Former U.N. Ambassador John Bolton has reportedly agreed to plead guilty to mishandling classified documents in a bid to avoid jail time.

Bolton would also be subject to a $2.25 million fine in a plea deal in which the government has agreed not to seek jail time, Reuters reported.

Bolton, 77, who served as national security adviser for President Donald Trump, is expected to plead guilty to one felony count of illegal retention of sensitive national security information, three sources familiar with the matter told the wire service.

A hearing is scheduled June 26 for Bolton to change his plea before a U.S. District Court judge in Maryland, according to a spokesperson for the U.S. attorney’s office.

While prosecutors can recommend punishment such as fines and supervision in lieu of jail time, ultimately the judge decides the sentence, which could include a maximum of five years in prison.

Bolton had pleaded not guilty to the charges in October 2025.

The plea deal represents a dramatic reversal for Bolton, who had loudly proclaimed his innocence after federal agents raided his Maryland home and Washington office in August 2025.

“These charges are not just about his focus on me or my diaries, but his intensive effort to intimidate his opponents, to ensure that he alone determines what is said about his conduct,” Bolton said at the time of his not guilty plea about Trump. “Dissent and disagreement are foundational to America’s constitutional system, and vitally important to our freedom. I look forward to the fight to defend my lawful conduct and to expose his abuse of power.”

The media, including panels at CNN, largely agreed with Bolton’s assessment.

Bolton’s lawyer, Abbe Lowell, insisted the underlying facts were investigated and resolved “years ago,” before Trump returned to the Oval Office.

The diary entries at the heart of the case were “unclassified, shared only with his immediate family,” the attorney said.

According to the indictment, Bolton regularly transmitted diary-like entries to two family members, neither of whom ever held a security clearance, containing information classified up to the Top Secret/SCI level.

Secrets revealed included covert U.S. government actions, intelligence about planned foreign missile launches, human intelligence sources and methods, and intercepted communications from adversary nations.

The former ambassador and national security adviser sent the documents through personal AOL and Google email accounts and a commercial messaging app, none of which were authorized for classified material.

The Department of Justice indictment charges eight separate transmission counts and an additional 10 counts of unauthorized retention of national defense information.

In total, prosecutors allege more than 1,000 pages of top-secret material flowed out through Bolton’s personal devices to unauthorized recipients.

The case took a turn when prosecutors revealed that between 2019 and 2021, Bolton’s email account was hacked by a cyber actor believed to be associated with Iran, a regime against which Bolton spent decades advocating military action.

“A representative for Bolton notified the U.S. Government of the hack in or about July 2021, but did not tell the U.S. Government that the account contained national defense information, including classified information, that Bolton had placed in the account from his time as National Security Advisor,” the indictment reads. “Nor did Bolton’s representative tell the U.S. Government that Bolton had shared some of that national defense information, including classified information, with Individuals 1 and 2 via personal email and a nongovernmental messaging application.”

Comparisons of the Bolton case have been made to the case of Gen. David Petraeus.

Petraeus pleaded guilty in 2015 to a single misdemeanor count for sharing diary materials with a biographer. Petraeus was levied a $100,000 fine after a judge increased the Department of Justice’s initial request of $40,000.

The escalation reflects both the volume of material involved and the deliberate posture of a Department of Justice that has made accountability for mishandling classified information a consistent priority.

The stepped-up enforcement comes after several high-profile cases regarding the handling of classified material by government officials, including cases involving Trump and former Secretary of State Hillary Clinton.

In his book, Bolton warned voters during the 2024 election cycle that Trump was “unfit to be president.”

“Trump really cares only about retribution for himself, and it will consume much of a second term,” the former Trump adviser wrote, according to Reuters.

The Bolton investigation was launched prior to Trump’s return to the White House in January 2025 and was pursued with the support of career federal prosecutors, the wire service said.

A request for comment from The Lion sent to Bolton’s representative was not returned before publication.