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Former President Donald Trump has consistently shown 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 can't delay further, it's damaging our reputation and credibility," the leader wrote last month in a Truth Social post.

"I was impeached me, and charged me (5 times!)" he declared, referencing the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in situations that many experts have stated appear 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, stand apart, legal experts and ex-prosecutors assert.

"In my opinion, comparing Bolton's case to Comey's is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Details of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the supposed improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, even to describe him "stunningly uninformed" and unfit for the presidency in his memoir.

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 stronger legal argument than the Justice Department presented against Comey.

"These actions that's being claimed is both more severe and appears to have occurred over a considerable period of time," commented 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 exit, prosecutors alleged that Bolton put the country at danger by improperly keeping and transmitting classified information to relatives using unprotected methods, including AOL. Several of the documents were marked highly classified.

The indictment alleges that at one point a unauthorized user gained access to Bolton's account where files were kept and sent an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

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

Political Motivation or a Strong Legal Argument?

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

Trump once suggested Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, authored a book about his experience in the Trump administration that was highly critical of the leader.

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

Nevertheless, he added, "if the DOJ is capable to demonstrate the allegations stated and show the material is properly designated, his conduct may certainly have violated the law".

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

"Situations that concern classified information pose challenges to try, but they may and are brought against equally low-level and senior officials, from occasionally," she said.

Similarities to Investigations into Former President and President

Trump similarly encountered allegations of wrongfully 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 leader.

A special counsel additionally found that former President Joe Biden wrongfully stored sensitive materials from his time as vice president, but did not criminally charge him.

Bolton's situation bears similarities to Trump's classified documents matters, said Mr Lesko, who previously held a top national security role at the DOJ.

Rigorous procedures govern the management of sensitive materials. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Due to the classified nature of the material at question in this matter, we lack a lot of particulars about why the prosecution believes elements like the personal notes and the additional information he shared by email, and why there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ brought this legal action will be under scrutiny, following Trump publicly posted his wish to see his critics prosecuted and some of those charges came to fruition.

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

"The Bolton prosecution and eventually the charge seemed to have followed the standard procedure including the rules and norms within the Department of Justice," he said.

Unlike Comey's short, concise charge, Bolton's was a increasingly "conventional" document that "explicitly outlines the details involving the facts and circumstances here," Mr Lesko said.

"It appears fairly aligned with a series of precedents... where government officials mishandled and shared classified material."