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

"We can't delay further, it's killing our standing and trustworthiness," the president stated last month in a social media message.

"I was impeached twice, and indicted me (five times!)" he said, referencing the multiple legal proceedings he faced after leaving the White House in 2021 and James's civil case.

Both have subsequently been indicted, in cases that numerous specialists have stated appear to be driven by politics and challenging to win in legal proceedings.

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

"In my opinion, comparing Bolton's case to Comey's is like comparing apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of sensitive materials. Since departing the White House in 2019, he has become a outspoken Trump critic, even to call him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts say that while there may be political motivations to go after Bolton, the procedures used to obtain an charge and the proof gathered against him indicate a possibly stronger case than the DOJ brought against Comey.

"These actions that's being alleged is both more serious and seems to have occurred over a significant period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and after his 2019 White House departure, prosecutors claimed that Bolton placed the nation at danger by improperly retaining and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were labeled highly classified.

The indictment alleges that at a certain time a unauthorized user accessed to Bolton's system where documents were stored and sent an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

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

Retribution or a Strong Case?

The schedule of his charge - arriving on the tails of charges against Comey - has revived concerns about political pressure on the legal system.

Trump once implied Bolton belonged in prison, and described him a "sleazebag". Bolton, for his part, authored a publication about his time in the Trump government that was sharply negative of the leader.

"There's no question that the schedule of this charge, when paired with others, has prompted questions about the validity of these allegations, and the reason these charges are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.

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

Prosecuting such a senior official for improperly handling classified documents is "rare" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information present difficulties to prosecute, but they can and are brought against equally low-level and senior personnel, from time to time," she explained.

Parallels to Investigations into Former President and Biden

Trump likewise faced allegations of improperly storing classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that case was ultimately dismissed by a federal judge and negated by his return as president.

A special counsel also found that former President Joe Biden improperly stored sensitive materials from his period as vice president, but failed to prosecute him.

Bolton's situation shares characteristics to Trump's sensitive materials matters, said Mr Lesko, who previously held a senior national security position at the Justice Department.

Strict procedures regulate the handling of sensitive materials. To win a guilty verdict, the government must demonstrate that Bolton knew the information he was transmitting was classified, and he had to intentionally transmit it to someone without authorization to obtain it.

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

A Increasingly Traditional Prosecution

The process by which the DOJ brought this case will be under scrutiny, following Trump openly expressed his desire to see his political opponents prosecuted and some of those charges materialized.

But Mr Lesko said in Bolton's case, prosecutors 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.

Unlike Comey's short, two-page indictment, Bolton's was a more "traditional" document that "explicitly outlines the details concerning the circumstances and situation here," Mr Lesko said.

"It seems fairly aligned with a series of precedents... where public servants improperly handled and transmitted classified material."