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Former President Donald Trump has consistently expressed his desire to see opponents probed, exerting 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 damaging our reputation and credibility," the president stated recently in a social media post.

"They impeached me, and charged me (five times!)" he declared, mentioning the four criminal cases he faced after departing the White House in 2021 and James's civil case.

Both have since been charged, in cases that many experts have said appear to be politically motivated and difficult to win in legal proceedings.

But the latest charges against a presidential opponent, ex national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors say.

"I would say, contrasting Bolton's charges to Comey's is like comparing apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Details of the Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has become a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unfit for the presidency in his book.

Experts contend that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence gathered against him suggest a possibly more substantial case than the Justice Department presented against Comey.

"This misconduct that's being claimed is simultaneously more serious 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.

During his time as Trump's national security adviser, and after his 2019 White House departure, authorities alleged that Bolton put the nation at risk by wrongfully retaining and sending sensitive documents to family members using unprotected methods, including AOL. Some of the documents were labeled top secret.

The charge alleges that at a certain time a hacker gained access to Bolton's account where documents were kept and transmitted an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to eighteen distinct counts of improperly handling classified information.

Political Motivation or a Substantial Legal Argument?

The schedule of his indictment - coming on the tails of charges against Comey - has renewed concerns about political pressure on the legal system.

Trump once implied Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, authored a publication about his time in the Trump government that was sharply negative of the leader.

"Undoubtedly that the timing of this charge, when paired with additional cases, has prompted doubts about the strength of these allegations, and why these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is capable to prove the allegations stated and show the material is correctly designated, his behavior may very well have violated the law".

Charging such a high-ranking official for mishandling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve sensitive materials pose difficulties to prosecute, but they may and are filed against equally junior and high-level officials, from time to time," she explained.

Similarities to Examinations into Trump and Biden

Trump similarly encountered allegations of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately dismissed by a court official and voided by his return as president.

A special counsel also found that former President Joe Biden improperly maintained classified documents from his time as vice president, but did not prosecute him.

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

Strict procedures govern the management of sensitive materials. To win a guilty verdict, the prosecution must prove that Bolton was aware the material he was sending was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the sensitive nature of the information at issue in this matter, we don't have a great deal of details about why the prosecution contends things like the personal notes and the additional material he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department initiated this legal action will be under scrutiny, following Trump publicly posted his wish to see his political opponents prosecuted and some of those indictments materialized.

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

"The Bolton prosecution and eventually the indictment appeared to have observed the standard process including the rules and norms within the DOJ," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a more "conventional" document that "explicitly sets forth the particulars concerning the circumstances and situation here," Mr Lesko said.

"It appears reasonably consistent with a series of cases... where government officials improperly handled and shared sensitive information."