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Former President Donald Trump has consistently shown his wish to see critics investigated, applying 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 killing our reputation and trustworthiness," the leader stated recently in a Truth Social message.

"I was impeached me, and indicted me (five 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 difficult to win in legal proceedings.

But the latest charges against a Trump critic, ex security advisor John Bolton, stand apart, legal specialists and ex-prosecutors assert.

"I would say, comparing Bolton's case to James' is like equating two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the supposed mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken presidential opponent, even to describe him "remarkably ignorant" and unsuitable for office in his book.

Experts contend that while there may be political motivations to target Bolton, the procedures used to obtain an indictment and the proof compiled against him suggest a possibly more substantial case than the DOJ brought against James.

"These actions that's being alleged is both more serious and seems to have occurred over a considerable duration," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and after his 2019 White House departure, authorities alleged that Bolton put the country at risk by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

The indictment states that at a certain time a hacker gained access to Bolton's account where files were kept and transmitted an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on recently to eighteen separate counts of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - coming on the tails of charges against James - has revived concerns about political pressure on the legal system.

Trump previously suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump government that was sharply negative of the leader.

"There's no question that the timing of this charge, when combined with others, has raised questions about the strength of these allegations, and why these charges are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to demonstrate the facts stated and demonstrate the material is properly designated, his behavior may very well have broken the statute".

Charging such a high-ranking figure for improperly handling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information present challenges to try, but they can and are filed against equally junior and high-level personnel, from occasionally," she said.

Parallels to Investigations into Former President and Biden

Trump similarly encountered charges of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately thrown out by a federal judge and negated by his return as leader.

A special counsel also determined that ex-President Joe Biden wrongfully maintained classified documents from his time as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's classified documents issues, said Mr Lesko, who also held a top national security role at the Justice Department.

Rigorous protocols regulate the handling of sensitive materials. To win a guilty verdict, the government must demonstrate that Bolton knew the information he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to receive it.

"Because of the classified character of the information at question in this matter, we lack a great deal of particulars about the reasons the prosecution contends things like the personal notes and the additional information he shared by electronic message, and why there were restricted," said Mr Jaffer.

A Increasingly Conventional Prosecution

The process by which the DOJ initiated this legal action will be under scrutiny, following Trump openly expressed his wish to see his critics charged and several of those indictments materialized.

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

"This Bolton case and eventually the charge seemed to have followed the standard process including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" document that "explicitly sets forth the details concerning the facts 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."