John R. Bolton, a national security adviser to President Trump in his first term, has reached a tentative deal with prosecutors to plead guilty to mishandling classified information when he compiled notes for a book that was harshly critical of the president, according to two people familiar with the matter.
A notice in Maryland federal court, where Mr. Bolton was indicted last year, indicates he is now scheduled for a re-arraignment — a hearing that can signal a planned guilty plea. The hearing is set for June 26.
Under the terms of the plea deal, which still requires approval from a judge, Mr. Bolton plans to plead guilty to a single count of illegal retention of classified information and pay a fine, facing anywhere from no prison time to five years of incarceration when he is sentenced, according to the people familiar with the negotiations, who spoke on condition of anonymity because they were not authorized to discuss them. If Mr. Bolton had gone to trial and lost, he could have faced decades in prison.
The plea would provide President Trump perhaps his most significant victory in his campaign to prosecute his perceived enemies, which so far has largely foundered once cases hit the courts.
But the case against Mr. Bolton, who has emerged as a persistent critic of Mr. Trump since leaving the administration in 2019, was always different from others that Mr. Trump has pushed the Justice Department to prosecute. The investigation into him was also pursued and gained momentum under the Biden administration, when U.S. intelligence agencies gathered what former officials have described as troubling evidence.
A Justice Department spokesperson declined to comment.
The original 18-count indictment against Mr. Bolton accused him of using personal email and a messaging app to share more than 1,000 pages of notes, which included national defense information, with two family members who did not have security clearances.
The information was shared as part of Mr. Bolton’s effort to write a memoir of his time in the first Trump White House. Those relatives were Mr. Bolton’s wife and daughter, according to people familiar with the matter. They spoke on the condition of anonymity to describe details of the case that were not in court filings.
After his indictment, Mr. Bolton said he was being treated unfairly by an administration determined to use the justice system to silence the president’s critics. His lawyer, Abbe Lowell, said the issues in the case had been investigated years ago and had not been deemed worthy of criminal charges.
The indictment charged that as he wrote notes for his 2020 book, “The Room Where It Happened,” Mr. Bolton indicated that he knew he was describing carefully guarded government secrets. One entry by Mr. Bolton began, “The intel briefer said,” while another read, “While in the Situation Room, I learned.”
The Trump administration fought unsuccessfully to prevent the publication of Mr. Bolton’s book. The criminal investigation ultimately focused not on what was in the published manuscript, but what Mr. Bolton had written in private notes.
Unlike some other investigations involving classified information, including charges filed in 2023 against Mr. Trump, Mr. Bolton was not accused of retaining the secret documents themselves, but rather of keeping diaries and sending emails that mentioned details of his daily work in national security.
Mr. Bolton’s emails, however, were later hacked by someone associated with the government of Iran, the indictment said.
“A representative for Bolton notified the U.S. government of the hack in or about July 2021, but did not tell the U.S. government that the account contained national defense information, including classified information, that Bolton had placed in the account from his time as national security adviser,” according to the filing.
One surreal section of the indictment described Mr. Bolton apparently being taunted by his hacker. A message on July 25, 2021, warned, “I do not think you would be interested in the F.B.I. being aware of the leaked content of John’s email (some of which have been attached).” The email went on to declare, “This could be the biggest scandal since Hillary’s emails were leaked, but this time on the G.O.P. side! Contact me before it’s too late.”
A representative for Mr. Bolton forwarded the email to the F.B.I.
CNN reported the plea deal earlier.
