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

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

"They impeached twice, and indicted me (five times!)" he said, referencing the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in situations that numerous specialists have said appear to be politically motivated and challenging to win in court.

But the latest charges against a Trump critic, former security advisor John Bolton, stand apart, legal experts and ex-prosecutors say.

"In my opinion, comparing Bolton's charges 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 federal charges related to the supposed improper handling of classified information. After departing the White House in 2019, he has become a vocal presidential opponent, going so far as to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the evidence gathered against him suggest a possibly stronger legal argument than the Justice Department presented against Comey.

"This misconduct that's being alleged is simultaneously more serious and appears to have taken place over a considerable 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 departure, authorities alleged that Bolton put the country at danger by wrongfully keeping and sending classified information to family members using insecure means, including AOL. Several of the materials were labeled highly classified.

The charge alleges that at one point a hacker gained access to Bolton's system where files were stored and transmitted an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

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

Retribution or a Substantial Case?

The timing of his charge - coming on the heels of charges against Comey - has revived concerns about political pressure on the justice system.

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

"There's no question that the timing of this indictment, when combined with others, has raised questions about the strength of these allegations, and the reason these counts are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is able to demonstrate the allegations alleged and show the information is correctly classified, his behavior may certainly have broken the law".

Prosecuting such a high-ranking figure 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 sensitive materials present challenges to prosecute, but they may and are filed against equally low-level and senior personnel, from time to time," she explained.

Parallels to Examinations into Trump and President

Trump similarly faced allegations of improperly storing sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was ultimately thrown out by a federal judge and voided by his re-election as president.

A special counsel additionally found that ex-President Joe Biden improperly stored classified documents from his period as vice president, but failed to prosecute him.

Bolton's situation shares characteristics to Biden's sensitive materials issues, noted Mr Lesko, who also held a top security position at the DOJ.

Strict procedures regulate the handling of sensitive materials. To win a guilty verdict, the prosecution must prove that Bolton was aware the information he was transmitting was classified, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the classified character of the information at issue in this case, we don't have a great deal of details about why the government contends things like the diary entries and the additional material he shared by email, and the reason there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department initiated this case will be closely examined, following Trump openly expressed his wish to see his critics charged and several of those indictments materialized.

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

"The Bolton prosecution and ultimately the charge seemed to have observed the standard procedure including the regulations and norms within the Department of Justice," he stated.

In contrast to Comey's short, two-page indictment, Bolton's was a increasingly "traditional" document that "explicitly outlines the details concerning the facts and situation in this instance," Mr Lesko said.

"It seems fairly consistent with a long line of cases... where public servants improperly handled and shared sensitive information."