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Former President Donald Trump has repeatedly shown his desire to see critics investigated, exerting influence on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and trustworthiness," the leader wrote last month in a Truth Social post.

"I was impeached me, and indicted me (5 times!)" he declared, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Each have since been indicted, in cases that many specialists have said appear to be politically motivated and difficult to win in court.

But the latest charges against a presidential opponent, former security advisor John Bolton, stand apart, legal experts and ex-prosecutors assert.

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

This Details of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has become a outspoken presidential opponent, even to describe him "remarkably ignorant" and unfit for the presidency in his book.

Experts contend that while there may be political motivations to go after Bolton, the methods used to obtain an charge and the evidence compiled against him suggest a potentially more substantial legal argument than the DOJ brought against James.

"These actions that's being alleged is simultaneously more severe and appears to have occurred 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 national security adviser, and after his 2019 White House exit, authorities alleged that Bolton placed the nation at risk by wrongfully retaining and sending classified information to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

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

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct counts of improperly handling sensitive materials.

Political Motivation or a Strong Case?

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

Trump previously implied Bolton belonged in prison, and described him a "sleazebag". Bolton, for his role, authored a publication about his experience in the Trump administration that was sharply negative of the leader.

"There's no question that the timing of this indictment, when combined with additional cases, has prompted questions about the validity of these allegations, and why these counts are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is able to prove the facts stated and show the material is properly classified, his conduct may very well have violated the statute".

Prosecuting such a high-ranking figure for improperly handling sensitive materials is "rare" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern sensitive materials pose challenges to prosecute, but they may and are brought against both junior and high-level officials, from occasionally," she said.

Similarities to Examinations into Trump and President

Trump similarly encountered allegations of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that matter was ultimately thrown out by a court official and voided by his return as president.

A special counsel additionally determined that former President Joe Biden wrongfully stored sensitive materials from his time as vice president, but failed to prosecute him.

Bolton's situation shares characteristics to Trump's classified documents matters, noted Mr Lesko, who also held a top security role at the Justice Department.

Rigorous protocols regulate the handling of sensitive materials. To secure a conviction, the prosecution must prove that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the sensitive character of the information at issue in this matter, we don't have a lot of particulars about why the government contends things like the personal notes and the other information he shared by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Conventional Prosecution

The process by which the DOJ initiated this case will be closely examined, following Trump publicly expressed his wish to see his critics charged and several of those charges materialized.

But Mr Lesko indicated in Bolton's case, authorities appear to have followed protocol.

"The Bolton case and eventually the indictment appeared to have observed the standard process including the rules and norms within the Department of Justice," he stated.

Unlike Comey's short, two-page indictment, Bolton's was a more "traditional" document that "clearly sets forth the particulars involving the facts and situation here," Mr Lesko said.

"It seems reasonably aligned with a series of precedents... where government officials improperly handled and transmitted sensitive information."