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Former President Donald Trump has repeatedly shown his wish to see opponents investigated, exerting pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and trustworthiness," the leader stated recently in a social media message.

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

Both have subsequently been charged, in cases that many specialists have said appear to be driven by politics and challenging to succeed in legal proceedings.

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

"In my opinion, contrasting Bolton's charges to James' is like comparing apples to oranges," stated Mark Lesko, a former acting US attorney 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 sensitive materials. After leaving the White House in 2019, he has emerged as a vocal Trump critic, even to describe him "remarkably ignorant" and unfit for the presidency in his book.

Experts say that while there may be political reasons to go after Bolton, the methods used to obtain an charge and the proof gathered against him suggest a possibly stronger case than the DOJ brought against James.

"These actions that's being claimed is simultaneously more severe and appears to have occurred over a considerable period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House departure, prosecutors claimed that Bolton placed the country at risk by improperly keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Some of the documents were labeled top secret.

The indictment alleges that at a certain time a unauthorized user gained access to Bolton's account where files were stored and transmitted an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

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

Retribution or a Strong Legal Argument?

The timing of his charge - coming on the tails of allegations against James - has renewed concerns about external influence on the justice system.

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

"There's no question that the schedule of this indictment, when paired with others, has prompted questions about the strength of these allegations, and the reason these charges are being filed at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is capable to prove the facts stated and demonstrate the information is properly designated, his conduct may very well have violated the statute".

Prosecuting such a senior official for mishandling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern sensitive materials pose difficulties to try, but they can and are brought against both junior and senior personnel, from occasionally," she said.

Similarities to Investigations into Former President and President

Trump likewise encountered charges of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that case was eventually thrown out by a court official and negated by his return as president.

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 situation bears similarities to Trump's sensitive materials matters, noted Mr Lesko, who also held a top security role at the Justice Department.

Strict procedures regulate the management of sensitive materials. To secure a conviction, the government must demonstrate that Bolton knew the information he was sending was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

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

A More Traditional Prosecution

The procedure by which the DOJ brought this legal action will be closely examined, following Trump publicly posted his desire to see his critics charged 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 indictment appeared to have observed the standard process including the rules and norms within the DOJ," he stated.

Unlike Comey's short, concise charge, Bolton's was a more "traditional" document that "clearly outlines the details concerning the circumstances and circumstances here," Mr Lesko said.

"It seems reasonably consistent with a series of precedents... where public servants improperly handled and shared classified material."