John Bolton, a frequent media commentator and critic of Donald Trump who once served as his national security adviser, plead guilty on Friday to one count of retaining national defense information.

Bolton entered the plea in federal court in Maryland.

The plea agreement calls for Bolton to pay a $2.25 million fine and for a sentence of no more than 60 months in prison. Sentencing is scheduled for Oct. 28. He had been charged with 18 counts related to the retention and transmission of sensitive information.

Last year, an FBI raid of Bolton’s Bethesda, MD home was a cable news sensation, coming as the Trump administration was threatening some of his president’s foes, including former FBI director James Comey.

But in Bolton’s case, prosecutors’ allegations stretched all the way back to when he was preparing his memoir, The Room Where It Happened, in 2019. They alleged that Bolton sent “diary-like” entries to relatives that contained information marked classified.

Bolton served as Trump’s national security adviser from 2018 to 2019.

In 2020, after Bolton left the Trump administration and published his book, the Justice Department sued over its publication. Federal officials claimed that Bolton failed to complete a review process to edit out classified information. But the DOJ dropped the lawsuit the following year.

Bolton has continued to provide commentary to media outlets even as he faced the guilty plea. That included a commentary in The Wall Street Journal criticizing Trump as he has worked toward a deal to end the war with Iran. He appeared on NewsNation on Wednesday.