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Ex-President Donald Trump has repeatedly expressed his desire to see opponents investigated, exerting pressure on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our reputation and credibility," the leader stated last month in a social media message.

"They impeached me, and charged me (five times!)" he said, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Each have since been indicted, in situations that numerous experts have stated appear to be politically motivated and difficult to succeed in court.

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

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

The Specifics of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the supposed improper handling of classified information. After leaving the White House in 2019, he has emerged as a outspoken presidential opponent, even to describe him "stunningly uninformed" and unsuitable for office in his book.

Experts contend that while there may be political reasons to target Bolton, the procedures used to obtain an charge and the proof gathered against him indicate a possibly stronger case than the DOJ presented against James.

"These actions that's being claimed is simultaneously more severe and appears to have occurred over a considerable period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and following his 2019 White House exit, authorities claimed that Bolton placed the country at danger by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

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

Bolton pleaded not guilty during a hearing on Friday to 18 separate counts of improperly handling classified information.

Retribution or a Substantial Legal Argument?

The timing of his charge - arriving on the heels of allegations against Comey - has revived questions about external influence on the legal system.

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

"Undoubtedly that the schedule of this indictment, when paired with others, has prompted questions about the validity of these charges, and why these charges are being filed now," said Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the Justice Department is able to prove the facts stated and show the information is correctly designated, his conduct may very well have broken the statute".

Charging such a high-ranking figure for improperly handling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

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

Similarities to Investigations into Trump and Biden

Trump similarly faced charges of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately dismissed by a court official and negated by his re-election as leader.

A independent investigator also determined that former President Joe Biden improperly maintained classified documents from his period as second-in-command, but failed to criminally charge him.

Bolton's case bears similarities to Trump's sensitive materials issues, noted Mr Lesko, who previously held a senior security role at the DOJ.

Strict protocols regulate the handling of sensitive materials. To win a conviction, the prosecution 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 receive it.

"Due to the classified nature of the information at issue in this case, we lack a lot of particulars about why the government believes things like the diary entries and the other information he shared by electronic message, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department brought this legal action will be under scrutiny, after Trump publicly expressed his wish to see his political opponents prosecuted and some of those charges came to fruition.

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

"The Bolton case and ultimately the charge seemed to have followed the regular process including the regulations and norms within the Department of Justice," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a increasingly "traditional" filing that "clearly outlines the particulars concerning the facts and situation here," Mr Lesko commented.

"It appears reasonably aligned with a series of precedents... where public servants improperly handled and shared classified material."