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Former President Donald Trump has consistently shown his desire to see critics investigated, applying pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our standing and credibility," the president stated last month in a social media message.

"I was impeached twice, and indicted me (5 times!)" he declared, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in cases that many experts have said seem to be politically motivated and challenging to succeed in court.

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

"In my opinion, comparing Bolton's charges to James' 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 Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged mishandling of sensitive materials. After leaving the White House in 2019, he has become a vocal Trump critic, even to call him "remarkably ignorant" and unfit for office in his memoir.

Specialists say that while there may be political motivations to target Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a potentially stronger legal argument than the DOJ brought against James.

"These actions that's being claimed is both more severe and appears to have taken place over a significant period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the nation at danger by wrongfully keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Some of the documents were labeled top secret.

The indictment states that at one point a hacker gained access to Bolton's system where documents were kept and transmitted an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on recently to eighteen separate charges of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The timing of his charge - coming on the heels of allegations against James - has renewed questions about external influence on the legal system.

Trump once implied Bolton belonged in prison, and described him a "disreputable person". Bolton, for his role, wrote a book about his time in the Trump government that was highly critical of the leader.

"There's no question that the timing of this indictment, when paired with others, has prompted doubts about the validity of these allegations, and the reason these counts are being filed at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "should the DOJ is capable to prove the allegations alleged and demonstrate the information is correctly classified, his behavior may certainly have broken the statute".

Charging such a high-ranking figure for improperly handling sensitive materials is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern classified information present challenges to try, but they may and are filed against both junior and high-level personnel, from occasionally," she explained.

Parallels to Examinations into Former President and Biden

Trump likewise encountered charges of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that matter was eventually dismissed by a federal judge and negated by his return as president.

A independent investigator additionally found that ex-President Joe Biden improperly stored sensitive materials from his period as vice president, but did not criminally charge him.

Bolton's case shares characteristics to Biden's sensitive materials matters, noted Mr Lesko, who previously held a top security position at the DOJ.

Strict procedures regulate the handling of classified documents. To win a guilty verdict, the prosecution must prove that Bolton was aware the information he was sending was classified, and he had to knowingly transfer it to someone not entitled to receive it.

"Due to the classified character of the information at question in this case, we don't have a lot of details about why the government contends elements like the diary entries and the additional information he communicated by electronic message, and why there were classified," said Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, after Trump openly expressed his desire to see his critics charged and some of those indictments materialized.

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

"This Bolton case and eventually the indictment seemed to have observed the regular procedure including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's short, two-page indictment, Bolton's was a more "conventional" document that "explicitly outlines the particulars concerning the facts and circumstances here," Mr Lesko commented.

"It seems fairly consistent with a series of precedents... where public servants mishandled and shared classified material."