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Former President Donald Trump has consistently expressed his wish to see critics probed, applying pressure on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our standing and credibility," the president stated recently in a Truth Social post.

"I was impeached twice, and charged me (5 times!)" he declared, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that many experts have stated seem to be politically motivated and challenging to win in legal proceedings.

But the most recent allegations against a presidential opponent, former security advisor John Bolton, differ significantly, legal specialists and ex-prosecutors assert.

"In my opinion, comparing Bolton's case to James' is like equating two different things," said 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 pertaining to the alleged improper handling of classified information. After departing the White House in 2019, he has become a vocal Trump critic, going so far as to call him "remarkably ignorant" and unsuitable for the presidency 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 proof gathered against him indicate a potentially more substantial legal argument than the DOJ brought against Comey.

"These actions that's being alleged is both more severe and appears 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.

During his time as Trump's national security adviser, and following his 2019 White House departure, authorities claimed that Bolton placed the nation at risk by wrongfully keeping and transmitting sensitive documents to family members using unprotected methods, including AOL. Several of the documents were marked highly classified.

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

Bolton entered a not guilty plea during a court appearance on recently to 18 separate charges of improperly handling classified information.

Retribution or a Strong Case?

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

Trump once suggested Bolton belonged in jail, and described him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the timing of this charge, when paired with additional cases, has raised doubts about the validity of these charges, and the reason these counts are being filed at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "should the DOJ is capable to prove the facts stated and show the information is properly classified, his conduct may certainly have broken the law".

Charging such a senior figure for mishandling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve classified information present challenges to prosecute, but they can and are filed against both junior and senior officials, from time to time," she said.

Similarities to Investigations into Former President and Biden

Trump similarly encountered charges of wrongfully storing classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually dismissed by a federal judge and voided by his re-election as leader.

A independent investigator also found that former President Joe Biden improperly maintained classified documents from his time as second-in-command, but did not prosecute him.

Bolton's case shares characteristics to Biden's classified documents matters, noted Mr Lesko, who previously held a top national security position at the DOJ.

Strict procedures regulate the handling of sensitive materials. To secure a conviction, the prosecution must prove that Bolton was aware the information he was sending was restricted, and he had to knowingly transfer it to someone without authorization to obtain it.

"Due to the sensitive nature of the material at issue in this case, we lack a lot of details about the reasons the prosecution contends things like the personal notes and the other information he shared by email, and the reason there were restricted," said Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the DOJ initiated this case will be under scrutiny, following Trump publicly expressed his wish to see his political opponents prosecuted and some of those indictments came to fruition.

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

"This Bolton prosecution and ultimately the charge appeared to have observed the regular process including the regulations and standards within the DOJ," he stated.

In contrast to Comey's short, concise indictment, Bolton's was a more "conventional" document that "explicitly sets forth the details concerning the facts and circumstances in this instance," Mr Lesko commented.

"It appears reasonably consistent with a long line of cases... where government officials mishandled and shared classified material."