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Ex-President Donald Trump has consistently shown his wish to see critics probed, applying pressure on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our standing and trustworthiness," the leader wrote recently in a social media post.

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

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

But the latest charges against a Trump critic, ex security advisor John Bolton, stand apart, legal experts and ex-prosecutors say.

"I would say, contrasting Bolton's charges to Comey's is like equating two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Details of the Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken Trump critic, going so far as to call him "remarkably ignorant" and unsuitable for the presidency in his book.

Specialists say that while there may be political reasons to target Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a potentially more substantial legal argument than the Justice Department brought against James.

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

During his time as Trump's national security adviser, and following his 2019 White House exit, authorities alleged that Bolton placed the country at danger by improperly retaining and sending classified information to family members using insecure means, including AOL. Some of the materials were labeled highly classified.

The indictment states that at a certain time a hacker accessed to Bolton's system where documents were kept and transmitted an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct counts of improperly handling classified information.

Retribution or a Strong Legal Argument?

The timing of his indictment - coming on the tails of charges against Comey - has revived questions about political pressure on the justice system.

Trump once suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump administration that was sharply negative of the president.

"Undoubtedly that the schedule of this indictment, when paired with others, has prompted questions about the validity of these allegations, and the reason these charges are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to demonstrate the facts stated and demonstrate the information is properly classified, his conduct may very well have broken the statute".

Prosecuting such a senior official for improperly handling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern classified information present difficulties to prosecute, but they can and are filed against both low-level and high-level personnel, from occasionally," she explained.

Similarities to Examinations into Former President and President

Trump similarly encountered charges of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually thrown out by a court official and negated by his re-election as leader.

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

Bolton's case shares characteristics to Biden's classified documents matters, noted Mr Lesko, who also held a senior security role at the DOJ.

Rigorous procedures govern the management of classified documents. To win a conviction, the government must prove that Bolton knew the information he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the classified nature of the material at issue in this matter, we lack a lot of particulars about why the prosecution contends elements like the personal notes and the other information he shared by email, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department brought this legal action will be under scrutiny, after Trump openly expressed his wish to see his critics prosecuted and some of those indictments came to fruition.

But Mr Lesko said in Bolton's case, prosecutors seem to have followed protocol.

"The Bolton prosecution and eventually the indictment seemed to have followed 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 increasingly "traditional" filing that "clearly sets forth the particulars concerning the facts and circumstances here," Mr Lesko commented.

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