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Former President Donald Trump has consistently expressed his desire to see opponents probed, applying pressure on the Justice Department 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 president wrote recently in a social media message.

"They impeached twice, and indicted me (five times!)" he said, referencing the four criminal cases he encountered after departing the White House in 2021 and James's civil case.

Both have subsequently been indicted, in cases that many specialists have stated seem to be driven by politics and challenging to succeed in legal proceedings.

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

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

The Details of Bolton's Case

Bolton has been formally charged on federal charges related to the supposed mishandling of classified information. Since departing the White House in 2019, he has become a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the procedures used to secure an charge and the evidence compiled against him indicate a potentially stronger case than the DOJ presented against Comey.

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

Throughout his time as Trump's national security adviser, and after his 2019 White House exit, prosecutors alleged that Bolton put the nation at danger by improperly retaining and transmitting classified information to relatives using insecure means, including AOL. Several of the documents were marked top secret.

The indictment states that at a certain time a unauthorized user accessed to Bolton's system where files were stored and transmitted an seeming warning 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 sensitive materials.

Political Motivation or a Strong Legal Argument?

The timing of his charge - arriving on the tails of charges against Comey - has revived concerns about external influence on the justice system.

Trump previously suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump administration that was sharply negative of the president.

"There's no question that the timing of this charge, when combined with additional cases, has raised doubts about the validity of these charges, and why these charges are being brought now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the DOJ is able to demonstrate the allegations stated and demonstrate the material is correctly designated, his behavior may very well have violated the statute".

Prosecuting such a senior figure for mishandling classified documents is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern classified information pose difficulties to prosecute, but they can and are filed against both junior and high-level personnel, from occasionally," she explained.

Similarities to Investigations into Trump and President

Trump similarly faced allegations of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was ultimately thrown out by a federal judge and voided by his re-election as president.

A special counsel additionally determined that former President Joe Biden wrongfully stored sensitive materials from his time as second-in-command, but did not prosecute him.

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

Strict protocols govern the management of classified documents. To secure a guilty verdict, the government must demonstrate that Bolton knew the information he was sending was restricted, and he had to intentionally transmit it to someone not entitled to obtain it.

"Because of the classified nature of the material at issue in this case, we lack a lot of details about why the government believes things like the personal notes and the other information he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the Justice Department brought this legal action will be under scrutiny, after Trump openly posted his desire to see his critics charged and several of those charges materialized.

But Mr Lesko indicated in Bolton's situation, authorities seem to have adhered to standard procedure.

"This Bolton case and eventually the indictment appeared to have followed the regular process including the regulations and norms within the DOJ," he stated.

In contrast to Comey's brief, concise indictment, Bolton's was a more "traditional" document that "explicitly sets forth the particulars involving the facts and situation in this instance," Mr Lesko said.

"It seems reasonably consistent with a series of cases... where government officials improperly handled and shared sensitive information."