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Former President Donald Trump has repeatedly expressed his desire to see critics probed, exerting pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our reputation and trustworthiness," the president stated recently in a Truth Social message.

"They impeached twice, and charged me (5 times!)" he declared, referencing the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Both have subsequently been charged, in situations that numerous specialists have said seem to be politically motivated and difficult to succeed in legal proceedings.

But the latest charges against a Trump critic, ex national security adviser John Bolton, stand apart, legal specialists and former prosecutors say.

"In my opinion, contrasting Bolton's charges to Comey's is like comparing two different things," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Details of the Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. After leaving the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unfit for office in his memoir.

Experts say that while there may be political reasons to go after Bolton, the procedures used to obtain an indictment and the proof compiled against him indicate a possibly stronger legal argument than the Justice Department brought against James.

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

Throughout his time as Trump's security advisor, and following his 2019 White House exit, prosecutors alleged that Bolton put the nation at danger by wrongfully keeping and transmitting sensitive documents to relatives using unprotected methods, including AOL. Some of the documents were labeled highly classified.

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

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

Political Motivation or a Substantial Legal Argument?

The timing of his charge - coming on the heels of allegations against Comey - has renewed concerns about external influence on the legal system.

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

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

However, he continued, "if the DOJ is capable to demonstrate the allegations stated and show the information is correctly designated, his behavior may very well have broken the law".

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

"Cases that involve sensitive materials present difficulties to try, but they can and are brought against equally junior and senior personnel, from time to time," she explained.

Similarities to Examinations into Former President and President

Trump similarly encountered charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was eventually thrown out by a court official and negated by his re-election as leader.

A special counsel also determined that former President Joe Biden improperly stored sensitive materials from his time as vice president, but failed to criminally charge him.

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

Strict protocols govern the management of classified documents. To secure a conviction, the prosecution must prove that Bolton was aware the material he was sending was classified, and he had to knowingly transfer it to someone not entitled to receive it.

"Because of the sensitive nature of the information at question in this matter, we don't have a great deal of details about why the prosecution contends things like the diary entries and the other material he shared by electronic message, and why there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department initiated this case will be closely examined, following Trump openly posted his wish to see his critics charged and some of those charges came to fruition.

But Mr Lesko indicated in Bolton's situation, prosecutors appear to have adhered to protocol.

"The Bolton prosecution and ultimately the charge seemed to have observed the regular process including the rules and norms within the DOJ," he stated.

In contrast to Comey's brief, concise indictment, Bolton's was a increasingly "conventional" document that "explicitly sets forth the details concerning the circumstances and situation in this instance," Mr Lesko said.

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