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Ex-President Donald Trump has repeatedly expressed his desire to see critics probed, exerting 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 standing and credibility," the president wrote last month in a Truth Social post.

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

Both have subsequently been indicted, in cases that many specialists have stated seem to be driven by politics and challenging to win in court.

But the most recent charges against a Trump critic, ex security advisor John Bolton, stand apart, legal experts and ex-prosecutors say.

"In my opinion, comparing Bolton's charges to Comey's is like comparing apples to oranges," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged improper handling of sensitive materials. After departing the White House in 2019, he has become a outspoken Trump critic, even to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the methods used to secure an charge and the proof gathered against him indicate a possibly more substantial legal argument than the Justice Department brought against James.

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

During his tenure as Trump's national security adviser, and after his 2019 White House departure, prosecutors alleged that Bolton placed the country at danger by improperly keeping and transmitting sensitive documents to relatives using unprotected methods, including AOL. Some of the documents were marked highly classified.

The indictment states that at a certain time a unauthorized user accessed to Bolton's system where files were kept and transmitted an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to 18 separate charges of mishandling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his indictment - arriving on the heels of charges against James - has revived questions about political pressure on the justice system.

Trump previously implied Bolton belonged in jail, and described him a "disreputable person". Bolton, for his role, authored a book about his time in the Trump government that was sharply negative of the leader.

"There's no question that the schedule of this indictment, when paired with others, has prompted questions about the validity of these allegations, and the reason these counts are being brought now," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the Justice Department is capable to prove the allegations alleged and show the information is properly classified, his behavior may very well have violated the law".

Prosecuting such a senior official for mishandling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information pose challenges to prosecute, but they can and are filed against equally low-level and high-level personnel, from time to time," she explained.

Similarities to Examinations into Former President and President

Trump likewise faced charges of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that case was ultimately dismissed by a federal judge and negated by his return as president.

A special counsel also determined that ex-President Joe Biden improperly maintained classified documents from his period as second-in-command, but did not criminally charge him.

Bolton's situation bears similarities to Trump's sensitive materials matters, said Mr Lesko, who previously held a top security position at the Justice Department.

Rigorous protocols regulate the handling of sensitive materials. To win a conviction, the government must demonstrate that Bolton knew the material he was transmitting was restricted, and he had to intentionally transmit it to someone without authorization to obtain it.

"Because of the classified nature of the information at question in this matter, we lack a great deal of details about why the prosecution believes elements like the personal notes and the additional material he communicated by email, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the DOJ brought this case will be closely examined, after Trump publicly expressed his desire to see his critics charged and some of those charges materialized.

But Mr Lesko indicated in Bolton's case, prosecutors seem to have adhered to protocol.

"This Bolton case and ultimately the charge seemed to have followed the standard procedure including the rules and standards within the DOJ," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the particulars concerning the circumstances and circumstances here," Mr Lesko commented.

"It seems reasonably consistent with a series of cases... where public servants improperly handled and transmitted sensitive information."