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Ex-President Donald Trump has consistently shown his wish to see critics investigated, exerting pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our standing and trustworthiness," the leader wrote recently in a Truth Social message.

"They impeached twice, and charged me (5 times!)" he said, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Each have subsequently been charged, in cases that many specialists have stated appear to be politically motivated and difficult to succeed in legal proceedings.

But the most recent charges against a presidential opponent, ex national security adviser John Bolton, differ significantly, legal specialists and former prosecutors say.

"I would say, contrasting 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 Details of Bolton's Case

Bolton has been formally charged on national allegations related to the alleged improper handling of classified information. After leaving the White House in 2019, he has become a vocal presidential opponent, going so far as to describe him "remarkably ignorant" and unfit for the presidency in his memoir.

Experts contend that while there may be political motivations to go after Bolton, the procedures used to secure an charge and the proof compiled against him indicate a possibly more substantial legal argument than the Justice Department presented against James.

"This misconduct that's being claimed is simultaneously 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.

Throughout his tenure as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton put the nation at danger by wrongfully keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Some of the materials were labeled top secret.

The indictment states that at a certain time a hacker gained access to Bolton's system where files were kept and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

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

Retribution or a Strong Case?

The timing of his charge - coming on the tails 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, authored a publication about his experience in the Trump government that was sharply negative of the leader.

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

However, he added, "should the DOJ is able to prove the allegations alleged and demonstrate the material is correctly designated, his conduct may very well have broken the statute".

Charging such a senior figure for improperly handling sensitive materials is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to try, but they may and are filed against equally junior and high-level personnel, from time to time," she said.

Similarities to Investigations into Trump and Biden

Trump likewise encountered allegations of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately dismissed by a federal judge and negated by his return as president.

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

Bolton's case bears similarities to Trump's classified documents issues, noted Mr Lesko, who previously held a senior national security role at the Justice Department.

Rigorous procedures regulate the handling of sensitive materials. To secure a guilty verdict, the government must prove that Bolton knew the information he was sending was classified, and he had to knowingly transmit it to someone not entitled to receive it.

"Because of the sensitive nature of the material at issue in this case, we lack a great deal of details about the reasons the government contends things like the personal notes and the additional material he shared by electronic message, and why there were restricted," explained Mr Jaffer.

A More Traditional Prosecution

The procedure by which the DOJ brought this case will be under scrutiny, after Trump openly expressed his desire to see his critics charged and several of those indictments materialized.

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

"This Bolton prosecution and eventually the indictment seemed to have observed the regular procedure including the rules and norms within the Department of Justice," he said.

In contrast to Comey's short, concise charge, Bolton's was a more "traditional" filing that "clearly sets forth the details involving the circumstances and situation in this instance," Mr Lesko said.

"It seems reasonably consistent with a series of cases... where government officials mishandled and transmitted classified material."