GREENBELT, Md. — Former Trump administration National Security Adviser John R. Bolton pleaded guilty on Friday to illegally retaining classified information, sealing a deal with federal prosecutors that could allow him to avoid a prison term.
Bolton, who became an outspoken critic of President Trump after serving in the Republican’s first administration, 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. His plea agreement with the Justice Department may enable him to avoid time behind bars, but the judge ultimately will decide his punishment.
The plea agreement recommends capping any prison sentence at five years, but the judge isn’t bound by that part of the deal. Bolton can withdraw his guilty plea if the judge issues a longer prison sentence or a fine greater than $2.25 million.
Bolton was charged last October with 18 counts of either retaining or disseminating classified information, including diary-like notes that he shared with relatives as he wrote a memoir about his career in government.
Other Trump adversaries have been charged with federal crimes during his second term in the White House. While some of those cases have collapsed under judicial scrutiny and amid claims of political retribution, Bolton didn’t mount a vigorous defense against his charges before cutting a deal.
FBI agents searched Bolton’s Maryland home and Washington office last August, but the investigation began before Trump returned to the White House in January 2025.
Bolton served for more than a year in Trump’s first administration before getting pushed out in 2019. He later published a book called “The Room Where it Happened” that presented an unflattering portrait of Trump’s leadership.
The Trump administration fought unsuccessfully to block the book’s release, claiming 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.”
Bolton’s indictment focused on notes that he shared with his wife and daughter rather than the contents of his book. After sending one document, Bolton wrote in a message to his relatives, “None of which we talk about!!!” In response, one of his relatives wrote, “Shhhhh,” prosecutors said.
