John Bolton, the former national security adviser to President Donald Trump who later became one of Trump’s most vocal critics, is expected to plead guilty Friday in federal court in Greenbelt, Maryland, to one count of illegally retaining sensitive national security information.
The charge relates specifically to diary entries Bolton kept during his work in Trump’s first term. The former adviser was accused of transmitting some of those materials to two relatives. As part of the plea agreement, Bolton will pay a $2.25 million fine, according to sources familiar with the deal.
In October 2025, Bolton pleaded not guilty to charges of mishandling classified information. A person close to Bolton, speaking to NBC, described the decision to change his plea as a difficult one.
“This was a very difficult decision for him,” the source said. “Most importantly, he is doing what leaders do and taking responsibility.”
The source added that Bolton understood the consequences of proceeding to trial.
“He understands that if he went to trial what that would mean, which essentially would be the disclosure of many, many more classified documents that he would need to reveal to defend himself,” the source said. “And given the Ukraine and the Middle East, he didn’t want to do that.”
Bolton served as Trump’s national security adviser from April 2018 to September 2019. After leaving the administration, he became one of Trump’s most prominent Republican critics, writing a memoir about his time in the White House that drew Trump’s ire.
A possible sentence for Bolton could range from no jail time to up to five years in prison. The exact sentence will be determined by the presiding judge.
MSI previously reported that Bolton had agreed to plead guilty to retaining classified documents and pay a fine exceeding $2 million, in an article published June 4, 2026. Read that report.