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Former President Donald Trump has consistently expressed his desire to see opponents investigated, applying pressure on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our standing and trustworthiness," the leader wrote recently in a social media message.

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

Each have subsequently been indicted, in situations that numerous experts have stated appear to be politically motivated and challenging to win in court.

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

"I would say, comparing Bolton's charges to Comey's is like equating apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been criminally indicted on federal charges related to the supposed mishandling of sensitive materials. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, even to call him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts contend that while there may be political motivations to target Bolton, the procedures used to obtain an charge and the evidence gathered against him indicate a possibly stronger case than the Justice Department presented against Comey.

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

During his time as Trump's security advisor, and after his 2019 White House departure, authorities alleged that Bolton placed the country at danger by wrongfully keeping and sending classified information to relatives using unprotected methods, including AOL. Several of the materials were marked top secret.

The charge states that at a certain time a hacker gained access to Bolton's system where files were stored and transmitted an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to eighteen distinct charges of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The timing of his charge - coming on the tails of allegations against Comey - has renewed concerns about external influence on the legal system.

Trump previously suggested Bolton belonged in jail, and described him a "disreputable person". Bolton, for his role, authored a publication about his time in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this charge, when combined with others, has prompted doubts about the validity of these allegations, and why these charges are being brought now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

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

Prosecuting such a high-ranking figure for mishandling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern sensitive materials pose difficulties to try, but they may and are filed against both low-level and high-level personnel, from occasionally," she said.

Similarities to Investigations into Trump and President

Trump similarly faced allegations of improperly keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was ultimately thrown out by a court official and voided by his return as leader.

A special counsel additionally determined that former President Joe Biden wrongfully maintained classified documents from his period as vice president, but failed to criminally charge him.

Bolton's case shares characteristics to Biden's classified documents issues, said Mr Lesko, who previously held a top national security position at the Justice Department.

Rigorous procedures govern the management of sensitive materials. To win a conviction, the prosecution must prove that Bolton knew the information he was sending was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Because of the classified nature of the material at question in this matter, we don't have a lot of particulars about the reasons the government believes things like the diary entries and the other material he communicated by electronic message, and the reason there were classified," explained Mr Jaffer.

A Increasingly Conventional Prosecution

The process by which the Justice Department initiated this case will be under scrutiny, after Trump publicly expressed his desire to see his critics charged and several of those charges materialized.

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

"The Bolton case and eventually the charge seemed to have followed the standard process including the regulations and norms within the DOJ," he stated.

Unlike Comey's short, concise indictment, Bolton's was a increasingly "conventional" filing that "clearly sets forth the details concerning the circumstances and circumstances here," Mr Lesko said.

"It seems reasonably consistent with a series of precedents... where public servants improperly handled and transmitted classified material."