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Former President Donald Trump has consistently shown his wish to see opponents probed, applying pressure on the DOJ 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 leader wrote last month in a Truth Social post.

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

Both have subsequently been charged, in situations that numerous specialists have said appear to be driven by politics and challenging to win in court.

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

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

This Specifics of the Case

Bolton has been criminally indicted on federal charges related to the alleged improper handling of classified information. Since leaving the White House in 2019, he has emerged as a vocal Trump critic, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists contend that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the evidence compiled against him indicate a possibly more substantial legal argument than the Justice Department brought against James.

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

Throughout his time as Trump's security advisor, and following his 2019 White House departure, authorities alleged that Bolton placed the country at risk by wrongfully retaining and sending classified information to relatives using unprotected methods, including AOL. Some of the materials were marked top secret.

The indictment states that at a certain time a unauthorized user gained access to Bolton's system where files were stored and sent an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on recently to 18 distinct counts of mishandling classified information.

Political Motivation or a Strong Case?

The schedule of his charge - coming on the heels of charges against James - has revived questions about political pressure on the legal 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 timing of this indictment, when paired with others, has prompted doubts about the strength of these allegations, and why these charges are being filed now," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to demonstrate the facts stated and show the material is correctly designated, his behavior may certainly have violated the law".

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

"Situations that involve sensitive materials pose difficulties to prosecute, but they may and are brought against both low-level and senior officials, from time to time," she said.

Similarities to Examinations into Former President and Biden

Trump similarly faced allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately thrown out by a court official and voided by his re-election as leader.

A special counsel additionally found that former President Joe Biden improperly stored sensitive materials from his period as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's sensitive materials matters, noted Mr Lesko, who previously held a senior security role at the DOJ.

Rigorous procedures govern the handling of sensitive materials. To secure a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was sending was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Due to the classified character of the material at issue in this case, we lack a lot of particulars about the reasons the government contends things like the personal notes and the additional information he shared by electronic message, and the reason there were classified," explained Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, after Trump openly expressed his desire to see his political opponents prosecuted and several of those indictments came to fruition.

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

"This Bolton case and eventually the charge seemed to have followed the regular procedure including the regulations and norms within the Department of Justice," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a increasingly "traditional" filing that "clearly sets forth the particulars concerning the facts and circumstances in this instance," Mr Lesko said.

"It seems fairly consistent with a series of cases... where public servants mishandled and transmitted classified material."