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Ex-President Donald Trump has repeatedly expressed his desire to see critics investigated, exerting influence on the Justice Department to prosecute former 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 stated recently in a Truth Social message.

"They impeached twice, and indicted me (5 times!)" he declared, referencing the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that numerous specialists have said seem to be driven by politics and challenging to succeed in court.

But the most recent allegations against a Trump critic, former security advisor John Bolton, differ significantly, legal experts and former prosecutors say.

"In my opinion, contrasting Bolton's case to Comey's is like equating two different things," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Details of the Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. After leaving the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Experts contend that while there may be political reasons to target Bolton, the procedures used to obtain an charge and the proof gathered against him suggest a possibly stronger case than the DOJ presented against James.

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

Throughout his time as Trump's national security adviser, and following his 2019 White House exit, authorities alleged that Bolton placed the nation at risk by wrongfully keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Some of the documents were labeled highly classified.

The indictment states that at a certain time a hacker accessed to Bolton's system where documents were kept and transmitted an seeming threat to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Strong Case?

The timing of his charge - coming on the tails of charges against Comey - has renewed questions about political pressure on the legal system.

Trump once suggested Bolton should be in prison, and described him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump administration that was highly critical of the president.

"There's no question that the schedule of this indictment, when combined with additional cases, has prompted questions about the validity of these allegations, and why these counts are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "should the DOJ is capable to demonstrate the allegations stated and demonstrate the information is correctly designated, his conduct may very well have broken the law".

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

"Cases that concern classified information present difficulties to try, but they can and are brought against both low-level and high-level officials, from time to time," she explained.

Similarities to Examinations into Former President and Biden

Trump similarly encountered allegations of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually dismissed by a federal judge and negated by his re-election as president.

A special counsel additionally found that former President Joe Biden wrongfully maintained classified documents from his time as vice president, but did not prosecute him.

Bolton's situation shares characteristics to Trump's sensitive materials issues, noted Mr Lesko, who also held a senior national security role at the DOJ.

Strict protocols regulate the handling of classified documents. To secure a guilty verdict, the prosecution must prove that Bolton knew the material he was sending was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the classified character of the material at issue in this case, we don't have a lot of particulars about the reasons the prosecution believes things like the diary entries and the other material he shared by email, and why there were classified," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the Justice Department initiated this legal action will be closely examined, following Trump openly posted his desire to see his political opponents prosecuted and several of those indictments materialized.

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

"This Bolton case and ultimately the indictment appeared to have observed the standard process including the rules and standards within the Department of Justice," he said.

Unlike Comey's short, concise indictment, Bolton's was a more "traditional" document that "clearly outlines the particulars involving the circumstances and situation in this instance," Mr Lesko said.

"It appears fairly aligned with a series of precedents... where public servants improperly handled and shared sensitive information."