Former Trump national security adviser John Bolton pleaded guilty in Maryland to one count of illegally retaining classified information, in a deal that could spare him prison time. He is scheduled to be sentenced Oct. 28 by U.S. District Judge Theodore Chuang
GREENBELT, Md. — The plea came on a Friday in a federal courtroom in Greenbelt, and for John Bolton the moment was crisp: former national security adviser Bolton pleaded guilty to illegally retaining classified information.
The case centers on a sealed agreement with federal prosecutors that could allow him to avoid a prison term, though the decision ultimately remains with the judge. Bolton is scheduled to be sentenced on Oct. 28 by U.S. District Judge Theodore Chuang in Greenbelt, Maryland.
Bolton pleaded guilty to a single count of illegally retaining classified information. The plea agreement recommends capping any prison sentence at five years. But the judge is not bound by that cap. Under the deal. Bolton retains a way out only if the judge goes further—he can withdraw his guilty plea if the court issues a longer prison sentence or imposes a fine greater than $2.25 million.
Bolton was charged last October with 18 counts involving either retaining or disseminating classified information. Prosecutors described that the allegations involved diary-like notes that he shared with relatives as he wrote a memoir about his career in government.
The indictment focused less on the contents of the published book and more on notes Bolton shared with his wife and daughter. After sending one document, Bolton wrote to his relatives, “None of which we talk about!!!” prosecutors said. In response, one relative wrote, “Shhhhh,” prosecutors said.
This is not Bolton’s first political rupture with the Trump orbit. After serving for more than a year in Trump’s first administration, Bolton was pushed out in 2019. In later years. he became one of Trump’s most outspoken critics. and he published a book titled “The Room Where it Happened” that presented an unflattering portrait of Trump’s leadership. The Trump administration had unsuccessfully fought to block the book’s release. arguing it contained classified information that could jeopardize national security. Trump derided Bolton as a “crazy” warmonger who would have led the country into “World War Six.”.
Federal investigators moved with force when the case was opened. FBI agents searched Bolton’s Maryland home and Washington, D.C., office last August. But the investigation began before Trump returned to the White House in January 2025.
Bolton, however, did not mount a vigorous defense before reaching the plea deal. Other Trump adversaries have faced federal criminal charges during his second term. and some cases have collapsed under judicial scrutiny amid claims of political retribution. In this case, Bolton cut a deal rather than pressing his fight in court.
When the sentencing date arrives on Oct. 28. the key question for Bolton will be how much room the judge leaves in a recommendation that caps imprisonment at five years—because even a single decision could determine whether the agreement holds. or whether Bolton chooses to step back from the plea entirely.
John Bolton pleaded guilty classified information Greenbelt Maryland Theodore Chuang Justice Department FBI search sentencing Oct. 28