John Bolton, the former national security adviser who later became one of Donald Trump’s fiercest Republican critics, is reportedly preparing to plead guilty in a classified documents case that has drawn major political attention since last year.Former Trump administration national security adviser John Bolton arrives for his arraignment at the federal courthouse in Greenbelt, Md., Oct. 17, 2025. (AP Photo/Rod Lamkey)According to CNN, Bolton has reached a provisional agreement with federal prosecutors to plead guilty to one count tied to the unlawful retention of classified national security information.Court filings reviewed by multiple outlets show Bolton is scheduled to appear in federal court in Greenbelt, Maryland, on June 26 to formally enter a new plea in the case.The Department of Justice originally charged Bolton in October 2025 as part of a series of prosecutions involving prominent Trump critics and former officials. According to CNBC, the plea agreement could include a prison sentence of up to 60 months along with a financial penalty of more than $2 million.