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

"We can't delay any longer, it's damaging our reputation and trustworthiness," the leader wrote recently in a social media message.

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

Each have subsequently been indicted, in cases that many experts have said seem to be politically motivated and challenging to win in court.

But the most recent 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 charges to James' is like equating apples to oranges," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Details of the Case

Bolton has been formally charged on federal charges related to the alleged mishandling of classified information. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Specialists say that while there may be political reasons to target Bolton, the procedures used to secure an indictment and the proof 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 occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's national security adviser, and after his 2019 White House exit, authorities claimed that Bolton put the country at risk by improperly 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 unauthorized user gained access to Bolton's system where documents were stored and sent an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on recently to 18 distinct charges of mishandling classified information.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the tails of charges against James - has renewed questions about external influence on the justice system.

Trump once implied Bolton belonged in prison, and described him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump administration that was highly critical of the president.

"Undoubtedly that the timing of this charge, when combined with others, has prompted doubts about the validity of these allegations, and why these counts are being filed now," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is capable to prove the allegations stated and demonstrate the information is properly designated, his behavior may very well have violated the statute".

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

"Cases that involve classified information pose difficulties to prosecute, but they may and are brought against both low-level and high-level officials, from time to time," she explained.

Parallels to Examinations into Trump and Biden

Trump similarly encountered charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was eventually dismissed by a court official and voided by his re-election as leader.

A independent investigator also determined that ex-President Joe Biden wrongfully stored classified documents from his period as second-in-command, but did not prosecute him.

Bolton's case bears similarities to Biden's sensitive materials matters, noted Mr Lesko, who previously held a top security role at the DOJ.

Strict procedures regulate the management of classified documents. To secure a guilty verdict, the prosecution must prove that Bolton was aware the material he was transmitting was classified, and he had to intentionally transfer it to someone without authorization to receive it.

"Because of the sensitive nature of the information at issue in this case, we don't have a lot of details about why the prosecution believes elements like the personal notes and the additional information he shared by email, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department initiated this case will be closely examined, after Trump openly expressed his wish to see his critics charged and some of those charges came to fruition.

But Mr Lesko said in Bolton's situation, authorities seem to have followed standard procedure.

"The Bolton prosecution and eventually the indictment seemed to have followed the standard procedure including the rules and standards within the DOJ," he said.

Unlike Comey's brief, concise charge, Bolton's was a more "traditional" filing that "explicitly outlines the particulars concerning the facts and circumstances in this instance," Mr Lesko said.

"It appears reasonably consistent with a series of precedents... where public servants improperly handled and shared sensitive information."