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Ex-President Donald Trump has consistently shown 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 can't delay further, it's damaging our standing and trustworthiness," the leader wrote last month in a social media message.

"They impeached twice, and charged me (5 times!)" he declared, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's civil case.

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

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

"In my opinion, contrasting Bolton's charges to James' is like equating two different things," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of the Case

Bolton has been criminally indicted on federal charges related to the supposed mishandling of classified information. Since leaving the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to call him "stunningly uninformed" and unsuitable for office in his book.

Experts say that while there may be political motivations to target Bolton, the methods used to secure an charge and the proof compiled against him indicate a possibly stronger case than the Justice Department brought against James.

"These actions that's being claimed is both more serious and appears to have occurred over a considerable period of time," 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 claimed that Bolton put the country at risk by improperly keeping and sending classified information to relatives using unprotected methods, including AOL. Some of the documents were marked top secret.

The charge states that at a certain time a unauthorized user gained access to Bolton's account where files were kept and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct counts of mishandling classified information.

Retribution or a Strong Legal Argument?

The timing of his indictment - arriving on the tails of allegations against Comey - has renewed concerns about external influence on the legal system.

Trump once suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, wrote a publication about his experience in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the timing of this indictment, when paired with additional cases, has raised doubts about the strength of these allegations, and why these charges are being brought at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he added, "should the DOJ is able to demonstrate the allegations alleged and demonstrate the information is correctly designated, his behavior may very well have violated the statute".

Charging such a senior official for mishandling classified documents is "rare" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials pose challenges to try, but they may and are filed against both low-level and high-level officials, from occasionally," she explained.

Similarities to Examinations into Former President and President

Trump likewise faced allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually dismissed by a federal judge and negated by his return as leader.

A independent investigator also found that former President Joe Biden improperly maintained classified documents from his time as second-in-command, but failed to criminally charge him.

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

Rigorous protocols govern the handling of sensitive materials. To secure a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was sending was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the classified nature of the material at question in this matter, we don't have a great deal of details about why the prosecution believes elements like the personal notes and the additional information he communicated by email, and the reason there were restricted," said Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the DOJ initiated this case will be under scrutiny, following Trump publicly posted his wish to see his critics prosecuted and several of those charges came to fruition.

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

"The Bolton prosecution and eventually the indictment appeared to have observed the regular procedure including the regulations and standards within the DOJ," he stated.

In contrast to Comey's short, two-page indictment, Bolton's was a more "traditional" filing that "clearly outlines the particulars concerning the facts and situation in this instance," Mr Lesko said.

"It seems reasonably aligned with a long line of precedents... where government officials mishandled and transmitted sensitive information."