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 potentially face time in prison for his actions.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.