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Ex-President Donald Trump has consistently expressed his desire to see critics investigated, exerting pressure on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our standing and credibility," the leader wrote last month in a social media message.

"I was impeached twice, and indicted me (5 times!)" he declared, mentioning the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Each have subsequently been indicted, in cases that many experts have stated appear to be driven by politics and challenging to win in court.

But the latest allegations against a Trump critic, ex national security adviser John Bolton, stand apart, legal specialists and former prosecutors assert.

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

The Details of Bolton's Legal Situation

Bolton has been formally charged on national allegations pertaining to the supposed mishandling of classified information. After leaving the White House in 2019, he has become a vocal presidential opponent, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his book.

Experts say that while there may be political reasons to go after Bolton, the methods used to obtain an indictment and the proof gathered against him indicate a possibly more substantial case than the Justice Department brought against James.

"This misconduct that's being claimed is both more serious and seems to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton put the nation at risk by improperly retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were marked top secret.

The indictment alleges that at a certain time a unauthorized user gained access to Bolton's system where files were stored and transmitted an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on recently to 18 distinct counts of mishandling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his charge - arriving on the heels of charges against Comey - has renewed questions about political pressure on the legal system.

Trump once implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, authored a publication about his time in the Trump government that was highly critical of the president.

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

Nevertheless, he continued, "should the Justice Department is able to prove the facts stated and demonstrate the material is correctly designated, his behavior may very well have violated the statute".

Prosecuting such a high-ranking figure 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.

"Cases that involve sensitive materials pose challenges to try, but they may and are brought against both low-level and senior personnel, from time to time," she said.

Parallels to Examinations into Former President and Biden

Trump similarly faced allegations of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that matter was ultimately dismissed by a court official and voided by his return as president.

A special counsel also found that former President Joe Biden improperly stored sensitive materials from his time as second-in-command, but did not criminally charge him.

Bolton's case shares characteristics to Biden's classified documents issues, said Mr Lesko, who previously held a top national security role at the Justice Department.

Rigorous protocols regulate the management of sensitive materials. To secure a guilty verdict, the government must prove that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the sensitive nature of the material at issue in this case, we don't have a great deal of details about the reasons the prosecution contends things like the personal notes and the additional information he shared by email, and why there were classified," said Mr Jaffer.

A More Traditional Prosecution

The process by which the Justice Department initiated this legal action will be closely examined, after Trump publicly expressed his wish to see his political opponents prosecuted and some of those indictments came to fruition.

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

"This Bolton case and ultimately the charge seemed to have observed the standard procedure including the regulations and norms within the Department of Justice," he stated.

In contrast to Comey's short, concise indictment, Bolton's was a increasingly "conventional" filing that "clearly sets forth the details involving the facts and situation in this instance," Mr Lesko said.

"It appears reasonably consistent with a long line of precedents... where public servants improperly handled and transmitted sensitive information."