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Former President Donald Trump has repeatedly shown his desire to see critics investigated, exerting 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 reputation and credibility," the president wrote last month in a Truth Social message.

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

Each have subsequently been charged, in cases that numerous experts have said appear to be politically motivated and difficult to win in court.

But the latest allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal experts and former prosecutors assert.

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

This Specifics of Bolton's Legal Situation

Bolton has been formally charged on federal charges pertaining to the alleged improper handling of sensitive materials. After leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political reasons to go after Bolton, the methods used to secure an indictment and the proof gathered against him indicate a potentially more substantial case than the DOJ presented against James.

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

During his tenure as Trump's national security adviser, and following his 2019 White House exit, authorities claimed that Bolton put the country at danger by improperly retaining and transmitting classified information to relatives using unprotected methods, including AOL. Several of the materials were marked top secret.

The indictment alleges that at one point a hacker accessed to Bolton's system where documents were kept and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on recently to 18 separate charges of mishandling sensitive materials.

Political Motivation or a Substantial Legal Argument?

The timing of his charge - arriving on the heels of charges against James - has revived questions about external influence on the legal system.

Trump previously implied Bolton belonged in jail, and described him a "disreputable person". Bolton, for his part, authored a publication about his time in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this indictment, when paired with others, has raised questions about the validity of these allegations, and the reason these counts are being filed at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to prove the allegations alleged and show the material is correctly designated, his conduct may very well have broken the law".

Charging such a high-ranking official for mishandling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern sensitive materials present difficulties to prosecute, but they may and are filed against both junior and high-level personnel, from occasionally," she said.

Parallels to Investigations into Trump and Biden

Trump similarly encountered allegations of improperly storing classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was ultimately thrown out by a court official and negated by his return as leader.

A independent investigator also found that ex-President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but did not criminally charge him.

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

Rigorous protocols govern the management of sensitive materials. To secure a conviction, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to receive it.

"Because of the sensitive character of the material at issue in this case, we don't have a great deal of details about the reasons the prosecution believes elements like the personal notes and the other information he shared by electronic message, and why there were classified," said Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department brought this legal action will be closely examined, following Trump openly posted his desire to see his political opponents charged and some of those indictments materialized.

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

"This Bolton prosecution and ultimately the charge seemed to have followed the standard procedure including the rules and standards within the Department of Justice," he said.

In contrast to Comey's brief, two-page indictment, Bolton's was a more "conventional" filing that "explicitly sets forth the particulars involving the circumstances and situation here," Mr Lesko commented.

"It appears reasonably aligned with a series of precedents... where government officials improperly handled and transmitted classified material."