President Donald Trump’s former national security adviser John Bolton walked into federal court with a very stern expression as he prepares to admit to stealing national security secrets. 

He is expected to plead guilty on Friday to a single charge of retaining classified information - a significant update in his criminal case, and one that may help him avoid jail time altogether.

Bolton could pay up to $2.24 million to settle his case and avoid jail time, according to CNN.

The agreement would resolve an eighteen-count federal indictment brought against Bolton last year, stemming from his alleged retention and transmission of classified and sensitive materials during Trump's first term. 

The deal could allow him to avoid jail time altogether, or serve five years or less behind bars — a sharp contrast to his original case, which carried a maximum penalty of up to ten years in prison for each charge.

Bolton is accused of sending more than 1,000 ‘diary-like’ entries to his wife and daughter during a period between 2018 and 2019, including classified information and information from intelligence briefings and meetings with foreign officials.

The re-arraignment comes after Bolton entered a ‘not guilty’ plea on all charges last fall, saying in a statement at the time that he was the ‘latest target’ of political weaponization at the Justice Department. 

Since taking office for a second term, Trump’s administration has opened federal criminal investigations into some of his most outspoken political foes, including former FBI Director James Comey, New York Attorney General Letitia James, and former Federal Reserve Chairman Jerome Powell.

But the investigation into Bolton’s actions differed significantly from other cases the administration has brought against the President’s perceived political foes.

The investigation into Bolton’s handling of classified materials moved forward in part during the Biden administration, and career prosecutors in the U.S. attorney’s office signed off on the charges — a contrast to the cases against Comey and James, which were brought by Trump’s former attorney, Lindsey Halligan.

Bolton appeared in court last year for his original arraignment and was ordered released by a magistrate judge on the condition that he remain in the continental United States and surrender his passport.

Trump has slammed his former aide as a 'lowlife' and 'not a smart guy.' 

'He doesn't talk, he's like a very quiet person except on television and then he can say something bad about Trump. He'll always do that. But he doesn't talk, he's very quiet,' Trump told reporters.