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Ex-President Donald Trump has repeatedly shown his wish to see opponents investigated, exerting influence on the DOJ to charge former 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 last month in a social media message.

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

Both have since been charged, in situations that many specialists have said appear to be politically motivated and difficult to succeed in legal proceedings.

But the most recent charges against a presidential opponent, former security advisor John Bolton, differ significantly, legal experts and ex-prosecutors say.

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

This Specifics of Bolton's Legal Situation

Bolton has been formally charged on federal charges pertaining 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 describe him "stunningly uninformed" and unfit for office in his book.

Experts say that while there may be political motivations to go after Bolton, the methods used to obtain an indictment and the evidence gathered against him suggest a potentially more substantial legal argument than the DOJ brought against James.

"These actions that's being claimed is simultaneously more severe and seems to have occurred 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 national security adviser, and following his 2019 White House exit, authorities alleged that Bolton placed the country at danger by improperly keeping and transmitting classified information to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

The indictment states that at one point a unauthorized user accessed to Bolton's system where files were kept and transmitted an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate counts of mishandling classified information.

Retribution or a Strong Legal Argument?

The timing of his indictment - arriving on the tails of allegations against James - has renewed 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 time in the Trump administration that was sharply negative of the president.

"There's no question that the timing of this indictment, when paired with others, has prompted doubts about the validity of these allegations, and why these counts are being filed at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is able to prove the allegations alleged and demonstrate the material is properly classified, 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 pose challenges to try, but they can and are brought against both junior and senior personnel, from occasionally," she said.

Similarities to Investigations into Former President and Biden

Trump similarly encountered charges of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was eventually thrown out by a federal judge and negated by his re-election as leader.

A independent investigator additionally determined that former President Joe Biden improperly stored classified documents from his time as vice president, but failed to prosecute him.

Bolton's case bears similarities to Trump's classified documents matters, noted Mr Lesko, who previously held a top national security role at the DOJ.

Rigorous protocols govern the management of classified documents. To secure a guilty verdict, the government must prove that Bolton knew the material he was transmitting was classified, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the sensitive character of the material at question in this case, we don't have a lot of particulars about the reasons the government believes elements like the personal notes and the additional material he shared by electronic message, and why there were restricted," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department brought this legal action will be under scrutiny, following Trump publicly posted his desire to see his critics prosecuted and several of those indictments came to fruition.

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

"The Bolton prosecution and eventually the charge seemed to have followed the regular procedure including the regulations and norms within the Department of Justice," he stated.

Unlike Comey's short, two-page charge, Bolton's was a more "conventional" document that "clearly sets forth the details involving the circumstances and circumstances in this instance," Mr Lesko commented.

"It seems reasonably consistent with a series of precedents... where government officials improperly handled and shared sensitive information."