John Bolton Pleads Not Guilty to Charges of Mishandling Classified Documents

John R. Bolton, the former national security adviser to President Trump who became one of his most outspoken critics, pleaded not guilty on Friday to charges he had mishandled classified information while a top White House aide.

Mr. Bolton appeared in federal court in Greenbelt, Md., a day after he was indicted by a grand jury.

The presiding judge, Timothy J. Sullivan, set two conditions to Mr. Bolton’s release, requiring him to hand over his passport to his lawyer, Abbe Lowell, and limiting his travel to the continental United States.

The 18-count indictment against Mr. Bolton accused him of using personal email and a messaging app to share more than 1,000 pages of “diary” notes about his day-to-day activities as Mr. Trump’s national security adviser in 2018 and 2019. The notes, which were sent to two family members who did not have security clearances, included national defense information, such as details classified as top secret, according to the indictment.

While Mr. Bolton is part of a string of perceived enemies of the president to become prosecutorial targets, the federal investigation into him gained momentum during the Biden administration, when U.S. intelligence agencies gathered what former officials have described as troubling evidence.

The prosecution appeared to follow normal department channels. Kelly O. Hayes, the U.S. attorney in Maryland, was among the career prosecutors to sign off on the charges in conjunction with the Justice Department’s national security division.

By contrast, Mr. Trump in recent weeks has removed or sidelined prosecutors in order to secure indictments against two of his longtime targets: James B. Comey, the former F.B.I. director, and Letitia James, New York’s attorney general.

If convicted of the charges, Mr. Bolton, 76, could spend the rest of his life in prison. Each count carries a maximum potential sentence of 10 years.