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Former President Donald Trump has consistently expressed his desire to see opponents investigated, exerting pressure on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and credibility," the president wrote last month in a Truth Social message.

"They impeached twice, and indicted me (five times!)" he declared, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in cases that many specialists have stated seem to be politically motivated and challenging to win in legal proceedings.

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

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

The Specifics of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the supposed improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken Trump critic, even to call him "stunningly uninformed" and unfit for office in his book.

Specialists say that while there may be political motivations to target Bolton, the methods used to obtain an charge and the proof compiled against him suggest a possibly more substantial legal argument than the Justice Department presented against James.

"This misconduct that's being claimed is both more serious and seems to have taken place over a considerable duration," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, authorities claimed that Bolton put the nation at risk by wrongfully retaining and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were labeled highly classified.

The charge states that at a certain time a unauthorized user gained access to Bolton's account where documents were kept and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on recently to 18 separate charges of improperly handling sensitive materials.

Political Motivation or a Substantial Legal Argument?

The timing of his indictment - coming on the heels of charges against James - has renewed concerns about political pressure on the justice system.

Trump once implied Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump administration that was sharply negative of the president.

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

However, he continued, "if the Justice Department is able to prove the allegations stated and demonstrate the information is correctly classified, his behavior may certainly have broken the statute".

Charging such a high-ranking figure for mishandling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose challenges to prosecute, but they may and are filed against both junior and high-level personnel, from occasionally," she explained.

Similarities to Examinations into Former President and President

Trump similarly faced charges of improperly storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that matter was eventually thrown out by a court official and negated by his return as president.

A independent investigator also found that ex-President Joe Biden wrongfully maintained classified documents from his period as vice president, but did not criminally charge him.

Bolton's case bears similarities to Biden's sensitive materials matters, noted Mr Lesko, who previously held a senior security position at the DOJ.

Rigorous procedures govern the management of classified documents. To secure a conviction, the prosecution must prove that Bolton was aware the material he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the classified character of the information at question in this matter, we lack a great deal of particulars about the reasons the prosecution contends elements like the diary entries and the other information he shared by email, and why there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The procedure by which the DOJ brought this case will be under scrutiny, following Trump openly posted his wish to see his critics prosecuted and some of those indictments materialized.

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

"This Bolton prosecution and eventually the indictment appeared to have observed the standard procedure including the rules and standards within the Department of Justice," he said.

Unlike Comey's short, concise charge, Bolton's was a more "conventional" document that "clearly outlines the particulars involving the facts and circumstances in this instance," Mr Lesko said.

"It seems reasonably aligned with a series of cases... where government officials mishandled and transmitted classified material."