Trump’s former security adviser, to plead guilty in classified documents case, faces $2.25 million fine

John Bolton, former United States national security adviser and one of Donald Trump’s most prominent Republican critics, has agreed to plead guilty to a single felony charge related to the retention of classified information, according to multiple US media reports, including CNN and The Associated Press.

The plea agreement marks a dramatic turn in a case that has drawn intense political attention because of Bolton’s long and contentious relationship with Trump. Under the deal, Bolton is expected to plead guilty to one count of illegally retaining sensitive national security documents and pay a fine of about $2.25 million.

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A hearing has been scheduled for June 26 in federal court in Greenbelt, Maryland. Court records indicate the proceeding will be a rearraignment, a step that often signals a plea agreement.

According to reports, the agreement would resolve an 18 count indictment filed by federal prosecutors in October. Bolton had been accused of retaining and sharing classified information contained in diary style notes from his time in government, including records of intelligence briefings, discussions with foreign leaders and high level national security meetings.

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The single count to which Bolton is expected to plead guilty carries a potential prison sentence of up to five years, though the plea deal could allow him to avoid jail time. Any final sentence will be determined by a judge.

Prosecutors alleged that Bolton shared classified material with two family members through his personal email account. The indictment claimed the documents included information classified at levels as high as top secret and contained details about intelligence sources, methods and foreign adversaries.

One document reportedly related to plans for a foreign missile launch, while another included details of covert United States government operations. According to court filings, Bolton once warned his relatives after sending a document, writing, “None of which we talk about!!!” One recipient allegedly replied, “Shhhhh.”

Federal prosecutors said Bolton shared more than a thousand pages documenting his daily activities while serving in government. However, the alleged transmission of classified information is not part of the charge to which he is expected to plead guilty.

The case stems from notes Bolton kept during his tenure in the first Trump administration, where he served as national security adviser from 2018 until his departure in 2019 following policy disputes with the president over issues including Iran, North Korea and Ukraine.

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Bolton later became one of Trump’s most outspoken critics. His 2020 memoir, The Room Where It Happened, offered a highly critical account of the administration and sparked a fierce legal battle after the Trump administration unsuccessfully sought to block its publication over concerns that it contained classified information.

The current plea agreement does not relate to information published in the book. Instead, it focuses on diary entries and notes that prosecutors said were shared with relatives.

Following his indictment, Bolton accused Trump of using the justice system to target political opponents. He described the prosecution as part of what he called an “intensive effort” by Trump to intimidate critics and control public discussion of his presidency.

The investigation itself has spanned multiple administrations. Trump’s first Justice Department opened criminal and civil inquiries into Bolton’s memoir in 2020 before those investigations were closed. A separate FBI inquiry was launched during Joe Biden’s presidency after suspected Iranian hackers breached Bolton’s email account.

Investigators subsequently discovered what prosecutors described as diary like entries containing classified information.

While the case unfolded amid broader concerns over politically charged prosecutions, AP reported that unlike some other investigations involving Trump adversaries, the Bolton case retained the backing of career prosecutors and investigators.

A formal plea is expected later this month, bringing the long running case against one of Washington’s most influential foreign policy figures closer to its conclusion.