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Ex-President Donald Trump has repeatedly shown his desire to see critics probed, exerting pressure on the Justice Department to charge 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 president stated last month in a social media post.

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

Each have subsequently been charged, in situations that many experts have said appear to be politically motivated and challenging to win in legal proceedings.

But the latest 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 Comey's is like comparing two different things," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of the Case

Bolton has been formally charged on national allegations related to the supposed mishandling of classified information. After leaving the White House in 2019, he has become a vocal 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 reasons to go after Bolton, the methods used to obtain an charge and the evidence gathered against him suggest a potentially more substantial case than the DOJ brought against Comey.

"This misconduct that's being claimed is both more serious and appears to have taken place over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and after his 2019 White House exit, prosecutors claimed that Bolton placed the country at risk by wrongfully keeping and transmitting classified information to relatives using insecure means, including AOL. Some of the documents were marked top secret.

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

Bolton pleaded not guilty during a hearing on recently to 18 separate counts of mishandling sensitive materials.

Retribution or a Strong Legal Argument?

The schedule of his indictment - coming on the tails of charges against Comey - has revived questions about external influence on the legal system.

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump administration that was sharply negative of the president.

"Undoubtedly that the schedule of this indictment, when paired with others, has prompted doubts about the strength of these allegations, and why these counts are being filed now," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "if the DOJ is able to demonstrate the allegations stated and demonstrate the material is correctly classified, his behavior may very well have violated the law".

Prosecuting such a high-ranking official for mishandling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose difficulties to try, but they can and are brought against both junior and high-level officials, from occasionally," she explained.

Similarities to Investigations into Former President and Biden

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

A special counsel also determined that ex-President Joe Biden wrongfully stored classified documents from his time as vice president, but failed to criminally charge him.

Bolton's case bears similarities to Trump's sensitive materials matters, noted Mr Lesko, who also held a top security position at the DOJ.

Strict procedures govern the handling of sensitive materials. To secure a conviction, the prosecution must demonstrate that Bolton knew the material he was sending was classified, and he had to knowingly transfer it to someone without authorization to obtain it.

"Due to the sensitive character of the material at issue in this matter, we lack a great deal of details about the reasons the prosecution believes elements like the personal notes and the additional material he shared by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ initiated this case will be under scrutiny, after Trump publicly expressed his desire to see his political opponents prosecuted and some of those indictments came to fruition.

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

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

Unlike Comey's short, two-page charge, Bolton's was a increasingly "conventional" filing that "clearly outlines the details involving the circumstances and circumstances in this instance," Mr Lesko said.

"It seems reasonably consistent with a long line of cases... where public servants mishandled and shared classified material."