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Former President Donald Trump has consistently expressed his desire to see critics probed, applying pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our reputation and trustworthiness," the president wrote last month in a social media message.

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

Each have subsequently been charged, in cases that many experts have stated seem to be driven by politics and challenging to succeed in legal proceedings.

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

"In my opinion, comparing Bolton's charges to Comey's is like comparing two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "stunningly uninformed" and unsuitable for office in his book.

Experts contend that while there may be political motivations to target Bolton, the procedures used to obtain an indictment and the proof gathered against him suggest a potentially stronger legal argument than the Justice Department brought against James.

"This misconduct that's being alleged is simultaneously more serious and appears to have occurred over a significant period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, prosecutors alleged that Bolton placed the nation at danger by improperly retaining and transmitting classified information to relatives using unprotected methods, including AOL. Several of the materials were labeled highly classified.

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

Bolton entered a not guilty plea during a court appearance on Friday to eighteen separate charges of improperly handling classified information.

Political Motivation or a Strong Case?

The timing of his charge - coming on the heels of allegations against James - has renewed questions about political pressure on the justice system.

Trump previously suggested Bolton should be in prison, and called him a "sleazebag". Bolton, for his role, authored a publication about his experience in the Trump administration that was sharply negative of the leader.

"There's no question that the timing of this charge, when combined with additional cases, has raised questions about the validity of these allegations, and the reason these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is capable to prove the facts alleged and show the material is correctly classified, his behavior may certainly have violated the law".

Charging such a high-ranking figure for mishandling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow 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 low-level and senior officials, from occasionally," she said.

Parallels to Investigations into Trump and President

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

A independent investigator also determined that former President Joe Biden wrongfully stored classified documents from his time as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's sensitive materials issues, said Mr Lesko, who previously held a top security position at the Justice Department.

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

"Because of the sensitive character of the information at issue in this case, we lack a lot of particulars about the reasons the government believes things like the personal notes and the other information he communicated by electronic message, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the DOJ brought this legal action will be closely examined, following Trump openly posted his wish to see his critics prosecuted and some of those indictments materialized.

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

"This Bolton prosecution and eventually the charge seemed to have followed the regular process including the rules and standards within the DOJ," he stated.

In contrast to Comey's short, concise charge, Bolton's was a more "traditional" document that "explicitly outlines the details involving the facts and circumstances here," Mr Lesko said.

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