John Bolton, former national security adviser under President Donald Trump, is expected to plead guilty on Friday to a single charge of retaining classified information. This development marks a significant shift in his criminal case, as he walks into federal court in Maryland with a stern expression.

The agreement would resolve an eighteen-count federal indictment brought against Bolton last year. He was accused of retaining and transmitting classified and sensitive materials during Trump's first term. The plea deal could allow Bolton to avoid jail time or serve five years or less, a stark contrast to the original charges which carried a maximum penalty of up to ten years per count.

Bolton is accused of sending over 1,000 "diary-like" entries to his wife and daughter between 2018 and 2019. These entries allegedly contained classified information and details from intelligence briefings and meetings with foreign officials.

This re-arraignment follows Bolton's initial plea of "not guilty" last fall, when he stated he was the "latest target" of political weaponization within the Justice Department. The investigation into Bolton's handling of classified materials reportedly continued during the Biden administration, with career prosecutors approving the charges.

Bolton previously appeared in court for his arraignment and was released on the condition that he remain within the continental United States and surrender his passport. The case against Bolton differs from other investigations into perceived political foes of the Trump administration, such as former FBI Director James Comey and New York Attorney General Letitia James, which were brought by Trump's former attorney.

President Trump has publicly criticized Bolton, calling him a "lowlife" and "not a smart guy."

Bolton's actions came under scrutiny after an FBI raid on his home in August, linked to allegations he used a private email server to transmit sensitive documents. The Friday morning FBI raid on the home of ex-National Security Advisor John Bolton was linked to allegations he used a private email server to send sensitive, classified documents Bolton, who has since turned against Trump after being fired from the White House, was home at the time of the raid. Bolton, who has since turned against Donald Trump after being fired from the White House in his first term, was home at the time of the 7:00 a.m. raid on his D.C.-area house in August, according to a source familiar

According to CNN, Bolton could pay up to $2.24 million to settle his case and avoid incarceration.