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

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

"I was impeached twice, and charged me (five times!)" he said, referencing the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in situations that many experts have said appear to be driven by politics and challenging to win in court.

But the latest charges against a presidential opponent, ex security advisor John Bolton, differ significantly, legal specialists and former prosecutors say.

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

The Details of Bolton's Legal Situation

Bolton has been formally charged on federal charges related to the alleged improper handling of sensitive materials. Since departing the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his book.

Specialists contend that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the evidence gathered against him indicate a potentially stronger case than the Justice Department brought against James.

"This misconduct that's being claimed is both more severe and appears to have occurred over a significant duration," 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, prosecutors claimed that Bolton put the nation at risk by wrongfully retaining and sending classified information to family members using unprotected methods, including AOL. Some of the materials were marked highly classified.

The charge states that at one point a hacker accessed to Bolton's system where documents were kept and sent an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct charges of improperly handling sensitive materials.

Retribution or a Strong Case?

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

Trump previously implied Bolton belonged in prison, and called him a "disreputable person". 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 indictment, when combined with others, has raised doubts about the validity of these allegations, and the reason these charges are being filed at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

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

Charging such a high-ranking official for mishandling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose challenges to prosecute, but they can and are filed against both junior and senior officials, from occasionally," she explained.

Similarities to Investigations into Trump and Biden

Trump similarly faced charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was eventually dismissed by a federal judge and voided by his return as president.

A special counsel additionally determined that former President Joe Biden improperly maintained classified documents from his time as vice president, but failed to prosecute him.

Bolton's case shares characteristics to Trump's classified documents matters, said Mr Lesko, who also held a senior national security role at the DOJ.

Strict protocols govern the handling of sensitive materials. To secure a guilty verdict, the government must prove that Bolton knew the material he was sending was restricted, and he had to knowingly transmit it to someone without authorization to receive it.

"Due to the sensitive character of the material at issue in this matter, we lack a lot of details about the reasons the prosecution contends things like the personal notes and the other information he communicated by email, and why there were classified," said Mr Jaffer.

A More Conventional Legal Action

The process by which the DOJ initiated this case will be closely examined, following Trump publicly expressed his desire to see his critics charged and several of those indictments materialized.

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

"This Bolton case and eventually the charge appeared to have observed the standard process including the rules and standards within the Department of Justice," he said.

Unlike Comey's short, two-page indictment, Bolton's was a increasingly "conventional" document that "explicitly outlines the details concerning the facts and situation here," Mr Lesko commented.

"It appears reasonably aligned with a long line of precedents... where public servants mishandled and transmitted classified material."