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Ex-President Donald Trump has repeatedly shown his desire to see critics investigated, exerting pressure on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

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

"I was impeached me, and indicted me (5 times!)" he said, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in situations that numerous specialists have stated seem to be driven by politics and difficult to succeed in court.

But the latest charges against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and former prosecutors say.

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

This Details of the Case

Bolton has been criminally indicted on national allegations pertaining to the alleged improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, even to call him "stunningly uninformed" and unsuitable for office in his book.

Experts contend that while there may be political motivations to target Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a possibly more substantial legal argument than the Justice Department presented against Comey.

"These actions that's being alleged is simultaneously more serious and seems to have taken place over a significant period of time," 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 after his 2019 White House departure, authorities alleged that Bolton placed the nation at risk by wrongfully retaining 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 unauthorized user accessed to Bolton's system where files were stored and transmitted an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on recently to 18 distinct charges of improperly handling sensitive materials.

Retribution or a Strong Case?

The schedule of his charge - arriving on the tails of allegations against James - has renewed concerns about political pressure on the legal system.

Trump once suggested Bolton belonged in prison, and called him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this indictment, when combined with additional cases, has raised doubts about the validity of these allegations, and the reason these charges are being filed now," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is capable to demonstrate the allegations alleged and show the material is properly designated, his conduct may certainly have broken the law".

Charging such a senior figure for improperly handling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern classified information pose difficulties to try, but they can and are filed against equally junior and high-level officials, from occasionally," she explained.

Similarities to Examinations into Former President and President

Trump likewise encountered charges of wrongfully storing classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was ultimately dismissed by a court official and negated by his re-election as leader.

A special counsel also determined that former President Joe Biden wrongfully maintained classified documents from his period as second-in-command, but failed to prosecute him.

Bolton's case bears similarities to Trump's sensitive materials matters, said Mr Lesko, who also held a senior national security role at the DOJ.

Rigorous procedures govern the management of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the material he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the sensitive character of the information at issue in this case, we lack a great deal of details about why the government contends things like the diary entries and the additional material he shared by electronic message, and the reason there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The process by which the DOJ initiated this legal action will be closely examined, after Trump publicly expressed his desire to see his critics prosecuted and several of those indictments came to fruition.

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

"The Bolton case and eventually the charge appeared to have followed the standard process including the rules and norms within the Department of Justice," he stated.

In contrast to Comey's short, concise charge, Bolton's was a more "conventional" document that "explicitly sets forth the details concerning the circumstances and situation here," Mr Lesko commented.

"It seems fairly aligned with a long line of cases... where government officials mishandled and transmitted classified material."