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Ex-President Donald Trump has consistently expressed his wish to see opponents probed, exerting pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our standing and credibility," the leader wrote recently in a Truth Social post.

"I was impeached me, and charged me (five times!)" he said, mentioning the multiple legal proceedings he faced after departing the White House in 2021 and James's civil case.

Each have since been charged, in cases that many specialists 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, differ significantly, legal experts and ex-prosecutors say.

"I would say, contrasting Bolton's charges to James' is like comparing two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been criminally indicted on national allegations related to the supposed mishandling of classified information. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "remarkably ignorant" and unfit for office in his book.

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

"These actions that's being claimed is both more serious and appears to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's national security adviser, and after his 2019 White House exit, prosecutors claimed that Bolton put the country at risk by improperly retaining and transmitting classified information to family members using insecure means, including AOL. Some of the documents were labeled top secret.

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

Bolton pleaded not guilty during a hearing on Friday to eighteen separate counts of improperly handling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his charge - arriving on the tails of allegations against James - has revived questions about political pressure on the legal system.

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

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

However, he added, "should the Justice Department is capable to demonstrate the allegations stated and show the information is correctly designated, his behavior may very well have broken the law".

Prosecuting such a high-ranking figure 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 pose difficulties to prosecute, but they can and are brought against both low-level and senior officials, from occasionally," she said.

Parallels to Examinations into Former President and Biden

Trump likewise faced allegations of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately dismissed by a federal judge and voided by his re-election as president.

A independent investigator also found that former President Joe Biden improperly maintained sensitive materials from his time as vice president, but did not criminally charge him.

Bolton's case bears similarities to Biden's classified documents matters, noted Mr Lesko, who also held a senior security role at the DOJ.

Rigorous procedures govern the management of classified documents. To secure a guilty verdict, the government must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Due to the classified character of the information at question in this matter, we lack a lot of details about why the government contends elements like the diary entries and the other material he shared by email, and why there were classified," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ brought this case will be under scrutiny, following Trump publicly posted his desire to see his political opponents charged and several of those charges materialized.

But Mr Lesko indicated in Bolton's situation, prosecutors seem to have followed protocol.

"This Bolton prosecution and ultimately the charge seemed to have followed the standard process including the regulations and standards within the DOJ," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a increasingly "conventional" document that "clearly sets forth the particulars involving the facts and circumstances here," Mr Lesko commented.

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