Trump now faces two new obstruction-of-justice charges related to the alleged attempt to erase the security camera video. In addition, the new indictment adds a felony count under the Espionage Act stemming from his alleged possession of the war plan. He now faces 32 counts of willfully retaining national defense information under the Espionage Act and eight counts related to alleged efforts to obstruct the investigation.

The new indictment alleges that on June 27, 2022, De Oliveira met with a Trump Organization employee in an audio closet at Mar-a-Lago and asked that person — unnamed in the indictment — to delete the security camera video sought by prosecutors in a grand jury subpoena days earlier.

“De Oliveira told [the employee] ‘the boss’ wanted the server deleted,” the new indictment alleges. The employee “responded that he would not know how to do that, and that he did not believe he would have the rights to do that,” the indictment adds.

Prosecutors claim that when the employee said a supervisor would need to be involved, De Oliveira repeated that “the boss” wanted the server deleted and De Oliveira then asked: “What are we going to do?”

The indictment indicates that De Oliveira spoke by phone and texted with Nauta, a longtime Trump aide who is also a defendant in the case, shortly after the exchange with the unnamed employee. De Oliveira and Nauta met in person just off the Mar-a-Lago grounds, and Trump called De Oliveira later that day, the indictment alleges. There is no indication of what was said in the phone calls.

De Oliveira, 56, of Palm Beach Gardens, Fla., is scheduled to be arraigned Monday in Miami federal court, according to a court docket. Trump and Nauta will also need to be re-arraigned on the new indictment, but it’s unclear when that will take place.

Smith’s team first obtained criminal charges against Trump and Nauta in Florida last month. They accused Trump of hoarding boxes containing classified documents at his Mar-a-Lago residence after he left the White House and attempting to thwart the government’s efforts to retrieve them, and they accused Nauta of helping Trump obstruct the investigation.

The updated indictment does not merely add new criminal charges and a new defendant; it also shows prosecutors making a concerted effort to undercut some of Trump’s recent public denials of the case they’ve brought against him. And it adds significant new elements to the legal peril he faces and underscores prosecutors’ deep penetration into his cloistered inner circle.

In a separate investigation, Smith’s team appears to be on the verge of indicting Trump in Washington, D.C., for his efforts to subvert the results of the 2020 election. Trump also faces criminal charges in Manhattan for falsifying business records in connection with a hush money scheme.

The new indictment in the Florida case adds new details about Trump’s alleged handling of the classified war plan, believed to be a plan of attack on Iran. It alleges that, on July 21, 2021, Trump shared the plan at his club in Bedminster, New Jersey, with two people working on a book being written by his former chief of staff, Mark Meadows. In the original indictment, prosecutors had revealed they had a recording of that conversation, but they hadn’t yet charged Trump with possessing the document.

The new indictment charges that Trump also had that classified war plan at his Mar-a-Lago estate in Palm Beach, Fla. It does not specify how the document reached either location.

Trump has publicly denied showing the actual document to the researchers, instead claiming he had shown them news clippings.

“I didn’t have a document, per se,” Trump said in a Fox News appearance last month. “There was nothing to declassify. These were newspaper stories, magazine stories, and articles.”

Each of the new obstruction-of-justice charges carries a maximum penalty of 20 years in prison. The charge of willfully retaining national defense secrets is punishable by up to 10 years in prison.

Due to the operation of federal sentencing guidelines and the sheer volume of charges Trump already faced, the new charges may not significantly affect Trump’s bottom-line sentence if he is convicted and given prison time. But they are likely to bolster the narrative prosecutors can present to a jury — and the public.

In a statement Thursday night, the Trump campaign called the new charges “desperate and flailing” and said Smith is “casting about for any way to salvage” the case against him.