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

"We cannot postpone further, it's killing our reputation and trustworthiness," the leader wrote recently in a Truth Social message.

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

Both have subsequently been indicted, in situations that many experts have said seem to be driven by politics and difficult to succeed in legal proceedings.

But the latest allegations against a presidential opponent, ex national security adviser John Bolton, stand apart, legal experts and ex-prosecutors assert.

"I would say, comparing Bolton's charges to Comey's is like comparing apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of the Case

Bolton has been criminally indicted on federal charges pertaining to the supposed improper handling of classified information. After leaving the White House in 2019, he has become a outspoken presidential opponent, even to call him "stunningly uninformed" and unfit for the presidency in his memoir.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the proof compiled against him indicate a possibly more substantial case than the DOJ presented against James.

"This misconduct that's being alleged is simultaneously more serious and appears to have occurred over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House departure, prosecutors alleged that Bolton placed the country at risk by wrongfully retaining and sending classified information to relatives using insecure means, including AOL. Some of the documents were marked top secret.

The indictment alleges that at a certain time a hacker accessed to Bolton's account where documents were stored and sent an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

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

Retribution or a Substantial Case?

The timing of his charge - arriving on the heels of charges against Comey - has renewed questions about external influence on the justice system.

Trump previously implied Bolton belonged in prison, 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 president.

"Undoubtedly that the schedule of this indictment, when paired with additional cases, has raised doubts about the validity of these charges, and why these counts are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "if the DOJ is capable to demonstrate the allegations alleged and demonstrate the material is correctly designated, his behavior may very well have violated the statute".

Charging such a senior official for mishandling classified documents is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials present difficulties to prosecute, but they can and are filed against equally low-level and high-level personnel, from time to time," she said.

Parallels to Investigations into Former President and Biden

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

A independent investigator also found that ex-President Joe Biden improperly maintained classified documents from his period as second-in-command, but did not prosecute him.

Bolton's case shares characteristics to Biden's classified documents issues, noted Mr Lesko, who also held a senior national security position at the Justice Department.

Strict protocols regulate the handling of classified documents. To win a conviction, the government must prove that Bolton knew the information he was sending was classified, and he had to knowingly transmit it to someone without authorization to obtain it.

"Due to the sensitive character of the information at question in this matter, we don't have a lot of details about the reasons the prosecution contends things like the diary entries and the additional material he shared by electronic message, and why there were restricted," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department brought this legal action will be closely examined, following Trump openly posted his wish to see his critics charged and some of those indictments materialized.

But Mr Lesko said in Bolton's situation, authorities seem to have followed protocol.

"The Bolton prosecution and ultimately the charge appeared to have observed the standard process including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's short, two-page charge, Bolton's was a increasingly "traditional" filing that "clearly outlines the particulars concerning the circumstances and circumstances here," Mr Lesko commented.

"It appears reasonably aligned with a long line of cases... where government officials improperly handled and transmitted sensitive information."