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

"We cannot postpone further, it's damaging our reputation and credibility," the president wrote last month in a social media post.

"I was impeached me, and indicted me (5 times!)" he said, referencing the four criminal cases he faced after departing the White House in 2021 and James's civil case.

Each have since been indicted, in situations that numerous experts have stated seem to be driven by politics and difficult to succeed in court.

But the most recent charges against a Trump critic, ex security advisor John Bolton, differ significantly, legal experts and former prosecutors say.

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

The Details of the Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed mishandling of sensitive materials. Since departing the White House in 2019, he has become a outspoken presidential opponent, going so far as to call him "remarkably ignorant" and unfit for the presidency in his memoir.

Specialists contend that while there may be political motivations to target Bolton, the methods used to secure an charge and the proof gathered against him indicate a potentially more substantial legal argument than the DOJ presented against Comey.

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

Throughout his time as Trump's national security adviser, and following his 2019 White House departure, authorities claimed that Bolton placed the nation at danger by improperly retaining and transmitting sensitive documents to family members using insecure means, including AOL. Some of the materials were marked top secret.

The indictment alleges that at one point a hacker gained access to Bolton's system where files were stored and transmitted an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to eighteen separate counts of mishandling sensitive materials.

Political Motivation or a Strong Case?

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

Trump once suggested Bolton should be in jail, and described him a "sleazebag". Bolton, for his part, authored a book 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 raised questions about the validity of these charges, and why these counts are being filed at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to demonstrate the facts stated and show the information is correctly classified, his conduct may certainly have violated the law".

Charging such a high-ranking figure for mishandling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials present difficulties to try, but they can and are brought against both low-level and high-level personnel, from occasionally," she explained.

Parallels to Investigations into Trump and Biden

Trump likewise faced allegations of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was ultimately dismissed by a federal judge and voided by his re-election as leader.

A independent investigator also found that former President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but did not prosecute him.

Bolton's situation bears similarities to Trump's sensitive materials matters, said Mr Lesko, who previously held a top national security role at the DOJ.

Rigorous protocols regulate the handling of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the material he was sending was restricted, and he had to intentionally transmit it to someone not entitled to obtain it.

"Due to the sensitive character of the material at issue in this case, we lack a lot of details about why the prosecution contends things like the diary entries and the additional information he communicated by electronic message, and why there were classified," said Mr Jaffer.

A More Traditional Legal Action

The process by which the DOJ brought this legal action will be closely examined, after Trump publicly posted his wish to see his critics charged and some of those indictments came to fruition.

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

"This Bolton case and ultimately the charge appeared to have followed the regular procedure including the rules and standards within the Department of Justice," he stated.

In contrast to Comey's short, two-page indictment, Bolton's was a increasingly "conventional" document that "clearly outlines the particulars involving the circumstances and situation here," Mr Lesko commented.

"It appears reasonably aligned with a series of precedents... where public servants mishandled and transmitted sensitive information."