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

"We cannot postpone further, it's killing our reputation and credibility," the leader wrote last month in a social media message.

"I was impeached me, and charged 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 numerous experts have stated appear to be politically motivated and difficult to win in court.

But the latest charges against a Trump critic, ex security advisor John Bolton, differ significantly, legal specialists and ex-prosecutors say.

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

The Specifics of the Legal Situation

Bolton has been formally charged on national allegations related to the supposed improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unfit for office in his memoir.

Specialists contend that while there may be political reasons to go after Bolton, the procedures used to obtain an charge and the evidence gathered against him indicate a potentially more substantial legal argument than the DOJ presented against Comey.

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

During his tenure as Trump's national security adviser, and after his 2019 White House exit, prosecutors alleged that Bolton placed the country at risk by improperly retaining and transmitting sensitive documents to family members using unprotected methods, including AOL. Some of the documents were marked top secret.

The indictment states that at one point a hacker accessed to Bolton's system where files were stored and sent an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate counts of mishandling sensitive materials.

Retribution or a Strong Case?

The timing of his charge - coming on the heels of allegations against Comey - has renewed questions about external influence on the justice system.

Trump previously implied Bolton should be in prison, 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 schedule of this indictment, when paired with additional cases, has raised questions about the validity of these allegations, and why these counts are being filed now," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "should the DOJ is capable to prove the facts stated and show the material is correctly designated, his conduct may very well have broken the statute".

Charging such a high-ranking official for improperly handling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve classified information pose difficulties to prosecute, but they may and are filed against both low-level and senior personnel, from occasionally," she said.

Parallels to Investigations into Trump and Biden

Trump likewise encountered charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was eventually thrown out by a court official and voided by his re-election as leader.

A special counsel also found that former President Joe Biden wrongfully stored sensitive materials from his period as second-in-command, but failed to prosecute him.

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

Strict procedures regulate the handling of sensitive materials. To secure a conviction, the prosecution must demonstrate that Bolton was aware the information he was transmitting was classified, and he had to intentionally transmit it to someone without authorization to obtain it.

"Due to the classified character of the information at question in this matter, we lack a lot of particulars about the reasons the prosecution believes elements like the diary entries and the other material he shared by email, and the reason there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department initiated this case will be under scrutiny, following Trump publicly expressed his wish to see his political opponents charged and several of those indictments materialized.

But Mr Lesko said in Bolton's situation, prosecutors seem to have followed protocol.

"The Bolton case and ultimately the charge seemed to have observed the regular process including the regulations and standards within the Department of Justice," he said.

Unlike Comey's brief, concise indictment, Bolton's was a more "conventional" document that "clearly outlines the details concerning the circumstances and situation here," Mr Lesko commented.

"It seems reasonably aligned with a long line of cases... where government officials mishandled and shared sensitive information."