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Former President Donald Trump has repeatedly expressed his wish to see critics probed, exerting pressure 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 trustworthiness," the president wrote recently in a social media message.

"I was impeached me, and indicted me (5 times!)" he declared, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Both have subsequently been charged, in cases that numerous specialists have said appear to be driven by politics and challenging to succeed in court.

But the most recent allegations against a Trump critic, ex security advisor John Bolton, stand apart, legal experts and ex-prosecutors say.

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

This Details of Bolton's Case

Bolton has been criminally indicted on national allegations related to the supposed improper handling of classified information. Since departing the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to call him "stunningly uninformed" and unfit for the presidency in his book.

Experts say that while there may be political reasons to target Bolton, the methods used to obtain an charge and the evidence gathered against him suggest a potentially stronger case 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," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and after his 2019 White House departure, authorities claimed that Bolton placed the country at danger by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled top secret.

The indictment states that at one point a unauthorized user gained access to Bolton's system where documents were kept and sent an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to 18 separate counts of mishandling classified information.

Retribution or a Substantial Case?

The timing of his charge - coming on the heels of charges against James - has revived concerns about political pressure on the justice system.

Trump previously implied Bolton should be in jail, and described him a "disreputable person". Bolton, for his role, wrote a publication about his time in the Trump government that was highly critical of the president.

"Undoubtedly that the timing of this charge, when paired with others, has raised doubts about the validity of these allegations, and the reason these counts are being filed at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "if the Justice Department is capable to demonstrate the allegations alleged and demonstrate the information is properly classified, his conduct may very well have violated the statute".

Prosecuting such a high-ranking figure for improperly handling classified documents is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern classified information pose difficulties to try, but they may and are filed against equally low-level and senior personnel, from occasionally," she explained.

Similarities to Investigations into Trump and President

Trump likewise faced allegations of wrongfully keeping classified documents 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 return as leader.

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

Bolton's situation bears similarities to Trump's sensitive materials issues, said Mr Lesko, who also held a senior security position at the Justice Department.

Rigorous protocols regulate the handling of classified documents. To win 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 without authorization to obtain it.

"Due to the classified character of the material at issue in this case, we don't have a lot of particulars about the reasons the prosecution believes things like the diary entries and the additional material he shared by email, and why there were classified," said Mr Jaffer.

A Increasingly Traditional Legal Action

The procedure by which the DOJ initiated this case will be under scrutiny, after Trump publicly posted his wish to see his critics prosecuted and several 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 indictment appeared to have followed the standard procedure including the rules and standards within the Department of Justice," he said.

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

"It seems reasonably aligned with a series of precedents... where government officials mishandled and shared sensitive information."