been asking witnesses questions about Boris Epshteyn, who has played a central role in coordinating lawyers on several of the investigations involving Mr. Trump, according to multiple people briefed on the matter. It was Mr. Epshteyn who first brought Mr. Corcoran into Mr. Trump’s orbit.
At least three lawyers have sat for interviews with the Justice Department during which questions about Mr. Epshteyn were asked — among them Ms. Bobb and, more recently, Alina Habba, people with knowledge of the matter said. A third lawyer close to Mr. Trump, Jesse Binnall, has also spoken with prosecutors about Mr. Epshteyn, the people said.
One person briefed on the interviews said that investigators were interested in discussions between Mr. Epshteyn and others about establishing a possible common-interest privilege in the documents case. A common-interest privilege creates a kind of umbrella privilege allowing groups of lawyers and clients to communicate with each other confidentially.
But prosecutors are asking questions about whether Mr. Epshteyn was trying to influence witness testimony, the person briefed on the interviews said.
Mr. Binnall declined to comment.
Lawyers representing or advising Mr. Trump have been central players in both the documents and Jan. 6 investigations.
A federal judge in California issued an opinion in a civil case last year arguing that there was reasonable evidence that Mr. Trump and another one of his lawyers, John Eastman, had conspired together to commit at least two crimes in their efforts to overturn the results of the 2020 election: conspiracy to defraud the United States and obstruction of an official proceeding before Congress.
Mr. Eastman had filed a lawsuit seeking to prevent the House select committee investigating Jan. 6 from obtaining some of his emails by arguing that many were protected by attorney-client privilege. But the judge, David O. Carter, overruled him, citing the crime-fraud exception as a reason to allow the committee to have the emails.
In June, federal agents armed with a search warrant seized Mr. Eastman’s phone in connection with the Jan. 6 investigation.
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