John Bolton, Donald Trump’s former national security adviser who’s now a fierce critic of the president, pleaded guilty Friday to mishandling classified information in a criminal case brought against him by Trump’s Justice Department.Bolton, 77, appeared in federal court in Maryland and agreed to plead guilty to a single count of unlawfully keeping classified national security information in diaries while preparing a memoir about his time in the White House. The deal is a significant reduction from the 18 charges initially in the indictment, though he could still face up to five years in prison.He has also agreed to pay a $2.25 million fine, prosecutors said.Asked by the judge if he was guilty of the charges, Bolton said, “I am, your honor, and I’m sorry for it.”John Bolton pleaded guilty to mishandling classified information in a criminal case brought against him by President Donald Trump’s Justice Department.Michael Dwyer, File/Associated PressA grand jury indicted Bolton in October 2025 on charges that he unlawfully transmitted and retained classified documents — a charge he initially denied.The guilty plea marks the first successful prosecution to emerge from Trump’s campaign of retribution against those he perceives as political enemies.Bolton, a longtime Republican, served as an adviser for 17 months before departing the White House, but he and the president had clashed over foreign policy and Trump’s handling of global conflicts. Those tensions reached a tipping point when Bolton published his critical memoir a year after leaving his position and described Trump as “stunningly uninformed” and unfit for office. Prosecutors alleged Bolton “abused” his position and accused him of using a non-government personal email account and messaging application to transmit information to family members who may have been helping Bolton with his 2020 memoir, “The Room Where It Happened.” The indictment alleged at least eight documents contained information classified at levels ranging from “secret” to “top secret.”At the time of the charges, Bolton pushed back sharply in a statement to reporters and referred to Trump, saying, “Now, I have become the latest target in weaponizing the Justice Department to charge those he deems to be his enemies with charges that were declined before or distort the facts.”The case also carries an unavoidable irony: Trump himself was indicted in June 2023 on charges of mishandling classified national defense documents after leaving office. A Trump-appointed judge dismissed the indictment in July 2024, ruling that Jack Smith, the special counsel who obtained the indictment against Trump, had been unlawfully appointed without congressional approval.