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Former President Donald Trump has repeatedly shown his wish to see critics investigated, exerting influence on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and credibility," the leader stated recently in a social media message.

"I was impeached twice, and indicted me (five times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Both have subsequently been indicted, in cases that many experts have said appear to be politically motivated and difficult to succeed in legal proceedings.

But the latest charges against a Trump critic, ex security advisor John Bolton, stand apart, legal specialists and ex-prosecutors say.

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

This Specifics of the Case

Bolton has been formally charged on federal charges pertaining to the supposed improper handling of sensitive materials. Since departing the White House in 2019, he has become a vocal presidential opponent, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

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

"This misconduct that's being alleged is both more serious and seems to have taken place 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, authorities alleged that Bolton put the country at danger by wrongfully retaining and sending classified information to family members using unprotected methods, including AOL. Some of the materials were marked top secret.

The charge alleges that at a certain time a hacker accessed to Bolton's system where files were stored and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Substantial Case?

The schedule of his indictment - coming on the heels of charges against James - has revived questions about external influence on the justice system.

Trump once suggested Bolton should be in jail, and called him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump government that was highly critical of the president.

"Undoubtedly that the schedule of this charge, when combined with others, has prompted doubts about the strength of these charges, and why these charges are being filed at this time," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the Justice Department is able to prove the facts stated and demonstrate the information is properly classified, his behavior may certainly have violated the law".

Prosecuting such a high-ranking 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.

"Situations that concern classified information present difficulties to try, but they can and are brought against both junior and senior personnel, from occasionally," she said.

Similarities to Examinations into Trump and President

Trump likewise encountered charges of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that case was ultimately dismissed by a federal judge and negated by his re-election as president.

A independent investigator additionally found that ex-President Joe Biden improperly stored classified documents from his time as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Biden's sensitive materials issues, noted Mr Lesko, who also held a top national security role at the DOJ.

Strict procedures regulate the handling of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was sending was classified, and he had to intentionally transmit it to someone not entitled to obtain it.

"Because of the sensitive character of the material at issue in this matter, we don't have a great deal of particulars about why the government contends things like the diary entries and the other material he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ initiated this legal action will be under scrutiny, following Trump openly expressed his wish to see his political opponents prosecuted and some of those indictments came to fruition.

But Mr Lesko said in Bolton's case, prosecutors appear to have adhered to standard procedure.

"This Bolton prosecution and ultimately the indictment seemed to have followed the standard process including the regulations and norms within the Department of Justice," he said.

In contrast to Comey's short, concise indictment, Bolton's was a more "conventional" filing that "explicitly sets forth the particulars concerning the circumstances and circumstances in this instance," Mr Lesko commented.

"It appears reasonably consistent with a series of precedents... where government officials mishandled and shared sensitive information."