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

"We can't delay any longer, it's damaging our standing and trustworthiness," the leader wrote last month in a Truth Social post.

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

Both have since been charged, in cases that numerous experts have stated appear to be driven by politics and challenging to win in court.

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

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

The Specifics of Bolton's Legal Situation

Bolton has been formally charged on federal charges related to the supposed improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, even to describe him "remarkably ignorant" and unsuitable for the presidency in his book.

Experts contend that while there may be political reasons to target Bolton, the methods used to obtain an indictment and the evidence compiled against him suggest a potentially more substantial case than the DOJ presented against James.

"These actions that's being claimed is both more serious and appears to have occurred over a significant duration," 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 exit, authorities alleged that Bolton placed the country at danger by wrongfully retaining and transmitting sensitive documents to family members using unprotected methods, including AOL. Several of the materials were marked top secret.

The charge alleges that at one point a hacker gained access to Bolton's system where documents were kept and transmitted an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct charges of mishandling classified information.

Retribution or a Strong Case?

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

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, authored a publication about his time in the Trump government that was sharply negative of the president.

"There's no question that the timing of this indictment, when paired with others, has raised doubts about the validity of these charges, and the reason these charges are being brought at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the Justice Department is able to demonstrate the allegations alleged and show the information is properly designated, his behavior may certainly have broken the law".

Charging such a senior figure for mishandling sensitive materials 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 prosecute, but they may and are filed against equally low-level and senior personnel, from time to time," she said.

Parallels to Investigations into Trump and President

Trump similarly faced charges of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually dismissed by a federal judge and voided by his return as president.

A special counsel additionally found that former President Joe Biden improperly maintained classified documents from his time as second-in-command, but failed to prosecute him.

Bolton's case shares characteristics to Biden's classified documents matters, said Mr Lesko, who previously held a senior national security position at the Justice Department.

Rigorous protocols regulate the handling of classified documents. To secure a conviction, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transfer it to someone without authorization to obtain it.

"Due to the sensitive character of the information at issue in this case, we lack a great deal of details about why the government believes elements like the diary entries and the additional information he communicated by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department initiated this case will be closely examined, following Trump openly expressed his desire to see his political opponents charged and several of those charges came to fruition.

But Mr Lesko indicated in Bolton's case, authorities appear to have followed protocol.

"This Bolton prosecution and ultimately the indictment seemed to have followed the standard procedure including the rules and standards within the Department of Justice," he stated.

Unlike Comey's short, two-page indictment, Bolton's was a increasingly "conventional" filing that "clearly outlines the particulars involving the circumstances and situation here," Mr Lesko commented.

"It seems reasonably consistent with a long line of cases... where government officials mishandled and shared sensitive information."