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Ex-President Donald Trump has repeatedly expressed his desire to see critics probed, applying pressure on the Justice Department to charge 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 indicted me (five times!)" he declared, mentioning the multiple legal proceedings he faced after leaving the White House in 2021 and James's civil case.

Each have subsequently been charged, in cases that many experts have said seem to be driven by politics and challenging to succeed in legal proceedings.

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

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

The Details of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to call him "remarkably ignorant" and unfit for office in his memoir.

Specialists contend that while there may be political motivations to target Bolton, the procedures used to obtain an charge and the evidence compiled against him indicate a potentially stronger legal argument than the Justice Department brought against James.

"These actions that's being claimed is simultaneously more serious and appears to have taken place over a significant duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and after his 2019 White House exit, authorities claimed that Bolton put the country at danger by wrongfully retaining and transmitting classified information to family members using insecure means, including AOL. Some of the materials were labeled top secret.

The charge alleges that at one point a unauthorized user gained access to Bolton's account where files were kept and sent 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 Friday to eighteen separate counts of improperly handling classified information.

Retribution or a Strong Legal Argument?

The timing of his charge - arriving on the heels of charges against Comey - has renewed questions about external influence on the legal system.

Trump previously implied Bolton should be in prison, and called him a "sleazebag". 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 indictment, when combined with additional cases, has prompted doubts about the strength of these charges, and why these charges are being brought now," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "if the Justice Department is able to prove the allegations alleged and show the information is correctly designated, his conduct may certainly have broken the statute".

Charging such a high-ranking official for mishandling sensitive materials is "uncommon" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

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

Parallels to Investigations into Trump and President

Trump likewise encountered charges of improperly storing classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was eventually thrown out by a court official and voided by his return as president.

A independent investigator also determined that ex-President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but failed to prosecute him.

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

Strict protocols regulate the handling of sensitive materials. To win a conviction, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to receive it.

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

A Increasingly Conventional Legal Action

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

But Mr Lesko said in Bolton's situation, prosecutors appear to have adhered to protocol.

"This Bolton case and ultimately the indictment seemed to have observed the regular procedure including the rules and norms within the DOJ," he said.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" filing that "clearly outlines the particulars concerning the facts and circumstances in this instance," Mr Lesko commented.

"It seems reasonably aligned with a series of cases... where government officials mishandled and transmitted classified material."