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Former President Donald Trump has repeatedly expressed his wish to see opponents investigated, applying influence on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our reputation and trustworthiness," the president wrote last month in a social media post.

"I was impeached twice, and indicted me (five times!)" he said, mentioning the multiple legal proceedings he faced after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in situations that numerous experts have said seem to be politically motivated and difficult to succeed in court.

But the most recent charges against a presidential opponent, former security advisor John Bolton, stand apart, legal experts and former prosecutors assert.

"I would say, comparing Bolton's charges to Comey's is like equating two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been criminally indicted on national allegations related to the supposed mishandling of classified information. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists say that while there may be political reasons to go after Bolton, the procedures used to obtain an indictment and the proof compiled against him suggest a potentially stronger case than the DOJ presented against Comey.

"These actions that's being alleged is simultaneously more severe and seems to have occurred over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton placed the country at risk by wrongfully keeping and transmitting classified information to family members using unprotected methods, including AOL. Several of the documents were marked highly classified.

The charge states that at a certain time a unauthorized user gained access to Bolton's system where files were kept and transmitted an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on recently to 18 separate charges of mishandling classified information.

Political Motivation or a Substantial Case?

The timing of his charge - arriving on the tails of allegations against James - has revived questions about political pressure on the justice system.

Trump once implied Bolton belonged in prison, and called him a "disreputable person". Bolton, for his role, wrote a publication about his time in the Trump government that was highly critical of the leader.

"There's no question that the timing of this charge, when paired with additional cases, has prompted doubts about the strength of these charges, and why these charges are being filed at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he continued, "if the Justice Department is able to prove the allegations alleged and show the material is properly classified, his conduct may certainly have broken the statute".

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

"Situations that involve classified information present difficulties to prosecute, but they can and are brought against both low-level and senior officials, from occasionally," she explained.

Similarities to Investigations into Trump and Biden

Trump likewise encountered charges of improperly 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 special counsel additionally determined that former President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but did not criminally charge him.

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

Strict protocols regulate the management of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

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

A More Conventional Prosecution

The process by which the Justice Department brought this legal action will be closely examined, after Trump publicly expressed his wish to see his critics charged and several of those charges came to fruition.

But Mr Lesko indicated in Bolton's situation, authorities appear to have adhered to protocol.

"This Bolton prosecution and ultimately the charge seemed to have followed the standard procedure including the rules and norms within the DOJ," he said.

Unlike Comey's brief, two-page indictment, Bolton's was a more "conventional" filing that "clearly sets forth the details involving the circumstances and situation here," Mr Lesko said.

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