John Bolton, who served as President Donald Trump’s national security adviser, pleaded guilty Friday to one federal charge of unlawfully retaining national defense information while serving in the White House, exposing the 77-year-old to a possible prison sentence of up to 10 years.

Bolton, a longtime Republican foreign policy figure, former U.S. ambassador to the United Nations, and outspoken Iran hawk, entered the guilty plea during a brief appearance in federal court outside Washington, D.C.

The plea resolves a criminal case that began after a federal grand jury indicted Bolton last October on 18 felony counts related to the alleged retention and transmission of classified material. Had he been convicted on all counts, Bolton faced the possibility of spending the remainder of his life behind bars. Federal agents searched both his Maryland residence and his Washington office on Aug. 22, 2025, as part of the investigation.

Authorities said the searches uncovered numerous sensitive government documents, including files concerning weapons of mass destruction, internal strategy discussions, classified travel memoranda, and materials related to the U.S. mission to the United Nations.

Prosecutors alleged that Bolton used email and various messaging applications to transmit documents classified up to the “top secret” level to individuals, exposing intelligence related to prospective U.S. military operations, foreign adversaries, and sensitive diplomatic matters.

Investigators also accused Bolton of sending more than 1,000 pages of personal diary-style notes and policy assessments through his private AOL email account to two people who allegedly lacked the necessary security clearances. Those recipients are widely believed to have been his wife and daughter.

According to investigators, that information was later compromised when Iranian-linked hackers breached Bolton’s AOL account in July 2021.

Bolton has remained a target of Iranian threats since the January 2020 U.S. strike that killed Iranian military commander Qassem Soleimani.

Friday’s guilty plea brought to a close an investigation that began during the closing months of President Trump’s first administration. According to FBI sources previously cited by The New York Post, the probe was later mysteriously “shelved” during the administration of President Joe Biden.

Separately, Bolton came under scrutiny in 2020 over his handling of classified information connected to his bestselling White House memoir, The Room Where It Happened, which chronicled his 17 months as national security adviser.

At the time, the Trump administration argued that publication of the manuscript could jeopardize national security. Bolton’s legal team maintained that the book was released only after a White House National Security Council official who had worked extensively with Bolton informed him that the manuscript no longer contained classified material.

Bolton’s attorney, Abbe Lowell, also argued that many of the documents seized during the August 2025 searches had previously been reviewed and cleared through the government’s pre-publication process for The Room Where It Happened. He further contended that many of the records were decades old and stemmed from Bolton’s lengthy career in public service.