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Former President Donald Trump has repeatedly expressed his desire to see critics investigated, applying influence on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and trustworthiness," the leader wrote last month in a social media message.

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

Each have since been charged, in situations that numerous specialists have stated appear to be driven by politics and difficult to win in court.

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

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

The Details of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unsuitable for office in his book.

Specialists say that while there may be political motivations to go after Bolton, the methods used to secure an charge and the proof compiled against him suggest a possibly more substantial case than the DOJ presented against James.

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

Throughout his tenure as Trump's national security adviser, and following his 2019 White House exit, authorities claimed that Bolton placed the nation at danger by wrongfully keeping and sending sensitive documents to family members using unprotected methods, including AOL. Some of the materials were marked top secret.

The charge states that at one point a unauthorized user accessed to Bolton's system where documents were kept and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to eighteen separate counts of improperly handling classified information.

Retribution or a Strong Legal Argument?

The timing of his charge - arriving on the tails of allegations against James - has revived concerns about political pressure on the legal system.

Trump previously suggested Bolton belonged in jail, and described him a "disreputable person". Bolton, for his part, wrote a publication about his experience in the Trump government that was highly critical of the leader.

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

However, he continued, "should the Justice Department is able to prove the allegations alleged and demonstrate the material is properly classified, his behavior may certainly have broken the statute".

Charging such a high-ranking figure for improperly handling sensitive materials is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve classified information present challenges to prosecute, but they can and are brought against equally low-level and senior personnel, from occasionally," she explained.

Parallels to Examinations into Former President and Biden

Trump similarly faced charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that case was eventually dismissed by a federal judge and negated by his return as leader.

A independent investigator additionally found that ex-President Joe Biden improperly maintained classified documents from his period as second-in-command, but did not prosecute him.

Bolton's case shares characteristics to Trump's classified documents issues, said Mr Lesko, who previously held a senior security role at the DOJ.

Strict protocols govern the handling of sensitive materials. To secure a conviction, the prosecution must prove that Bolton knew the information he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the classified character of the material at issue in this matter, we don't have a great deal of details about the reasons the prosecution contends things like the diary entries and the additional information he communicated by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ initiated this case will be closely examined, after Trump publicly expressed his wish to see his critics charged and several of those charges materialized.

But Mr Lesko said in Bolton's situation, authorities seem to have adhered to protocol.

"This Bolton prosecution and eventually the indictment appeared to have followed the regular process including the regulations and standards within the DOJ," he said.

In contrast to Comey's short, two-page charge, Bolton's was a more "conventional" document that "clearly outlines the details concerning the facts and circumstances here," Mr Lesko commented.

"It appears fairly aligned with a long line of cases... where government officials mishandled and transmitted sensitive information."