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Ex-President Donald Trump has repeatedly expressed his desire to see opponents investigated, exerting pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our reputation and credibility," the president wrote last month in a Truth Social post.

"They impeached me, and charged me (5 times!)" he declared, referencing the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in situations that numerous experts have stated appear to be politically motivated and challenging to succeed in legal proceedings.

But the most recent charges against a presidential opponent, former national security adviser John Bolton, stand apart, legal experts and former prosecutors assert.

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

This Details of the Case

Bolton has been formally charged on national allegations related to the supposed mishandling of classified information. Since leaving the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Specialists say that while there may be political motivations to target Bolton, the methods used to obtain an indictment and the proof gathered against him suggest a potentially more substantial legal argument than the DOJ presented against James.

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

Throughout his time as Trump's security advisor, and after his 2019 White House departure, authorities alleged that Bolton put the nation at danger by improperly keeping and transmitting classified information to family members using insecure means, including AOL. Several of the materials were labeled highly classified.

The indictment states that at a certain time a unauthorized user gained access to Bolton's account where files were stored and sent an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to 18 separate charges of mishandling classified information.

Retribution or a Strong Legal Argument?

The schedule of his indictment - arriving on the tails of allegations against James - has renewed concerns about external influence on the legal system.

Trump previously suggested Bolton belonged in jail, and called him a "sleazebag". Bolton, for his role, authored a publication about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this charge, when paired with others, has raised doubts about the validity of these allegations, and why these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to prove the facts stated and demonstrate the information is correctly classified, his behavior may certainly have broken the statute".

Prosecuting such a senior official for improperly handling classified documents is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern classified information present difficulties to prosecute, but they can and are filed against both junior and senior officials, from occasionally," she explained.

Parallels to Investigations into Former President and Biden

Trump similarly faced allegations of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately thrown out by a federal judge and voided by his re-election as leader.

A independent investigator additionally determined that former President Joe Biden improperly maintained sensitive materials from his period as vice president, but did not criminally charge him.

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

Strict procedures regulate the management of sensitive materials. To secure a guilty verdict, the government must demonstrate that Bolton knew the material he was sending was classified, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the classified nature of the material at issue in this matter, we don't have a great deal of details about why the prosecution believes things like the personal notes and the additional material he shared by electronic message, and why there were restricted," said Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department brought this case will be under scrutiny, following Trump publicly expressed his desire to see his critics prosecuted and several of those indictments came to fruition.

But Mr Lesko said in Bolton's situation, authorities seem to have followed protocol.

"The Bolton prosecution and ultimately the indictment seemed to have observed the standard process including the regulations and standards within the DOJ," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a more "traditional" document that "clearly outlines the details involving the facts and situation here," Mr Lesko said.

"It seems fairly consistent with a long line of precedents... where government officials improperly handled and shared classified material."