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Former President Donald Trump has repeatedly expressed his wish to see critics probed, applying pressure on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our standing and trustworthiness," the president stated recently in a Truth Social post.

"I was impeached twice, and charged me (5 times!)" he declared, mentioning the four criminal cases he faced after departing the White House in 2021 and James's civil case.

Both have since been indicted, in situations that numerous specialists have said appear to be politically motivated 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 ex-prosecutors say.

"In my opinion, comparing Bolton's case to James' is like equating two different things," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Details of the Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed improper handling of sensitive materials. After leaving the White House in 2019, he has become a vocal presidential opponent, even to call him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists contend that while there may be political motivations to target Bolton, the procedures used to secure an charge and the proof compiled against him indicate a potentially stronger legal argument than the Justice Department presented against James.

"These actions that's being alleged is simultaneously more serious and seems to have taken place over a significant period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and after his 2019 White House exit, prosecutors claimed that Bolton put the nation at danger by improperly keeping and transmitting classified information to relatives using unprotected methods, including AOL. Several of the documents were marked highly classified.

The indictment alleges that at a certain time a hacker gained access to Bolton's system where files were stored and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

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

Retribution or a Strong Legal Argument?

The timing of his charge - coming on the tails of allegations against James - has revived questions about political pressure on the justice system.

Trump once suggested Bolton should be in prison, and described him a "sleazebag". Bolton, for his role, authored a book about his experience in the Trump administration that was highly critical of the president.

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

However, he continued, "should the DOJ is capable to prove the allegations stated and show the material is properly classified, his behavior may certainly have violated the statute".

Prosecuting such a senior figure 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 involve classified information present challenges to prosecute, but they may and are brought against both low-level and senior officials, from occasionally," she said.

Parallels to Investigations into Former President and Biden

Trump likewise faced allegations of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was eventually thrown out by a federal judge and negated by his return as leader.

A independent investigator additionally determined that ex-President Joe Biden wrongfully maintained sensitive materials from his period as vice president, but failed to prosecute him.

Bolton's case bears similarities to Biden's classified documents matters, said Mr Lesko, who also held a top national security position at the Justice Department.

Strict protocols govern the management of sensitive materials. To secure a guilty verdict, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to intentionally transmit it to someone without authorization to obtain it.

"Because of the sensitive nature of the material at issue in this case, we lack a great deal of details about the reasons the government contends elements like the diary entries and the other information he shared by email, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Prosecution

The process by which the DOJ brought this case will be closely examined, following Trump publicly expressed his wish to see his political opponents charged and some of those charges materialized.

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

"The Bolton prosecution and ultimately the indictment seemed to have observed the regular procedure including the rules and standards within the DOJ," he stated.

In contrast to Comey's brief, two-page charge, Bolton's was a more "conventional" filing that "explicitly sets forth the details involving the circumstances and circumstances here," Mr Lesko commented.

"It seems reasonably consistent with a long line of cases... where government officials mishandled and transmitted sensitive information."