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

"We can't delay further, it's killing our standing and trustworthiness," the president stated recently in a social media post.

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

Both have since been charged, in situations that many experts have said appear to be driven by politics and difficult to win in legal proceedings.

But the latest charges against a presidential opponent, ex national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors say.

"In my opinion, contrasting Bolton's case to Comey's is like comparing two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been criminally indicted on national allegations pertaining to the supposed mishandling of classified information. Since departing the White House in 2019, he has emerged as a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Experts contend that while there may be political reasons to target Bolton, the methods used to obtain an indictment and the proof compiled against him indicate a potentially more substantial legal argument than the Justice Department brought against James.

"These actions that's being alleged is both more serious and seems to have taken place 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 national security adviser, and after his 2019 White House exit, authorities claimed that Bolton placed the nation at danger by wrongfully keeping and transmitting classified information to relatives using unprotected methods, including AOL. Some of the materials were labeled top secret.

The charge alleges that at a certain time a hacker gained access to Bolton's account where documents were kept and sent an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on recently to 18 distinct charges of mishandling classified information.

Retribution or a Strong Legal Argument?

The schedule of his charge - coming on the heels of charges against James - has renewed concerns about political pressure on the justice system.

Trump once implied Bolton should be in prison, and described him a "sleazebag". Bolton, for his part, authored a book about his experience in the Trump government that was highly critical of the president.

"There's no question that the timing of this indictment, when paired with others, has prompted questions about the strength of these allegations, and the reason these charges are being brought now," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to demonstrate the allegations alleged and demonstrate the information is correctly designated, his conduct may very well have broken the statute".

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

"Cases that concern sensitive materials pose difficulties to prosecute, but they can and are brought against both junior and high-level personnel, from occasionally," she explained.

Similarities to Investigations into Former President and Biden

Trump likewise faced allegations of improperly storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was ultimately dismissed by a court official and voided by his re-election as leader.

A independent investigator also determined that former President Joe Biden improperly stored classified documents from his time as second-in-command, but did not criminally charge him.

Bolton's situation bears similarities to Biden's classified documents issues, said Mr Lesko, who also held a top national security position at the DOJ.

Strict protocols govern the handling of sensitive materials. To win a guilty verdict, the government must prove that Bolton was aware the material he was sending was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the sensitive character of the material at question in this matter, we lack a lot of details about why the prosecution believes things like the diary entries and the additional material he shared by email, and why there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the Justice Department initiated this legal action will be under scrutiny, after Trump publicly posted his wish to see his critics prosecuted and some of those indictments materialized.

But Mr Lesko indicated in Bolton's situation, prosecutors appear to have followed protocol.

"This Bolton case and eventually the indictment seemed to have observed the standard procedure including the rules and standards within the Department of Justice," he stated.

Unlike Comey's short, concise charge, Bolton's was a more "conventional" filing that "explicitly outlines the details involving the circumstances and circumstances in this instance," Mr Lesko said.

"It seems reasonably consistent with a long line of cases... where public servants mishandled and transmitted classified material."