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Former President Donald Trump has repeatedly shown his wish 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 can't delay further, it's damaging our standing and trustworthiness," the president wrote recently in a Truth Social post.

"I was impeached me, and indicted me (5 times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's civil case.

Both have since been indicted, in situations that many specialists have stated appear to be politically motivated and difficult to win in legal proceedings.

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

"In my opinion, comparing Bolton's charges to Comey's is like equating apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a possibly stronger legal argument than the DOJ brought against James.

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

Throughout his tenure as Trump's security advisor, and following his 2019 White House departure, prosecutors alleged that Bolton placed the nation at danger by wrongfully retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were labeled top secret.

The indictment alleges that at one point a hacker gained access to Bolton's system where files were kept and sent an seeming 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 18 separate charges of mishandling sensitive materials.

Retribution or a Strong Case?

The schedule of his charge - arriving on the tails of charges against James - has renewed concerns about external influence on the legal system.

Trump once suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his role, wrote a book about his time in the Trump administration that was highly critical of the leader.

"Undoubtedly that the schedule of this indictment, when combined with others, has raised questions about the strength of these charges, and the reason these charges are being filed at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "should the DOJ is capable to prove the facts stated and demonstrate the information is correctly classified, his behavior may very well have violated the statute".

Prosecuting such a senior figure for mishandling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information present difficulties to prosecute, but they may and are brought against both junior and high-level personnel, from time to time," she explained.

Parallels to Investigations into Trump and Biden

Trump likewise encountered charges of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually dismissed by a federal judge and negated by his return as leader.

A independent investigator additionally determined that ex-President Joe Biden improperly maintained sensitive materials from his period as second-in-command, but failed to prosecute him.

Bolton's case shares characteristics to Biden's sensitive materials issues, said Mr Lesko, who previously held a top security position at the DOJ.

Strict procedures govern the management of classified documents. To win a conviction, the prosecution must prove that Bolton knew the material he was transmitting was classified, and he had to knowingly transfer it to someone without authorization to receive it.

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

A Increasingly Conventional Legal Action

The process by which the DOJ initiated this case will be under scrutiny, after Trump openly expressed his desire to see his critics prosecuted and some of those indictments materialized.

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

"This Bolton case and ultimately the charge seemed to have observed the standard process including the rules and standards within the DOJ," he said.

Unlike Comey's short, concise charge, Bolton's was a more "traditional" document that "clearly outlines the particulars concerning the circumstances and circumstances in this instance," Mr Lesko said.

"It seems fairly consistent with a long line of precedents... where public servants mishandled and shared classified material."