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Ex-President Donald Trump has repeatedly shown his wish to see opponents investigated, applying pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our standing and trustworthiness," the president wrote recently in a Truth Social message.

"They impeached me, and charged me (5 times!)" he said, referencing the multiple legal proceedings he faced after leaving the White House in 2021 and James's civil case.

Both have since been charged, in situations that many specialists have stated seem to be driven by politics and challenging to succeed in court.

But the most recent charges against a Trump critic, ex security advisor John Bolton, stand apart, legal experts and ex-prosecutors say.

"I would say, comparing Bolton's case to Comey's is like comparing apples to oranges," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Specifics of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. After departing the White House in 2019, he has emerged as a vocal Trump critic, even to call him "remarkably ignorant" and unsuitable for office in his book.

Experts contend that while there may be political motivations to target Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a potentially more substantial legal argument than the Justice Department brought against James.

"This misconduct that's being claimed is simultaneously more severe and seems to have taken place over a considerable duration," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton placed the nation at risk by wrongfully keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were labeled highly classified.

The charge alleges that at a certain time a hacker gained access to Bolton's system where documents were stored and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on recently to eighteen separate charges of improperly handling classified information.

Political Motivation or a Substantial Case?

The schedule of his indictment - arriving on the heels of charges against James - has revived concerns about political pressure on the legal system.

Trump previously implied Bolton should be in jail, and called him a "disreputable person". Bolton, for his role, authored a book about his experience in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this charge, when paired with others, has prompted questions about the validity of these charges, and the reason these charges are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is capable to demonstrate the allegations alleged and demonstrate the information is correctly designated, his conduct may certainly have violated the law".

Prosecuting such a senior figure for mishandling sensitive materials is "rare" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information present challenges to prosecute, but they can and are filed against equally junior and senior officials, from occasionally," she explained.

Similarities to Examinations into Former President and Biden

Trump similarly encountered allegations of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was eventually dismissed by a court official and voided by his re-election as president.

A special counsel also determined that former President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Biden's classified documents issues, said Mr Lesko, who also held a top national security position at the Justice Department.

Strict procedures govern the management of sensitive materials. To win a guilty verdict, the government must demonstrate that Bolton knew the material he was sending was classified, and he had to knowingly transfer it to someone without authorization to receive it.

"Due to the classified character of the material at question in this matter, we lack a lot of details about why the government believes elements like the personal notes and the additional information he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The procedure by which the Justice Department initiated this case will be under scrutiny, after Trump openly expressed his desire to see his critics prosecuted and some of those charges came to fruition.

But Mr Lesko indicated in Bolton's situation, authorities seem to have adhered to standard procedure.

"This Bolton prosecution and eventually the indictment seemed to have followed the regular procedure including the rules and norms within the DOJ," he said.

Unlike Comey's brief, concise indictment, Bolton's was a more "conventional" filing that "clearly outlines the details concerning the circumstances and situation here," Mr Lesko commented.

"It appears reasonably aligned with a long line of cases... where government officials improperly handled and transmitted sensitive information."