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Ex-President Donald Trump has consistently expressed his desire to see critics investigated, applying pressure on the DOJ to charge 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 president wrote last month in a social media post.

"I was impeached me, and indicted me (5 times!)" he declared, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Each have since been charged, in cases that numerous specialists have said appear to be politically motivated and difficult to succeed in legal proceedings.

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

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

The Details of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to call him "remarkably ignorant" and unsuitable for office in his book.

Specialists contend that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the evidence compiled against him indicate a possibly stronger legal argument than the DOJ brought against Comey.

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

Throughout his time as Trump's national security adviser, and after his 2019 White House departure, prosecutors alleged that Bolton placed the nation at risk by improperly retaining and transmitting classified information to relatives using unprotected methods, including AOL. Several of the materials were labeled highly classified.

The indictment alleges that at one point a unauthorized user accessed to Bolton's account where files were stored and sent an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct counts of mishandling classified information.

Retribution or a Strong Legal Argument?

The schedule of his charge - arriving on the heels of allegations against James - has revived concerns about political pressure on the justice system.

Trump once suggested Bolton belonged in prison, and described him a "disreputable person". Bolton, for his part, authored a publication about his experience in the Trump administration that was sharply negative of the president.

"Undoubtedly that the schedule of this indictment, when combined with others, has raised questions about the strength of these allegations, and the reason these counts are being filed now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is able to demonstrate the allegations stated and show the material is properly designated, his behavior may very well have violated the law".

Charging such a high-ranking official for mishandling classified documents is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present challenges to try, but they can and are brought against both junior and high-level personnel, from occasionally," she explained.

Parallels to Examinations into Former President and President

Trump likewise faced charges of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that matter was eventually thrown out by a federal judge and voided by his return as president.

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

Bolton's situation shares characteristics to Biden's sensitive materials matters, noted Mr Lesko, who previously held a top national security role at the Justice Department.

Strict procedures govern the handling of classified documents. To secure a guilty verdict, the government must prove that Bolton was aware the material he was sending was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the sensitive nature of the information at question in this matter, we don't have a lot of particulars about the reasons the government believes things like the personal notes and the other information he communicated by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Traditional Prosecution

The process by which the DOJ brought this legal action will be under scrutiny, after Trump publicly expressed his desire to see his political opponents charged and some of those charges materialized.

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

"This Bolton case and ultimately the charge seemed to have observed the standard procedure including the rules and standards within the DOJ," he stated.

In contrast to Comey's short, two-page indictment, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details involving the circumstances and circumstances here," Mr Lesko commented.

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