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Ex-President Donald Trump has consistently shown his desire to see opponents investigated, exerting influence on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

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

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

Each have subsequently been charged, in cases that many experts have stated seem to be politically motivated and challenging to succeed in court.

But the most recent allegations against a Trump critic, former security advisor John Bolton, stand apart, legal specialists and former prosecutors say.

"In my opinion, contrasting Bolton's case to James' is like comparing apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the supposed mishandling of classified information. Since leaving the White House in 2019, he has become a vocal Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for office in his book.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the proof gathered against him indicate a possibly more substantial legal argument than the Justice Department brought against Comey.

"These actions that's being alleged is both more severe and appears to have occurred over a significant duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's national security adviser, and following his 2019 White House exit, authorities claimed that Bolton placed the country at danger by wrongfully retaining and sending classified information to family members using unprotected methods, including AOL. Some of the materials were labeled top secret.

The charge states that at one point a hacker accessed to Bolton's system where documents were stored and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on recently to eighteen distinct counts of improperly handling classified information.

Retribution or a Substantial Case?

The schedule of his indictment - arriving on the tails of allegations against James - has renewed concerns about external influence on the justice system.

Trump once implied Bolton should be in prison, and called him a "sleazebag". Bolton, for his part, wrote a publication about his time in the Trump administration that was sharply negative of the president.

"Undoubtedly that the schedule of this indictment, when combined with others, has raised questions about the strength of these allegations, and the reason these counts are being filed now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is able to demonstrate the facts stated and demonstrate the information is correctly classified, his conduct may certainly have broken the statute".

Prosecuting such a high-ranking official for mishandling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials present difficulties to try, but they can and are brought against both junior and senior personnel, from time to time," she said.

Similarities to Examinations into Former President and President

Trump similarly encountered allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was ultimately dismissed by a court official and voided by his return as president.

A independent investigator additionally determined that former President Joe Biden improperly stored classified documents from his period as second-in-command, but did not prosecute him.

Bolton's case bears similarities to Trump's classified documents issues, said Mr Lesko, who also held a senior security role at the Justice Department.

Strict procedures govern the handling of sensitive materials. To secure a conviction, the government must prove that Bolton was aware the material he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the classified nature of the material at issue in this matter, we lack a lot of particulars about why the government believes elements like the diary entries and the additional material he communicated by email, and why there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the Justice Department initiated this case will be under scrutiny, after Trump openly expressed his desire to see his critics charged and some of those charges came to fruition.

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

"The Bolton prosecution and ultimately the indictment appeared to have observed the regular procedure including the regulations and standards within the DOJ," he stated.

In contrast to Comey's brief, two-page charge, Bolton's was a more "conventional" document that "explicitly outlines the particulars concerning the circumstances and circumstances in this instance," Mr Lesko said.

"It seems reasonably consistent with a series of cases... where government officials improperly handled and shared classified material."