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Former President Donald Trump has repeatedly expressed his wish to see critics probed, applying pressure on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our standing and credibility," the leader wrote recently in a social media message.

"They impeached me, and indicted me (5 times!)" he said, mentioning the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Both have subsequently been charged, in cases that numerous experts have stated appear to be driven by politics and challenging to win in court.

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

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

This Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of classified information. Since leaving the White House in 2019, he has become a vocal Trump critic, even to call him "remarkably ignorant" and unfit for the presidency in his memoir.

Experts say that while there may be political reasons to target Bolton, the methods used to obtain an charge and the proof compiled against him suggest a possibly more substantial legal argument than the Justice Department presented against James.

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

During his time as Trump's security advisor, and following his 2019 White House departure, authorities claimed that Bolton put the nation at risk by wrongfully keeping and sending classified information to relatives using insecure means, including AOL. Several of the documents were labeled top secret.

The charge states that at one point a hacker accessed to Bolton's account where files were stored and sent an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate counts of improperly handling classified information.

Political Motivation or a Substantial Case?

The timing of his charge - arriving 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 described him a "disreputable person". Bolton, for his part, wrote a book about his time in the Trump government that was highly critical of the leader.

"Undoubtedly that the schedule of this indictment, when paired with others, has raised doubts about the validity of these allegations, and why these charges are being brought now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

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

Charging such a senior figure for improperly handling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to prosecute, but they can and are filed against both junior and senior officials, from time to time," she explained.

Parallels to Examinations into Former President and Biden

Trump likewise encountered allegations of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was ultimately dismissed by a court official and negated by his return as president.

A special counsel also determined that former President Joe Biden wrongfully maintained classified documents from his time as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Biden's classified documents issues, said Mr Lesko, who also held a senior national security role at the DOJ.

Rigorous procedures govern the handling of classified documents. To win a guilty verdict, the prosecution must prove that Bolton knew the material he was sending was restricted, and he had to intentionally transmit it to someone not entitled to obtain it.

"Due to the classified character of the material at question in this matter, we don't have a great deal of particulars about why the prosecution contends things like the personal notes and the other information he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A More Traditional Prosecution

The process by which the DOJ brought this case will be closely examined, following Trump publicly expressed his wish to see his political opponents charged and some of those indictments materialized.

But Mr Lesko said in Bolton's case, authorities seem to have adhered to protocol.

"The Bolton prosecution and ultimately the charge appeared to have observed the regular process including the regulations and standards within the DOJ," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a increasingly "traditional" filing that "clearly outlines the details involving the facts and circumstances in this instance," Mr Lesko said.

"It seems reasonably aligned with a series of precedents... where public servants improperly handled and shared classified material."