Ex-Trump advisor turned foe pleads guilty in classified docs case — could get prison

President Donald Trump's former National Security Advisor John Bolton intends to plead guilty to Justice Department charges related to classified information cited in his book, CNN reported.

Bolton, a loud opponent of Trump's, was charged in 2025 with 18 felony counts for mishandling classified information. At the end of Trump's first administration, Bolton published a book that Trump claimed wasn't authorized and likely contained classified information in it.

CNN crime and justice reporter Katelyn Polantz said explained, "This is a man that Trump very much hates and very much wanted to see prosecuted."

Bolton was also accused of sending more than 1,000 pages of diary-like emails and encrypted app messages to his wife and daughter that contained top secret or "SCI level" classifications.

While he was charged with 18 counts, Bolton will plead guilty to one count of illegal retention of sensitive national security documents and pay a more than $2 million fine, sources told CNN.

The docket shows that Bolton's hearing is scheduled for June 26.

CNN law enforcement analyst John Miller explained that Bolton was always "caught between a rock and a hard place."

"This guilty plea is John Bolton saying, 'Let's get a recommendation from prosecutors on a sentence. Let's get a deal with the government. Let's boil this down to one count and try to get out of it,'" said Miller.

CNN legal analyst Elie Honig said that it's different from other cases in which Trump has gone after his foes in that the ones against New York Attorney General Letitia James and FBI Director James Comey are part of a political agenda.

"I think the Bolton case is entirely separate for a couple of main reasons. One, as Katelyn Polantz just told us, the reporting is that this investigation goes back to the Biden administration and predates the current Trump administration. And two, the conduct that John Bolton has been charged with and now apparently will be pleading to some of it is quite serious. It's quite straightforward."

He agreed with Miller's assessment, saying that it "is not some manufactured crime."

"John Bolton took the highest level sensitive and classified information, which he got in his capacity as a key White House adviser, and he disseminated it to others," Honig said. "That is a straightforward crime. And so I do not categorize the Bolton case along with those other cases. I think it's fundamentally different."