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Former President Donald Trump has repeatedly expressed his desire to see opponents investigated, applying 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 damaging our standing and trustworthiness," the president wrote recently in a Truth Social message.

"I was impeached me, and indicted me (five 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 indicted, in cases that many specialists have stated appear to be politically motivated and difficult to win in legal proceedings.

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

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

The Details of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged mishandling of sensitive materials. Since departing the White House in 2019, he has emerged as a outspoken presidential opponent, even to describe him "remarkably ignorant" and unsuitable for office in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the procedures used to secure an charge and the evidence compiled against him suggest a possibly stronger case than the Justice Department brought against Comey.

"These actions that's being alleged is both more severe and seems to have taken place 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, authorities alleged that Bolton put the nation at risk by wrongfully keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the materials were labeled highly classified.

The charge alleges that at one point a unauthorized user gained access to Bolton's system where documents were kept and transmitted an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on Friday to 18 separate charges of improperly handling sensitive materials.

Retribution or a Substantial Case?

The schedule of his indictment - coming on the heels of allegations against Comey - has revived questions about political pressure on the legal system.

Trump previously suggested Bolton should be in prison, and described him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump government that was highly critical of the leader.

"There's no question that the timing of this indictment, when combined with others, has raised doubts about the strength of these allegations, and the reason these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "should the DOJ is capable to demonstrate the allegations alleged and show the material is properly classified, his conduct may certainly have broken the statute".

Charging such a senior official for mishandling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose difficulties to prosecute, but they can and are brought against both low-level and senior personnel, from occasionally," she explained.

Parallels to Investigations into Former President and Biden

Trump similarly faced charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was eventually thrown out by a court official and voided by his return as leader.

A independent investigator also determined 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 classified documents matters, noted Mr Lesko, who also held a top national security role at the DOJ.

Strict protocols regulate the handling of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the sensitive character of the information at issue in this case, we lack a lot of details about the reasons the prosecution believes things like the diary entries and the additional information he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ brought this case will be closely examined, following Trump openly posted his desire to see his critics charged and some of those indictments came to fruition.

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

"The Bolton case and ultimately the indictment seemed to have observed the regular process including the rules and norms within the Department of Justice," he said.

In contrast to Comey's short, concise charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears reasonably aligned with a series of cases... where public servants mishandled and shared sensitive information."