In a high-profile case involving former U.S. President Donald Trump, two of his aides are set to enter pleas in federal court in Florida on Thursday. Walt Nauta, Trump's valet, and Carlos De Oliveira, a property manager at Trump's Mar-a-Lago resort home in Palm Beach, are facing charges of obstruction of justice and false statements related to allegations that they unlawfully took classified documents with them after Trump left office. The charges stem from a year-long investigation by Special Counsel Jack Smith's team into Trump's retention of classified documents, including some of the country's most closely held secrets.

According to prosecutors, Trump stored the documents haphazardly at Mar-a-Lago, even keeping them in places like bathrooms, showers, and ballrooms. Furthermore, he allegedly showed classified information to unauthorized individuals at his golf resort in Bedminster, New Jersey. Nauta is accused of moving boxes of documents at Mar-a-Lago to hide them from Trump's lawyer and federal investigators, as well as attempting to delete security camera footage. Both Nauta and De Oliveira are also accused of lying to the FBI.

This criminal case is one of three that Trump faces as he campaigns for the 2024 Republican presidential nomination. He has pleaded not guilty to 40 counts of unauthorized retention of national defense information, obstruction of justice, and false statements. In addition to the charges in Florida, Trump is also facing charges in Georgia related to his efforts to reverse his election loss in that state.

Carlos De Oliveira is scheduled to appear before U.S. Magistrate Judge Shaniek Mills Maynard in Fort Pierce, Florida, to enter a plea on the four charges brought against him. Last week, he was released on a $100,000 signature bond but did not enter a plea as he had not yet retained counsel in Florida. Walt Nauta, on the other hand, is set to appear for a second arraignment in the case. Trump, however, has waived his right to appear at the proceeding and has pleaded not guilty to the additional charges.

The new indictment against De Oliveira includes charges of altering, destroying, mutilating, or concealing an object, corruptly altering, destroying, mutilating, or concealing a document or record, conspiracy to obstruct justice, and making false statements during a voluntary interview with federal investigators. The indictment also includes new charges against Trump, including obstruction counts and an additional count of unlawful retention of national defense information.

The case against Trump involving the handling of government documents recovered from Mar-a-Lago is the first of two cases brought against him by Special Counsel Jack Smith. A federal grand jury last week indicted Trump on charges related to his efforts to remain in office after the 2020 presidential election. He faces four charges, including falsifying business records. Trump has pleaded not guilty to all charges and has labeled them as part of a political plot against him.

In a separate development, the use of an out-of-state grand jury by Special Counsel Jack Smith to investigate the case has been called into question. Federal Judge Aileen Cannon, who is overseeing the case, denied a motion to seal filings and requested additional information about the use of the out-of-state grand jury. Cannon has asked for clarification on the legal propriety of using an out-of-district grand jury to investigate and seek post-indictment hearings on matters related to the case.

The trial in the classified documents case is scheduled to begin in May 2024, amid the Republican presidential primaries. Trump and his aides maintain their innocence and continue to portray the charges as politically motivated attacks against him. The former president has also hinted at the possibility of a fourth indictment in the near future, as part of an ongoing investigation by a district attorney into his efforts to reverse the outcome of the 2020 election.