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Former President Donald Trump has consistently shown his wish to see critics investigated, exerting pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our reputation and trustworthiness," the president stated last month in a Truth Social post.

"They impeached me, and charged me (five times!)" he said, mentioning the four criminal cases he encountered after leaving the White House in 2021 and James's civil case.

Both have subsequently been indicted, in cases that many specialists have said seem to be driven by politics and difficult to succeed in legal proceedings.

But the most recent charges against a Trump critic, former national security adviser John Bolton, stand apart, legal experts and ex-prosecutors assert.

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

This Details of Bolton's Case

Bolton has been criminally indicted on federal charges related to the supposed improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Specialists say that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the proof gathered against him suggest a possibly more substantial case than the DOJ brought against Comey.

"These actions that's being claimed is both more severe 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 time as Trump's security advisor, and after his 2019 White House exit, prosecutors alleged that Bolton put the nation at risk by wrongfully retaining and transmitting sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled top secret.

The charge alleges that at one point a unauthorized user accessed to Bolton's system where documents were stored and transmitted an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on Friday to eighteen separate counts of mishandling classified information.

Political Motivation or a Strong Legal Argument?

The timing of his charge - arriving on the tails of charges against James - has revived questions about external influence on the justice system.

Trump once implied Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, authored a book about his time in the Trump government that was sharply negative of the leader.

"There's no question that the timing of this charge, when paired with additional cases, has prompted questions about the validity of these allegations, and why these charges are being brought at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "if the DOJ is capable to demonstrate the facts stated and demonstrate the information is correctly designated, his behavior may very well have broken the law".

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.

"Situations that concern classified information present difficulties to try, but they may and are brought against equally low-level and senior officials, from occasionally," she said.

Parallels to Examinations into Trump and Biden

Trump similarly encountered charges of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was ultimately thrown out by a federal judge and voided by his return as president.

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

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

Rigorous procedures govern the handling of classified documents. To secure a guilty verdict, the government must prove that Bolton knew the information he was sending was classified, and he had to intentionally transfer it to someone not entitled to receive it.

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

A More Traditional Legal Action

The process by which the DOJ initiated this case will be closely examined, after Trump publicly expressed his wish to see his critics charged and some of those indictments came to fruition.

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

"This Bolton prosecution and eventually the charge appeared to have observed the regular procedure including the regulations and norms within the DOJ," he said.

In contrast to Comey's short, two-page indictment, Bolton's was a more "traditional" document that "explicitly sets forth the particulars involving the facts and situation here," Mr Lesko commented.

"It appears fairly aligned with a long line of precedents... where government officials mishandled and shared classified material."