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Former President Donald Trump has consistently shown his wish to see critics investigated, exerting pressure on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's killing our standing and trustworthiness," the leader wrote recently in a Truth Social post.

"They impeached me, and charged me (five times!)" he declared, mentioning the multiple legal proceedings he faced after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in situations that many experts have said appear to be driven by politics and difficult to win in legal proceedings.

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

"In my opinion, contrasting Bolton's charges to Comey's is like equating apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the supposed 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 "remarkably ignorant" and unsuitable for the presidency in his book.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an charge and the proof compiled against him indicate a possibly more substantial case than the DOJ brought against Comey.

"This misconduct that's being alleged is both more severe and appears to have taken place over a significant duration," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and following his 2019 White House exit, prosecutors alleged that Bolton put the country at risk by wrongfully keeping and transmitting sensitive documents to family members using insecure means, including AOL. Several of the materials were labeled top secret.

The indictment alleges that at one point a unauthorized user gained access to Bolton's account where documents were kept and sent an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

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

Retribution or a Strong Case?

The timing of his charge - arriving on the heels of charges against Comey - has revived concerns about external influence on the legal system.

Trump once implied Bolton should be in prison, and called him a "disreputable person". Bolton, for his role, authored a publication about his time in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this charge, when combined with additional cases, has prompted doubts about the strength of these charges, and why these counts are being brought at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to demonstrate the allegations alleged and demonstrate the information is properly classified, his conduct may very well have broken the statute".

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

"Situations that concern sensitive materials present challenges to try, but they may and are filed against both junior and senior personnel, from occasionally," she explained.

Similarities to Investigations into Trump and Biden

Trump similarly faced charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was eventually thrown out by a court official and voided by his return as president.

A independent investigator additionally determined that ex-President Joe Biden wrongfully stored classified documents from his time as second-in-command, but failed to criminally charge him.

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

Strict procedures govern the handling of sensitive materials. To win a conviction, the government must prove that Bolton knew the material he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Due to the sensitive character of the material at question in this case, we lack a lot of details about the reasons the government believes elements like the diary entries and the additional material he shared by electronic message, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the DOJ initiated this case will be under scrutiny, after Trump openly posted his desire to see his political opponents charged and some of those indictments came to fruition.

But Mr Lesko said in Bolton's situation, prosecutors seem to have followed protocol.

"The Bolton prosecution and ultimately the indictment appeared to have followed the regular process including the rules and norms within the Department of Justice," he stated.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" document that "clearly outlines the particulars involving the facts and situation here," Mr Lesko commented.

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