John Bolton, a former national security adviser for United States President Donald Trump who has since become one of his fiercest critics, pleaded guilty in federal court on Friday to mishandling classified information and faces up to five years in prison.

“I’m sorry for it,” Bolton told US District Judge Theodore D. Chuang during the hearing.

Reuters previously reported that Bolton would plead guilty under a deal with prosecutors that included a sentencing range from no prison time to as many as five years behind bars, with the final sentence to be determined by a judge.

As part of the agreement, Bolton agreed to pay a $2.25 million fine. Bolton, 77, must make half that payment within five days of sentencing and the full payment within 90 days of sentencing.

He also committed to up to 100 hours of community service and to meet with intelligence and Justice Department officials for a debriefing. Bolton will also forfeit his government pension.

Chuang scheduled sentencing for October 28.

Bolton is accused of sharing sensitive information with two relatives for possible use in a memoir he was writing, including notes on intelligence briefings and meetings with senior government officials and foreign leaders. Prosecutors said he shared more than 1,000 pages in the form of diary entries. He pleaded not guilty to 18 criminal charges last year.

The book detailed Bolton’s tenure as Trump’s national security adviser during his first term. In the book, Bolton described the president as unfit for office, sparking a public feud. But prosecutors said on Friday that no classified information was published in Bolton’s book, The Room Where It Happened.

Authorities said Bolton’s personal email was hacked by someone believed to be linked to Iran, which prosecutors reiterated on Friday.

Kelly O. Hayes, the US attorney for the district of Maryland, told reporters after the hearing that that was exactly why it was dangerous to share classified information on personal accounts.

“He put our national security at grave risk,” she said of Bolton.

Bolton, who served as national security adviser during Trump’s first term in office, is one of several notable political opponents who have faced prosecution from Trump’s Justice Department, erasing longstanding norms that had separated law enforcement efforts from partisan considerations.

But unlike other cases brought against Trump critics, the Bolton investigation began before Trump returned to office in 2025 and had the backing of career federal prosecutors.