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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 can't delay any longer, it's killing our reputation and trustworthiness," the leader stated last month in a Truth Social post.

"I was impeached twice, and charged me (5 times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in situations that many experts have stated seem to be driven by politics and difficult to win in court.

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

"In my opinion, comparing Bolton's case to James' is like equating two different things," stated Mark Lesko, a ex federal prosecutor 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 improper handling of sensitive materials. After leaving the White House in 2019, he has emerged as a outspoken presidential opponent, even to describe him "stunningly uninformed" and unfit for the presidency in his memoir.

Specialists say that while there may be political reasons to go after Bolton, the methods used to secure an charge and the proof gathered against him suggest a possibly stronger case than the DOJ presented against James.

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

During his tenure as Trump's security advisor, and following his 2019 White House departure, authorities alleged that Bolton placed the nation at risk by wrongfully retaining and sending sensitive documents to relatives using insecure means, including AOL. Some of the materials were labeled highly classified.

The indictment states that at one point a hacker gained access to Bolton's account where documents were kept and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to eighteen separate counts of mishandling classified information.

Political Motivation or a Substantial Legal Argument?

The schedule of his charge - coming on the heels of allegations against James - has revived questions about political pressure on the justice system.

Trump once implied Bolton should be in jail, and called him a "disreputable person". Bolton, for his role, authored a publication about his time in the Trump administration that was sharply negative of the leader.

"There's no question that the timing of this indictment, when combined with others, has prompted doubts about the strength of these allegations, and the reason these charges are being filed at this time," said Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "should the Justice Department is able to demonstrate the allegations stated and show the material is properly classified, his behavior may very well have broken the law".

Charging such a senior figure for improperly handling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern classified information present difficulties to try, but they can and are brought against both junior and high-level personnel, from time to time," she said.

Similarities to Investigations into Trump and President

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

A special counsel additionally found that ex-President Joe Biden improperly stored sensitive materials from his time as second-in-command, but did not criminally charge him.

Bolton's situation bears similarities to Trump's classified documents issues, noted Mr Lesko, who previously held a senior national security position at the DOJ.

Rigorous protocols regulate the management of sensitive materials. To secure a conviction, the government 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 receive it.

"Because of the sensitive nature of the material at issue in this matter, we don't have a great deal of details about why the government believes things like the diary entries and the other information he communicated by electronic message, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the DOJ brought this case 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 said in Bolton's case, prosecutors appear to have adhered to standard procedure.

"The Bolton case and ultimately the charge seemed to have observed the standard process including the rules and standards within the Department of Justice," he stated.

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

"It seems fairly consistent with a series of cases... where government officials mishandled and transmitted classified material."