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

"We can't delay further, it's killing our standing and trustworthiness," the leader stated recently in a social media message.

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

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

But the most recent charges against a Trump critic, former national security adviser John Bolton, stand apart, legal experts and former prosecutors say.

"In my opinion, contrasting Bolton's case to James' is like comparing apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the supposed mishandling of sensitive materials. Since departing the White House in 2019, he has become a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unfit for office in his memoir.

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

"This misconduct that's being claimed is simultaneously more serious and appears to have occurred over a significant 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 put the country at risk by improperly keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the materials were labeled top secret.

The indictment states that at a certain time a unauthorized user accessed to Bolton's system where files were stored and sent an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on recently to eighteen distinct counts of improperly handling classified information.

Political Motivation or a Substantial Legal Argument?

The timing of his indictment - coming on the tails of allegations against Comey - has revived concerns about political pressure on the justice system.

Trump previously suggested Bolton belonged in prison, and called him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump administration that was sharply negative of the president.

"There's no question that the timing of this charge, when paired with others, has prompted questions about the strength of these allegations, and why these charges are being brought at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "if the Justice Department is capable to prove the allegations alleged and show the information is properly designated, his conduct may very well have broken the statute".

Charging such a high-ranking official for improperly handling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information pose challenges to prosecute, but they can and are filed against equally low-level and high-level personnel, from occasionally," she said.

Similarities to Investigations into Trump and Biden

Trump similarly faced allegations of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually dismissed by a federal judge and voided by his return as leader.

A special counsel additionally found that former President Joe Biden improperly stored classified documents from his time as second-in-command, but failed to criminally charge him.

Bolton's case bears similarities to Trump's classified documents issues, noted Mr Lesko, who also held a senior security role at the Justice Department.

Strict protocols regulate the management of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was sending was classified, and he had to intentionally transfer it to someone without authorization to receive it.

"Due to the classified character of the material at issue in this matter, we lack a lot of details about why the government believes elements like the personal notes and the other material he communicated by email, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ brought this case will be under scrutiny, after Trump openly posted his wish to see his critics charged and some of those indictments came to fruition.

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

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

Unlike Comey's brief, two-page indictment, Bolton's was a increasingly "conventional" document that "explicitly outlines the details involving the facts and situation here," Mr Lesko commented.

"It seems fairly consistent with a series of precedents... where government officials improperly handled and transmitted sensitive information."