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Ex-President Donald Trump has consistently expressed his wish to see critics probed, applying influence on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's killing our reputation and credibility," the leader wrote recently in a social media post.

"I was impeached twice, and indicted me (5 times!)" he said, referencing the multiple legal proceedings he faced after leaving the White House in 2021 and James's civil case.

Both have since been indicted, in situations that numerous experts have stated seem to be politically motivated and difficult to win in court.

But the most recent charges against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and ex-prosecutors assert.

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

This Details of Bolton's Legal Situation

Bolton has been formally charged on federal charges related to the alleged mishandling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal Trump critic, even to describe him "stunningly uninformed" and unsuitable for the presidency in his book.

Experts contend that while there may be political motivations to target Bolton, the methods used to secure an indictment and the evidence compiled against him indicate a potentially more substantial legal argument than the Justice Department brought against Comey.

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

During his time as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton placed the country at risk by improperly retaining and transmitting sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

The charge states that at a certain time a unauthorized user gained access to Bolton's account where files were kept 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 Friday to eighteen distinct charges of mishandling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his charge - arriving on the heels of allegations against James - has renewed concerns about political pressure on the legal system.

Trump once implied Bolton should be in prison, and described him a "sleazebag". Bolton, for his part, wrote a publication about his time in the Trump administration that was sharply negative of the leader.

"There's no question that the schedule of this indictment, when combined with additional cases, has prompted doubts about the strength of these allegations, and the reason 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 able to prove the facts stated and demonstrate the material is correctly designated, his behavior may very well have broken the statute".

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

"Situations that concern classified information present challenges to try, but they may and are filed against equally low-level and senior personnel, from occasionally," she said.

Parallels to Investigations into Trump and President

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

A independent investigator also determined that ex-President Joe Biden wrongfully stored classified documents from his time as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's classified documents issues, noted Mr Lesko, who previously held a senior security role at the DOJ.

Strict protocols regulate the handling of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was sending was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the classified character of the material at issue in this matter, we lack a lot of details about why the government contends things like the personal notes and the additional information he communicated by email, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ initiated this case will be closely examined, following Trump publicly posted his desire to see his political opponents charged and several of those indictments came to fruition.

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

"The Bolton case and ultimately the indictment seemed to have observed the standard procedure including the rules and standards within the Department of Justice," he said.

Unlike Comey's short, concise charge, Bolton's was a more "traditional" filing that "explicitly outlines the details involving the circumstances and situation here," Mr Lesko commented.

"It appears reasonably aligned with a long line of cases... where public servants improperly handled and transmitted sensitive information."