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Ex-President Donald Trump has consistently expressed his desire to see critics probed, applying influence on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's damaging our standing and credibility," the president wrote last month in a social media post.

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

Both have since been indicted, in situations that many experts have stated appear to be driven by politics and challenging to win in court.

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

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

The Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged mishandling of classified information. Since leaving the White House in 2019, he has emerged as a vocal Trump critic, even to describe him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the methods used to obtain an charge and the evidence compiled against him indicate a possibly more substantial case than the Justice Department brought against Comey.

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

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, prosecutors alleged that Bolton put the nation at danger by wrongfully retaining and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were labeled top secret.

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

Bolton entered a not guilty plea during a hearing on recently to 18 separate charges of mishandling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his indictment - coming on the tails of charges against Comey - has renewed questions about political pressure on the justice system.

Trump once implied Bolton should be in prison, and called him a "disreputable person". Bolton, for his role, authored a book about his experience in the Trump administration that was highly critical of the leader.

"Undoubtedly that the timing of this charge, when paired with additional cases, has raised questions about the strength of these charges, and why these charges are being filed at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the DOJ is capable to prove the allegations stated and show the information is properly designated, his behavior may very well have broken the statute".

Charging such a high-ranking official for improperly handling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose difficulties to prosecute, but they may and are brought against equally junior and senior officials, from time to time," she said.

Parallels to Examinations into Trump and President

Trump similarly faced charges of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually dismissed by a court official and negated by his return as president.

A special counsel also determined that former President Joe Biden improperly stored classified documents from his time as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's sensitive materials issues, said Mr Lesko, who previously held a senior national security role at the Justice Department.

Rigorous protocols regulate the handling of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the classified character of the information at question in this matter, we don't have a lot of details about the reasons the prosecution believes elements like the diary entries and the additional material he shared by email, and the reason there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department initiated this case will be closely examined, following Trump openly posted his wish to see his political opponents charged and several of those charges came to fruition.

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

"The Bolton prosecution and eventually the charge appeared to have observed the standard procedure including the regulations and standards within the Department of Justice," he said.

In contrast to Comey's short, two-page indictment, Bolton's was a more "conventional" filing that "clearly outlines the details concerning the facts and situation in this instance," Mr Lesko said.

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