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

"We can't delay further, it's damaging our reputation and credibility," the president wrote recently in a Truth Social message.

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

Both have since been indicted, in situations that many specialists have said seem to be driven by politics and difficult to win in court.

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

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

The Specifics of Bolton's Legal Situation

Bolton has been formally charged on national allegations pertaining to the supposed mishandling of classified information. After departing the White House in 2019, he has become a outspoken presidential opponent, even to call him "remarkably ignorant" and unsuitable for office in his book.

Specialists contend that while there may be political motivations to target Bolton, the methods used to secure an charge and the proof compiled against him suggest a potentially more substantial case than the Justice Department brought against James.

"These actions that's being alleged is simultaneously more severe and seems to have taken place over a significant duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House departure, authorities claimed that Bolton put the country at danger by improperly keeping and sending classified information to relatives using unprotected methods, including AOL. Several of the materials were marked highly classified.

The indictment alleges that at a certain time a hacker accessed to Bolton's account where documents were kept and sent an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on recently to eighteen separate charges of improperly handling sensitive materials.

Political Motivation or a Substantial Case?

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

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

"Undoubtedly that the timing of this indictment, when combined with additional cases, has raised questions about the strength of these charges, and why these counts are being filed now," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is capable to prove the allegations stated and show the information is properly designated, his conduct may very well have broken the statute".

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

"Situations that concern sensitive materials present difficulties to try, but they can and are brought against both junior and senior personnel, from time to time," she explained.

Parallels to Investigations into Former President and President

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

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

Bolton's case shares characteristics to Biden's classified documents matters, noted Mr Lesko, who also held a senior security role at the Justice Department.

Strict procedures regulate the handling of sensitive materials. To win a conviction, the government must prove that Bolton knew the material he was transmitting was classified, and he had to intentionally transfer it to someone without authorization to receive it.

"Due to the sensitive nature of the information at issue in this matter, we don't have a lot of particulars about the reasons the government contends things like the diary entries and the additional information he shared by electronic message, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the Justice Department initiated this case will be under scrutiny, following Trump openly posted his desire to see his political opponents charged and several of those indictments materialized.

But Mr Lesko indicated in Bolton's situation, authorities appear to have adhered to standard procedure.

"This Bolton case and eventually the charge seemed to have observed the regular procedure including the regulations and standards within the Department of Justice," he said.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" filing that "clearly outlines the details concerning the circumstances and circumstances in this instance," Mr Lesko commented.

"It appears reasonably aligned with a long line of cases... where public servants improperly handled and shared sensitive information."