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Ex-President Donald Trump has consistently expressed his wish to see critics probed, exerting influence on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our reputation and trustworthiness," the president wrote recently in a Truth Social post.

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

Both have subsequently been charged, in cases that many experts have stated appear to be politically motivated and difficult to succeed in court.

But the most recent allegations against a Trump critic, former security advisor John Bolton, stand apart, legal specialists and ex-prosecutors say.

"I would say, contrasting Bolton's case to James' is like equating apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of sensitive materials. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unfit for office in his book.

Specialists contend that while there may be political reasons to target Bolton, the methods used to secure an indictment and the proof compiled against him suggest a potentially more substantial case than the DOJ brought against James.

"This misconduct that's being alleged is simultaneously more serious and seems to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and following his 2019 White House exit, prosecutors alleged that Bolton put the country at danger by improperly retaining and sending sensitive documents to family members using insecure means, including AOL. Several of the documents were marked top secret.

The charge alleges that at a certain time a hacker gained access to Bolton's system where documents were kept and sent an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on recently to eighteen distinct charges of improperly handling classified information.

Retribution or a Strong Legal Argument?

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

Trump previously implied Bolton should be in jail, and called him a "disreputable person". Bolton, for his part, wrote a publication about his experience in the Trump government that was sharply negative of the leader.

"Undoubtedly that the timing of this charge, when combined with additional cases, has raised doubts about the validity of these charges, and why these charges are being brought now," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is capable to demonstrate the allegations alleged and demonstrate the information is correctly classified, his behavior may very well have broken the statute".

Prosecuting such a high-ranking official for mishandling classified documents is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve sensitive materials pose challenges to try, but they may and are brought against equally low-level and high-level officials, from time to time," she explained.

Similarities to Investigations into Former President and President

Trump likewise faced charges of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was ultimately thrown out by a court official and negated by his return as president.

A independent investigator also determined that ex-President Joe Biden improperly stored sensitive materials from his period as vice president, but failed to criminally charge him.

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

Rigorous procedures regulate the management of sensitive materials. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was sending was classified, and he had to knowingly transmit it to someone without authorization to receive it.

"Due to the classified character of the material at question in this matter, we lack a great deal of particulars about why the government believes elements like the personal notes and the additional material he communicated by email, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Prosecution

The process by which the Justice Department brought this case will be closely examined, after Trump publicly posted his desire to see his critics charged and several of those indictments came to fruition.

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

"The Bolton case and eventually the charge seemed to have followed the standard process including the rules and norms within the DOJ," he said.

Unlike Comey's brief, concise indictment, Bolton's was a increasingly "traditional" document that "explicitly outlines the particulars involving the facts and circumstances here," Mr Lesko said.

"It seems reasonably consistent with a series of cases... where public servants mishandled and shared sensitive information."