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Former President Donald Trump has repeatedly shown his desire to see critics probed, applying pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's damaging our reputation and credibility," the leader wrote last month in a social media message.

"I was impeached twice, and charged me (5 times!)" he declared, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's lawsuit.

Both have since been indicted, in cases that numerous experts have said seem to be politically motivated and challenging to win in legal proceedings.

But the most recent charges against a presidential opponent, ex security advisor John Bolton, stand apart, legal specialists and former prosecutors say.

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

The Details of the Case

Bolton has been criminally indicted on federal charges related to the alleged improper handling of classified information. After leaving the White House in 2019, he has emerged as a outspoken presidential opponent, even to call him "remarkably ignorant" and unfit for the presidency in his memoir.

Experts say that while there may be political motivations to target Bolton, the procedures used to obtain an indictment and the proof gathered against him suggest a potentially stronger legal argument than the DOJ presented against Comey.

"These actions that's being claimed is both more serious and seems to have taken place over a considerable duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the country at danger by wrongfully keeping and transmitting sensitive documents to family members using unprotected methods, including AOL. Several of the documents were labeled top secret.

The charge states that at a certain time a hacker accessed to Bolton's system where documents were stored and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct counts of mishandling sensitive materials.

Political Motivation or a Strong Case?

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

Trump previously implied Bolton should be in prison, and called him a "disreputable person". Bolton, for his role, wrote a book about his time in the Trump administration that was highly critical of the leader.

"Undoubtedly that the schedule of this charge, when combined with additional cases, has raised doubts about the validity of these charges, and the reason these charges are being brought at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to demonstrate the facts stated and show the information is properly classified, his conduct may very well have violated the statute".

Charging such a high-ranking official for mishandling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information pose difficulties to try, but they can and are brought against both low-level and high-level officials, from occasionally," she explained.

Similarities to Examinations into Former President and Biden

Trump likewise faced allegations of improperly storing classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was ultimately thrown out by a court official and negated by his return as president.

A independent investigator also determined that former President Joe Biden wrongfully stored sensitive materials from his time as vice president, but did not prosecute him.

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

Rigorous protocols regulate the handling of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was sending was classified, and he had to intentionally transfer it to someone not entitled to receive it.

"Because of the classified nature of the material at issue in this case, we lack a lot of details about why the prosecution believes elements like the diary entries and the other information he communicated by electronic message, and why there were classified," said Mr Jaffer.

A More Conventional Legal Action

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

But Mr Lesko indicated in Bolton's situation, authorities appear to have adhered to protocol.

"The Bolton prosecution and eventually the indictment appeared to have observed the standard procedure including the rules and norms within the Department of Justice," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a increasingly "traditional" filing that "explicitly sets forth the details concerning the facts and situation in this instance," Mr Lesko commented.

"It appears fairly consistent with a series of cases... where public servants mishandled and transmitted sensitive information."