Donald Trump's former national security advisor turned nemesis, John Bolton, is expected to plead guilty to mishandling classified documents. Bolton, 77, intends to plead guilty to a single count of illegal retention of sensitive national security documents, sources told CNN. Bolton was indicted last year on 18 counts related to mishandling classified material. Bolton has agreed to pay a $2 million fine as part of the deal, according to one of the sources. One count of illegally retaining documents can land him in prison for up to five years. The deal comes after Bolton was charged with allegedly keeping classified material at his Bethesda, Maryland, home. 

Prosecutors allege he withheld 'more than a thousand pages of information about his day-to-day activities.' He used his personal email account to share the sensitive materials with two unauthorized individuals. According to CNN, those individuals were his wife and daughter. Bolton was initially charged with 18 counts: eight counts for transmission of national defense information and 10 for retention of national defense information. The original 18-count indictment alleged that Bolton used his personal email and a messaging app to circulate over 1,000 pages of notes, including sensitive information.

He is scheduled to appear for a hearing on June 26, according to court documents. Bolton, who worked for Trump during his first term from 2018 to 2019, was unceremoniously fired via social media after having policy disputes over Iran, North Korea and Afghanistan. Less than a year after his firing, Bolton released a tell-all book about his time in Trump's administration, titled 'The Room Where It Happened.' The memoir was highly critical of the President, and Trump slammed Bolton as a 'washed up creepster' around the time it was published in June, 2020.

'Washed up creepster John Bolton is a lowlife who should be in jail, money seized, for disseminating, for profit, highly classified information,' Trump wrote. The President also gave multiple interviews at the time, in which he doubled down on calls to imprison Bolton. 'He released massive amounts of classified, and confidential, but classified information. That's illegal and you go to jail for that,' Trump said during a 2020 Fox News interview.

The Department of Justice under Trump's first term opened criminal and civil probes into Bolton over the book in 2020, but the inquiries were halted within a year. The DOJ under Joe Biden later opened a new inquiry into Bolton the following year. Bolton's reported plea deal marks a victory for the Trump administration's efforts to prosecute its political opponents. Trump has also pursued cases against his first-term FBI Director James Comey for alleged threats and lying to Congress; New York Attorney General Letitia James, who sued the President; and Democratic Senator Adam Schiff, who led an impeachment inquiry against Trump.