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

"We can't delay further, it's killing our standing and credibility," the president stated last month in a Truth Social post.

"I was impeached twice, and indicted me (five times!)" he declared, mentioning the four criminal cases he faced after leaving the White House in 2021 and James's civil case.

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

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

"I would say, contrasting Bolton's case to James' is like equating apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been criminally indicted on national allegations pertaining to the supposed mishandling of classified information. After leaving the White House in 2019, he has emerged as a outspoken Trump critic, even to call him "remarkably ignorant" and unsuitable for office in his book.

Experts contend that while there may be political reasons to go after Bolton, the procedures used to obtain an indictment and the evidence gathered against him suggest a possibly more substantial legal argument than the Justice Department presented against James.

"These actions that's being alleged is both more severe and appears to have occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's security advisor, and after his 2019 White House exit, authorities alleged that Bolton placed the nation at danger by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the materials were labeled highly classified.

The indictment alleges that at a certain time a hacker accessed to Bolton's account where documents were kept and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on Friday to eighteen distinct counts of mishandling classified information.

Political Motivation or a Strong Legal Argument?

The timing of his charge - coming on the heels of allegations against Comey - has revived questions about political pressure on the justice system.

Trump previously suggested Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, 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 combined with additional cases, has raised doubts about the strength of these charges, and the reason these counts are being filed at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "should the DOJ is capable to demonstrate the facts stated and demonstrate the material is properly classified, his conduct may very well have violated the law".

Charging such a senior figure for improperly handling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials present challenges to prosecute, but they may and are filed against both low-level and senior officials, from time to time," she said.

Parallels to Investigations into Former President and President

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

A independent investigator also found that former President Joe Biden improperly stored sensitive materials from his period as vice president, but did not prosecute him.

Bolton's situation bears similarities to Biden's sensitive materials matters, said Mr Lesko, who also held a top security position at the DOJ.

Strict procedures regulate the handling of classified documents. To win a guilty verdict, the prosecution must prove that Bolton knew the material he was transmitting was classified, and he had to knowingly transmit it to someone not entitled to receive it.

"Because of the sensitive nature of the information at question in this matter, we lack a great deal of particulars about the reasons the government contends elements like the personal notes and the additional material he communicated by email, and why there were classified," said Mr Jaffer.

A Increasingly Traditional Legal Action

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

But Mr Lesko said in Bolton's situation, prosecutors appear to have followed standard procedure.

"This Bolton case and ultimately the indictment seemed to have observed the standard procedure including the regulations and standards within the DOJ," he stated.

Unlike Comey's short, concise indictment, Bolton's was a increasingly "conventional" filing that "explicitly sets forth the details involving the facts and circumstances in this instance," Mr Lesko said.

"It appears reasonably consistent with a series of precedents... where public servants improperly handled and transmitted sensitive information."