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Former President Donald Trump has consistently expressed his desire to see critics probed, applying influence on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our reputation and credibility," the leader stated recently in a social media message.

"I was impeached twice, and charged me (5 times!)" he said, mentioning the multiple legal proceedings he encountered after leaving the White House in 2021 and James's civil case.

Both have subsequently been charged, in cases that numerous experts have stated appear to be politically motivated and challenging to win in court.

But the latest charges against a Trump critic, former security advisor John Bolton, stand apart, legal experts and former prosecutors assert.

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

The Details of Bolton's Case

Bolton has been formally charged on federal charges related to the alleged improper handling of classified information. Since departing the White House in 2019, he has become a vocal presidential opponent, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the proof compiled against him indicate a possibly more substantial legal argument than the DOJ presented against James.

"These actions that's being claimed is both more serious and seems to have occurred over a significant duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and following his 2019 White House departure, authorities claimed that Bolton put 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 a certain time a unauthorized user accessed to Bolton's account where documents were stored and sent an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on recently to eighteen distinct charges of mishandling classified information.

Retribution or a Substantial Case?

The timing of his indictment - coming on the heels of charges against Comey - has renewed questions about external influence on the justice system.

Trump once suggested Bolton belonged in jail, and called him a "sleazebag". Bolton, for his role, authored a book about his time in the Trump government that was sharply negative of the president.

"There's no question that the timing of this charge, when combined with additional cases, has raised questions about the validity of these allegations, and the reason these counts are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the Justice Department is capable to prove the facts alleged and demonstrate the information is correctly designated, his conduct may certainly have broken the law".

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

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

Similarities to Investigations into Former President and President

Trump likewise encountered charges of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that matter was ultimately dismissed by a federal judge and voided by his return as president.

A special counsel also determined that former President Joe Biden wrongfully stored classified documents from his time as second-in-command, but did not prosecute him.

Bolton's case shares characteristics to Trump's classified documents matters, said Mr Lesko, who also held a senior security role at the DOJ.

Strict procedures regulate the handling of sensitive materials. To win a guilty verdict, the government must demonstrate that Bolton was aware the information he was sending was classified, and he had to intentionally transmit it to someone without authorization to obtain it.

"Due to the sensitive nature of the information at question in this matter, we lack a great deal of particulars about the reasons the government believes elements like the personal notes and the additional information he shared by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department initiated this legal action will be under scrutiny, following Trump openly expressed his desire to see his political opponents prosecuted and some of those indictments materialized.

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

"The Bolton prosecution and ultimately the charge appeared to have observed the standard procedure including the rules and norms within the DOJ," he stated.

Unlike Comey's brief, two-page indictment, Bolton's was a increasingly "traditional" document that "clearly sets forth the particulars concerning the facts and situation in this instance," Mr Lesko said.

"It appears reasonably consistent with a series of precedents... where government officials mishandled and shared classified material."