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

"We cannot postpone further, it's killing our standing and trustworthiness," the leader wrote recently in a Truth Social message.

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

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

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

"I would say, comparing Bolton's case to James' is like comparing two different things," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Details of the Case

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of sensitive materials. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists say that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the proof gathered against him indicate a possibly more substantial case than the Justice Department presented against James.

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

During his time as Trump's security advisor, and following his 2019 White House exit, prosecutors claimed that Bolton put the country at danger by improperly retaining and sending classified information to relatives using insecure means, including AOL. Several of the materials were marked top secret.

The charge states that at a certain time a unauthorized user gained access to Bolton's account where files were kept and sent an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on Friday to eighteen distinct charges of improperly handling sensitive materials.

Retribution or a Substantial Case?

The schedule of his indictment - coming on the tails of allegations against James - has revived concerns about external influence on the legal system.

Trump previously implied Bolton should be in prison, and described him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump administration that was highly critical of the leader.

"There's no question that the timing of this indictment, when combined with others, has raised doubts about the validity of these charges, and why these counts are being brought at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "if the DOJ is capable to prove the allegations stated and demonstrate the material is properly classified, his conduct may very well have broken the law".

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

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

Parallels to Investigations into Former President and Biden

Trump likewise encountered charges of improperly storing sensitive materials at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually dismissed by a court official and negated by his return as president.

A special counsel additionally determined that ex-President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's classified documents issues, noted Mr Lesko, who previously held a top security role at the DOJ.

Rigorous protocols govern the management of sensitive materials. To win a conviction, the government must demonstrate that Bolton was aware the material he was sending was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the sensitive character of the material at question in this case, we don't have a lot of details about the reasons the prosecution contends elements like the personal notes and the other material he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the Justice Department brought this case will be under scrutiny, following Trump openly posted his wish to see his political opponents prosecuted and some of those charges materialized.

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

"The Bolton case and eventually the indictment seemed to have followed the regular process including the regulations and norms within the Department of Justice," he said.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" document that "clearly outlines the details involving the circumstances and circumstances in this instance," Mr Lesko commented.

"It appears fairly consistent with a series of cases... where government officials mishandled and shared sensitive information."