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Former President Donald Trump has consistently expressed his desire to see critics investigated, applying pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our standing and credibility," the leader wrote recently in a social media post.

"I was impeached twice, and indicted me (5 times!)" he said, mentioning the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Both have since been indicted, in situations that many specialists have said seem to be politically motivated and challenging to succeed in legal proceedings.

But the latest charges against a Trump critic, ex national security adviser John Bolton, differ significantly, legal experts and former prosecutors assert.

"I would say, contrasting Bolton's charges to James' is like comparing apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the alleged mishandling of classified information. After departing the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the evidence gathered against him indicate a possibly more substantial case than the Justice Department presented against James.

"This misconduct that's being claimed is both more severe and seems to have taken place over a considerable 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 exit, prosecutors alleged that Bolton put the country at risk by improperly retaining and transmitting sensitive documents to family members using insecure means, including AOL. Some of the materials were marked top secret.

The charge states that at one point a hacker accessed to Bolton's system where files were stored and sent an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

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

Retribution or a Substantial Case?

The timing of his charge - coming on the tails of charges against James - has renewed concerns about political pressure on the justice system.

Trump once suggested Bolton should be in jail, and called him a "disreputable person". Bolton, for his part, wrote a book about his time in the Trump administration that was highly critical of the leader.

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

Nevertheless, he added, "should the DOJ is capable to demonstrate the facts alleged and show the information is correctly classified, his behavior may very well have broken the law".

Prosecuting such a senior official for improperly handling sensitive materials is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve classified information pose challenges to prosecute, but they can and are filed against both low-level and senior officials, from time to time," she said.

Parallels to Investigations into Former President and President

Trump similarly faced allegations of improperly keeping classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that case was ultimately thrown out by a federal judge and voided by his re-election as president.

A special counsel additionally determined that ex-President Joe Biden improperly stored sensitive materials from his period as vice president, but did not prosecute him.

Bolton's situation shares characteristics to Trump's sensitive materials matters, said Mr Lesko, who also held a top national security position at the DOJ.

Rigorous protocols regulate the management of classified documents. To secure a conviction, the prosecution must prove that Bolton was aware the material he was transmitting was restricted, and he had to intentionally transmit it to someone not entitled to obtain it.

"Because of the sensitive nature of the material at question in this matter, we don't have a great deal of details about the reasons the government believes elements like the diary entries and the additional information he communicated by email, and the reason there were restricted," said Mr Jaffer.

A Increasingly Traditional Prosecution

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

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

"This Bolton case and ultimately the indictment seemed to have observed the regular process including the regulations and standards within the DOJ," he said.

In contrast to Comey's brief, two-page indictment, Bolton's was a more "traditional" filing that "clearly sets forth the details involving the facts and situation here," Mr Lesko said.

"It seems fairly aligned with a series of cases... where government officials improperly handled and transmitted classified material."