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Former President Donald Trump has consistently shown his wish to see opponents 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 damaging our standing and credibility," the president wrote last month in a Truth Social message.

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

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

But the latest charges against a presidential opponent, former national security adviser John Bolton, stand apart, legal experts and ex-prosecutors say.

"I would say, contrasting Bolton's charges to Comey's is like equating two different things," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts contend that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a potentially stronger legal argument than the Justice Department presented against James.

"This misconduct that's being alleged is simultaneously more serious and seems to have taken place over a significant duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and after his 2019 White House exit, authorities claimed that Bolton placed the nation at risk by wrongfully keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Some of the materials were labeled highly classified.

The charge alleges that at one point a hacker gained access to Bolton's account where files were kept and sent an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on recently to 18 distinct counts of improperly handling classified information.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the tails of allegations against Comey - has revived concerns about external influence on the legal system.

Trump previously implied Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this charge, when paired with additional cases, has raised questions about the validity of these allegations, and why these counts are being brought now," said Jamil Jaffer, creator and director of the National Security Institute.

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

Charging such a senior figure for improperly handling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve classified information pose difficulties to try, but they can and are brought against both low-level and senior personnel, from time to time," she explained.

Parallels to Investigations into Trump and Biden

Trump likewise faced charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and obstructing their recovery, but that matter was ultimately dismissed by a federal judge and negated by his return as president.

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

Bolton's case bears similarities to Biden's sensitive materials matters, said Mr Lesko, who also held a senior national security position at the Justice Department.

Strict protocols govern the handling of sensitive materials. To win a conviction, the prosecution must demonstrate that Bolton was aware the information he was sending was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the sensitive character of the information at issue in this matter, we lack a great deal of particulars about why the prosecution contends things like the personal notes and the other information he shared by email, and why there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The process by which the Justice Department initiated this case will be under scrutiny, following Trump publicly posted his wish to see his critics charged and some of those charges came to fruition.

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

"The Bolton case and eventually the indictment appeared to have followed the standard procedure including the regulations and norms within the DOJ," he stated.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" filing that "clearly outlines the particulars concerning the circumstances and situation here," Mr Lesko said.

"It appears fairly consistent with a series of cases... where public servants mishandled and transmitted classified material."