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Ex-President Donald Trump has repeatedly expressed his desire to see opponents investigated, applying 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 trustworthiness," the leader wrote recently in a social media post.

"They impeached me, and indicted me (5 times!)" he declared, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Each have since been charged, in situations that many specialists have said seem to be driven by politics and challenging to win in legal proceedings.

But the latest allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and ex-prosecutors say.

"I would say, contrasting Bolton's case to Comey's is like equating apples to oranges," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Details of the Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the supposed mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a vocal Trump critic, even to describe him "stunningly uninformed" and unfit for office in his book.

Experts contend that while there may be political reasons to go after Bolton, the procedures used to secure an indictment and the evidence compiled against him suggest a potentially more substantial legal argument than the DOJ brought against James.

"This misconduct that's being claimed is simultaneously more serious and seems to have taken place over a significant duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's national security adviser, and after his 2019 White House departure, prosecutors claimed that Bolton put the country at danger by improperly keeping and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were labeled top secret.

The indictment states that at one point a hacker accessed to Bolton's system where files were stored and transmitted an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Strong Case?

The schedule of his charge - arriving on the heels of allegations against Comey - has renewed questions about political pressure on the justice system.

Trump previously implied Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, 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 charge, when combined with additional cases, has raised questions about the validity of these charges, and why these counts are being brought now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "if the DOJ is able to demonstrate the allegations stated and demonstrate the material is properly classified, his conduct may very well have violated the law".

Charging such a senior official for improperly handling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to prosecute, but they can and are brought against equally junior and high-level personnel, from occasionally," she explained.

Similarities to Examinations into Former President and President

Trump likewise encountered allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was ultimately thrown out by a federal judge and voided by his return as president.

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

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

Strict protocols govern the handling of classified documents. To win a conviction, the government must prove that Bolton knew the information he was sending was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the sensitive character of the information at issue in this matter, we lack a lot of particulars about why the government contends things like the personal notes and the other material he shared by email, and why there were classified," explained Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department brought this case will be under scrutiny, after Trump openly expressed his wish to see his political opponents prosecuted and some of those indictments came to fruition.

But Mr Lesko indicated in Bolton's situation, prosecutors seem to have adhered to protocol.

"The Bolton case and eventually the charge appeared to have followed the standard process including the rules and norms within the DOJ," he said.

In contrast to Comey's brief, two-page charge, Bolton's was a increasingly "traditional" document that "clearly outlines the details involving the facts and situation in this instance," Mr Lesko said.

"It seems reasonably aligned with a long line of cases... where public servants improperly handled and transmitted classified material."