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Ex-President Donald Trump has consistently shown his wish to see critics probed, applying pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

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

"They impeached twice, and charged me (5 times!)" he declared, referencing the multiple legal proceedings he faced after leaving the White House in 2021 and James's lawsuit.

Both have since been indicted, in situations that numerous specialists have stated appear to be politically motivated and challenging to win in court.

But the most recent charges against a presidential opponent, 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 two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been formally charged on federal charges related to the supposed mishandling of classified information. After departing the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "remarkably ignorant" and unfit for the presidency in his book.

Specialists say that while there may be political motivations to target Bolton, the procedures used to obtain an charge and the proof gathered against him suggest a possibly more substantial case than the DOJ brought against James.

"These actions that's being claimed is simultaneously more serious and appears to have occurred over a considerable period of time," commented Carissa Byrne Hessick, a professor 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 nation at risk by wrongfully retaining and transmitting classified information to family members using insecure means, including AOL. Some of the materials were marked top secret.

The charge states that at one point a hacker gained access to Bolton's account where files were kept and sent an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct counts of improperly handling classified information.

Political Motivation or a Substantial Case?

The schedule of his charge - coming on the heels of charges against James - has renewed concerns about external influence on the legal system.

Trump once implied Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, wrote a book about his time in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this indictment, when combined with others, has prompted questions about the strength of these charges, and why these charges are being filed at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "if the DOJ is able to demonstrate the facts alleged and show the material is correctly classified, his conduct may very well have broken the statute".

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

"Cases that involve classified information present challenges to prosecute, but they can and are brought against both junior and high-level officials, from time to time," she explained.

Parallels to Examinations into Former President and President

Trump similarly faced charges of improperly storing classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually dismissed by a court official and negated by his re-election as president.

A independent investigator also found that ex-President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but failed to criminally charge him.

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

Rigorous procedures regulate the handling of classified documents. To secure a conviction, the government must prove that Bolton was aware the material he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Because of the sensitive nature of the information at issue in this matter, we lack a lot of details about the reasons the government believes things like the personal notes and the additional information he communicated by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Traditional Prosecution

The process by which the DOJ initiated this legal action will be closely examined, after Trump openly expressed his desire to see his political opponents charged and several of those indictments materialized.

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

"The Bolton case and ultimately the indictment appeared to have observed the standard procedure including the rules and standards within the DOJ," he said.

In contrast to Comey's short, concise charge, Bolton's was a increasingly "traditional" filing that "explicitly sets forth the particulars concerning the facts and situation here," Mr Lesko said.

"It seems fairly consistent with a long line of cases... where government officials mishandled and shared sensitive information."