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Former President Donald Trump has consistently shown his wish to see critics probed, exerting influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our standing and credibility," the leader wrote recently in a Truth Social post.

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

Both have since been charged, in cases that numerous experts have stated appear to be driven by politics and difficult to win in legal proceedings.

But the latest allegations against a presidential opponent, former national security adviser John Bolton, differ significantly, legal experts and former prosecutors say.

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

This Specifics of the Case

Bolton has been criminally indicted on national allegations related to the alleged mishandling of classified information. Since departing the White House in 2019, he has emerged as a vocal presidential opponent, even to describe him "stunningly uninformed" and unfit for office in his book.

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

"This misconduct that's being alleged is simultaneously more severe and appears to have occurred over a considerable period of time," said 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 departure, prosecutors alleged that Bolton placed the nation at risk by wrongfully retaining and sending classified information to family members using unprotected methods, including AOL. Several of the materials were marked top secret.

The indictment alleges that at a certain time a unauthorized user gained access to Bolton's account where documents were stored and sent an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to eighteen distinct counts of mishandling classified information.

Retribution or a Strong Legal Argument?

The schedule of his indictment - arriving on the tails of charges against James - has renewed concerns about political pressure on the justice system.

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

"Undoubtedly that the timing of this charge, when combined with additional cases, has prompted questions about the validity of these charges, and the reason these counts are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "if the DOJ is capable to demonstrate the facts alleged and demonstrate the material is properly designated, his conduct may certainly have broken the statute".

Prosecuting such a senior figure for improperly handling classified documents is "rare" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to try, but they can and are filed against equally junior and senior officials, from occasionally," she said.

Parallels to Investigations into Former President and Biden

Trump similarly encountered allegations of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was eventually thrown out by a court official and negated by his return as leader.

A independent investigator also determined that ex-President Joe Biden wrongfully stored sensitive materials from his period as second-in-command, but did not 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.

Rigorous procedures govern the management of classified documents. To secure a guilty verdict, the government must demonstrate that Bolton knew the information he was sending was restricted, and he had to intentionally transmit it to someone without authorization to receive it.

"Due to the sensitive nature of the information at issue in this matter, we don't have a great deal of particulars about the reasons the government believes things like the diary entries and the additional information he communicated by email, and why there were restricted," said Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ initiated this case will be closely examined, after Trump openly expressed his wish to see his political opponents charged and some of those indictments came to fruition.

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

"This Bolton prosecution and ultimately the charge seemed to have observed the standard process including the regulations and standards within the DOJ," he said.

In contrast to Comey's short, concise charge, Bolton's was a increasingly "conventional" filing that "explicitly sets forth the details involving the facts and situation here," Mr Lesko said.

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