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

"We can't delay any longer, it's damaging our reputation and trustworthiness," the president wrote recently in a social media post.

"They impeached twice, and charged me (five times!)" he said, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Each have subsequently been indicted, in cases that many experts have stated appear to be politically motivated and challenging to win in legal proceedings.

But the latest charges against a Trump critic, ex national security adviser John Bolton, differ significantly, legal specialists and former prosecutors say.

"In my opinion, contrasting Bolton's case to James' is like equating apples to oranges," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of the Case

Bolton has been formally charged on federal charges pertaining to the alleged improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "stunningly uninformed" and unsuitable for office in his book.

Experts contend that while there may be political motivations to target Bolton, the methods used to secure an indictment and the proof gathered against him suggest a possibly more substantial case than the DOJ presented against Comey.

"This misconduct that's being alleged is simultaneously more serious 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 tenure as Trump's national security adviser, and after his 2019 White House exit, authorities alleged that Bolton placed the country at danger by improperly retaining and sending classified information to family members using unprotected methods, including AOL. Several of the documents were marked top secret.

The indictment states that at a certain time a unauthorized user accessed to Bolton's account where files were stored and transmitted an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on recently to 18 distinct charges of mishandling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his charge - coming on the tails of charges against Comey - has revived concerns about external influence on the legal system.

Trump previously suggested Bolton belonged in prison, and called him a "disreputable person". Bolton, for his role, authored a publication about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the timing of this charge, when combined with additional cases, has raised doubts about the strength of these allegations, and why these counts are being filed at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "if the Justice Department is capable to prove the allegations stated and demonstrate the information is correctly designated, his conduct may certainly have violated the statute".

Charging such a senior official 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 challenges to try, but they can and are filed against both low-level and senior officials, from time to time," she said.

Parallels to Examinations into Trump and President

Trump likewise encountered allegations of improperly storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was ultimately dismissed by a federal judge and voided by his return as president.

A special counsel also determined that former President Joe Biden improperly stored sensitive materials from his period as vice president, but did not criminally charge him.

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

Strict protocols govern the management of sensitive materials. To secure a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to receive it.

"Because of the sensitive character of the information at question in this case, we don't have a lot of details about the reasons the government believes things like the diary entries and the additional information he shared by email, and the reason there were restricted," said Mr Jaffer.

A More Traditional Legal Action

The process by which the Justice Department brought this legal action will be under scrutiny, following Trump openly posted his wish to see his political opponents charged and some of those indictments materialized.

But Mr Lesko indicated in Bolton's case, prosecutors seem to have adhered to protocol.

"This Bolton prosecution and eventually the indictment seemed to have followed the standard process including the regulations and norms within the DOJ," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a increasingly "traditional" document that "clearly sets forth the details concerning the circumstances and circumstances in this instance," Mr Lesko said.

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