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Former President Donald Trump has repeatedly expressed his desire to see critics investigated, applying influence on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

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

"They impeached twice, and indicted me (five times!)" he said, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's lawsuit.

Both have since been charged, in situations that many experts have stated seem to be driven by politics and challenging to win in legal proceedings.

But the most recent allegations against a presidential opponent, former national security adviser John Bolton, stand apart, legal specialists and former prosecutors say.

"I would say, comparing Bolton's case to Comey's is like comparing apples to oranges," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been criminally indicted on federal charges related to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has become a outspoken Trump critic, even to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Experts contend 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 more substantial legal argument than the Justice Department brought against Comey.

"These actions that's being alleged is both more serious and seems 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 following his 2019 White House departure, prosecutors alleged that Bolton placed the nation at risk by improperly retaining and sending sensitive documents to relatives using unprotected methods, including AOL. Some of the materials were labeled top secret.

The charge alleges that at one point a hacker accessed to Bolton's account where documents were stored and sent an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate counts of mishandling sensitive materials.

Political Motivation or a Strong Case?

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

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

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

However, he continued, "should the Justice Department is able to prove the allegations stated and demonstrate the information is properly designated, his behavior may certainly have broken the law".

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

"Situations that involve sensitive materials pose challenges to prosecute, but they may and are filed against both junior and senior officials, from occasionally," she explained.

Parallels to Examinations into Trump and Biden

Trump similarly encountered allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually dismissed by a federal judge and negated by his re-election as president.

A independent investigator also determined that ex-President Joe Biden improperly maintained sensitive materials from his period as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Trump's sensitive materials issues, said Mr Lesko, who previously held a senior national security position at the Justice Department.

Rigorous protocols govern the management of sensitive materials. To win a conviction, the government must demonstrate that Bolton knew the material he was transmitting was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the sensitive nature of the material at issue in this case, we don't have a great deal of particulars about why the prosecution believes things like the diary entries and the other information he communicated by email, and the reason there were restricted," said Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ brought this legal action will be under scrutiny, after Trump openly posted his wish to see his political opponents charged and some of those indictments came to fruition.

But Mr Lesko indicated in Bolton's case, authorities appear to have adhered to protocol.

"The Bolton prosecution and eventually the charge appeared to have followed the standard procedure including the regulations and standards within the DOJ," he stated.

Unlike Comey's short, concise indictment, Bolton's was a increasingly "traditional" document that "explicitly sets forth the details involving the circumstances and circumstances in this instance," Mr Lesko said.

"It appears fairly consistent with a long line of precedents... where government officials mishandled and shared classified material."