John Bolton Nears Guilty Plea in Classified Information Case

John Bolton, a prominent critic of Donald Trump who served as his national security adviser, is poised to plead guilty to mishandling classified information. The agreement with federal prosecutors includes a $2.25 million fine, according to three sources familiar with the deal.

Bolton is expected to enter a guilty plea to one count of retaining classified information, specifically related to diary entries detailing his work during Trump’s first term.

The court hearing is scheduled for Friday in Greenbelt, Maryland. While the deal recommends a sentencing range from no prison time up to five years behind bars, a federal judge will ultimately determine the final sentence.

This case is one of several initiated by Trump’s Justice Department against individuals critical of the president, a pattern that has been seen as departing from long-standing norms designed to shield federal law enforcement from political pressures.

Bolton was initially accused of sharing sensitive information with two relatives for a book he was writing, including notes from intelligence briefings and meetings with senior government officials and foreign leaders.

He had previously pleaded not guilty to 18 criminal charges, encompassing both the transmission and retention of national defense information.

Neither the Justice Department nor a spokesperson for Bolton offered comment on the matter.

Bolton transitioned from a key adviser in Trump’s first term to one of his most outspoken critics, famously describing Trump in a memoir as "unfit to serve as president."

Sources familiar with the plea agreement clarified that it does not allege wrongdoing concerning Bolton’s book itself, but rather that Bolton acknowledges making a mistake.

Trump’s Justice Department had previously attempted, unsuccessfully, to block the publication of Bolton’s book, which criticized Trump’s temperament and decision-making, alleging it contained classified information.

Unlike some other cases brought against Trump’s critics, the investigation into Bolton began before Trump returned to office in 2025 and was supported by career federal prosecutors.

The Justice Department also brought criminal cases against former FBI Director James Comey and New York Attorney General Letitia James, both of whom had led investigations into Trump or his businesses.

Those cases were later dismissed by a federal judge, though a second set of charges has since been brought against Comey.

Other critics of Trump have also faced investigations, with a wide-ranging probe currently seeking to establish that prior investigations of Trump constituted a criminal conspiracy against him.