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Ex-President Donald Trump has repeatedly expressed his wish to see opponents investigated, applying influence on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our reputation and trustworthiness," the leader wrote recently in a Truth Social message.

"I was impeached me, and indicted me (5 times!)" he declared, mentioning the multiple legal proceedings he faced after leaving the White House in 2021 and James's civil case.

Both have subsequently been charged, in situations that many experts have stated seem to be politically motivated and difficult to succeed in legal proceedings.

But the most recent allegations against a presidential opponent, ex national security adviser John Bolton, stand apart, legal experts and ex-prosecutors say.

"I would say, contrasting Bolton's case to James' is like comparing two different things," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Specifics of the Legal Situation

Bolton has been formally charged on national allegations pertaining to the supposed mishandling of sensitive materials. Since leaving the White House in 2019, he has become a vocal presidential opponent, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Experts say that while there may be political motivations to target Bolton, the methods used to obtain an charge and the evidence compiled against him suggest a potentially stronger legal argument than the Justice Department presented against Comey.

"This misconduct that's being claimed is simultaneously more severe and appears to have taken place over a significant duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the country at risk by improperly keeping and transmitting sensitive documents to family members using unprotected methods, including AOL. Several of the materials were marked top secret.

The indictment alleges that at one point a hacker gained access to Bolton's system where documents were kept and transmitted an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on recently to eighteen distinct charges of improperly handling sensitive materials.

Retribution or a Substantial Case?

The schedule of his indictment - coming on the heels of charges against James - has revived concerns about external influence on the legal system.

Trump previously suggested Bolton should be in jail, and described him a "disreputable person". Bolton, for his role, wrote a publication about his time in the Trump administration that was highly critical of the leader.

"Undoubtedly that the timing of this charge, when combined with others, has prompted doubts about the strength of these allegations, and the reason these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the DOJ is able to prove the allegations stated and demonstrate the material is correctly classified, his behavior may very well have broken the law".

Prosecuting such a senior official for improperly handling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern classified information pose challenges to prosecute, but they may and are brought against both junior and senior personnel, from occasionally," she explained.

Parallels to Investigations into Former President and President

Trump likewise encountered allegations of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually dismissed by a court official and negated by his return as leader.

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

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

Strict protocols regulate the management of classified documents. To win a conviction, the government must demonstrate that Bolton knew the information he was sending was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the sensitive character of the material at issue in this matter, we don't have a great deal of details about the reasons the government believes things like the diary entries and the other material he communicated by email, and the reason there were restricted," said Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the DOJ brought this case will be under scrutiny, after Trump openly expressed his wish to see his critics prosecuted and some of those indictments materialized.

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

"This Bolton case and eventually the indictment appeared to have followed the standard procedure including the regulations and norms within the Department of Justice," he stated.

Unlike Comey's brief, concise charge, Bolton's was a more "traditional" document that "clearly sets forth the particulars involving the circumstances and circumstances in this instance," Mr Lesko commented.

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