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Ex-President Donald Trump has repeatedly expressed his wish to see critics investigated, 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 standing and credibility," the leader wrote recently in a Truth Social post.

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

Each have since been indicted, in situations that many experts have said appear to be politically motivated and challenging to succeed in court.

But the latest charges against a presidential opponent, former security advisor John Bolton, differ significantly, legal experts and former prosecutors assert.

"I would say, contrasting Bolton's case to James' is like equating two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

This Details of Bolton's Case

Bolton has been formally charged on national allegations pertaining to the supposed mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unfit for office in his memoir.

Experts say that while there may be political motivations to target Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a potentially stronger legal argument than the DOJ presented against Comey.

"These actions that's being alleged 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 claimed that Bolton placed the country at risk by wrongfully retaining and transmitting sensitive documents to family members using unprotected methods, including AOL. Some of the materials were marked top secret.

The charge alleges that at a certain time a unauthorized user accessed to Bolton's account where documents were stored and sent an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to 18 separate charges of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the heels of charges against Comey - has revived concerns about external influence on the justice system.

Trump once implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his role, authored a book about his time in the Trump government that was highly critical of the leader.

"There's no question that the schedule of this charge, when paired with additional cases, has raised doubts about the strength of these charges, and why these counts are being brought at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "should the Justice Department is able to demonstrate the facts stated and demonstrate the material is properly designated, his conduct may certainly have violated the statute".

Charging such a senior official for mishandling classified documents is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose challenges to try, but they may and are brought against equally junior and senior personnel, from time to time," she explained.

Similarities to Examinations into Trump and Biden

Trump similarly faced allegations of improperly keeping classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that case was ultimately dismissed by a federal judge and voided by his return as leader.

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

Bolton's situation shares characteristics to Biden's classified documents matters, noted Mr Lesko, who previously held a senior national security role at the DOJ.

Strict protocols regulate the handling of classified documents. To win a conviction, the government must demonstrate that Bolton knew the information he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to receive it.

"Due to the sensitive character of the information at question in this case, we lack a great deal of particulars about why the government contends elements like the diary entries and the additional information he communicated by email, and why there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The process by which the Justice Department brought this case will be closely examined, following Trump publicly posted his desire to see his political opponents charged and several of those indictments came to fruition.

But Mr Lesko said in Bolton's case, authorities appear to have adhered to standard procedure.

"This Bolton case and eventually the indictment appeared to have followed the regular process including the rules and standards within the DOJ," he stated.

Unlike Comey's brief, concise charge, Bolton's was a increasingly "traditional" filing that "clearly sets forth the details involving the facts and circumstances in this instance," Mr Lesko said.

"It seems fairly aligned with a long line of precedents... where government officials improperly handled and transmitted sensitive information."