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Ex-President Donald Trump has repeatedly expressed his desire to see opponents probed, applying influence on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our reputation and credibility," the leader stated last month in a Truth Social post.

"I was impeached twice, and indicted me (5 times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in cases that many experts have said appear to be politically motivated and challenging to succeed in court.

But the most recent charges against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and former prosecutors assert.

"I would say, contrasting Bolton's case to James' is like comparing two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Details of the Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the supposed improper handling of sensitive materials. Since departing the White House in 2019, he has become a outspoken Trump critic, going so far as to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists contend that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the proof gathered against him suggest a possibly stronger case than the Justice Department brought against Comey.

"These actions that's being claimed is both more serious and seems to have occurred over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and after his 2019 White House exit, authorities alleged that Bolton put the country at danger by wrongfully keeping and sending sensitive documents to relatives using insecure means, including AOL. Several of the documents were labeled highly classified.

The charge states that at one point a hacker accessed to Bolton's system where files were stored and sent an apparent warning to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to 18 separate counts of improperly handling sensitive materials.

Retribution or a Strong Case?

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

Trump previously implied Bolton belonged in prison, and described him a "disreputable person". Bolton, for his role, authored a book about his experience in the Trump government that was highly critical of the leader.

"There's no question that the timing of this indictment, when combined with additional cases, has prompted doubts about the strength 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 continued, "should the DOJ is able to prove the allegations alleged and show the material is properly classified, his behavior may certainly have violated the law".

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

"Cases that concern sensitive materials present difficulties to try, but they can and are brought against both low-level and senior officials, from time to time," she explained.

Parallels to Examinations into Former President and President

Trump similarly encountered charges of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that matter was eventually thrown out by a federal judge and voided by his return as leader.

A special counsel also determined that ex-President Joe Biden improperly maintained sensitive materials from his time as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Biden's sensitive materials matters, said Mr Lesko, who previously held a senior national security position at the DOJ.

Strict procedures regulate the management of sensitive materials. To secure a conviction, the government must demonstrate that Bolton knew the information he was sending was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Due to the classified nature of the material at issue in this matter, we don't have a great deal of particulars about why the government contends things like the personal notes and the other information he communicated by email, and why there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The process by which the Justice Department initiated this case will be closely examined, after Trump openly expressed his desire to see his political opponents prosecuted and some of those indictments came to fruition.

But Mr Lesko said 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 norms within the DOJ," he said.

Unlike Comey's brief, concise charge, Bolton's was a more "traditional" document that "explicitly outlines the particulars involving the facts and circumstances here," Mr Lesko commented.

"It seems reasonably consistent with a long line of precedents... where government officials improperly handled and shared sensitive information."