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Ex-President Donald Trump has consistently expressed his wish to see opponents investigated, exerting pressure on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

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

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

Each have since been charged, in situations that numerous experts have said seem to be politically motivated and challenging to succeed in court.

But the latest allegations against a Trump critic, former security advisor John Bolton, differ significantly, legal experts and ex-prosecutors assert.

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

This Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed mishandling of classified information. After leaving the White House in 2019, he has become a vocal Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his book.

Specialists say that while there may be political motivations to target Bolton, the methods used to obtain an indictment and the proof gathered against him indicate a potentially more substantial legal argument than the DOJ brought against Comey.

"This misconduct that's being alleged is simultaneously more serious and seems to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic 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 claimed that Bolton placed the nation at risk by improperly keeping and transmitting classified information to family members using insecure means, including AOL. Several of the materials were marked highly classified.

The charge states that at one point a unauthorized user accessed to Bolton's account where files were kept and sent an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

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

Political Motivation or a Strong Legal Argument?

The timing of his indictment - coming on the heels of charges against James - has renewed questions about external influence on the legal system.

Trump previously suggested Bolton belonged in prison, and described him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this charge, when paired with additional cases, has raised doubts about the strength of these charges, and why these counts are being brought at this time," said Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the DOJ is able to demonstrate the allegations stated and show the information is properly designated, his behavior may very well have broken the law".

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

"Cases that concern sensitive materials pose challenges to try, but they may and are filed against both junior and senior personnel, from time to time," she explained.

Parallels to Examinations into Former President and Biden

Trump likewise encountered charges of improperly storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately thrown out by a federal judge and negated by his return as president.

A special counsel additionally found that ex-President Joe Biden improperly stored sensitive materials from his time as vice president, but failed to criminally charge him.

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

Rigorous procedures govern the management of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Because of the classified character of the material at issue in this matter, we don't have a lot of details about the reasons the prosecution believes things like the diary entries and the other information he shared by electronic message, and why there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The process by which the DOJ brought this legal action will be under scrutiny, following Trump publicly expressed his desire to see his political opponents prosecuted and some of those indictments materialized.

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

"The Bolton case and eventually the indictment seemed to have observed the standard procedure including the regulations and standards within the DOJ," he stated.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" filing that "explicitly sets forth the details involving the facts and situation in this instance," Mr Lesko said.

"It appears fairly consistent with a series of precedents... where public servants improperly handled and shared classified material."