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

"We cannot postpone any longer, it's killing our reputation and credibility," the leader wrote last month in a Truth Social message.

"I was impeached twice, and charged me (five times!)" he said, mentioning the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Each have subsequently been indicted, in situations that many experts have stated seem to be driven by politics and challenging to succeed in court.

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

"I would say, comparing Bolton's charges to Comey's is like equating apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of the Case

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. After departing the White House in 2019, he has emerged as a outspoken Trump critic, even to call him "stunningly uninformed" and unfit for office in his book.

Experts say that while there may be political reasons to target Bolton, the procedures used to secure an charge and the evidence compiled against him suggest a possibly more substantial case than the DOJ brought against Comey.

"This misconduct that's being alleged is simultaneously more serious and appears to have occurred over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton placed the country at danger by improperly retaining and sending classified information to family members using insecure means, including AOL. Some of the documents were marked highly classified.

The charge states that at one point a unauthorized user gained access to Bolton's system where files were stored and transmitted an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

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

Retribution or a Strong Case?

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

Trump once implied Bolton should be in jail, and described him a "sleazebag". Bolton, for his part, wrote a publication about his experience in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the schedule of this charge, when paired with additional cases, has raised doubts about the validity of these charges, and why these counts are being filed at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to demonstrate the allegations alleged and demonstrate the information is properly designated, his behavior may certainly have broken the law".

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

"Situations that concern classified information present challenges to prosecute, but they may and are brought against equally low-level and high-level personnel, from occasionally," she said.

Parallels to Examinations into Former President and President

Trump likewise faced charges of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was eventually thrown out by a federal judge and voided by his re-election as president.

A special counsel additionally determined that former President Joe Biden improperly stored classified documents from his time as vice president, but did not criminally charge him.

Bolton's case shares characteristics to Trump's classified documents issues, said Mr Lesko, who also held a top national security role at the DOJ.

Rigorous protocols regulate the handling of classified documents. To win a guilty verdict, the prosecution must prove that Bolton knew the information he was sending was restricted, and he had to intentionally transfer it to someone without authorization to obtain it.

"Because of the classified character of the information at question in this matter, we don't have a lot of particulars about why the government believes elements like the personal notes and the additional material he communicated by email, and why there were classified," said Mr Jaffer.

A More Traditional Prosecution

The procedure by which the DOJ initiated this case will be under scrutiny, after Trump openly posted his wish to see his critics prosecuted and some of those indictments came to fruition.

But Mr Lesko indicated in Bolton's case, prosecutors appear to have followed standard procedure.

"The 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, two-page indictment, Bolton's was a more "conventional" document that "clearly outlines the particulars involving the circumstances and situation in this instance," Mr Lesko commented.

"It appears reasonably consistent with a series of precedents... where government officials mishandled and shared sensitive information."