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

"We can't delay any longer, it's killing our reputation and trustworthiness," the president wrote recently in a Truth Social message.

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

Both have subsequently been charged, in situations that numerous experts have said appear to be driven by politics and challenging to win in legal proceedings.

But the most recent charges against a Trump critic, former security advisor John Bolton, stand apart, legal specialists and former prosecutors assert.

"I would say, comparing Bolton's charges to Comey's is like equating two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Details of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the alleged mishandling of classified information. After departing the White House in 2019, he has become a outspoken presidential opponent, even to describe him "remarkably ignorant" and unsuitable for the presidency in his book.

Experts contend that while there may be political reasons to go after Bolton, the methods used to secure an charge and the proof compiled against him suggest a possibly more substantial legal argument than the DOJ presented against James.

"This misconduct that's being alleged is simultaneously more severe and seems to have taken place over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and following his 2019 White House departure, authorities alleged that Bolton placed the country at danger by improperly retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were labeled top secret.

The indictment states that at one point a hacker gained access to Bolton's system where files were kept and transmitted an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on recently to 18 distinct counts of improperly handling sensitive materials.

Retribution or a Substantial Legal Argument?

The schedule of his indictment - coming on the heels of allegations against Comey - has renewed questions about external influence on the legal system.

Trump once suggested Bolton should be in prison, and called him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump administration that was sharply negative of the president.

"There's no question that the timing of this charge, when combined with additional cases, has raised doubts about the strength of these allegations, and why these charges are being brought at this time," said Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "if the Justice Department is capable to demonstrate the facts alleged and demonstrate the information is correctly designated, his behavior may very well have violated the law".

Charging such a high-ranking figure for improperly handling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern classified information present challenges to try, but they may and are filed against equally low-level and high-level officials, from time to time," she explained.

Similarities to Investigations into Former President and Biden

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

A independent investigator also determined that ex-President Joe Biden improperly stored classified documents from his time as second-in-command, but did not prosecute him.

Bolton's case shares characteristics to Biden's sensitive materials matters, said Mr Lesko, who also held a top security role at the Justice Department.

Rigorous protocols regulate the management of sensitive materials. To secure a guilty verdict, the prosecution must prove that Bolton was aware the information he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Due to the sensitive nature of the material at issue in this matter, we don't have a great deal of particulars about the reasons the government contends things like the personal notes and the additional material he shared by email, and the reason there were restricted," said Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the Justice Department brought this case will be under scrutiny, after Trump openly posted his wish to see his political opponents prosecuted and several of those charges materialized.

But Mr Lesko said in Bolton's case, prosecutors appear to have adhered to protocol.

"This Bolton prosecution and ultimately the charge seemed to have followed the standard procedure including the rules and norms within the DOJ," he stated.

Unlike Comey's brief, concise charge, Bolton's was a more "conventional" document that "explicitly outlines the particulars involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears fairly consistent with a long line of precedents... where public servants improperly handled and transmitted sensitive information."