John Bolton, President Trump’s former national security adviser turned sharp critic, returned to a federal courtroom today to plead guilty on a national security-related charge, marking the latest chapter in Trump’s apparent retribution tour against his political foes. 

Bolton had previously pleaded not guilty to charges related to mishandling classified information. But Bolton reached a plea deal with federal prosecutors at the end of May that would see him plead guilty to a single felony count of retaining classified information.

When asked if it was his intention to plead guilty, Bolton responded, “I am, your honor, and I’m very sorry for that.”

U.S. District Judge Theodore Chuang set a sentencing hearing for October 28. Bolton is facing up to five years in jail and a $2.25 million fine, per the terms of the plea agreement.

U.S. Attorney Kelly Hayes, who attended the arraignment, would not comment when asked if the government will seek prison time.

The single guilty count of keeping classified information in a private diary entry marks a significant reduction in the severity of charges against Bolton. He had been facing 18 counts of retaining and leaking national defense information after he was indicted by a federal grand jury last October. 

The 26-page indictment charged Bolton with illegally retaining national defense information, including some labeled “top secret,” in his home and transmitting it by using personal email and messaging accounts.

The plea deal resolves a massive indictment that threatened Bolton with millions of dollars in legal fees and decades in prison. In MS NOW’s earlier reporting of the expected plea deal, sources said Bolton is not admitting to leaking classified information to the media or a foreign government, and that the only people who were exposed to the state secrets were his wife and daughter.

Bolton had served as Trump’s national security adviser before becoming a frequent and sharp critic of the president. He was viewed as an early target of Trump’s campaign to weaponize the Justice Department against his political enemies. 

The case against Bolton was brought around the same time as some of the Trump DOJ’s cases against other perceived enemies, including Former FBI Director James Comey and New York Attorney General Letitia James. But the case against Bolton has always been deemed more serious than those against the president’s other targets for prosecution. 

Last August, the FBI executed a search warrant at Bolton’s home in Maryland. During that search, agents seized both electronic and printed copies of Bolton’s diary entries, which allegedly included classified information. He was accused of keeping and sharing more than 1,000 pages of that classified information.

The Bolton case was also brought by a respected career prosecutor, Thomas Sullivan, who runs the national security unit in the Maryland U.S. attorney’s office. Both the original case against Comey and the only case successfully brought against James were presented by Lindsey Halligan, a Trump ally and former insurance attorney who had been acting as the interim U.S. attorney for the Eastern District of Virginia. She was later declared unlawfully appointed, resulting in the dismissal of those two cases. 

Though the indictment was returned last October, Bolton’s case was progressing slowly due to the significant amount of highly classified material. U.S. District Judge Theodore Chuang, who was presiding over the case, had not even set a trial date yet. 

The plea deal marks a victory of sorts for both Bolton and Trump. For Bolton, the deal liberates him from the significant prison time he would have faced upon conviction, as well as the piling legal fees as the case continued. For Trump, the deal marks the first successful conviction by his DOJ against one of his perceived political enemies.

This article has been updated to reflect Bolton’s plea and additional details from his court appearance

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