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Prosecutors have urged a federal judge to hold Donald Trump’s office in contempt of court for failing to fully comply with a May subpoena to return all classified documents in his possession, according to people familiar with the matter — a sign of how contentious the private talks have become over whether the former president still holds any secret papers.

In recent days, Justice Department lawyers have asked U.S. District Judge Beryl A. Howell to hold Trump’s office in contempt, according to the people, who spoke on the condition of anonymity to describe sealed court proceedings. The hearing is scheduled for Friday, according to two people with knowledge of the matter.

The request came after months of mounting frustration from the Justice Department with Trump’s team — frustration that spiked in June after the former president’s lawyers provided assurances that a diligent search had been conducted for classified documents at his Mar-a-Lago Club and residence. But the FBI amassed evidence suggesting — and later confirmed through a court-authorized search — that many more remained.

One of the key areas of disagreement centers on the Trump legal team’s repeated refusal to designate a custodian of records to sign a document attesting that all classified materials have been returned to the federal government, according to two of these people. The Justice Department has repeatedly sought an unequivocal sworn written assurance from Trump’s team that all such documents have been returned, and Trump’s team has been unwilling to designate a custodian of records to sign such a statement while also giving assurances that they have handed documents back.

Adriana Usero

The precise wording of the filing could not be determined because it remains under seal. Trump is under investigation for three potential crimes: mishandling classified documents, obstruction and destruction of government records.

Trump spokesman Steven Cheung said the former president’s lawyers “continue to be cooperative and transparent.” He added: “This is a political witch hunt unlike anything like this country has ever seen.”

A Justice Department spokesman declined to comment.

Trump’s team has searched a number of his other properties in recent weeks, in response to the Justice Department concerns and instructions from the judge, and <a href="https://www.washingtonpost.com/nation/2022/12/07/trump-tower-bedminster-records-search/?itid=ap_jacquelinealemany" target=_blank>turned over two items with classification markings to the government</a>. Trump’s advisers told the FBI the items were found in a storage facility used by the former president in West Palm Beach, Fla. Other Trump properties searched in recent weeks include his Bedminster golf course in New Jersey and his home and office at Trump Tower in Manhattan. People familiar with those searches by a private firm say no classified documents were found at those locations.

Wilfredo Lee

Trump’s side has taken the position that such a request is unreasonable — that no lawyer could sign such a blanket certification in good faith or advise any client to do so, as opposed to attesting that a search of a given location has been completed in good faith. Some of Trump’s lawyers are also wary of making any claim under oath based on Trump’s word alone, two people familiar with the matter said.

The government’s request for a finding of contempt underscores the fundamental distrust that has existed since the spring between the government trying to retrieve sensitive documents and a former president whose responses have proved untrustworthy. That distrust has led to a legal impasse in sealed papers over what constitutes a complete search for classified papers.

When the government first issued a subpoena in May for any documents with classified markings, the official recipient of that subpoena was the office of the former president’s custodian of records — a role Trump’s team ultimately told the government was held by attorney Christina Bobb.

In June, Bobb signed an attestation that a diligent search had been conducted for any such material, but the FBI collected convincing evidence that was not the case. The government received a court-authorized search warrant in August, which turned up 103 more classified documents at Mar-a-Lago that had not been turned over in response to the subpoena.

But after months of back-and-forth, the core question has still not been answered to the Justice Department’s satisfaction: Are there any more classified items still in the former president’s possession? Prosecutors, having been burned before by empty promises, now want unqualified vows from someone in the official role of the custodian of records that there are no more classified skeletons in any of Trump’s closets.

Prosecutors have asked the judge to find Trump’s side in contempt as long as none of his advisers are willing to assume the role of custodian of records responsible for a complete answer to the question, these people said. In recent months, Bobb has publicly said she is not doing legal work related to the documents case but only advising Trump’s PAC on election issues.

If the judge were to agree, the most likely scenario would be a daily fine until the demands of the contempt motion are met. How large of a fine, or who would be forced to pay it, would be up to the judge.

It is not uncommon for large organizations to designate a records custodian who can take formal legal responsibility for the company or entity’s files. In Trump’s case, the subpoena sent in May was formally directed to his office’s custodian of records. No individual was named in the request.

Prosecutors have said in court filings that after Trump’s lawyers received the May subpoena, they asked for additional time to comply with it before agreeing to meet on June 3 to turn over records. The night before the scheduled meeting, Bobb — a lawyer and former One America News host —<b> </b>was called by Trump adviser Boris Epshteyn and asked to join lawyer Evan Corcoran at the meeting with Justice Department lawyers, according to a person familiar with the account she later gave to the FBI.<b> </b>Bobb had not previously met Corcoran.

At the June 3 meeting, Bobb gave the Justice Department a letter that began by saying she had been designated to serve as the office’s custodian of records, for purposes of the subpoena, according to people familiar with the conversation. The certification, with a redacted name, has been included in court filings. The letter said Bobb had been told a “diligent search” had been conducted of boxes “moved from the White House to Florida,” and that all documents responsive to the subpoena were being turned over.

The person close to Bobb has said she told the FBI she was skeptical of the letter and insisted on adding a disclaimer saying it was based on information provided to her by others.

Last month, Attorney General Merrick Garland appointed a special counsel to take over the investigation into the classified documents, along with an investigation into Trump’s attempts to overturn the 2020 election. In recent weeks, a number of Trump advisers have appeared in front of a grand jury hearing evidence in the classified documents case.

Stephen Ryan, a white-collar criminal defense attorney, said it is usually not difficult to figure out who should serve as the custodian of records for a company. “In the normal course of business, if you’re a real business, you have records and you have custodians of those records that you can call on,” he said. “It’s the person who holds custody of the records as part of their day-to-day activities.”

In this case, however, there is no representative of Trump who has actually maintained control of the records. “The department is in effect asking for something that doesn’t exist,” he said. “This is an extraordinary problem that is factually relatively unique.”

At this point, he said, “no one wants to put their head in the custodian noose.”

Finalist, Pulitzer Prize for Public Service, National Emmy Award nominee, Society of Professional Journalists Sigma Delta Chi Award for Public Service, Ursula and Gilbert Farfel Prize for Excellence in Investigative Reporting, American Immigration Lawyers Association Media Leadership Award,

Harvard University, B.A. in English

Spencer S. Hsu is an investigative reporter, two-time Pulitzer finalist and national Emmy Award nominee. Hsu has covered homeland security, immigration, Virginia politics and Congress.

Spencer Hsu

White House Correspondents Award for Deadline Reporting

University of South Carolina

Josh Dawsey is a political enterprise and investigations reporter for The Washington Post. He joined the paper in 2017 and previously covered the White House. Before that, he covered the White House for Politico, and New York City Hall and New Jersey Gov. Chris Christie for the Wall Street Journal.

Josh Dawsey

Harvard University, BA IN Government

Jacqueline Alemany is a Congressional Investigations reporter for The Washington Post. Previously, she was the author of The Early 202, The Post's flagship early morning newsletter featuring news critical to the nation’s many power centers. Alemany is also an on-air contributor to NBC News and MSNBC.

Jacqueline Alemany

Pulitzer Prize co-finalist for Feature Writing, 2017

Pulitzer Prize co-finalist for International Reporting, 2017

Part of team that won Pulitzer Prize for National Reporting, 2018

Part of team that won Pulitzer Prize for Public Service, 2022

"October Surprise: How the FBI Tried to Save Itself and Crashed an Election"

McGill University, BA 

Devlin Barrett writes about the FBI and the Justice Department, and is the author of "October Surprise: How the FBI Tried to Save Itself and Crashed an Election." He was part of reporting teams that won Pulitzer Prizes in 2018 and 2022. In 2017 he was a co-finalist for the Pulitzer for Feature Writing and the Pulitzer for International Reporting. 

Devlin Barrett

Pulitzer Prize for Public Service, 2022, for coverage fo the attack on Jan. 6

George Polk Award, 2022, for coverage of the attack on Jan. 6

Pulitzer Prize for National Reporting, 2018, for coverage of Russian interference 

George Polk Award, 2018, for coverage of Russian interference 

George Polk Award, 2014, for coverage of the Virginia governor's interactions with a wealthy donor

Harvard University, BA in history

Rosalind Helderman is an investigative reporter on the national staff of The Washington Post. She was part of teams awarded the Pulitzer Prize for Public Service in 2022 and the Pulitzer Prize for National Reporting in 2018. She joined The Post in 2001. 