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

"We cannot postpone any longer, it's killing our standing and trustworthiness," the president wrote last month in a Truth Social message.

"They impeached twice, and charged me (five times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's civil case.

Both have subsequently been indicted, in cases that many experts have said seem to be driven by politics and challenging to succeed in court.

But the most recent allegations against a Trump critic, ex national security adviser John Bolton, stand apart, legal experts and ex-prosecutors assert.

"I would say, comparing Bolton's case to James' is like equating apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been criminally indicted on national allegations related to the supposed improper handling of sensitive materials. Since leaving the White House in 2019, he has become a vocal presidential opponent, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists say that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence gathered against him indicate a potentially stronger case than the DOJ brought against Comey.

"This misconduct that's being alleged is both more serious and appears to have occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and after his 2019 White House exit, prosecutors alleged that Bolton placed the country at danger by wrongfully retaining and sending sensitive documents to family members using insecure means, including AOL. Several of the documents were marked highly classified.

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

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

Retribution or a Substantial Case?

The timing of his indictment - arriving on the heels of charges against Comey - has revived questions about external influence on the justice system.

Trump once implied Bolton should be in prison, and called him a "disreputable person". Bolton, for his part, authored a publication about his time in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this indictment, when paired with others, has prompted doubts about the strength of these charges, and the reason these counts are being filed at this time," said Jamil Jaffer, founder and director of the National Security Institute.

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

Prosecuting such a senior figure for mishandling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information present challenges to try, but they can and are filed against equally low-level and high-level personnel, from time to time," she said.

Parallels to Examinations into Former President and Biden

Trump similarly faced charges of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that case was ultimately thrown out by a court official and negated by his return as president.

A independent investigator additionally determined that former President Joe Biden improperly stored sensitive materials from his time as vice president, but failed to criminally charge him.

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

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

"Because of the sensitive nature of the information at issue in this matter, we don't have a lot of particulars about why the prosecution contends elements like the diary entries and the additional information he communicated by electronic message, and why there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the Justice Department initiated this case will be closely examined, after Trump openly posted his wish to see his political opponents prosecuted and several of those indictments came to fruition.

But Mr Lesko said in Bolton's situation, authorities appear to have followed protocol.

"The Bolton case and eventually the indictment seemed to have observed the regular procedure including the rules and standards within the DOJ," he said.

In contrast to Comey's short, concise charge, Bolton's was a more "traditional" filing that "clearly sets forth the particulars concerning the facts and situation here," Mr Lesko commented.

"It seems fairly consistent with a series of precedents... where public servants improperly handled and shared classified material."