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

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

"They impeached me, and indicted 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 charged, in cases that numerous specialists have said seem to be politically motivated and difficult to win in legal proceedings.

But the most recent allegations against a presidential opponent, ex national security adviser John Bolton, stand apart, legal specialists and former prosecutors assert.

"I would say, contrasting Bolton's case to Comey's is like comparing apples to oranges," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Legal Situation

Bolton has been formally charged on national allegations related to the supposed improper handling of classified information. Since departing the White House in 2019, he has become a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unfit for the presidency in his book.

Experts say that while there may be political motivations to go after Bolton, the methods used to secure an charge and the evidence compiled against him suggest a potentially more substantial legal argument than the Justice Department brought against James.

"These actions that's being alleged is both more serious and seems to have taken place over a considerable period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House departure, authorities alleged that Bolton placed the country at danger by wrongfully keeping and sending sensitive documents to family members using unprotected methods, including AOL. Several of the documents were marked highly classified.

The charge alleges that at one point a unauthorized user gained access to Bolton's account where files were stored and sent an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to 18 separate charges of improperly handling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his charge - arriving on the tails of charges against Comey - has revived concerns about external influence on the justice system.

Trump once suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, wrote a book about his experience in the Trump government that was highly critical of the leader.

"There's no question that the timing of this indictment, when combined with additional cases, has prompted questions about the validity of these allegations, and the reason these charges are being brought at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "should the DOJ is capable to demonstrate the facts stated and demonstrate the information is correctly designated, his behavior may very well have violated the law".

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

"Situations that involve classified information pose difficulties to prosecute, but they may and are filed against both low-level and high-level personnel, from occasionally," she said.

Parallels to Investigations into Trump and Biden

Trump likewise faced charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that matter was ultimately dismissed by a court official and voided by his re-election as president.

A independent investigator also found that former President Joe Biden improperly stored sensitive materials from his period as second-in-command, but did not prosecute him.

Bolton's case bears similarities to Biden's sensitive materials issues, noted Mr Lesko, who previously held a top security position at the Justice Department.

Strict procedures regulate the management of classified documents. To win a conviction, the prosecution must demonstrate that Bolton knew the information he was sending was classified, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the classified nature of the information at question in this case, we don't have a great deal of details about why the prosecution contends things like the diary entries and the additional material he shared by email, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The process by which the DOJ initiated this legal action will be under scrutiny, following Trump publicly posted his wish to see his critics prosecuted and some of those charges materialized.

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

"The Bolton prosecution and eventually the charge appeared to have followed the regular procedure including the rules and norms within the Department of Justice," he said.

Unlike Comey's brief, two-page charge, Bolton's was a increasingly "conventional" document that "clearly outlines the details involving the facts and situation here," Mr Lesko commented.

"It seems reasonably aligned with a long line of precedents... where government officials improperly handled and transmitted sensitive information."