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Former President Donald Trump has consistently expressed his wish to see opponents probed, applying influence on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our standing and trustworthiness," the leader wrote recently in a social media message.

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

Both have since been charged, in cases that numerous experts have said seem to be politically motivated and difficult to win in court.

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

"In my opinion, contrasting Bolton's charges to James' is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the alleged improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unfit for the presidency in his book.

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 Justice Department brought against James.

"This misconduct that's being claimed is both more severe and appears to have taken place 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 after his 2019 White House exit, prosecutors alleged that Bolton placed the country at risk by wrongfully keeping and transmitting classified information to relatives using unprotected methods, including AOL. Several of the documents were marked highly classified.

The charge states that at one point a unauthorized user gained access to Bolton's account where files were stored and sent an apparent 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 separate counts of improperly handling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his indictment - arriving on the tails of charges against Comey - has renewed concerns about external influence on the legal system.

Trump previously implied Bolton should be in jail, and called him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump government that was highly critical of the president.

"There's no question that the schedule of this charge, when combined with others, has raised questions about the validity of these charges, and why these counts are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is able to demonstrate the facts stated and demonstrate the material is correctly designated, his conduct may very well have broken the law".

Prosecuting such a high-ranking figure for mishandling 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 sensitive materials pose difficulties to prosecute, but they can and are filed against both junior and high-level personnel, from time to time," she explained.

Similarities to Examinations into Former President and President

Trump similarly faced charges 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 federal judge and voided by his return as leader.

A special counsel additionally determined that former President Joe Biden wrongfully maintained classified documents from his period as vice president, but failed to prosecute him.

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

Strict procedures regulate the handling of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the material he was sending was restricted, and he had to intentionally transmit it to someone without authorization to obtain it.

"Due to the classified nature of the information at question in this matter, we don't have a great deal of details about why the government contends things like the personal notes and the additional material he shared by email, and why there were classified," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, after Trump publicly posted his wish to see his political opponents charged and some of those indictments materialized.

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

"The Bolton prosecution and eventually the indictment appeared to have followed the standard procedure including the rules and norms within the Department of Justice," he stated.

In contrast to Comey's brief, two-page indictment, Bolton's was a more "traditional" filing that "clearly outlines the particulars involving the facts and situation here," Mr Lesko said.

"It seems fairly aligned with a series of precedents... where public servants improperly handled and transmitted classified material."