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

"We cannot postpone further, it's damaging our standing and trustworthiness," the leader stated last month in a social media message.

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

Each have subsequently been charged, in situations that numerous experts have said appear to be politically motivated and challenging to succeed in court.

But the most recent charges against a Trump critic, ex security advisor John Bolton, stand apart, legal specialists and ex-prosecutors say.

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

This Details of Bolton's Case

Bolton has been formally charged on national allegations pertaining to the alleged mishandling of sensitive materials. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, even to call him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political motivations to target Bolton, the procedures used to obtain an indictment and the proof gathered against him indicate a possibly stronger legal argument than the Justice Department brought against James.

"These actions that's being claimed is simultaneously more serious and appears to have occurred over a considerable 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 exit, prosecutors alleged that Bolton put the country at danger by wrongfully keeping and sending classified information to relatives using insecure means, including AOL. Several of the documents were labeled highly classified.

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

Bolton pleaded not guilty during a hearing on Friday to 18 distinct charges of improperly handling sensitive materials.

Retribution or a Substantial Case?

The schedule of his indictment - arriving on the tails of allegations against James - has renewed concerns about external influence on the legal system.

Trump once suggested Bolton should be in jail, and described him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the timing of this charge, when combined with additional cases, has prompted questions about the strength of these charges, and why these charges are being filed at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is capable to prove the facts alleged and demonstrate the material is correctly classified, his conduct may certainly have broken the law".

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

"Cases that involve sensitive materials pose difficulties to try, but they may and are brought against both junior and high-level personnel, from time to time," she said.

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 obstructing their recovery, but that matter was eventually dismissed by a court official and voided by his re-election as leader.

A independent investigator also found that ex-President Joe Biden improperly maintained sensitive materials from his time as second-in-command, but did not criminally charge him.

Bolton's case bears similarities to Trump's classified documents matters, said Mr Lesko, who also held a top national security position at the Justice Department.

Strict procedures regulate the handling of classified documents. To secure a conviction, the prosecution must prove that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the classified nature of the information at issue in this matter, we don't have a lot of particulars about why the government contends things like the diary entries and the additional material he communicated by email, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the Justice Department brought this legal action will be under scrutiny, following Trump openly posted his desire to see his political opponents charged and some of those charges materialized.

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

"This Bolton prosecution and ultimately the charge seemed to have observed the standard procedure including the rules and norms within the Department of Justice," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a more "traditional" filing that "clearly sets forth the details involving the circumstances and situation here," Mr Lesko commented.

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