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

"We can't delay further, it's damaging our standing and credibility," the president wrote recently in a Truth Social post.

"I was impeached twice, and indicted me (five times!)" he declared, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Both have subsequently been charged, in situations that numerous experts have said appear to be driven by politics and challenging to win in court.

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

"In my opinion, contrasting Bolton's case to James' is like equating apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Details of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged mishandling of sensitive materials. After leaving the White House in 2019, he has become a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists say that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence gathered against him indicate a potentially stronger case than the Justice Department brought against James.

"This misconduct that's being alleged is simultaneously more serious and seems 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 departure, prosecutors claimed that Bolton placed the country at risk by wrongfully retaining and sending classified information to family members using insecure means, including AOL. Several of the materials were labeled top secret.

The charge alleges that at a certain time a hacker accessed to Bolton's system where documents were stored and sent an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

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

Retribution or a Strong Case?

The schedule of his charge - coming on the tails of allegations against Comey - has revived questions about external influence on the justice system.

Trump once suggested Bolton belonged in jail, and described him a "disreputable person". Bolton, for his role, authored a book about his time in the Trump government that was sharply negative of the leader.

"Undoubtedly that the schedule of this indictment, when paired with additional cases, has prompted questions about the validity of these allegations, and why these counts are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "if the Justice Department is capable to prove the facts alleged and demonstrate the material is properly classified, his behavior may very well have violated the statute".

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

"Cases that concern classified information present challenges to prosecute, but they can and are brought against both low-level and senior officials, from time to time," she said.

Similarities to Investigations into Trump and President

Trump similarly faced allegations of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that case was ultimately dismissed by a court official and negated by his re-election as leader.

A independent investigator additionally found that ex-President Joe Biden improperly stored sensitive materials from his period as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Trump's classified documents issues, noted Mr Lesko, who also held a senior national security position at the Justice Department.

Rigorous procedures govern the handling of classified documents. To win a conviction, the prosecution must demonstrate that Bolton knew the material he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to obtain it.

"Due to the classified nature of the information at question in this case, we don't have a great deal of details about the reasons the prosecution contends elements like the diary entries and the other material he communicated by electronic message, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department brought this case will be under scrutiny, following Trump openly expressed his wish to see his critics charged and some of those indictments materialized.

But Mr Lesko said in Bolton's situation, prosecutors seem to have followed standard procedure.

"The Bolton prosecution and ultimately the indictment appeared to have followed the standard process including the rules and norms within the DOJ," he said.

Unlike Comey's brief, two-page indictment, Bolton's was a more "traditional" filing that "explicitly outlines the particulars concerning the circumstances and situation in this instance," Mr Lesko said.

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