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Ex-President Donald Trump has repeatedly shown his wish to see critics probed, exerting pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our reputation and trustworthiness," the leader wrote last month in a social media message.

"I was impeached twice, and charged me (five times!)" he declared, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's lawsuit.

Both have subsequently been indicted, in situations that numerous specialists have stated seem to be driven by politics and difficult to succeed in court.

But the most recent allegations against a presidential opponent, former security advisor John Bolton, stand apart, legal specialists and ex-prosecutors say.

"In my opinion, contrasting Bolton's case to James' is like equating apples to oranges," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been criminally indicted on federal charges related to the alleged improper handling of classified information. 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 office in his book.

Experts say that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the evidence compiled against him suggest a potentially more substantial legal argument than the Justice Department brought against James.

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

Throughout his tenure as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the nation at danger by wrongfully retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were marked highly classified.

The charge states that at one point a hacker gained access to Bolton's system where files were kept and sent an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on recently to eighteen distinct charges of improperly handling classified information.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the tails of allegations against Comey - has renewed questions about political pressure on the justice system.

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

"There's no question that the schedule of this indictment, when paired with others, has prompted questions about the strength of these charges, and the reason these counts are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is capable to prove the facts alleged and show the information is properly designated, his conduct may very well have broken the law".

Prosecuting such a senior official for mishandling sensitive materials 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 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 Trump and Biden

Trump similarly encountered charges of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately thrown out by a court official and voided by his return as president.

A special counsel additionally found that ex-President Joe Biden wrongfully stored sensitive materials from his period as vice president, but did not prosecute him.

Bolton's case shares characteristics to Trump's classified documents issues, said Mr Lesko, who also held a senior security position at the Justice Department.

Rigorous protocols regulate the management of classified documents. To win a conviction, the prosecution must prove that Bolton was aware the material he was transmitting was classified, and he had to intentionally transfer it to someone not entitled to obtain it.

"Due to the classified nature of the material at issue in this matter, we don't have a lot of particulars about why the prosecution believes things like the diary entries and the other material he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Prosecution

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

But Mr Lesko said in Bolton's situation, authorities seem to have adhered to protocol.

"This Bolton case and eventually the indictment appeared to have followed the regular process including the rules and standards within the Department of Justice," he stated.

In contrast to Comey's short, concise indictment, Bolton's was a more "traditional" filing that "explicitly outlines the details involving the circumstances and circumstances here," Mr Lesko commented.

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