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Former President Donald Trump has repeatedly expressed his desire to see critics probed, exerting pressure 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 killing our standing and trustworthiness," the president stated recently in a social media post.

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

Each have subsequently been charged, in cases that many specialists have stated seem to be driven by politics and difficult to win in court.

But the most recent charges against a Trump critic, ex national security adviser John Bolton, differ significantly, legal specialists and ex-prosecutors say.

"In my opinion, comparing Bolton's case to James' is like equating apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Details of Bolton's Legal Situation

Bolton has been formally charged on national allegations pertaining to the supposed improper handling of classified information. Since leaving the White House in 2019, he has become a vocal presidential opponent, going so far as to call him "remarkably ignorant" and unsuitable for office in his memoir.

Experts contend that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a potentially more substantial case than the Justice Department brought against James.

"This misconduct that's being claimed is simultaneously more serious and seems 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 exit, prosecutors alleged that Bolton put the country at danger by wrongfully retaining and sending sensitive documents to family members using unprotected methods, including AOL. Some of the materials were marked top secret.

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

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

Political Motivation or a Substantial Legal Argument?

The schedule of his charge - arriving on the heels of allegations against Comey - has revived concerns about external influence on the legal system.

Trump previously suggested Bolton belonged in prison, and described him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump government that was sharply negative of the leader.

"Undoubtedly that the schedule of this charge, when combined with others, has prompted doubts about the strength of these charges, and the reason these counts are being filed now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

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

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

"Cases that involve sensitive materials present challenges to try, but they can and are filed against both junior and senior officials, from time to time," she said.

Parallels to Examinations into Former President and President

Trump likewise faced allegations of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually dismissed by a court official and voided by his re-election as president.

A special counsel also found that former President Joe Biden improperly stored classified documents from his time as vice president, but did not criminally charge him.

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

Strict protocols regulate the management of classified documents. To secure a guilty verdict, the prosecution must prove that Bolton was aware the material he was sending was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the classified nature of the material at question in this case, we don't have a great deal of details about the reasons the prosecution contends things like the diary entries and the other information he communicated by electronic message, and why there were restricted," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the DOJ initiated this legal action will be under scrutiny, following Trump publicly posted his wish to see his critics prosecuted and some of those indictments came to fruition.

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

"This Bolton prosecution and eventually the indictment appeared to have followed the standard procedure including the regulations and norms within the DOJ," he said.

In contrast to Comey's short, concise indictment, Bolton's was a increasingly "conventional" filing that "clearly sets forth the particulars involving the facts and situation in this instance," Mr Lesko said.

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