• John Bolton plans to plead guilty to retaining classified information.
• He faces a $2.25 million fine and potentially a prison sentence capped at five years.
• The charges stem from his sharing of sensitive information with family members during his tenure as national security adviser.

John Bolton, former national security adviser under President Trump, is set to plead guilty to one count of retaining classified national security information, thereby resolving a criminal case in which he was originally indicted on 18 counts. Bolton's plea agreement comes as he prepares to pay a fine of $2.25 million, and it could allow him to avoid prison time altogether, according to multiple sources, including CBS News, India Times, and Reuters.

Scheduled for June 26 in a federal court in Maryland, Bolton's plea hearing will formally address his handling of sensitive information, which he reportedly shared in "diary-like" entries with two family members while preparing a memoir. Although he initially pleaded not guilty to the broader charges last year, the specific allegations involved sharing over 1,000 pages of previously classified information related to intelligence briefings, meetings, and government discussions, as noted by Los Angeles Times and South China Morning Post.

Federal prosecutors allege that Bolton's communications included sensitive matters such as foreign military activities and intelligence sources, underscoring the seriousness of the charges against him. While he had been originally charged with various counts of disseminating classified information, the plea will focus on his retention and mishandling of specific documents, aligning with prosecutors' claims that he improperly utilized personal email accounts for these communications, according to CBS News, India Times, and Reuters.

Bolton served as national security adviser from 2018 to 2019 and became known for his hawkish stance on foreign policy. His turbulent relationship with Trump deepened after he published a memoir critical of the president, which raised further scrutiny over his handling of classified material during and post-tenure. This ongoing investigation had notably resurfaced during the Biden administration following breaches involving Bolton's email account, leading to renewed legal action against him, as detailed by Los Angeles Times, South China Morning Post, and Reuters.