John Bolton to plead guilty to mishandling classified documents
Former national security adviser John Bolton is expected to plead guilty in a Maryland federal court to mishandling classified information as part of a plea deal. He faces charges of illegally retaining sensitive documents and paying a $2.25 million fine. Bolton, who served from 2018 to 2019, was investigated over the mishandling of classified material spanning two administrations, after hackers revealed that he kept highly classified journal entries and personal notes, some shared with his family via personal email accounts.He was indicted in October 2025 for possessing, transmitting, and distributing classified documents categorized as “secret” and “top secret,” including over 1,000 pages of personal records. Bolton has been a frequent critic of Trump, writing a memoir about his tenure and publicly exchanging barbs with the former president, who also criticized Bolton, describing him as a “lowlife” and accusing him of wanting to go to war indiscriminately. Trump remarked that Bolton was involved in creating problems related to war and accused him of criminal behavior for mishandling classified information.
Former national security adviser John Bolton is expected to plead guilty to mishandling classified information in a federal court in Maryland on Friday. The move comes as part of a plea deal agreed to earlier this month, as the Washington Examiner previously reported. Bolton is expected to plead guilty to one count of illegally retaining sensitive documents and pay a $2.25 million fine, according to multiple sources.
Bolton’s violations come after he served as national security adviser from 2018 to 2019. The investigation of his mishandling of classified information spanned two presidential administrations, starting in the first Trump administration and lasting into the Biden administration, after hackers, believed to be Iranian, accessed Bolton’s email account, revealing that Bolton wrote private journal entries that contained highly classified information while he was national security adviser. The New York Times reported he could possibly face time in prison for his actions.
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A grand jury indicted Bolton in October 2025 for the discovery of his journal entries, private notes, and other classified material from his time as national security adviser. He was accused of illegally possessing and transmitting classified national defense information, sharing over 1,000 pages of his personal records over a personal email account to unauthorized people who are believed to be family members, specifically his wife and daughter.
He was charged with eight counts of transmission and 10 counts of retaining classified national defense information. The classified materials he possessed and distributed were reportedly categorized at the “secret” and “top secret” levels, according to multiple sources.
Bolton’s time in the Trump administration was short-lived, but he has feuded with the president throughout Trump’s two separate terms. Bolton wrote a book, The Room Where It Happened, in 2020 about his time as national security adviser during Trump’s first term. Trump criticized Bolton and accused him of violating laws for allegedly disclosing classified information in the book.
Since his time at the NSA, Bolton has been a regular critic of Trump, offering commentary on a variety of things stemming from his mannerisms, temperament, and policy decisions. Trump has also criticized Bolton, calling him a “lowlife” and questioning his intelligence. He also claimed Bolton wanted to “go to war with everybody.”
“Well, I was never much of a fan of John Bolton,” Trump said earlier in June. “I never thought he was a smart person, that he was a radical right in terms of war, not in terms of other things. He was. He wanted to go to war with anybody that opened their mouth, anybody that talked, and I used him for a purpose, you know.”
“He was involved with [George W. Bush], and he created a lot of problems, but he always wanted to kill people in war, and that was okay for me, as long as I didn’t listen to him, which I never did,” Trump said.
“He’s a, he’s a bad guy, John Bolton, he’s a dirty guy, and we caught him, and then we caught him, and you know, he wrote a book,” Trump said. “You look at all the information he took, I mean, if you look at that case, it’s a great honor to have helped from the standpoint of encouragement.”
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