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Former President Donald Trump has repeatedly expressed his wish to see critics investigated, applying influence on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our standing and trustworthiness," the leader wrote recently in a Truth Social post.

"They impeached me, and charged me (5 times!)" he declared, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's civil case.

Each have subsequently been indicted, in situations that numerous specialists have said seem to be driven by politics and difficult to succeed in court.

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

"In my opinion, comparing Bolton's case to James' is like equating apples to oranges," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on national allegations pertaining to the alleged improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Experts say that while there may be political reasons to target Bolton, the methods used to secure an charge and the evidence compiled against him suggest a potentially more substantial legal argument than the DOJ presented against Comey.

"These actions that's being claimed is both more severe and seems to have occurred over a considerable period of time," commented 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 claimed that Bolton put the country at risk by improperly retaining and sending sensitive documents to relatives using insecure means, including AOL. Several of the documents were labeled highly classified.

The indictment alleges that at a certain time a unauthorized user gained access to Bolton's account where files were stored and transmitted 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.

Retribution or a Substantial Case?

The timing of his charge - coming on the tails of charges against James - has renewed questions about political pressure on the justice system.

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

"There's no question that the schedule of this indictment, when combined with others, has prompted questions about the strength of these allegations, and why these charges are being filed now," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is able to demonstrate the allegations stated and demonstrate the information is correctly classified, his conduct may very well have broken the law".

Prosecuting such a high-ranking figure for mishandling classified documents is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present difficulties to try, but they can and are filed against equally junior and senior officials, from time to time," she said.

Parallels to Examinations into Former President and Biden

Trump similarly encountered charges of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was eventually dismissed by a court official and negated by his re-election as leader.

A independent investigator additionally determined that ex-President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Biden's classified documents matters, noted Mr Lesko, who previously held a senior security role at the DOJ.

Rigorous protocols govern the management of sensitive materials. To win a conviction, the government must prove that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

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

A More Traditional Prosecution

The process by which the Justice Department brought this legal action will be under scrutiny, after Trump publicly expressed his wish to see his critics charged and several of those charges materialized.

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

"This Bolton case and eventually the charge appeared to have observed the standard process including the regulations and standards within the DOJ," he stated.

In contrast to Comey's short, two-page indictment, Bolton's was a more "traditional" document that "explicitly sets forth the particulars involving the circumstances and circumstances in this instance," Mr Lesko said.

"It seems reasonably consistent with a long line of precedents... where public servants improperly handled and shared classified material."