Trump Nemesis Reaches Plea Deal on Mishandling Classified Docs
Former national security adviser John Bolton is set to plead guilty after being indicted last year.

Photo Illustration by Elizabeth Brockway/The Daily Beast/Reuters
President Donald Trump’s former national security adviser John Bolton has reached a tentative plea deal with prosecutors over his mishandling of classified documents.
The former close Trump ally turned harsh critic of the president is expected to plead guilty to one count of illegal retention of sensitive national security documents.
The agreement was first reported by CNN and The New York Times on Thursday.
Bolton has also agreed to pay a fine in excess of $2 million. The former ambassador could face anywhere from no prison time to up to five years behind bars. Any agreement would have to be signed off by a judge.
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A notice in the Maryland federal court where Bolton was indicted last year indicated that he is now scheduled for a re-arraignment on June 26. The hearing could indicate he would plead guilty.

GREENBELT, MARYLAND - OCTOBER 17: Former U.S. National Security Advisor John Bolton leaves federal court after pleading not guilty to charges of mishandling classified material on October 17, 2025 in Greenbelt, Maryland. Bolton was indicted by a federal grand jury on Thursday. (Photo by Alex Kent/Getty Images)
Alex Kent/Getty Images
The Daily Beast has asked Bolton for comment.
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Bolton was one of several perceived political foes of Trump whom the president has targeted since returning to office.
His expected guilty plea would be the president’s greatest victory in his retribution campaign to date, as the Justice Department has launched a series of investigations and brought a series of indictments.
The Trump administration has brought charges against former FBI Director James Comey and New York Attorney General Letitia James in the past year, while Federal Reserve Chairman Jerome Powell, Federal Reserve Governor Lisa Cook, Sen. Adam Schiff, and others have all been the targets of investigations since the president returned to office.
The agreement would resolve an 18-count indictment brought against Bolton last year. He previously pleaded not guilty to charges last October.
The former national security adviser, who served in the Trump administration in 2018 and 2019, was accused of using a personal email and messaging app to share more than 1,000 pages of notes that included national security information with two family members who did not have security clearance.
At the time, Bolton was working on a memoir, The Room Where It Happened, about his time serving in Trump’s White House, which was published in 2020.

John Bolton has denied the allegations and said he looks forward to fighting Donald Trump's “abuse of power.”
Jabin Botsford/The Washington Post via Getty Images
After the FBI raided Bolton’s home last August, the president blasted his former adviser turned critic as a “lowlife” and a “sleazebag” but claimed he didn’t know anything about the probe.
He also said he did not know about the indictment last October, but called him a “bad person” and claimed “that’s the way it goes.”
While Trump himself was indicted in 2023 for retaining classified documents after leaving office, Bolton was accused not of keeping the documents but of writing diaries and sending emails that detailed his national security work.
After Bolton was indicted last year, he argued that he had become a target of weaponization by the Justice Department against Trump’s enemies and vowed to defend what he called lawful conduct and expose Trump’s abuse of power.
The White House referred all inquiries to the Justice Department. The Justice Department declined to comment.
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