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Ex-President Donald Trump has consistently shown his wish to see critics investigated, exerting influence on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our reputation and trustworthiness," the leader wrote recently in a Truth Social post.

"They impeached me, and indicted me (five times!)" he said, mentioning the multiple legal proceedings he faced after departing the White House in 2021 and James's civil case.

Each have since been charged, in situations that many specialists have said appear to be politically motivated and challenging to succeed in legal proceedings.

But the most recent allegations against a Trump critic, ex national security adviser John Bolton, differ significantly, legal specialists and former prosecutors say.

"In my opinion, contrasting Bolton's charges to Comey's is like comparing apples to oranges," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been formally charged on federal charges related to the alleged improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Experts say that while there may be political reasons to go after Bolton, the procedures used to obtain an charge and the proof compiled against him indicate a potentially more substantial case than the DOJ presented against James.

"These actions that's being claimed is both more serious and appears to have occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton placed the nation at danger by wrongfully retaining and sending sensitive documents to relatives using insecure means, including AOL. Some of the materials were labeled highly classified.

The charge alleges that at a certain time a hacker gained access to Bolton's account where files were kept and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on Friday to eighteen separate charges of mishandling sensitive materials.

Retribution or a Strong Case?

The schedule of his indictment - coming on the tails of charges against Comey - has revived concerns about external influence on the justice system.

Trump previously suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, authored a publication about his experience in the Trump administration that was sharply negative of the president.

"Undoubtedly that the schedule of this charge, when combined with others, has raised doubts about the validity of these allegations, and the reason these charges are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "if the DOJ is able to prove the facts stated and demonstrate the information is properly classified, his behavior may certainly have broken the law".

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

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

Similarities to Examinations into Trump and Biden

Trump similarly encountered allegations of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was eventually thrown out by a court official and negated by his re-election as president.

A independent investigator additionally found that ex-President Joe Biden wrongfully stored sensitive materials from his time as vice president, but did not criminally charge him.

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

Strict procedures regulate the handling of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton knew the material he was sending was restricted, and he had to knowingly transmit it to someone without authorization to receive it.

"Due to the classified character of the material at issue in this case, we lack a great deal of details about why the government contends things like the personal notes and the other information he communicated by electronic message, and why there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The process by which the DOJ brought this case will be closely examined, after Trump openly expressed his desire to see his critics charged and several of those indictments materialized.

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

"The Bolton case and ultimately the indictment seemed to have observed the regular process including the rules and standards within the DOJ," he stated.

In contrast to Comey's short, concise indictment, Bolton's was a more "conventional" document that "clearly outlines the particulars involving the facts and circumstances here," Mr Lesko commented.

"It seems reasonably aligned with a long line of precedents... where public servants mishandled and shared classified material."