John Bolton, President Donald Trump’s former national security adviser and later one of his most prominent Republican critics, pleaded guilty Friday in federal court in Greenbelt, Maryland, to illegally retaining classified information, resolving a case that had placed him at the center of another Washington fight over classified material. AP reported that sentencing is scheduled for October 28.
Bolton’s classified-information case is no longer about proving 18 separate counts at trial but how US District Judge Theodore Chuang weighs one admitted felony against a plea deal that could spare the former national security adviser from prison.
The financial penalty is unusually large for a classified-information plea. Reuters reported that Bolton agreed to pay a $2.25 million fine, with half due within five days of sentencing and the full amount due within 90 days. Reuters also reported that the deal requires up to 100 hours of community service, debriefings with intelligence and Justice Department officials, and forfeiture of his government pension.
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AP reported that the agreement recommends capping any prison term at five years, although Chuang is not bound by that recommendation. Bolton may withdraw the plea if the sentence exceeds five years or if the fine rises above $2.25 million.
Bolton, 77, told Chuang, “I’m sorry for it,” Reuters reported from the hearing.
The plea deal ends the immediate trial risk for both sides. The Justice Department said in October 2025 that a federal grand jury had charged Bolton with eight counts of transmission of national defense information and 10 counts of unlawful retention. The department alleged that he used personal email and messaging accounts to transmit sensitive documents classified as high as Top Secret, and that he retained national defense information at his home.
The indictment stage carried much heavier theoretical exposure. The Justice Department said each unlawful retention count and each transmission count carried a maximum penalty of 10 years in prison if convicted.
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The central tension in the case was not simply that Bolton wrote a memoir. It was how prosecutors said he handled notes and material connected to his time inside the national security apparatus.
AP reported that the charges involved diary-like notes Bolton shared with relatives while preparing a memoir about his career in government. Reuters reported that Bolton was accused of sharing sensitive information with two relatives for possible use in the memoir, including notes on intelligence briefings and meetings with senior US officials and foreign leaders.
That distinction matters. Reuters reported that prosecutors said Friday no classified information was published in Bolton’s 2020 book, The Room Where It Happened. The criminal case therefore centered on retention and transmission conduct, not on the publication of classified material in the book itself.
Bolton’s book was a flashpoint in his break with Trump. AP reported that the Trump administration unsuccessfully tried to block its release and argued it contained classified information that could endanger national security.
Bolton became an outspoken Trump critic after leaving the first Trump administration in 2019. AP reported that other Trump adversaries have faced federal charges during Trump’s second term, some of which have collapsed under judicial scrutiny and amid claims of political retribution.
But Reuters reported that the Bolton investigation began before Trump returned to office in 2025 and had the backing of career federal prosecutors. AP also reported that FBI agents searched Bolton’s Maryland home and Washington, DC, office in August, while noting that the investigation predated Trump’s return to the White House.
The Justice Department’s original statement framed the case around national security, not memoir politics. Prosecutors alleged that the material involved intelligence about future attacks, foreign adversaries, foreign-policy relations, adversary leaders, and intelligence sources and collection methods.
Reuters reported that authorities said Bolton’s personal email was hacked by someone believed to be linked to Iran, a point prosecutors reiterated Friday.
