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Ex-President Donald Trump has consistently shown his wish to see critics probed, exerting influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our reputation and trustworthiness," the president stated last month in a Truth Social message.

"They impeached twice, and charged me (five times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's civil case.

Both have subsequently been charged, in cases that numerous experts have stated seem to be politically motivated and difficult to win in legal proceedings.

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

"In my opinion, comparing Bolton's case to James' is like equating two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on national allegations pertaining to the supposed improper handling of classified information. Since leaving the White House in 2019, he has become a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists contend that while there may be political reasons to target Bolton, the procedures used to secure an indictment and the proof compiled against him indicate a possibly more substantial legal argument than the DOJ presented against James.

"This misconduct that's being claimed is both 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 tenure as Trump's national security adviser, and after his 2019 White House exit, prosecutors alleged that Bolton put the country at danger by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were marked highly classified.

The charge states that at one point a hacker accessed to Bolton's account where documents were kept and sent an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on recently to 18 distinct counts of mishandling classified information.

Political Motivation or a Strong Legal Argument?

The timing of his charge - arriving on the heels of allegations against Comey - has revived questions about external influence on the legal system.

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

"Undoubtedly that the timing of this indictment, when combined with others, has raised doubts about the validity of these charges, and the reason these charges are being filed now," said Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the DOJ is able to demonstrate the facts stated and demonstrate the material is properly classified, his conduct may very well have broken the law".

Charging such a senior figure for mishandling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present challenges to try, but they can and are filed against equally low-level and senior officials, from occasionally," she explained.

Parallels to Investigations into Trump and President

Trump similarly encountered allegations of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually dismissed by a federal judge and voided by his return as president.

A special counsel also found that former President Joe Biden improperly stored sensitive materials from his period as second-in-command, but failed to prosecute him.

Bolton's case shares characteristics to Biden's sensitive materials matters, noted Mr Lesko, who also held a top national security role at the DOJ.

Rigorous procedures govern the management of sensitive materials. To win a conviction, the government must prove that Bolton was aware the material he was sending was restricted, and he had to intentionally transmit it to someone not entitled to receive it.

"Because of the sensitive character of the material at issue in this matter, we lack a great deal of details about the reasons the government believes things like the diary entries and the other material he shared by electronic message, and why there were classified," said Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department brought this legal action will be under scrutiny, following 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, authorities appear to have adhered to protocol.

"The Bolton case and ultimately the indictment appeared to have observed the standard process including the regulations and norms within the DOJ," he stated.

In contrast to Comey's brief, concise indictment, Bolton's was a increasingly "conventional" document that "explicitly outlines the details concerning the facts and situation in this instance," Mr Lesko said.

"It seems reasonably aligned with a long line of precedents... where public servants improperly handled and shared sensitive information."