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Former President Donald Trump has repeatedly expressed his wish 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 cannot postpone further, it's damaging our standing and trustworthiness," the president wrote recently in a social media post.

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

Each have since been charged, in situations that numerous experts have stated seem to be politically motivated and challenging to win in legal proceedings.

But the latest charges against a presidential opponent, former national security adviser John Bolton, stand apart, legal experts and former prosecutors say.

"In my opinion, comparing Bolton's case to Comey's is like equating apples to oranges," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of the Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has emerged as a outspoken presidential opponent, even to describe him "remarkably ignorant" and unsuitable for office in his book.

Experts contend that while there may be political motivations to target Bolton, the methods used to secure an charge and the proof gathered against him suggest a potentially more substantial legal argument than the Justice Department brought against Comey.

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

During his tenure as Trump's national security adviser, and following his 2019 White House departure, prosecutors alleged that Bolton placed the nation at risk by improperly keeping and sending classified information to relatives using insecure means, including AOL. Several of the materials were labeled top secret.

The charge states that at one point a hacker gained access to Bolton's account where documents were kept and sent an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to 18 separate charges of mishandling classified information.

Retribution or a Substantial Case?

The schedule of his indictment - coming on the tails of charges against Comey - has revived questions about political pressure on the legal system.

Trump once implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his role, authored a publication about his experience in the Trump administration that was sharply negative of the leader.

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

Nevertheless, he added, "should the DOJ is capable to demonstrate the facts alleged and demonstrate the information is correctly classified, his behavior may certainly have violated the statute".

Prosecuting such a high-ranking figure for mishandling sensitive materials is "uncommon" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern sensitive materials pose challenges to try, but they can and are filed against equally low-level and high-level personnel, from time to time," she said.

Similarities to Examinations into Trump and President

Trump similarly faced charges of wrongfully keeping sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was ultimately thrown out by a federal judge and negated by his return as leader.

A independent investigator also found that former President Joe Biden wrongfully maintained classified documents from his time as vice president, but failed to criminally charge him.

Bolton's situation shares characteristics to Biden's classified documents matters, noted Mr Lesko, who previously held a top security role at the Justice Department.

Strict protocols govern the handling of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the sensitive character of the information at issue in this matter, we lack a great deal of details about the reasons the government contends elements like the personal notes and the other information he communicated by electronic message, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the DOJ brought this case will be under scrutiny, after Trump openly posted his wish to see his critics prosecuted and some of those indictments came to fruition.

But Mr Lesko said in Bolton's situation, prosecutors appear to have followed standard procedure.

"This Bolton case and ultimately the charge appeared to have followed the regular process including the rules and norms within the DOJ," he stated.

Unlike Comey's short, concise indictment, Bolton's was a more "traditional" filing that "explicitly outlines the particulars concerning the circumstances and situation in this instance," Mr Lesko commented.

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