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

"We can't delay any longer, it's damaging our standing and trustworthiness," the president stated recently in a Truth Social post.

"They impeached twice, and charged me (5 times!)" he said, mentioning the four criminal cases he faced after leaving the White House in 2021 and James's civil case.

Each have since been charged, in situations that numerous experts have stated seem to be driven by politics and difficult to win in court.

But the most recent charges against a Trump critic, ex national security adviser John Bolton, differ significantly, legal experts and former prosecutors assert.

"I would say, comparing Bolton's case to James' is like comparing two different things," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of the Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a vocal presidential opponent, even to describe him "stunningly uninformed" and unfit for the presidency in his book.

Experts contend that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the proof gathered against him indicate a possibly more substantial legal argument than the Justice Department presented against Comey.

"This misconduct that's being alleged is both more severe and seems to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, prosecutors claimed that Bolton placed the nation at danger by improperly keeping and transmitting sensitive documents to family members using insecure means, including AOL. Some of the documents were marked highly classified.

The indictment states that at a certain time a hacker gained access to Bolton's account where documents were kept 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 eighteen distinct counts of mishandling sensitive materials.

Political Motivation or a Strong Case?

The schedule of his charge - arriving on the tails of charges against Comey - has revived questions about external influence on the legal system.

Trump previously suggested Bolton should be in jail, and described him a "sleazebag". Bolton, for his part, authored a publication about his experience in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the schedule of this indictment, when paired with others, has raised questions about the validity of these allegations, and the reason these charges are being brought at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "if the DOJ is capable to prove the allegations stated and demonstrate the material is properly designated, his conduct may very well have broken the statute".

Prosecuting such a high-ranking figure for mishandling classified documents is "rare" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to try, but they may and are brought against both junior and high-level personnel, from time to time," she explained.

Similarities to Investigations into Trump and President

Trump similarly faced charges of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was ultimately thrown out by a court official and negated by his re-election as president.

A independent investigator additionally found that former President Joe Biden improperly maintained sensitive materials from his time as second-in-command, but did not prosecute him.

Bolton's case shares characteristics to Trump's classified documents matters, noted Mr Lesko, who previously held a senior national security role at the Justice Department.

Strict procedures regulate the management of classified documents. To secure a guilty verdict, the government must prove that Bolton was aware the material he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the sensitive character of the material at question in this matter, we don't have a great deal of particulars about the reasons the prosecution contends things like the diary entries and the other material he shared by email, and the reason there were restricted," said Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the Justice Department initiated this legal action will be closely examined, after Trump openly posted his wish to see his political opponents charged and some of those charges materialized.

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

"The Bolton prosecution and ultimately the charge seemed to have observed the standard process including the rules and norms within the Department of Justice," he said.

Unlike Comey's short, two-page indictment, Bolton's was a increasingly "conventional" document that "explicitly outlines the details involving the circumstances and situation here," Mr Lesko commented.

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