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Former President Donald Trump has repeatedly shown his wish to see opponents investigated, exerting pressure on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our standing and trustworthiness," the president wrote last month in a social media message.

"They impeached twice, and indicted me (five times!)" he said, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's lawsuit.

Each have subsequently been indicted, in situations that numerous experts have said appear to be politically motivated and difficult to succeed in court.

But the most recent allegations against a Trump critic, ex security advisor John Bolton, stand apart, legal specialists and former prosecutors say.

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

This Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged improper handling of classified information. After departing the White House in 2019, he has become a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unsuitable for office in his memoir.

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

"This misconduct that's being alleged is simultaneously more serious and appears 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 national security adviser, and after his 2019 White House departure, prosecutors alleged that Bolton placed the country at danger by wrongfully retaining and transmitting sensitive documents to family members using unprotected methods, including AOL. Some of the materials were labeled top secret.

The charge states that at a certain time a hacker gained access to Bolton's system where documents were stored and transmitted an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

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

Political Motivation or a Substantial Legal Argument?

The schedule of his charge - arriving on the tails of charges against Comey - has renewed concerns about political pressure on the justice system.

Trump previously implied Bolton should be in prison, and called him a "sleazebag". Bolton, for his role, authored a book about his experience in the Trump administration that was highly critical of the leader.

"There's no question that the schedule of this charge, when paired with others, has raised questions about the validity of these allegations, and why these charges are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "should the Justice Department is able to demonstrate the facts stated and demonstrate the information is correctly classified, his behavior may certainly have violated the statute".

Prosecuting such a senior official for mishandling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information present difficulties to prosecute, but they may and are filed against equally junior and high-level personnel, from time to time," she explained.

Parallels to Investigations into Former President and President

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

A independent investigator additionally determined that ex-President Joe Biden wrongfully maintained classified documents from his time as vice president, but did not criminally charge him.

Bolton's situation shares characteristics to Trump's classified documents issues, noted Mr Lesko, who also held a senior security role at the DOJ.

Rigorous procedures govern the handling of classified documents. To secure a guilty verdict, the prosecution must prove that Bolton was aware the material he was sending was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the classified nature of the material at issue in this case, we lack a lot of details about the reasons the government believes elements like the personal notes and the other information he shared by email, and why there were classified," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the Justice Department initiated this case will be closely examined, following Trump openly posted his desire to see his critics prosecuted and several of those charges came to fruition.

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

"The Bolton prosecution and ultimately the indictment appeared to have observed the standard procedure including the rules and norms within the Department of Justice," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a more "conventional" filing that "explicitly sets forth the details involving the facts and circumstances in this instance," Mr Lesko said.

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