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Ex-President Donald Trump has repeatedly expressed his wish to see opponents investigated, exerting pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our standing and credibility," the president wrote last month in a Truth Social message.

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

Each have since been indicted, in cases that many experts have said appear to be driven by politics and challenging to succeed in court.

But the latest allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal experts and former prosecutors assert.

"I would say, contrasting Bolton's case to Comey's is like comparing apples to oranges," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Specifics of the Case

Bolton has been formally charged on national allegations related to the alleged mishandling of classified information. After departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unfit for office in his memoir.

Experts say that while there may be political reasons to go after Bolton, the procedures used to obtain an indictment and the proof gathered against him indicate a potentially more substantial legal argument than the DOJ presented against James.

"This misconduct that's being alleged is simultaneously more severe and seems to have occurred over a significant duration," 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 following his 2019 White House exit, prosecutors claimed that Bolton put the country at danger by improperly keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were marked top secret.

The charge alleges that at one point a unauthorized user accessed to Bolton's account where documents were kept and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to eighteen separate counts of improperly handling sensitive materials.

Retribution or a Substantial Legal Argument?

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

Trump once suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, wrote a book about his time in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this charge, when paired with others, has raised questions about the strength of these charges, and the reason these counts are being brought at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "should the Justice Department is able to demonstrate the allegations alleged and show the material is correctly designated, his conduct may certainly have violated the law".

Prosecuting such a high-ranking figure for mishandling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials present difficulties to prosecute, but they may and are brought against both junior and senior officials, from occasionally," she said.

Similarities to Examinations into Former President and President

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

A independent investigator also determined that former President Joe Biden wrongfully maintained classified documents from his period as vice president, but did not prosecute him.

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

Strict procedures regulate the handling of sensitive materials. To secure a guilty verdict, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the sensitive character of the information at issue in this matter, we don't have a lot of details about the reasons the prosecution believes elements like the diary entries and the additional material he shared by email, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the Justice Department initiated this legal action will be under scrutiny, following Trump publicly expressed his wish to see his critics charged and some of those charges materialized.

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

"The Bolton prosecution and eventually the indictment appeared to have followed the regular procedure including the rules and standards within the DOJ," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a more "traditional" filing that "explicitly outlines the particulars involving the circumstances and situation here," Mr Lesko commented.

"It appears fairly aligned with a long line of precedents... where government officials mishandled and transmitted classified material."