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

"We can't delay further, it's damaging our standing and trustworthiness," the leader wrote last month in a social media message.

"They impeached me, and charged me (five times!)" he declared, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been indicted, in situations that numerous specialists have said appear to be politically motivated and difficult to win in legal proceedings.

But the most recent allegations against a presidential opponent, ex security advisor John Bolton, stand apart, legal specialists and former prosecutors say.

"I would say, contrasting Bolton's case to Comey's is like comparing apples to oranges," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on federal charges related to the alleged mishandling of sensitive materials. Since leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "stunningly uninformed" and unfit for the presidency in his book.

Experts contend that while there may be political motivations to go after Bolton, the procedures used to secure an charge and the proof gathered against him suggest a possibly stronger legal argument than the Justice Department brought against Comey.

"These actions that's being claimed is simultaneously more severe and seems to have taken place over a considerable period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and after his 2019 White House departure, prosecutors claimed that Bolton put the nation at danger by improperly retaining and transmitting classified information to relatives using insecure means, including AOL. Several of the documents were marked highly classified.

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

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct counts of mishandling classified information.

Retribution or a Strong Case?

The schedule of his charge - coming on the heels of allegations against James - has renewed questions about political pressure on the legal system.

Trump once implied Bolton should be in prison, and described him a "sleazebag". Bolton, for his part, wrote a publication about his experience in the Trump administration that was highly critical of the leader.

"There's no question that the timing of this charge, when paired with additional cases, has prompted doubts about the validity of these allegations, and why these counts are being brought now," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is capable to demonstrate the facts alleged and demonstrate the material is correctly classified, his behavior may very well have broken the law".

Charging such a high-ranking figure for mishandling sensitive materials is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve sensitive materials present difficulties to prosecute, but they may and are filed against equally low-level and high-level personnel, from occasionally," she said.

Parallels to Examinations into Trump and President

Trump similarly faced allegations of improperly storing classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that matter was eventually dismissed by a court official and negated by his return as leader.

A independent investigator additionally determined that ex-President Joe Biden wrongfully stored classified documents from his time as second-in-command, but did not prosecute him.

Bolton's case shares characteristics to Biden's sensitive materials issues, said Mr Lesko, who also held a senior national security role at the DOJ.

Strict protocols regulate the management of classified documents. To win a conviction, the government must prove that Bolton knew the information he was sending was classified, and he had to intentionally transmit it to someone without authorization to receive it.

"Because of the sensitive character of the material at question in this matter, we don't have a lot of details about the reasons the government contends elements like the personal notes and the additional information he communicated by email, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Prosecution

The process by which the Justice Department brought this legal action will be under scrutiny, after Trump publicly expressed his wish to see his critics prosecuted and some of those indictments came to fruition.

But Mr Lesko said in Bolton's situation, prosecutors appear to have adhered to standard procedure.

"The Bolton prosecution and eventually the charge seemed to have observed the regular process including the regulations and norms within the Department of Justice," he said.

In contrast to Comey's brief, two-page charge, Bolton's was a more "conventional" document that "clearly sets forth the particulars concerning the facts and circumstances here," Mr Lesko said.

"It appears reasonably aligned with a long line of precedents... where public servants mishandled and shared sensitive information."