ToplineFormer Trump national security adviser-turned-nemesis John Bolton has reportedly agreed to plead guilty to mishandling classified documents from his time working in the first Trump administration—a rare win for President Donald Trump in his retribution campaign against his enemies after mostly failed cases.Former National Security Advisor John Bolton attends the Copenhagen Democracy Summit at the Royal Danish Playhouse on May 12, 2026. (Photo by Liselotte Sabroe / Ritzau Scanpix / AFP via Getty Images)Ritzau Scanpix/AFP via Getty ImagesKey FactsBolton will plead guilty to illegal retention of classified information and pay a fine, multiple outlets reported Thursday, citing unnamed sources. The fine is more than $2 million, CNN reported, and the charge carries a sentence of up to five years in prison.Bolton was charged with 18 counts alleging he kept 1,000 pages of notes, including classified information, chronicling his work in Trump’s White House and reportedly shared them with his wife and daughter.While Bolton has alleged he is Trump’s “latest target in weaponizing the Justice Department” against his enemies, the Bolton investigation is different from some of the other efforts against Trump’s political foes. Trump’s first Justice Department initiated investigations into Bolton, and while prosecutors under President Joe Biden dropped the cases, they opened a new probe when Bolton’s email was broken into by suspected Iranian hackers. What To Watch ForBolton, who initially pleaded not guilty in the case in October, is scheduled for a hearing in the case on June 26.TangentAlmost all of the Trump administration’s attempts to prosecute his allies have failed. A case accusing New York Attorney General Letitia James of criminal mortgage fraud was dismissed by a judge, and several other similar mortgage fraud accusations against Trump enemies have yet to amount to criminal charges. The Trump DOJ’s initial case accusing former FBI Director James Comey of lying to Congress was dismissed, and the Justice Department brought a subsequent case against him accusing him of threatening Trump by posting an image to social media of sea shells arranged to spell “86 47.” The pending case has been widely panned on both sides of the aisle. A case accusing six Democratic lawmakers of anti-subordination for a video urging military members to disobey illegal orders also failed when a grand jury declined to indict them. Key BackgroundBolton allegedly kept the notes for his 2020 book, “The Room Where It Happened,” and made references suggesting he knew some of the information was classified, according to the indictment against him. Trump’s first administration tried to block his book from being released, then filed a lawsuit to stop him from collecting the proceeds, before ultimately opening the criminal investigation into his handling of classified documents. Bolton and Trump have regularly traded barbs since Bolton left the Trump administration in 2019 (Bolton said he resigned and Trump said he was fired). Bolton described Trump as “stunningly uninformed” in his book and criticized Trump for meeting Russian President Vladimir Putin in Alaska in August. Trump revoked Bolton’s security clearance and canceled his security detail after taking office last year, telling reporters Bolton is a “very dumb person” in explaining the decision. further readingJohn Bolton—Ex-National Security Advisor—Becomes Third Trump Foe Indicted (Forbes)John Bolton Pleads Not Guilty—Here’s Why His Charges Are More Serious Than Other Trump Foes (Forbes)FBI Raids Trump Critic And His Former National Security Adviser John Bolton’s Home And Office (Forbes)