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Ex-President Donald Trump has consistently expressed his wish to see critics 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 further, it's damaging our standing and credibility," the leader stated recently in a social media message.

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

Each have subsequently been charged, in situations that numerous specialists have stated appear to be politically motivated and difficult to succeed in legal proceedings.

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

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

The Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed mishandling of classified information. After leaving the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to describe him "stunningly uninformed" and unsuitable for the presidency in his book.

Experts contend that while there may be political motivations to go after Bolton, the methods used to secure an charge and the evidence gathered against him indicate a potentially more substantial legal argument than the DOJ presented against James.

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

During his tenure as Trump's national security adviser, and after his 2019 White House departure, prosecutors alleged that Bolton placed the country at danger by improperly retaining and transmitting sensitive documents to family members using insecure means, including AOL. Several of the materials were marked top secret.

The charge alleges that at one point a unauthorized user accessed to Bolton's account where documents were stored and transmitted an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on recently to 18 separate charges of improperly handling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his charge - arriving on the tails of allegations against James - has revived concerns about political pressure on the justice system.

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, wrote a publication about his experience in the Trump government that was highly critical of the president.

"Undoubtedly that the timing of this charge, when paired with others, has prompted doubts about the strength of these allegations, and why these counts are being filed now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "if the DOJ is able to demonstrate the facts alleged and show the information is properly designated, his conduct may certainly have violated the law".

Charging such a senior official for improperly handling classified documents is "rare" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern sensitive materials present difficulties to prosecute, but they can and are brought against both low-level and high-level personnel, from time to time," she said.

Similarities to Investigations into Trump and President

Trump similarly faced charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was eventually thrown out by a federal judge and negated by his re-election as president.

A special counsel also found that ex-President Joe Biden improperly stored sensitive materials from his time as vice president, but failed to prosecute him.

Bolton's situation bears similarities to Biden's sensitive materials matters, said Mr Lesko, who also held a senior security position at the DOJ.

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

"Because of the sensitive nature of the material at issue in this case, we don't have a great deal of particulars about the reasons the prosecution contends things like the personal notes and the other material he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department brought this legal action will be closely examined, after Trump openly expressed his wish to see his critics charged and some of those charges materialized.

But Mr Lesko said in Bolton's case, authorities appear to have adhered to standard procedure.

"The Bolton case and eventually the indictment appeared to have observed the standard procedure including the rules and standards within the DOJ," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a more "conventional" filing that "clearly sets forth the particulars involving the circumstances and circumstances in this instance," Mr Lesko said.

"It appears reasonably consistent with a long line of cases... where public servants improperly handled and shared sensitive information."