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Ex-President Donald Trump has repeatedly expressed his wish to see opponents probed, applying influence on the Justice Department to charge 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 stated recently in a social media message.

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

Both have subsequently been charged, in cases that many experts have stated appear to be politically motivated and difficult to win in court.

But the latest charges against a presidential opponent, ex national security adviser John Bolton, differ significantly, legal experts and former prosecutors assert.

"In my opinion, contrasting Bolton's case to Comey's is like comparing apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Legal Situation

Bolton has been formally charged on federal charges pertaining to the alleged improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "stunningly uninformed" and unfit for the presidency in his book.

Experts say that while there may be political motivations to target Bolton, the methods used to secure an charge and the evidence compiled against him indicate a potentially stronger case than the Justice Department presented against James.

"These actions that's being claimed is both more severe and seems to have taken place 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 security advisor, and following his 2019 White House departure, authorities claimed that Bolton placed the country at risk by improperly retaining and sending sensitive documents to relatives using insecure means, including AOL. Some of the documents were marked highly classified.

The charge alleges that at one point a hacker accessed to Bolton's system where files were stored and sent an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to 18 separate counts of improperly handling classified information.

Political Motivation or a Substantial Legal Argument?

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

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump government that was sharply negative of the leader.

"Undoubtedly that the timing of this charge, when combined with others, has prompted questions about the validity of these charges, and the reason these charges are being filed at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "should the DOJ is able to prove the facts alleged and demonstrate the information is properly designated, his behavior may very well have violated the law".

Prosecuting such a senior 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 sensitive materials pose difficulties to prosecute, but they can and are filed against equally junior and senior officials, from occasionally," she explained.

Parallels to Investigations into Trump and Biden

Trump likewise faced allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was eventually dismissed by a federal judge and voided by his re-election as leader.

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

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

Strict protocols regulate the handling of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the material he was sending was classified, and he had to intentionally transmit it to someone without authorization to receive it.

"Due to the sensitive nature of the material at question in this matter, we lack a lot of particulars about why the prosecution believes things like the diary entries and the other information he communicated by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Traditional Legal Action

The process by which the DOJ initiated this legal action will be under scrutiny, following Trump publicly expressed his wish to see his critics charged and several of those charges materialized.

But Mr Lesko said in Bolton's situation, prosecutors appear to have followed standard procedure.

"The Bolton case and eventually the indictment appeared to have followed the regular procedure including the rules and norms within the Department of Justice," he said.

Unlike Comey's short, concise charge, Bolton's was a increasingly "conventional" document that "explicitly outlines the particulars concerning the facts and situation in this instance," Mr Lesko said.

"It seems fairly aligned with a series of cases... where public servants mishandled and transmitted classified material."