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Ex-President Donald Trump has repeatedly shown his desire to see opponents probed, exerting pressure on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our reputation and credibility," the leader wrote last month in a social media message.

"They impeached twice, and indicted me (five times!)" he declared, referencing the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

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

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

"I would say, contrasting Bolton's charges 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 Details of the Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the supposed mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to describe him "stunningly uninformed" and unsuitable for office in his book.

Experts contend that while there may be political reasons to go after Bolton, the methods used to obtain an charge and the proof compiled against him suggest a potentially stronger legal argument than the Justice Department brought against James.

"These actions that's being alleged is simultaneously more serious and seems to have taken place over a considerable period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, authorities alleged that Bolton put the country at risk by improperly keeping and sending classified information to relatives using insecure means, including AOL. Several of the documents were marked top secret.

The charge states that at one point a hacker accessed to Bolton's system where files were stored and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Substantial Legal Argument?

The timing of his indictment - arriving on the tails of charges against James - has renewed questions about external influence on the legal system.

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

"Undoubtedly that the timing of this charge, when combined with additional cases, has raised doubts about the validity of these charges, and why these counts are being brought now," said Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the DOJ is capable to prove the allegations alleged and show the information is properly designated, his behavior may very well have violated the law".

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

"Cases that involve classified information present difficulties to try, but they may and are brought against both low-level and senior officials, from time to time," she explained.

Similarities to Investigations into Trump and President

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

A independent investigator additionally determined that ex-President Joe Biden wrongfully maintained sensitive materials from his period as vice president, but failed to prosecute him.

Bolton's case shares characteristics to Biden's sensitive materials issues, said Mr Lesko, who previously held a top national security role at the DOJ.

Strict protocols govern the handling of classified documents. To secure a guilty verdict, the prosecution must prove that Bolton knew the information he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Due to the sensitive character of the information at question in this case, we lack a lot of particulars about the reasons the government contends things like the personal notes and the other information he communicated by email, and why there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The process by which the Justice Department initiated this legal action will be under scrutiny, after Trump publicly expressed his desire to see his critics prosecuted and some of those indictments materialized.

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

"This Bolton case and eventually the indictment seemed to have observed the standard procedure including the rules and norms within the DOJ," he said.

In contrast to Comey's short, concise indictment, Bolton's was a increasingly "traditional" document that "explicitly sets forth the details involving the circumstances and circumstances here," Mr Lesko said.

"It appears fairly aligned with a series of cases... where public servants mishandled and transmitted classified material."