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

"We cannot postpone any longer, it's killing our standing and trustworthiness," the president stated recently in a Truth Social message.

"They impeached twice, and indicted me (five times!)" he declared, referencing the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that numerous experts have stated appear to be driven by politics and difficult to win in legal proceedings.

But the latest allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal experts and former prosecutors assert.

"In my opinion, contrasting Bolton's charges to James' is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of the Case

Bolton has been criminally indicted on national allegations related to the supposed mishandling of classified information. Since departing the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Experts say that while there may be political reasons to target Bolton, the methods used to obtain an charge and the evidence compiled against him indicate a possibly more substantial case than the Justice Department presented against Comey.

"These actions that's being alleged is both more severe and appears to have taken place over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and after his 2019 White House exit, authorities alleged that Bolton put the nation at danger by wrongfully keeping and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were marked highly classified.

The charge states that at one point a unauthorized user gained access to Bolton's system where files were stored and transmitted an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on recently to 18 separate counts of improperly handling sensitive materials.

Political Motivation or a Strong Case?

The schedule of his charge - arriving on the heels of charges against James - has renewed questions about political pressure on the justice system.

Trump once implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump administration that was sharply negative of the leader.

"There's no question that the schedule of this charge, when paired with others, has raised questions about the validity of these allegations, and the reason these charges are being filed at this time," said Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the DOJ is able to prove the allegations alleged and demonstrate the information is correctly classified, his behavior may certainly have broken the statute".

Prosecuting such a high-ranking official for improperly handling sensitive materials is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials pose difficulties to try, but they can and are brought against equally low-level and senior officials, from time to time," she said.

Similarities to Examinations into Trump and Biden

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

A independent investigator also found that former President Joe Biden wrongfully stored classified documents from his period as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's classified documents issues, said Mr Lesko, who previously held a top national security position at the Justice Department.

Rigorous protocols govern the management of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to obtain it.

"Due to the sensitive nature of the material at question in this case, we lack a great deal of details about the reasons the prosecution contends things like the diary entries and the additional information he shared by email, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ brought this legal action will be under scrutiny, following Trump publicly expressed his wish to see his critics prosecuted and several of those indictments materialized.

But Mr Lesko said in Bolton's situation, prosecutors seem to have adhered to protocol.

"This Bolton prosecution and eventually the charge appeared to have followed the regular process including the rules and standards within the Department of Justice," he said.

In contrast to Comey's brief, concise charge, Bolton's was a more "traditional" document that "clearly outlines the details concerning the circumstances and situation in this instance," Mr Lesko said.

"It seems reasonably consistent with a long line of precedents... where public servants mishandled and shared sensitive information."