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Former President Donald Trump has repeatedly expressed his wish to see opponents investigated, applying influence on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our standing and trustworthiness," the leader wrote last month in a Truth Social message.

"I was impeached me, and indicted me (five times!)" he declared, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Both have subsequently been charged, in cases that many experts have stated appear to be driven by politics and difficult to succeed in legal proceedings.

But the latest allegations against a Trump critic, former security advisor John Bolton, differ significantly, legal experts and former prosecutors say.

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

This Details of Bolton's Case

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 presidential opponent, even to describe him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the proof gathered against him suggest a potentially stronger case than the DOJ brought against Comey.

"This misconduct that's being claimed is simultaneously more serious and seems to have taken place over a significant period of time," 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 following his 2019 White House exit, authorities alleged that Bolton put the nation at risk by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the materials were marked highly classified.

The indictment alleges that at one point a unauthorized user accessed to Bolton's system where files were kept and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate counts of improperly handling classified information.

Political Motivation or a Substantial Legal Argument?

The timing of his charge - coming on the heels of charges against Comey - has revived concerns about external influence on the legal system.

Trump previously suggested Bolton should be in jail, and called him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the timing of this charge, when combined with others, has raised doubts about the validity of these allegations, and why these charges are being brought at this time," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is able to demonstrate the allegations stated and demonstrate the material is correctly classified, his behavior may very well have broken the law".

Charging such a senior official for improperly handling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present difficulties to prosecute, but they may and are filed against both low-level and senior officials, from time to time," she said.

Similarities to Investigations into Former President and Biden

Trump similarly faced allegations of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and hindering their return, but that case was eventually thrown out by a federal judge and negated by his re-election as leader.

A independent investigator additionally determined that ex-President Joe Biden improperly stored classified documents from his time as second-in-command, but did not prosecute him.

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

Strict protocols govern the management of classified documents. To win a conviction, the prosecution must prove that Bolton was aware the material he was sending was restricted, and he had to intentionally transfer it to someone without authorization to receive it.

"Due to the classified nature of the information at issue in this matter, we lack a great deal of particulars about why the prosecution believes elements like the diary entries and the additional material he shared by email, and why there were restricted," said Mr Jaffer.

A Increasingly Traditional Legal Action

The procedure by which the Justice Department brought this case will be closely examined, after Trump publicly expressed his wish to see his critics prosecuted and some of those charges materialized.

But Mr Lesko said in Bolton's case, authorities seem to have adhered to protocol.

"This Bolton prosecution and eventually the indictment seemed to have observed the standard procedure including the rules and norms within the DOJ," he stated.

Unlike Comey's short, two-page charge, Bolton's was a increasingly "conventional" document that "clearly sets forth the details involving the circumstances and circumstances here," Mr Lesko said.

"It appears fairly aligned with a series of precedents... where government officials improperly handled and transmitted sensitive information."