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Ex-President Donald Trump has repeatedly shown 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 reputation and credibility," the leader stated recently in a social media message.

"I was impeached twice, and charged me (5 times!)" he declared, referencing the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Each have subsequently been indicted, in cases that numerous specialists have stated seem to be driven by politics and challenging to win in legal proceedings.

But the most recent charges against a Trump critic, ex security advisor John Bolton, differ significantly, legal experts and ex-prosecutors assert.

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

The Specifics of the Case

Bolton has been formally charged on national allegations pertaining to the supposed mishandling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, even to describe him "remarkably ignorant" and unsuitable for office in his book.

Experts say that while there may be political motivations to target Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a possibly more substantial legal argument than the Justice Department brought against James.

"This misconduct that's being alleged is both more serious and appears to have occurred over a considerable duration," 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 following his 2019 White House departure, prosecutors alleged that Bolton placed the country at risk by wrongfully retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Some of the materials were labeled top secret.

The indictment alleges that at a certain time a hacker gained access to Bolton's account where documents were kept and sent an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to 18 separate counts of mishandling classified information.

Political Motivation or a Substantial Legal Argument?

The timing of his charge - arriving on the tails of allegations against James - has renewed questions about external influence on the legal system.

Trump previously suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his role, 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 additional cases, has raised doubts about the validity of these allegations, and the reason these counts are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "should the DOJ is able to demonstrate the facts stated and demonstrate the information is properly designated, his conduct may certainly have broken the law".

Prosecuting such a senior figure for mishandling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information present difficulties to prosecute, but they can and are brought against equally junior and high-level personnel, from time to time," she explained.

Parallels to Examinations into Former President and Biden

Trump likewise encountered allegations of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was ultimately thrown out by a federal judge and negated by his return as leader.

A special counsel also determined that former President Joe Biden improperly stored sensitive materials from his time as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Trump's classified documents matters, said Mr Lesko, who previously held a top security role at the DOJ.

Rigorous protocols govern the management of sensitive materials. To secure a conviction, the government must demonstrate that Bolton was aware the information he was sending was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the classified nature of the material at issue in this case, we don't have a lot of details about why the prosecution contends things like the personal notes and the other material he shared by email, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The process by which the DOJ initiated this case will be under scrutiny, after Trump publicly expressed his desire to see his political opponents charged and some of those indictments came to fruition.

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

"The Bolton case and ultimately the charge seemed to have followed the regular procedure including the rules and norms within the DOJ," he stated.

In contrast to Comey's short, concise indictment, Bolton's was a increasingly "conventional" document that "clearly sets forth the particulars concerning the facts and situation here," Mr Lesko commented.

"It seems fairly consistent with a series of precedents... where government officials mishandled and transmitted sensitive information."