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Former President Donald Trump has consistently shown his desire to see critics investigated, applying influence on the DOJ to charge 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 president stated recently in a Truth Social message.

"I was impeached twice, and charged me (5 times!)" he said, referencing 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 difficult to succeed in court.

But the latest allegations against a Trump critic, ex security advisor John Bolton, differ significantly, legal experts and ex-prosecutors say.

"I would say, comparing 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.

This Specifics of the Case

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

Specialists say that while there may be political motivations to target Bolton, the methods used to obtain an charge and the proof compiled against him indicate a potentially more substantial case than the Justice Department presented against James.

"These actions that's being claimed is simultaneously more severe and seems to have occurred over a considerable duration," commented 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, authorities alleged that Bolton placed the country at danger by wrongfully keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the documents were marked highly classified.

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

Bolton entered a not guilty plea during a court appearance on recently to eighteen distinct charges of improperly handling sensitive materials.

Political Motivation or a Strong Case?

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

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

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

Nevertheless, he continued, "should the DOJ is capable to prove the allegations stated and demonstrate the information is correctly classified, his conduct may certainly have violated the law".

Prosecuting such a senior figure for improperly handling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern sensitive materials pose difficulties to try, but they may and are brought against both junior and high-level officials, from occasionally," she said.

Parallels to Examinations into Former President and Biden

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

A independent investigator also found that ex-President Joe Biden improperly stored classified documents from his period as vice president, but did not prosecute him.

Bolton's situation shares characteristics to Biden's sensitive materials matters, noted Mr Lesko, who also held a top security role at the Justice Department.

Rigorous procedures regulate the management of classified documents. To secure a guilty verdict, the prosecution must prove that Bolton knew the information he was sending was classified, and he had to intentionally transfer it to someone without authorization to obtain it.

"Because of the sensitive nature of the material at question in this matter, we lack a lot of details about the reasons the prosecution contends things like the personal notes and the additional material he shared by email, and why there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department initiated this case will be closely examined, following Trump publicly posted his desire to see his political opponents prosecuted and some of those charges came to fruition.

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

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

Unlike Comey's short, two-page charge, Bolton's was a increasingly "traditional" document that "clearly outlines the particulars involving the facts and situation here," Mr Lesko said.

"It seems reasonably aligned with a long line of precedents... where government officials mishandled and transmitted classified material."