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Former President Donald Trump has repeatedly expressed his desire to see critics probed, applying pressure on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our standing and credibility," the president stated recently in a Truth Social post.

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

Both have since been charged, in situations that many specialists have said seem to be politically motivated and difficult to win in court.

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

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

The Details of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the supposed improper handling of classified information. After departing the White House in 2019, he has become a outspoken Trump critic, even to call him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists say that while there may be political motivations to target Bolton, the procedures used to obtain an charge and the evidence compiled against him indicate a possibly more substantial legal argument than the DOJ brought against James.

"This misconduct that's being claimed is both more severe and seems to have occurred over a significant period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and after his 2019 White House departure, prosecutors alleged that Bolton put the country at risk by wrongfully keeping and sending classified information to relatives using insecure means, including AOL. Some of the materials were marked highly classified.

The indictment alleges that at one point a hacker accessed to Bolton's account where documents were kept and sent an apparent warning to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct charges of improperly handling classified information.

Political Motivation or a Strong Case?

The schedule of his indictment - coming on the heels of allegations against James - has renewed concerns about political pressure on the legal system.

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

"There's no question that the timing of this indictment, when paired with others, has raised questions about the validity of these allegations, and why these counts are being brought at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "should the Justice Department is able to demonstrate the allegations alleged and demonstrate the information is properly designated, his behavior may very well have broken the statute".

Prosecuting such a high-ranking official for improperly handling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern sensitive materials present challenges to try, but they can and are filed against both junior and senior personnel, from time to time," she said.

Parallels to Examinations into Trump and Biden

Trump similarly encountered charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was ultimately dismissed by a court official and negated by his re-election as leader.

A special counsel additionally found that former President Joe Biden wrongfully stored classified documents from his time as vice president, but failed to criminally charge him.

Bolton's case shares characteristics to Biden's sensitive materials issues, said Mr Lesko, who also held a senior security position at the Justice Department.

Strict procedures regulate the handling of classified documents. To secure a conviction, the prosecution must prove that Bolton was aware the information he was sending was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the classified nature of the material at question in this matter, we don't have a great deal of particulars about why the government contends things like the personal notes and the additional information he shared by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the DOJ initiated this legal action will be under scrutiny, after Trump publicly expressed his desire to see his critics charged and several of those indictments materialized.

But Mr Lesko indicated in Bolton's situation, authorities seem to have followed protocol.

"This Bolton case and eventually the charge appeared to have followed the standard process including the regulations and standards within the DOJ," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a more "traditional" filing that "clearly sets forth the details concerning the circumstances and situation here," Mr Lesko commented.

"It seems reasonably consistent with a long line of precedents... where public servants mishandled and shared sensitive information."