A judge has questioned how Donald Trump could have overlooked sensitive documents that turned up in his bedroom after the FBI searched the former US president’s Florida home.
The files were found in his private quarters months after federal agents discovered over 100 classified records as they executed a search warrant at Mar-a-Lago in Palm Beach in the summer of 2022.
The judge also noted the prosecution’s belief that Mr Trump was “likely instructing his agents to avoid the surveillance cameras” at the golf club.
He denies 40 federal charges of unlawful retention of national defence information.
His co-defendants, aide Walt Nauta and former employee Carlos de Oliveira, have also pleaded not guilty.
The trial is unlikely to begin before November’s US election, in which Mr Trump is the presumptive Republican nominee.
Joe Biden was also found to have willfully retained classified files, but he was not accused of obstructing that inquiry and a justice department investigator decided not to charge him, concluding that a jury would view the US president as “a well-meaning, elderly man with a poor memory”.
In the Trump case, a newly unsealed filing said the former president’s lawyers had turned over four additional documents with classification markings that were found in December 2022, four months after the FBI raid at the property.
US District Judge Beryl Howell, an Obama appointee, wrote in the March 2023 opinion: “Notably, no excuse is provided as to how the former president could miss the classified-marked documents found in his own bedroom at Mar-a-Lago.”
In June 2022, federal investigators won a court order to gain access to the security camera footage at the estate.
After Mr Trump learned of this subpoena, prosecutors allege there was a “scramble” by Mr Nauta to change his travel plans and fly from New Jersey to Mar-a-Lago in 2022 to ensure boxes were moved “off-camera”, according to the opinion unsealed on Tuesday.
The judge notes “the curious absence of any video footage” capturing the return of certain boxes to a storage room.
On Wednesday, Judge Aileen Cannon, the Trump appointee currently presiding over the case, was scheduled to hear arguments on the latest request by the former president to dismiss the indictment.
He argues it fails to clearly articulate a crime and instead amounts to “a personal and political attack” against him.
His co-accused, Mr Nauta, will also seek to have his case thrown out.
He argues it amounts to selective prosecution because he opted not to co-operate in the probe.
Mr Trump is facing dozens of other charges in three other criminal cases.
He is currently in trial in New York over an alleged cover-up of hush-money payments to an adult-film star in 2016.