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Former President Donald Trump has repeatedly expressed his desire to see critics investigated, exerting influence on the Justice Department to charge former 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 last month in a Truth Social message.

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

Each have subsequently been indicted, in situations that many experts have stated seem to be politically motivated and difficult to succeed in legal proceedings.

But the most recent charges against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and former prosecutors assert.

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

This Specifics of the Legal Situation

Bolton has been criminally indicted on national allegations related to the alleged improper handling of classified information. After leaving the White House in 2019, he has emerged as a outspoken presidential opponent, even to call him "remarkably ignorant" and unfit for office in his book.

Experts contend that while there may be political reasons to go after Bolton, the methods used to obtain an indictment and the proof compiled against him indicate a potentially more substantial case than the Justice Department brought against Comey.

"This misconduct that's being alleged is both more severe and seems to have occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and following his 2019 White House departure, prosecutors alleged that Bolton put the nation at danger by wrongfully keeping and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were marked highly classified.

The indictment states that at a certain time a unauthorized user gained access to Bolton's system where documents were kept 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 Friday to eighteen distinct counts of mishandling classified information.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the tails of allegations against James - has revived questions about external influence on the legal system.

Trump previously suggested Bolton should be in prison, and called him a "sleazebag". Bolton, for his role, authored a book about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this charge, when paired with additional cases, has raised questions about the strength of these allegations, and the reason these counts are being filed now," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is able to demonstrate the allegations stated and show the information is properly designated, his behavior may very well have violated the law".

Prosecuting such a high-ranking official for mishandling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present difficulties to prosecute, but they may and are brought against equally junior and senior officials, from occasionally," she explained.

Parallels to Investigations into Trump and Biden

Trump likewise faced allegations of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that matter was eventually dismissed by a court official and negated by his return as leader.

A independent investigator additionally found that ex-President Joe Biden improperly stored classified documents from his period as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Biden's sensitive materials matters, said Mr Lesko, who previously held a senior national security position at the Justice Department.

Rigorous protocols regulate the handling of sensitive materials. To win a conviction, the government must demonstrate that Bolton knew the information he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to obtain it.

"Because of the classified character of the information at question in this matter, we don't have a lot of particulars about the reasons the prosecution believes things like the diary entries and the other material he communicated by email, and the reason there were classified," explained Mr Jaffer.

A More Conventional Legal Action

The procedure by which the DOJ initiated this legal action will be under scrutiny, after Trump publicly posted his desire to see his political opponents prosecuted and some of those indictments materialized.

But Mr Lesko indicated in Bolton's situation, prosecutors appear to have adhered to protocol.

"This Bolton case and ultimately the charge seemed to have followed the regular procedure including the regulations and norms within the DOJ," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a more "traditional" filing that "clearly outlines the details involving the circumstances and situation in this instance," Mr Lesko said.

"It seems fairly aligned with a series of cases... where government officials mishandled and shared sensitive information."