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Ex-President Donald Trump has consistently shown his wish to see critics investigated, exerting pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's damaging our reputation and credibility," the leader wrote recently in a social media message.

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

Both have subsequently been charged, in cases that numerous specialists have said seem to be driven by politics and difficult to win in court.

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

"In my opinion, comparing Bolton's case to Comey's is like equating apples to oranges," stated 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 mishandling of classified information. Since departing the White House in 2019, he has become a outspoken presidential opponent, even to describe him "stunningly uninformed" and unfit for the presidency in his book.

Experts contend that while there may be political motivations to target Bolton, the methods used to secure an indictment and the proof gathered against him suggest a possibly stronger case than the DOJ presented against Comey.

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

During his time as Trump's national security adviser, and following his 2019 White House exit, prosecutors claimed that Bolton placed the country at risk by improperly keeping and transmitting classified information to relatives using insecure means, including AOL. Several of the documents were marked highly classified.

The indictment alleges that at one point a unauthorized user gained access to Bolton's system where documents were stored and transmitted an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on recently to 18 distinct charges of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the heels of allegations against James - has revived concerns about political pressure on the justice system.

Trump once implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, authored a publication about his time in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this charge, when paired with others, has prompted questions about the strength of these allegations, and why these charges are being brought at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "if the DOJ is capable to demonstrate the allegations stated and show the information is correctly designated, his behavior may very well have violated the statute".

Prosecuting such a high-ranking figure for improperly handling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information pose challenges to prosecute, but they can and are filed against both junior and high-level officials, from occasionally," she said.

Similarities to Investigations into Former President and Biden

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

A special counsel also determined that former President Joe Biden wrongfully maintained sensitive materials from his period as vice president, but did not prosecute him.

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

Strict protocols govern the management of sensitive materials. To secure a conviction, the prosecution must demonstrate that Bolton knew the information he was transmitting was classified, and he had to intentionally transfer it to someone not entitled to obtain it.

"Because of the sensitive nature of the material at issue in this matter, we don't have a lot of details about the reasons the government contends things like the diary entries and the other information he communicated by email, and the reason there were restricted," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, following Trump openly expressed his wish to see his political opponents prosecuted and several of those charges materialized.

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

"The Bolton prosecution and eventually the charge seemed to have followed the standard procedure including the rules and norms within the DOJ," he stated.

In contrast to Comey's short, concise charge, Bolton's was a increasingly "conventional" document that "clearly outlines the details involving the circumstances and circumstances here," Mr Lesko said.

"It seems fairly consistent with a long line of cases... where public servants mishandled and shared classified material."