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Ex-President Donald Trump has consistently expressed his desire to see opponents probed, exerting pressure on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's killing our reputation and trustworthiness," the president wrote last month in a social media post.

"I was impeached twice, and indicted me (5 times!)" he said, mentioning the four criminal cases he encountered after leaving the White House in 2021 and James's civil case.

Each have since been indicted, in cases that numerous experts have said appear to be driven by politics and difficult to win in court.

But the latest charges against a Trump critic, ex national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors say.

"I would say, comparing Bolton's case to Comey's is like comparing two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

This Details of Bolton's Case

Bolton has been formally charged on federal charges related to the supposed improper handling of classified information. Since departing the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "stunningly uninformed" and unfit for office in his memoir.

Experts say that while there may be political motivations to target Bolton, the methods used to obtain an indictment and the evidence compiled against him indicate a possibly more substantial case than the Justice Department presented against Comey.

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

Throughout his time as Trump's security advisor, and following his 2019 White House departure, prosecutors claimed that Bolton placed the country at danger by wrongfully retaining and sending classified information to family members using unprotected methods, including AOL. Several of the documents were labeled top secret.

The charge states that at a certain time a unauthorized user accessed to Bolton's account where files were stored and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct counts of mishandling sensitive materials.

Political Motivation or a Substantial Case?

The timing of his charge - coming on the tails of allegations against James - has renewed questions about political pressure on the justice system.

Trump once suggested Bolton should be in jail, and called him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump government that was sharply negative of the leader.

"Undoubtedly that the schedule of this indictment, when combined with additional cases, has raised doubts about the strength of these allegations, and why these counts are being filed now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is capable to demonstrate the allegations alleged and show the material is correctly designated, his behavior may very well have violated the statute".

Charging such a high-ranking official for improperly handling classified documents is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information pose challenges to try, but they may and are brought against equally junior and high-level officials, from time to time," she said.

Similarities to Investigations into Former President and Biden

Trump likewise faced allegations of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually thrown out by a court official and negated by his re-election as president.

A special counsel additionally found that former President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's sensitive materials issues, noted Mr Lesko, who also held a top national security position at the Justice Department.

Strict procedures regulate the management of classified documents. To win a conviction, the prosecution must prove that Bolton knew the information he was sending was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Due to the sensitive character of the information at issue in this matter, we lack a lot of details about why the prosecution believes elements like the diary entries and the other material he communicated by email, and the reason there were restricted," said Mr Jaffer.

A More Traditional Legal Action

The procedure by which the Justice Department brought this case will be under scrutiny, after Trump openly posted his wish to see his critics prosecuted and several of those charges came to fruition.

But Mr Lesko said in Bolton's case, authorities seem to have followed protocol.

"This Bolton case and ultimately the charge seemed to have observed the regular procedure including the regulations and norms within the DOJ," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a increasingly "traditional" document that "clearly sets forth the details involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears reasonably consistent with a long line of cases... where public servants improperly handled and shared classified material."