A federal judge in Washington was set to hear arguments at a closed-door hearing on Friday about whether to force a representative of Donald J. Trump’s presidential office to swear under oath that there are no more classified documents at any of Mr. Trump’s properties, according to two people familiar with the matter.
The judge, Beryl A. Howell, is also being asked to decide whether to impose financial penalties or issue a contempt finding if no one from Mr. Trump’s office agrees to formally vow that, to the best of their knowledge, all of the classified materials he took from the White House when he left office last year have been returned to the government.
The hearing, in Federal District Court in Washington, is being held at the request of federal prosecutors who asked Judge Howell in recent days to declare Mr. Trump in contempt of court for failing to obey a grand jury subpoena that was issued in May seeking the return of all of the classified records in his office’s possession.
The request by the government came after months of frustration with the former president and his lawyers, who have repeatedly made assurances to prosecutors that the sensitive materials had all been returned — only to find out there were more.
No matter what Judge Howell decides, the fact that she has been asked to mull a contempt finding suggests that the Justice Department has taken a newly aggressive stance toward Mr. Trump’s long-delayed response to the government’s efforts to retrieve a trove sensitive records that he took from the White House to Mar-a-Lago, his private club and residence in Florida.
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Around Thanksgiving, a team of experts hired by Mr. Trump concluded searches that included other locations — among them, Trump Tower in New York; his golf club in Bedminster, N.J.; and a storage facility near Mar-a-Lago. At the storage facility, the team discovered at least two documents that bore classification markings, prompting lawyers for the former president to immediately notify prosecutors about them.
Nonetheless, that discovery contradicted an affidavit that some of Mr. Trump’s other lawyers had drafted and signed in June, saying that they had done a “diligent” search of his properties and that to the best of their knowledge no classified material remained in his possession.
The new bid by prosecutors to persuade Judge Howell to use her authority to hold Mr. Trump and his legal team accountable for the return of the materials came weeks after the Justice Department named a special counsel, Jack Smith, to oversee the investigation into whether Mr. Trump had illegally kept national security documents at his private property and obstructed the government’s attempts to get them back.
Some lawyers who have worked with Mr. Smith’s team have said they were told that the Justice Department would no longer pull punches in seeking to enforce court orders or subpoenas.
The attestation in June was signed by a lawyer for Mr. Trump named Christina Bobb and drafted by another named Evan Corcoran. When the F.B.I. subsequently searched Mar-a-Lago in August, it found more than 100 additional documents bearing classification markings.
The initial grand jury subpoena was issued in May after officials with the National Archives, after nearly a year of attempts, retrieved 15 boxes of material from Mr. Trump’s club at Mar-a-Lago in January and discovered that they contained dozens of classified documents.
It is unclear whether Judge Howell will rule from the bench on Friday, reserve judgment or seek to have the two sides work out their disputes.