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Ex-President Donald Trump has repeatedly expressed his desire to see opponents probed, applying pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our standing and trustworthiness," the president wrote recently in a Truth Social post.

"I was impeached me, and indicted me (five times!)" he said, referencing the four criminal cases he faced after departing the White House in 2021 and James's civil case.

Each have subsequently been indicted, in situations that numerous experts have said appear to be politically motivated and challenging to succeed in legal proceedings.

But the latest allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and former prosecutors say.

"In my opinion, contrasting Bolton's charges to Comey's is like equating two different things," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Details of the Case

Bolton has been formally charged on federal charges pertaining to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to call him "remarkably ignorant" and unsuitable for office in his book.

Experts contend that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the proof compiled against him suggest a possibly more substantial legal argument than the DOJ brought against Comey.

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

During his tenure as Trump's national security adviser, and after his 2019 White House departure, authorities claimed that Bolton placed the nation at danger by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the materials were labeled top secret.

The indictment states that at a certain time a unauthorized user gained access to Bolton's system where documents were stored and transmitted an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to 18 separate charges of mishandling classified information.

Retribution or a Substantial Case?

The timing of his charge - arriving on the heels of allegations against Comey - has revived questions about political pressure on the justice system.

Trump once suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his role, authored a book about his time in the Trump government that was highly critical of the leader.

"There's no question that the schedule of this charge, when paired with additional cases, has prompted questions about the validity of these charges, and the reason these counts are being filed at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "if the DOJ is able to demonstrate the allegations stated and show the material is correctly designated, his behavior may very well have violated the law".

Charging such a high-ranking official for improperly handling classified documents is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present challenges to try, but they may and are brought against equally junior and senior officials, from time to time," she said.

Parallels to Investigations into Former President and Biden

Trump likewise faced allegations of wrongfully keeping sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that case was eventually dismissed by a court official and voided by his re-election as leader.

A independent investigator additionally determined that former President Joe Biden improperly maintained classified documents from his time as vice president, but did not prosecute him.

Bolton's case bears similarities to Biden's classified documents matters, noted Mr Lesko, who previously held a top national security position at the Justice Department.

Strict protocols govern the management of classified documents. To win a guilty verdict, the prosecution must prove that Bolton knew the information he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to obtain it.

"Due to the classified nature of the material at question in this matter, we don't have a great deal of particulars about why the government contends things like the personal notes and the additional information he shared by email, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The process by which the DOJ brought this legal action will be under scrutiny, after Trump openly expressed his desire to see his political opponents prosecuted and several of those indictments came to fruition.

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

"This Bolton case and eventually the charge seemed to have followed the standard process including the rules and standards within the DOJ," he stated.

In contrast to Comey's brief, concise indictment, Bolton's was a more "traditional" filing that "clearly sets forth the particulars involving the circumstances and circumstances in this instance," Mr Lesko commented.

"It seems fairly consistent with a long line of precedents... where government officials improperly handled and shared classified material."