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Former President Donald Trump has repeatedly shown his wish to see opponents probed, exerting influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our reputation and trustworthiness," the president stated recently in a social media post.

"I was impeached twice, and charged me (5 times!)" he declared, referencing the multiple legal proceedings he faced after leaving the White House in 2021 and James's lawsuit.

Each have since been indicted, in cases that numerous experts have stated appear to be driven by politics and challenging to succeed in legal proceedings.

But the latest allegations against a Trump critic, ex national security adviser John Bolton, stand apart, legal specialists and ex-prosecutors say.

"In my opinion, comparing Bolton's case to James' is like equating two different things," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of the Case

Bolton has been criminally indicted on federal charges related to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has emerged as a vocal Trump critic, even to call him "remarkably ignorant" and unsuitable for the presidency in his book.

Experts contend that while there may be political motivations to go after Bolton, the procedures used to obtain an charge and the proof compiled against him indicate a potentially stronger legal argument than the DOJ presented against Comey.

"These actions that's being claimed is both more serious and seems to have taken place over a significant period of time," said 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, authorities claimed that Bolton placed the nation at danger by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were marked top secret.

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

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

Political Motivation or a Strong Case?

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

Trump previously suggested Bolton should be in prison, and described him a "sleazebag". Bolton, for his part, authored a book about his experience in the Trump administration that was sharply negative of the president.

"There's no question that the timing of this indictment, when paired with additional cases, has prompted doubts about the validity of these charges, and why these charges are being brought now," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the Justice Department is able to prove the facts alleged and show the material is properly designated, his behavior may certainly have broken the law".

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

"Cases that involve sensitive materials pose difficulties to prosecute, but they may and are filed against equally junior and senior officials, from occasionally," she said.

Similarities to Examinations into Former President and Biden

Trump likewise faced charges of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that matter was eventually dismissed by a court official and voided by his return as president.

A special counsel additionally determined that former President Joe Biden improperly maintained classified documents from his period as vice president, but did not criminally charge him.

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

Strict procedures govern the management of sensitive materials. To secure a guilty verdict, the government must prove that Bolton knew the material he was transmitting was restricted, and he had to intentionally transmit it to someone not entitled to obtain it.

"Due to the classified nature of the information at issue in this matter, we don't have a lot of particulars about the reasons the prosecution contends elements like the diary entries and the other information he shared by electronic message, and the reason there were restricted," said Mr Jaffer.

A Increasingly Conventional Legal Action

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

But Mr Lesko said in Bolton's case, authorities seem to have adhered to protocol.

"This Bolton case and eventually the charge appeared to have followed the standard process including the regulations and standards within the DOJ," he said.

In contrast to Comey's brief, concise charge, Bolton's was a increasingly "conventional" document that "explicitly outlines the details involving the facts and situation here," Mr Lesko said.

"It seems fairly aligned with a series of precedents... where government officials improperly handled and transmitted sensitive information."