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

"We cannot postpone any longer, it's damaging our reputation and credibility," the president wrote last month in a social media message.

"They impeached twice, and indicted me (5 times!)" he said, referencing the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Both have since been charged, in situations that numerous experts have said seem to be driven by politics and challenging to succeed in legal proceedings.

But the most recent allegations against a presidential opponent, former security advisor John Bolton, differ significantly, legal experts and former prosecutors say.

"I would say, comparing Bolton's charges to Comey's is like comparing apples to oranges," stated Mark Lesko, a former federal prosecutor 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 alleged improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a vocal Trump critic, even to call him "remarkably ignorant" and unsuitable for the presidency in his book.

Specialists say that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a potentially stronger legal argument than the DOJ brought against Comey.

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

Throughout his time as Trump's security advisor, and after his 2019 White House departure, prosecutors alleged that Bolton placed the nation at risk by improperly retaining and sending classified information to relatives using insecure means, including AOL. Several of the materials were marked top secret.

The indictment alleges that at one point a unauthorized user accessed to Bolton's system where documents were kept and sent an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on recently to 18 separate charges of mishandling classified information.

Retribution or a Strong Legal Argument?

The schedule of his indictment - coming on the tails of allegations against James - has renewed questions about external influence on the justice system.

Trump once implied Bolton belonged in jail, and described him a "disreputable person". Bolton, for his part, authored a book about his time in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this charge, when paired with others, has raised doubts about the strength of these allegations, and the reason these counts are being brought now," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "if the DOJ is capable to demonstrate the allegations stated and show the information is properly classified, his conduct may certainly have broken the law".

Prosecuting such a high-ranking official for improperly handling 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 sensitive materials present challenges to try, but they may and are filed against equally junior and high-level officials, from time to time," she explained.

Parallels to Examinations into Trump and Biden

Trump likewise encountered allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that matter was eventually dismissed by a court official and negated by his re-election as president.

A special counsel additionally found that ex-President Joe Biden improperly stored classified documents from his period as vice president, but did not prosecute him.

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

Strict protocols govern the handling of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the material he was sending was classified, and he had to intentionally transfer it to someone without authorization to obtain it.

"Because of the sensitive nature of the information at issue in this case, we don't have a lot of particulars about why the government contends elements like the personal notes and the other information he shared by electronic message, and why there were restricted," said Mr Jaffer.

A Increasingly Conventional Prosecution

The process by which the Justice Department brought this case will be closely examined, following Trump publicly posted his desire to see his critics prosecuted and several of those indictments came to fruition.

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

"This Bolton prosecution and ultimately the indictment seemed to have observed the regular process including the regulations and standards within the DOJ," he said.

Unlike Comey's short, two-page charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details involving the circumstances and situation in this instance," Mr Lesko said.

"It seems fairly consistent with a series of precedents... where government officials mishandled and shared classified material."