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Ex-President Donald Trump has repeatedly shown his wish to see critics investigated, exerting pressure on the Justice Department to charge ex 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 leader wrote recently in a Truth Social message.

"They impeached me, and charged me (five times!)" he said, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that many specialists have stated appear to be politically motivated and difficult to succeed in court.

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

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

The Details of the Case

Bolton has been criminally indicted on national allegations related to the supposed mishandling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, even to describe him "stunningly uninformed" and unfit for office in his memoir.

Experts say that while there may be political motivations to go after Bolton, the methods used to secure an charge and the proof compiled against him indicate a potentially more substantial case than the DOJ presented against Comey.

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

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, prosecutors alleged that Bolton put the country at danger by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were marked highly classified.

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

Bolton entered a not guilty plea during a hearing on recently to 18 separate charges of mishandling classified information.

Retribution or a Strong Case?

The timing of his charge - coming on the tails of allegations against Comey - has revived questions about political pressure on the legal system.

Trump once implied Bolton should be in jail, and described him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump administration that was highly critical of the president.

"There's no question that the schedule of this charge, when combined with additional cases, has prompted questions about the strength of these charges, and the reason these charges are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "if the DOJ is capable to prove the facts alleged and show the material is properly designated, his conduct may very well have broken the law".

Prosecuting such a high-ranking figure for improperly handling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern sensitive materials present challenges to prosecute, but they can and are brought against both low-level and senior personnel, from occasionally," she said.

Similarities to Investigations into Trump and President

Trump similarly encountered charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was ultimately thrown out by a court official and negated by his return as leader.

A independent investigator additionally determined that ex-President Joe Biden improperly stored sensitive materials from his time as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's classified documents matters, said Mr Lesko, who also held a senior security role at the Justice Department.

Rigorous protocols govern the management of classified documents. To win a conviction, the prosecution must demonstrate that Bolton was aware the information he was sending was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Because of the classified character of the information at question in this matter, we don't have a lot of details about why the prosecution contends things like the personal notes and the additional information he communicated by electronic message, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Conventional Prosecution

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

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

"This Bolton case and ultimately the indictment appeared to have followed the standard process including the rules and norms within the DOJ," he stated.

In contrast to Comey's brief, concise indictment, Bolton's was a increasingly "conventional" filing that "clearly outlines the particulars concerning the facts and situation in this instance," Mr Lesko said.

"It seems fairly consistent with a long line of cases... where government officials improperly handled and transmitted sensitive information."