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Former President Donald Trump has repeatedly shown his desire to see critics investigated, exerting influence 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 damaging our standing and credibility," the president stated last month in a Truth Social message.

"They impeached me, and indicted me (5 times!)" he declared, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Both have since been indicted, in cases that numerous experts have stated seem to be driven by politics and challenging to succeed in court.

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

"In my opinion, comparing Bolton's charges to James' is like equating two different things," said Mark Lesko, a ex acting US attorney 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. Since leaving the White House in 2019, he has become a vocal Trump critic, even to call him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Experts say that while there may be political motivations to go after Bolton, the methods used to secure an charge and the evidence gathered against him indicate a potentially stronger legal argument than the Justice Department presented against Comey.

"This misconduct that's being claimed is simultaneously more severe and appears to have occurred over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the nation at danger by improperly retaining and transmitting sensitive documents to family members using unprotected methods, including AOL. Several of the materials were marked highly classified.

The indictment states that at one point a unauthorized user gained access to Bolton's system where documents were kept and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on recently to 18 distinct counts of improperly handling sensitive materials.

Political Motivation or a Strong Case?

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

Trump once implied Bolton should be in jail, and called him a "disreputable person". Bolton, for his role, wrote a publication about his experience in the Trump government that was highly critical of the president.

"Undoubtedly that the schedule of this indictment, 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, founder and executive director of the National Security Institute.

Nevertheless, he added, "if the DOJ is able to demonstrate the facts alleged and show the information is properly classified, his conduct may certainly have broken the law".

Prosecuting such a high-ranking figure for mishandling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to prosecute, but they may and are filed against both low-level and senior officials, from time to time," she said.

Parallels to Investigations into Former President and Biden

Trump likewise faced allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was eventually dismissed by a court official and voided by his return as leader.

A special counsel also found that ex-President Joe Biden improperly maintained classified documents from his period as vice president, but failed to criminally charge him.

Bolton's case bears similarities to Biden's sensitive materials issues, noted Mr Lesko, who also held a senior national security role at the Justice Department.

Strict protocols govern the handling of sensitive materials. To win 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 receive it.

"Because of the sensitive nature of the material at issue in this matter, we don't have a great deal of particulars about why the government contends things like the personal notes and the additional material he shared by electronic message, and why there were classified," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, after Trump publicly expressed his wish to see his political opponents prosecuted and several of those indictments came to fruition.

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

"This Bolton prosecution and eventually the indictment seemed to have observed the regular procedure including the regulations and standards within the DOJ," he said.

Unlike Comey's brief, concise charge, Bolton's was a more "conventional" filing that "clearly sets forth the details involving the circumstances and circumstances here," Mr Lesko said.

"It seems fairly consistent with a series of precedents... where government officials mishandled and shared classified material."