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

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

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

Both have subsequently been charged, in situations that many specialists have said seem to be driven by politics and difficult to succeed in legal proceedings.

But the latest allegations against a Trump critic, former security advisor John Bolton, stand apart, legal experts and ex-prosecutors assert.

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

This Details of the Case

Bolton has been criminally indicted on federal charges related to the alleged improper handling of sensitive materials. Since departing the White House in 2019, he has become a vocal presidential opponent, even to call him "remarkably ignorant" and unfit for office in his memoir.

Experts say that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the evidence compiled against him suggest a potentially more substantial legal argument than the DOJ presented against James.

"This misconduct that's being claimed is simultaneously more severe and appears to have taken place over a considerable period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and following his 2019 White House departure, authorities claimed that Bolton placed the country at danger by improperly keeping and transmitting sensitive documents to family members using insecure means, including AOL. Some of the documents were marked highly classified.

The charge states that at a certain time a unauthorized user accessed to Bolton's system where documents were kept and transmitted an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on recently to eighteen separate counts of mishandling sensitive materials.

Retribution or a Substantial Case?

The timing of his charge - arriving on the tails of allegations against James - has renewed questions about external influence on the legal system.

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

"There's no question that the timing of this charge, when paired with additional cases, has prompted questions about the strength of these allegations, and the reason these charges are being brought at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is able to prove the allegations alleged and demonstrate the material is properly designated, his behavior may very well have broken the statute".

Prosecuting such a high-ranking figure for improperly handling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials present difficulties to prosecute, but they can and are brought against equally junior and high-level personnel, from occasionally," she said.

Parallels to Investigations into Trump and President

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

A special counsel also determined that former President Joe Biden wrongfully maintained classified documents from his time as vice president, but failed to prosecute him.

Bolton's case bears similarities to Biden's sensitive materials issues, noted Mr Lesko, who previously held a top national security position at the DOJ.

Rigorous procedures govern the management of classified documents. To secure a guilty verdict, the prosecution must prove that Bolton was aware the information he was transmitting was classified, and he had to knowingly transmit it to someone without authorization to obtain it.

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

A Increasingly Conventional Prosecution

The process by which the Justice Department brought this case will be under scrutiny, following Trump publicly posted his desire to see his political opponents charged and some of those charges came to fruition.

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

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

Unlike Comey's brief, two-page charge, Bolton's was a more "conventional" document that "clearly sets forth the particulars involving the circumstances and situation here," Mr Lesko said.

"It seems fairly consistent with a series of cases... where public servants improperly handled and transmitted classified material."