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Ex-President Donald Trump has repeatedly shown his desire to see opponents probed, 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 credibility," the president wrote last month in a social media post.

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

Both have since been indicted, in cases that many experts have stated appear to be driven by politics and challenging to win in legal proceedings.

But the most recent charges against a Trump critic, ex national security adviser John Bolton, stand apart, legal experts and ex-prosecutors assert.

"In my opinion, 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 Specifics of the Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "stunningly uninformed" and unfit for the presidency in his book.

Experts contend that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the evidence gathered against him indicate a possibly stronger legal argument than the Justice Department presented against Comey.

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

During his time as Trump's security advisor, and after his 2019 White House exit, prosecutors alleged that Bolton placed the nation at danger by wrongfully keeping and sending classified information to family members using insecure means, including AOL. Several of the documents were marked top secret.

The indictment states that at one point a hacker gained access to Bolton's system where files were kept and sent an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on recently to eighteen distinct counts of mishandling classified information.

Retribution or a Substantial Legal Argument?

The timing of his charge - arriving on the heels of charges against Comey - has revived questions about political pressure on the justice system.

Trump previously suggested Bolton should be in jail, and described him a "disreputable person". 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 indictment, when combined with additional cases, has raised questions about the validity of these allegations, and the reason these counts are being filed now," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he added, "if the DOJ is able to prove the allegations stated and show the information is correctly designated, his conduct may certainly have broken the statute".

Charging such a senior official for improperly handling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern classified information pose difficulties to prosecute, but they can and are filed against both junior and high-level personnel, from occasionally," she said.

Similarities to Examinations into Former President and Biden

Trump likewise faced charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that case was eventually dismissed by a federal judge and voided by his return as president.

A independent investigator also found that former President Joe Biden wrongfully stored classified documents from his period as second-in-command, but failed to criminally charge him.

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

Rigorous procedures govern 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 not entitled to obtain it.

"Due to the sensitive character of the material at question in this matter, we don't have a great deal of particulars about why the prosecution contends elements like the personal notes and the additional information he shared by electronic message, and why there were restricted," explained Mr Jaffer.

A Increasingly Conventional Prosecution

The process by which the Justice Department brought this legal action will be closely examined, following Trump openly expressed his wish to see his critics prosecuted and several of those indictments materialized.

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

"This Bolton prosecution and ultimately the charge appeared to have observed the standard procedure including the rules and standards within the Department of Justice," he stated.

Unlike Comey's short, concise charge, Bolton's was a increasingly "conventional" document that "clearly sets forth the particulars concerning the facts and circumstances in this instance," Mr Lesko commented.

"It appears fairly aligned with a long line of precedents... where public servants mishandled and transmitted classified material."