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Former President Donald Trump has repeatedly shown his desire to see critics investigated, applying pressure on the Justice Department to charge former 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 post.

"I was impeached twice, and charged me (five times!)" he declared, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Each have since been indicted, in cases that numerous specialists have said seem to be driven by politics and difficult to win in court.

But the most recent charges against a presidential opponent, former national security adviser John Bolton, differ significantly, legal specialists and ex-prosecutors say.

"I would say, contrasting Bolton's case to James' is like comparing apples to oranges," stated Mark Lesko, a ex 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 supposed improper handling of sensitive materials. After leaving the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unsuitable for office in his book.

Experts say that while there may be political reasons to go after Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a potentially more substantial legal argument than the Justice Department brought against James.

"These actions that's being claimed is both more severe and appears to have occurred over a significant period of time," said Carissa Byrne Hessick, a academic 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 placed the nation at risk by wrongfully keeping and transmitting classified information to family members using unprotected methods, including AOL. Some of the documents were labeled top secret.

The indictment states that at a certain time a unauthorized user gained access to Bolton's account where files were kept and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on recently to eighteen distinct charges of improperly handling classified information.

Political Motivation or a Strong Case?

The timing of his charge - arriving on the tails of charges against Comey - has revived questions about external influence on the legal system.

Trump previously suggested Bolton should be in prison, and called him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump administration that was sharply negative of the president.

"There's no question that the timing of this charge, when combined with additional cases, has prompted questions about the validity of these charges, and the reason these counts are being filed now," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "should the Justice Department is capable to prove the facts stated and show the material is properly classified, his behavior may very well have violated the statute".

Charging such a high-ranking official for improperly handling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern classified information pose difficulties to prosecute, but they may and are brought against both junior and senior officials, from time to time," she explained.

Parallels to Investigations into Former President and President

Trump similarly faced charges of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually thrown out by a court official and negated by his return as leader.

A special counsel also determined that former President Joe Biden wrongfully maintained sensitive materials from his period as vice president, but did not prosecute him.

Bolton's case shares characteristics to Biden's classified documents issues, noted Mr Lesko, who also held a senior security position at the Justice Department.

Strict protocols govern the management 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 not entitled to obtain it.

"Due to the classified character of the material at question in this case, we lack a great deal of particulars about why the government believes elements like the diary entries and the additional information he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The process by which the Justice Department brought this legal action will be under scrutiny, following Trump publicly posted his desire to see his critics charged and some of those charges came to fruition.

But Mr Lesko indicated in Bolton's situation, prosecutors appear to have followed protocol.

"The Bolton case and eventually the indictment seemed to have followed the regular procedure including the rules and standards within the Department of Justice," he said.

In contrast to Comey's brief, concise charge, Bolton's was a more "conventional" filing that "explicitly outlines the particulars involving the facts and situation in this instance," Mr Lesko commented.

"It seems reasonably aligned with a long line of cases... where government officials improperly handled and transmitted sensitive information."