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Ex-President Donald Trump has repeatedly expressed his wish to see opponents probed, exerting pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and trustworthiness," the leader stated last month in a Truth Social message.

"I was impeached twice, 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 cases that many specialists have said seem to be politically motivated and challenging to succeed in legal proceedings.

But the latest allegations against a Trump critic, ex security advisor John Bolton, differ significantly, legal specialists and former prosecutors assert.

"I would say, contrasting 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 Case

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

Specialists say that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the evidence compiled against him suggest a potentially stronger case than the DOJ brought against James.

"These actions that's being alleged is simultaneously more serious and appears to have occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and following his 2019 White House exit, prosecutors claimed that Bolton placed the nation at danger by wrongfully retaining and sending classified information to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

The indictment states that at one point a unauthorized user gained access to Bolton's account where documents were kept and sent an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on recently to eighteen distinct counts of mishandling sensitive materials.

Retribution or a Strong Case?

The timing of his charge - arriving on the tails of charges against James - has renewed concerns about political pressure on the justice system.

Trump previously implied Bolton should be in jail, and described him a "disreputable person". Bolton, for his role, wrote 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 combined with additional cases, has prompted doubts about the strength of these allegations, and why these counts are being brought now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the Justice Department is capable to prove the facts alleged and show the information is correctly classified, his behavior may very well have broken the statute".

Prosecuting such a high-ranking official for mishandling sensitive materials is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve classified information pose challenges to try, but they may and are filed against equally low-level and senior officials, from occasionally," she explained.

Parallels to Examinations into Former President and President

Trump similarly encountered charges of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately dismissed by a court official and negated by his re-election as president.

A independent investigator also found that ex-President Joe Biden improperly stored classified documents from his time as vice president, but failed to prosecute him.

Bolton's situation bears similarities to Biden's sensitive materials matters, said Mr Lesko, who previously held a top security role at the Justice Department.

Strict procedures regulate the management of sensitive materials. To secure a guilty verdict, the government must demonstrate that Bolton knew the information he was sending was restricted, and he had to knowingly transfer it to someone not entitled to receive it.

"Due to the classified character of the information at issue in this matter, we lack a lot of particulars about why the government contends things like the diary entries and the other information he shared by email, and the reason there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department initiated this case will be under scrutiny, following Trump publicly expressed his desire to see his political opponents prosecuted and some of those indictments came to fruition.

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

"The Bolton prosecution and eventually the charge seemed to have followed the regular process including the rules and norms within the DOJ," he said.

Unlike Comey's brief, concise indictment, Bolton's was a more "traditional" document that "clearly outlines the particulars concerning the facts and situation here," Mr Lesko commented.

"It appears reasonably consistent with a series of precedents... where public servants improperly handled and transmitted sensitive information."