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

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

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

Both have since been indicted, in situations that numerous experts have stated appear to be driven by politics and challenging to win in court.

But the latest allegations against a presidential opponent, former security advisor John Bolton, stand apart, legal experts and ex-prosecutors say.

"In my opinion, comparing Bolton's case to Comey's is like equating 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 formally charged on national allegations related to the supposed mishandling of classified information. After leaving the White House in 2019, he has become a vocal Trump critic, even to call him "remarkably ignorant" and unfit for the presidency in his book.

Specialists contend that while there may be political motivations to target Bolton, the methods used to secure an charge and the evidence compiled against him suggest a potentially more substantial case than the Justice Department brought against James.

"This misconduct that's being claimed is simultaneously more severe and appears to have taken place over a significant duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, authorities claimed that Bolton put the country at risk by wrongfully retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Some of the materials were labeled highly classified.

The indictment alleges that at one point a unauthorized user gained access to Bolton's account where files were kept and sent an apparent warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to 18 separate counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - coming on the heels of allegations against James - has renewed concerns about political pressure on the legal system.

Trump once suggested Bolton should be in jail, and called him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump government that was sharply negative of the leader.

"There's no question that the schedule of this charge, when paired with additional cases, has raised questions about the validity of these allegations, and why these counts are being brought now," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to prove the facts alleged and show the material is properly classified, his behavior may very well have violated the law".

Prosecuting such a senior figure for improperly handling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials present challenges to try, but they can and are brought against both junior and senior officials, from occasionally," she said.

Parallels to Investigations into Former President and Biden

Trump likewise encountered charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually dismissed by a court official and voided by his re-election as leader.

A independent investigator additionally found that former President Joe Biden wrongfully maintained sensitive materials from his time as vice president, but did not prosecute him.

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

Rigorous protocols govern the management of sensitive materials. To win a conviction, the government must demonstrate that Bolton knew the material he was sending was classified, and he had to intentionally transmit it to someone without authorization to obtain it.

"Because of the sensitive character of the information at issue in this matter, we lack a great deal of details about why the prosecution believes things like the personal notes and the additional information he communicated by electronic message, and the reason there were classified," said Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ brought this legal action will be closely examined, following Trump publicly posted his wish to see his political opponents charged and several of those indictments came to fruition.

But Mr Lesko said in Bolton's case, authorities seem to have adhered to standard procedure.

"The Bolton prosecution and ultimately the charge seemed to have followed the standard procedure including the regulations and standards within the Department of Justice," he said.

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

"It seems fairly aligned with a long line of precedents... where government officials mishandled and shared classified material."