GREENBELT, Md. -- John Bolton, a national-security adviser to President Trump during his first term, pleaded guilty Friday to mishandling classified information when he collected notes for a memoir that painted an unflattering portrait of the president and his White House.

Bolton, 77 years old, had agreed earlier this month to plead guilty to a single count of unlawfully retaining national-defense information, as part of a deal with prosecutors in which he also agreed to pay a $2.25 million fine. Under the deal's terms, he faces up to five years in prison at sentencing but could receive considerably less time in custody, or none at all.

The plea deal also directs Bolton to conduct 100 hours of community service, at the direction of the Justice Department, to help with issues related to the unlawful handling and disclosure of classified information.

Bolton formally entered his guilty plea during a nearly hourlong hearing in federal court in Maryland. Judge Theodore D. Chuang scheduled his sentencing for Oct. 28. When the judge asked Bolton if he was entering the plea because he was, in fact, guilty, Bolton responded: "I am, your honor," adding he was "sorry for it."

When Bolton was initially charged last year, his criminal case added to a string of prosecutions the Trump administration was bringing against the president's perceived political enemies, including New York Attorney General Letitia James and James Comey, a former director of the Federal Bureau of Investigation.

Bolton's plea provides Trump with perhaps the most significant win in that crusade, which has otherwise fallen flat with dismissed charges and grand juries refusing to sign off on some indictments.

Bolton characterized his prosecution as part of an effort to intimidate Trump critics, saying at the time that he looked forward to exposing "his abuse of power." While the case came against the backdrop of the president's attacks, it stood apart from the prosecutions of other prominent Trump critics in that it arose out of a longer, more conventional investigation that had gathered steam under the Biden administration, and career prosecutors viewed it as on firmer footing.

In an 18-count indictment last year, prosecutors alleged that Bolton shared more than 1,000 pages of diarylike dispatches to two relatives -- identified by people familiar with the investigation as his wife and daughter -- in preparation for his memoir published in 2020, "The Room Where It Happened."

Bolton pleaded guilty to a single unlawful retention charge relating to a document that, according to the indictment, revealed intelligence about an adversary's knowledge of planned U.S. actions, a covert action program and "human intelligence using sensitive sources and methods." The document also contained intelligence collected on the leader of an adversary nation's military group, according to the indictment.

The indictment indicated that classified information might have been exposed when Iranian hackers got into Bolton's personal email account and gained access to the material he had shared. Prosecutors portrayed Bolton as driven by his eagerness to memorialize his day-to-day life in Trump's first term.

If Bolton had gone to trial and lost, he could have faced decades in prison on those alleged offenses, including charges that he transmitted national-defense information. With the plea deal, Bolton has substantially lowered his potential sentence by avoiding a conviction on the more serious charge of transmitting national-defense information and admitting only to a single count of unlawful retention, legal experts said.

Bolton's case added to the Justice Department's history prosecuting the alleged mishandling or sharing of sensitive national-security information, under a 1917 law called the Espionage Act. While the Justice Department has brought many lower-profile cases against current and former government officials accused of mishandling sensitive information, investigations involving current and former presidents and other top government officials have garnered national attention and thrust the Justice Department into the political spotlight in recent years.

For the Justice Department, the plea deal headed off the risks of a high-profile trial that would have been complicated by what prosecutors view as the paradox of cases like the one against Bolton: The need to prove charges can highlight or further expose the same classified information that was allegedly mishandled.

Bolton's agreement to pay a significant fine could lessen his prison time, or spare him from a term behind bars altogether, when Chuang sentences him, legal experts said.

"It's a recognition that a custodial sentence is realistic," said James Melendres, a former national-security prosecutor. "It's on the table."

Write to C. Ryan Barber at ryan.barber@wsj.com

(END) Dow Jones Newswires

June 26, 2026 10:57 ET (14:57 GMT)

Copyright (c) 2026 Dow Jones & Company, Inc.