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Former President Donald Trump has repeatedly expressed his desire to see critics probed, exerting influence 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 reputation and trustworthiness," the president wrote last month in a social media post.

"They impeached twice, and indicted me (5 times!)" he said, mentioning the multiple legal proceedings he encountered after leaving the White House in 2021 and James's civil case.

Both have since been indicted, in situations that many specialists have stated seem to be driven by politics and difficult to succeed in court.

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

"I would say, contrasting Bolton's charges to Comey's is like equating two different things," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Specifics of the Case

Bolton has been formally charged on federal charges pertaining to the supposed improper handling of classified information. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for office in his memoir.

Experts say that while there may be political motivations to target Bolton, the procedures used to secure an charge and the proof gathered against him suggest a possibly stronger case than the Justice Department presented against James.

"These actions that's being alleged is both more severe and seems to have taken place over a considerable duration," commented Carissa Byrne Hessick, a professor 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 claimed that Bolton put the country at danger by improperly keeping and transmitting classified information to relatives using unprotected methods, including AOL. Some of the materials were labeled top secret.

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

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate charges of mishandling classified information.

Retribution or a Strong Case?

The timing of his indictment - arriving on the heels of allegations against James - has revived questions about political pressure on the justice system.

Trump previously suggested Bolton belonged in jail, and described him a "sleazebag". Bolton, for his part, authored a book about his time in the Trump government that was highly critical of the president.

"Undoubtedly that the timing of this indictment, when combined with others, has raised questions about the validity of these charges, and why these charges are being brought at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

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

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

"Cases that involve sensitive materials present challenges to prosecute, but they can and are filed against equally junior and senior officials, from time to time," she explained.

Similarities to Examinations into Trump and President

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

A special counsel also determined that former President Joe Biden improperly stored sensitive materials from his time as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's sensitive materials matters, said Mr Lesko, who previously held a top national security role at the DOJ.

Rigorous procedures regulate the management of classified documents. To secure a conviction, the government must prove that Bolton knew 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 information at question in this matter, we don't have a lot of particulars about the reasons the government contends elements like the diary entries and the other information he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A Increasingly Traditional Legal Action

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

But Mr Lesko indicated in Bolton's situation, prosecutors appear to have followed protocol.

"The Bolton prosecution and eventually the charge seemed to have followed the standard process including the regulations and norms within the Department of Justice," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a more "conventional" filing that "explicitly sets forth the particulars concerning the circumstances and situation here," Mr Lesko said.

"It appears fairly consistent with a long line of cases... where government officials improperly handled and transmitted sensitive information."