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

"We cannot postpone any longer, it's killing our reputation and trustworthiness," the leader wrote recently in a Truth Social post.

"I was impeached me, 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 subsequently been charged, in cases that numerous specialists have said appear to be politically motivated and difficult to succeed in court.

But the latest allegations against a presidential opponent, ex national security adviser John Bolton, stand apart, legal specialists and former prosecutors assert.

"I would say, comparing Bolton's charges to James' is like equating apples to oranges," said Mark Lesko, a ex 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 improper handling of sensitive materials. Since leaving the White House in 2019, he has become a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unfit for office in his book.

Specialists say that while there may be political motivations to target Bolton, the procedures used to secure an indictment and the proof gathered against him indicate a possibly more substantial legal argument than the DOJ brought against Comey.

"These actions that's being claimed is both more severe and appears to have occurred over a significant period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House departure, prosecutors alleged that Bolton put the nation at danger by improperly keeping and transmitting classified information to relatives using insecure means, including AOL. Several of the documents were marked top secret.

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

Bolton entered a not guilty plea during a court appearance on recently to eighteen separate counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the tails of allegations against James - has revived questions about political pressure on the justice system.

Trump previously suggested Bolton belonged in prison, and called him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump administration that was highly critical of the leader.

"There's no question that the schedule of this charge, when combined with others, has prompted questions about the validity of these charges, and the reason these charges are being brought now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "if the DOJ is capable to demonstrate the allegations alleged and show the information is properly designated, his conduct may certainly have broken the law".

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

"Situations that concern classified information pose challenges to try, but they can and are filed against both low-level and senior officials, from time to time," she said.

Parallels to Investigations into Former President and Biden

Trump similarly encountered charges of wrongfully keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was ultimately dismissed by a federal judge and negated by his re-election as president.

A independent investigator additionally determined that former President Joe Biden wrongfully maintained sensitive materials from his time as vice president, but did not prosecute him.

Bolton's situation bears similarities to Biden's classified documents issues, said Mr Lesko, who previously held a top national security role at the Justice Department.

Strict protocols regulate the management of sensitive materials. To win a conviction, the prosecution must demonstrate that Bolton knew the material he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Due to the classified character of the material at question in this matter, we don't have a lot of details about the reasons the government contends elements like the personal notes and the other material he shared by email, and why there were classified," explained Mr Jaffer.

A More Conventional Prosecution

The process by which the Justice Department initiated this legal action will be closely examined, after Trump openly posted his wish to see his critics prosecuted and several of those indictments materialized.

But Mr Lesko said in Bolton's case, prosecutors appear to have adhered to protocol.

"The Bolton prosecution and eventually the indictment appeared to have observed the regular procedure including the rules and standards within the Department of Justice," he said.

In contrast to Comey's brief, two-page indictment, Bolton's was a increasingly "conventional" filing that "clearly outlines the particulars concerning the circumstances and situation here," Mr Lesko said.

"It seems reasonably consistent with a long line of precedents... where government officials mishandled and shared classified material."