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Former President Donald Trump has repeatedly expressed his desire to see opponents probed, applying influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and trustworthiness," the president wrote last month in a social media message.

"I was impeached me, and charged me (5 times!)" he said, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's civil case.

Each have since been charged, in cases that many specialists have stated appear to be driven by politics and difficult to win in legal proceedings.

But the latest charges against a Trump critic, former security advisor John Bolton, stand apart, legal experts and former prosecutors say.

"I would say, contrasting Bolton's charges to Comey's is like comparing apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Details of the Legal Situation

Bolton has been criminally indicted on national allegations related to the alleged mishandling of classified information. After departing the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "remarkably ignorant" and unsuitable for office in his book.

Experts contend that while there may be political reasons to go after Bolton, the procedures used to secure an charge and the evidence compiled against him suggest a possibly stronger legal argument than the Justice Department brought against James.

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

During his time as Trump's national security adviser, and after his 2019 White House exit, authorities claimed that Bolton placed the nation at danger by improperly keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the documents were marked top secret.

The indictment states that at one point a unauthorized user accessed to Bolton's account where files were kept and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on recently to 18 distinct charges of mishandling classified information.

Retribution or a Substantial Case?

The timing of his indictment - arriving on the heels of allegations against Comey - has revived questions about external influence on the justice system.

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, authored a publication about his time in the Trump government that was highly critical of the president.

"Undoubtedly that the schedule of this charge, when paired with others, has prompted doubts about the strength of these charges, and the reason these counts are being brought now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "if the Justice Department is capable to demonstrate the allegations alleged and demonstrate the material is correctly designated, his conduct may very well have broken the law".

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

"Cases that concern sensitive materials pose challenges to prosecute, but they may and are filed against both low-level and senior personnel, from occasionally," she explained.

Parallels to Investigations into Former President and President

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

A independent investigator also determined that former President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but did not prosecute him.

Bolton's case bears similarities to Trump's classified documents issues, said Mr Lesko, who previously held a senior security role at the Justice Department.

Strict protocols regulate the management of sensitive materials. To secure a guilty verdict, the government must demonstrate that Bolton was aware the information he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Because of the classified nature of the information at issue in this case, we don't have a lot of particulars about why the government believes things like the personal notes and the additional information he communicated by electronic message, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department brought this case will be under scrutiny, after Trump openly posted his wish to see his political opponents charged and some of those charges came to fruition.

But Mr Lesko said in Bolton's case, authorities appear to have adhered to standard procedure.

"The Bolton case and eventually the indictment appeared to have followed the regular procedure including the rules and norms within the Department of Justice," he stated.

In contrast to Comey's brief, two-page charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details concerning the circumstances and situation in this instance," Mr Lesko commented.

"It appears fairly aligned with a long line of cases... where public servants improperly handled and transmitted classified material."