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Former President Donald Trump has repeatedly shown his wish to see critics investigated, applying influence on the Justice Department to prosecute 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 leader stated last month in a Truth Social 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 lawsuit.

Each have since been charged, in situations that many specialists have said seem to be driven by politics and challenging to win in court.

But the most recent charges against a presidential opponent, former security advisor John Bolton, stand apart, legal experts and former prosecutors say.

"In my opinion, comparing Bolton's charges to James' is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on federal charges related to the alleged improper handling of sensitive materials. Since leaving the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts contend that while there may be political reasons to go after Bolton, the procedures used to obtain an indictment and the evidence gathered against him indicate a possibly stronger case than the DOJ presented against Comey.

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

During his time as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the nation at danger by improperly keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the documents were labeled top secret.

The indictment states that at one point a unauthorized user accessed to Bolton's account where files were kept and sent an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct charges of mishandling sensitive materials.

Political Motivation or a Substantial Legal Argument?

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

Trump once implied Bolton belonged in prison, and described him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump administration that was highly critical of the leader.

"There's no question that the timing of this indictment, when paired with additional cases, has raised questions about the validity of these charges, and the reason these charges are being brought now," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the Justice Department is able to demonstrate the facts stated and demonstrate the information is correctly classified, his behavior may certainly have broken the statute".

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

"Situations that involve sensitive materials pose difficulties to try, but they can and are filed against both low-level and senior officials, from time to time," she said.

Parallels to Investigations into Trump and Biden

Trump similarly encountered charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their recovery, but that matter was eventually thrown out by a federal judge and negated by his re-election as president.

A independent investigator additionally found that ex-President Joe Biden wrongfully stored sensitive materials from his period as vice president, but did not criminally charge him.

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

Strict protocols govern the management of classified documents. To win a guilty verdict, the government must prove that Bolton knew the material he was transmitting was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Due to the sensitive character of the information at issue in this matter, we don't have a lot of details about the reasons the prosecution believes elements like the personal notes and the other material he shared by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Conventional Prosecution

The procedure by which the Justice Department brought this case will be under scrutiny, following Trump openly posted his desire to see his political opponents prosecuted and several of those charges came to fruition.

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

"This Bolton case and ultimately the charge appeared to have followed the regular process including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a increasingly "traditional" filing that "clearly outlines the particulars involving the circumstances and circumstances in this instance," Mr Lesko said.

"It appears fairly aligned with a long line of precedents... where public servants mishandled and transmitted sensitive information."