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Ex-President Donald Trump has repeatedly expressed his wish to see critics probed, exerting influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our reputation and credibility," the president wrote recently in a Truth Social message.

"I was impeached me, and indicted me (five times!)" he said, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that numerous experts have said appear to be politically motivated and challenging to win in court.

But the most recent charges against a Trump critic, ex national security adviser John Bolton, differ significantly, legal experts and former prosecutors assert.

"In my opinion, comparing Bolton's charges to James' is like equating two different things," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of the Case

Bolton has been formally charged on national allegations related to the alleged improper handling of classified information. After leaving the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to describe him "stunningly uninformed" and unfit for office in his book.

Experts say that while there may be political motivations to go after Bolton, the methods used to obtain an charge and the evidence gathered against him indicate a potentially more substantial legal argument than the DOJ presented against James.

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

Throughout his time as Trump's security advisor, and following his 2019 White House exit, prosecutors alleged that Bolton placed the country at danger by improperly retaining and sending sensitive documents to relatives using insecure means, including AOL. Some of the materials were labeled highly classified.

The indictment states that at a certain time a hacker accessed to Bolton's system where documents were stored and transmitted 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 eighteen distinct charges of improperly handling classified information.

Retribution or a Substantial Case?

The schedule of his charge - coming on the tails of charges against James - has renewed concerns about external influence on the legal system.

Trump previously implied Bolton should be in jail, and called him a "sleazebag". Bolton, for his part, wrote a book about his time in the Trump administration that was highly critical of the leader.

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

However, he continued, "if the Justice Department is able to prove the facts alleged and demonstrate the material is correctly classified, his conduct may very well have violated the statute".

Charging such a high-ranking official for mishandling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials present difficulties to try, but they can and are filed against equally low-level and senior personnel, from time to time," she said.

Similarities to Examinations into Former President and President

Trump similarly faced allegations of improperly keeping classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually dismissed by a federal judge and negated by his return as leader.

A special counsel also found that ex-President Joe Biden wrongfully stored classified documents from his time as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's classified documents issues, said Mr Lesko, who also held a top national security position at the Justice Department.

Rigorous protocols govern the management of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the sensitive character of the material at issue in this matter, we lack a great deal of details about why the prosecution believes elements like the personal notes and the additional material he shared by email, and the reason there were classified," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department brought this case will be under scrutiny, after Trump publicly posted his desire to see his political opponents charged and some of those indictments came to fruition.

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

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

Unlike Comey's short, two-page indictment, Bolton's was a more "conventional" filing that "explicitly sets forth the particulars concerning the circumstances and situation in this instance," Mr Lesko said.

"It appears fairly aligned with a long line of precedents... where government officials mishandled and transmitted sensitive information."