Special counsel Jack Smith expanded his classified documents case against former President Donald Trump, making significant new allegations that Trump and his employees attempted to delete Mar-a-Lago security footage sought by the grand jury investigating the mishandling of the government records.

The new charges were presented in what's known as a superseding indictment that was handed up by a grand jury in Florida on Thursday. A third defendant, Mar-a-Lago employee Carlos De Oliveira, was also added to the case. He is accused alongside Trump and Walt Nauta of obstructing the investigation with the alleged bid to delete security footage at Trump's Florida resort.

Trump also faces a new charge stemming from the allegedly mishandled classified documents that are at the core of the case, with prosecutors identifying a new document -- reported by CNN to be possible Iran attack plans -- that they say Trump unlawfully retained.

Trump and Nauta pleaded not guilty to the initial round of charges Smith brought in the case last month.

The filing of the new charges illustrates the depth and breadth of legal jeopardy that Trump finds himself. A potential indictment against Trump in Smith's election subversion probe continues to loom against the former president and possible charges are expected in weeks to come in the Fulton County, Georgia, investigation into Trump and his allies' post-election conduct as well.

Here's what to know about the new charges in the classified documents case.

Trump 'requested' deletion of security footage

The indictment accuses Trump of being part of the effort to delete security footage from Mar-a-Lago after it was subpoenaed, saying that Trump "requested" that a resort employee delete footage in order "to prevent the footage from being provided to a federal grand jury."

The newest defendant in the case places the former president in the middle of the attempts to delete the security footage. According to the indictment, De Oliveira told another Trump employee, who was director of IT at Mar-a-Lago, "that 'the boss' wanted the server deleted," according to the indictment.

This happened in June 2022 after prosecutors had subpoenaed for the security footage.

When the unnamed Trump employee, identified as Employee 4, responded that he would not know how to do that and did not believe he would have the rights to do that, De Oliveira pressed him further, again referencing "the boss," prosecutors said.

"De Oliveira then insisted to Trump Employee 4 that 'the boss' wanted the server deleted and asked, 'what are we going to do?'" the indictment alleges.

According to the indictment, De Oliveira asked the IT employee how long the server retained security footage. He was told it was approximately 45 days. De Oliveira also said that the conversation "should remain between the two of them," according to the indictment.

De Oliveira also spoke by phone twice with Trump after Trump's lawyers were notified of plans to subpoena the security footage.

Trump and Nauta had already been charged with obstruction over the moving of boxes, but now the latest charges add a new dimension to the obstruction case that goes beyond hiding the documents themselves.

Trump's alleged mishandling of an Iran attack plan adds to the charges

The new indictment brings the number of counts Trump faces for retaining national defense information to up 32, with prosecutors adding a new count to the 31 they previously brought for a classified document described by prosecutors as a top secret "presentation concerning military activity in a foreign country."

Trump allegedly touted the document -- which CNN previously reported related to Iran attack plans -- in a taped July 2021 interview with biographers at his Bedminster, New Jersey, golf club.

The new changes and details in the superseding indictment contradict Trump's past denials about the document in question. Trump had previously denied that the document he discussed in the audio tapes was a government document, describing it instead as a news clipping.

"There was no document," Trump told Fox News last month. "That was a massive amount of papers and everything else talking about Iran and other things."

"And it may have been held up or may not, but that was not a document. I didn't have a document, per se. There was nothing to declassify. These were newspaper stories, magazine stories and articles," Trump said in the interview.

A new defendant

The new court filings lay out the role De Oliveira allegedly played in an attempt Nauta and Trump made to delete footage that was being sought by a grand jury subpoena. De Oliveira, 56, was also charged with making false statements in a January interview with the FBI, when he was asked about the movement of boxes at the Florida resort.

Prosecutors describe the new defendant as Mar-a-Lago's property manager who previously worked as a valet at the resort.

After the FBI executed a search warrant on Mar-a-Lago last August, Nauta discussed with an unidentified employee De Oliveira's loyalty, according to prosecutors, and requested that the employee confirm De Oliveira's loyalty in a group signal chat with a representatives for Trump's political action committee.

"That same day, TRUMP called DE OLIVEIRA and told DE OLIVEIRA that TRUMP would get DE OLIVEIRA an attorney," the indictment says.

What happens next

De Oliveira is scheduled for an arraignment on the new charges in Miami's federal courthouse on Monday morning, set to take places before Chief Magistrate Judge Edwin G. Torres.

It's not yet clear how the new charges will affect the pace of the case against Trump and Nauta. Currently, the trial -- which is slated to take place in Ft. Pierce, Florida, in front of US District Judge Aileen Cannon -- is scheduled to start in late May 2024.

But even before the new charges were unveiled, it was possible for that trial date to be pushed further back.

Thursday night, Trump told Fox News that the new charges amount to "election interference at the highest level" and "prosecutorial misconduct." He also claimed that his position in the 2024 presidential election polls has made him a target of the Justice Department.

Attorneys for De Olivera and Nauta have declined to comment.