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Former President Donald Trump has repeatedly expressed his desire to see opponents probed, exerting influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our standing and credibility," the president stated last month in a social media post.

"I was impeached me, and indicted me (five times!)" he said, referencing the multiple legal proceedings he faced after leaving the White House in 2021 and James's lawsuit.

Each have since been charged, in situations that numerous experts have said seem to be politically motivated and challenging to win in legal proceedings.

But the most recent allegations against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors assert.

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

The Details of the Case

Bolton has been formally charged on federal charges pertaining to the supposed improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal presidential opponent, even to call him "remarkably ignorant" and unsuitable for the presidency in his book.

Specialists contend that while there may be political reasons to target Bolton, the methods used to obtain an indictment and the proof compiled against him indicate a possibly stronger legal argument than the Justice Department presented against James.

"This misconduct that's being alleged is simultaneously more serious and seems to have taken place over a significant 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 exit, authorities alleged that Bolton placed the country at danger by wrongfully keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were labeled highly classified.

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

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

Retribution or a Strong Legal Argument?

The timing of his indictment - coming on the tails of allegations against James - has revived questions about political pressure on the legal system.

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

"There's no question that the timing of this indictment, when paired with others, has prompted questions about the validity of these charges, and why these counts are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "should the DOJ is capable to prove the allegations alleged and demonstrate the material is correctly designated, his conduct may certainly have broken the law".

Prosecuting such a high-ranking figure for mishandling classified documents is "rare" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information present challenges to try, but they can and are brought against equally junior and high-level officials, from occasionally," she explained.

Parallels to Examinations into Trump and President

Trump similarly faced allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was ultimately dismissed by a federal judge and voided by his re-election as president.

A special counsel additionally found that former President Joe Biden wrongfully maintained classified documents from his period as second-in-command, but did not prosecute him.

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

Rigorous protocols regulate the management of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the material he was transmitting was classified, and he had to intentionally transmit it to someone without authorization to obtain it.

"Because of the sensitive nature of the information at issue in this case, we lack a great deal of details about the reasons the government believes elements like the diary entries and the additional information he shared by email, and why there were restricted," said Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ initiated this legal action will be under scrutiny, after Trump openly posted his wish to see his critics charged and several of those charges materialized.

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

"The Bolton case and eventually the charge appeared to have observed the standard process including the regulations and standards within the DOJ," he said.

In contrast to Comey's short, two-page indictment, Bolton's was a increasingly "traditional" document that "clearly sets forth the particulars involving the facts and circumstances here," Mr Lesko said.

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