John Bolton, the former national security adviser who became one of Donald Trump’s most vocal critics, is now expected to plead guilty in a case centered on his alleged mishandling of classified materials. The reversal marks a significant turn in a prosecution that legal observers had already flagged as unusually strong.

A Shift From Not Guilty

Bolton had initially entered a not guilty plea in the case. That stance is now poised to change, with a plea hearing scheduled for June 26, according to a spokesperson for the U.S. attorney’s office in Maryland, who declined to elaborate further.

For the moment, it remains unclear which of the charges Bolton intends to admit to. He was indicted on 18 counts of mishandling classified information, and any plea will only become official once a judge formally accepts it.

What Prosecutors Allege

The accusations trace back to Bolton’s tenure as national security adviser during Trump’s first term, spanning 2018 to 2019. Federal prosecutors say he shared more than 1,000 pages of diary-like updates detailing his sensitive work with two relatives. Those family members were reportedly helping him prepare a book that he ultimately published in 2020.

The indictment paints a troubling picture of how that information was handled. Among the central claims:

• Bolton allegedly transmitted classified material through a personal email account.
• That account was later breached by a hacker whom U.S. authorities believe was connected to the Iranian government.
• Additional sensitive materials were uncovered by FBI agents during an August search of his home in Bethesda, Maryland, and his office in downtown Washington.

The Justice Department declined to comment on the development, and news of Bolton’s plans was first reported by CNN.

A Case Standing Apart

The political backdrop adds another dimension to the story. While the investigation that produced the indictment began under President Joe Biden’s administration, the charges materialized as the Justice Department under Trump’s second term has pursued a series of cases against individuals the president views as adversaries.

Yet Bolton’s situation differs in a meaningful way. Several other attempted prosecutions of Trump’s perceived foes, including those targeting former FBI director James Comey and New York Attorney General Letitia James, have stumbled in the courts. By contrast, legal experts have characterized the case against Bolton as comparatively robust, a distinction that may help explain why it now appears headed toward a guilty plea rather than a courtroom fight.

As the June 26 hearing approaches, the key remaining questions are which specific counts Bolton will concede and what consequences a plea agreement might carry, details that will come into sharper focus only once the arrangement is presented to and accepted by the judge.