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Ex-President Donald Trump has repeatedly shown his desire to see opponents probed, exerting influence on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our reputation and credibility," the leader wrote last month in a social media post.

"I was impeached twice, and charged me (five times!)" he said, mentioning the multiple legal proceedings he encountered after leaving the White House in 2021 and James's civil case.

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

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

"I would say, contrasting Bolton's charges to Comey's is like equating two different things," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Details of the Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the alleged improper handling of classified information. After leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to call him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts contend that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the proof compiled against him suggest a potentially stronger case than the DOJ brought against James.

"These actions that's being alleged is simultaneously more severe and seems to have occurred over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton put the nation at danger by improperly keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were labeled top secret.

The indictment alleges that at one point a hacker gained access to Bolton's system where files were stored and sent an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to eighteen distinct counts of mishandling sensitive materials.

Political Motivation or a Substantial Case?

The timing of his indictment - coming on the heels of charges against Comey - has renewed questions about political pressure on the legal system.

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

"There's no question that the timing of this charge, when combined with others, has prompted doubts about the strength of these charges, and why these counts are being brought now," said Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "should the Justice Department is capable to prove the allegations stated and show the material is properly classified, his conduct may very well have broken the law".

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

"Cases that concern classified information present difficulties to prosecute, but they may and are filed against both low-level and high-level officials, from time to time," she explained.

Parallels to Examinations into Trump and President

Trump similarly encountered charges of wrongfully storing sensitive materials 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 re-election as leader.

A independent investigator additionally determined that ex-President Joe Biden wrongfully maintained classified documents from his period as vice president, but did not criminally charge him.

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

Rigorous procedures regulate the management of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton knew the material he was sending was restricted, and he had to intentionally transfer it to someone not entitled to obtain it.

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

A More Traditional Legal Action

The procedure by which the DOJ brought this case will be under scrutiny, after Trump publicly expressed his wish to see his critics charged and some of those indictments materialized.

But Mr Lesko indicated in Bolton's case, prosecutors appear to have followed protocol.

"This Bolton case and ultimately the charge appeared to have observed the regular procedure including the regulations and norms within the DOJ," he said.

Unlike Comey's brief, two-page indictment, Bolton's was a increasingly "conventional" filing that "clearly outlines the details involving the facts and circumstances here," Mr Lesko commented.

"It appears fairly aligned with a series of cases... where government officials mishandled and shared sensitive information."