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

"We cannot postpone further, it's damaging our reputation and credibility," the president stated last month in a Truth Social message.

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

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

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

"I would say, contrasting Bolton's case to Comey's is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. After departing the White House in 2019, he has emerged as a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Specialists say that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence compiled against him indicate a possibly more substantial case than the Justice Department brought against Comey.

"This misconduct that's being alleged is both more serious and seems to have occurred over a significant period of time," 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 nation at risk by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the materials were labeled highly classified.

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

Bolton pleaded not guilty during a court appearance on Friday to 18 separate charges of improperly handling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his charge - coming on the heels of allegations against Comey - has renewed questions about external influence on the legal system.

Trump once suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his role, authored a publication about his time in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this indictment, when combined with additional cases, has raised questions about the validity of these allegations, and the reason these counts are being filed at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "if the Justice Department is able to prove the allegations alleged and show the information is correctly classified, his behavior may certainly have broken the statute".

Prosecuting such a high-ranking official for mishandling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information pose difficulties to prosecute, but they can and are brought against both junior and high-level personnel, from time to time," she said.

Parallels to Investigations into Trump and Biden

Trump likewise faced allegations of improperly storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that matter was ultimately dismissed by a federal judge and voided by his return as leader.

A independent investigator additionally found that former President Joe Biden improperly maintained classified documents from his period as second-in-command, but did not prosecute him.

Bolton's situation bears similarities to Trump's classified documents issues, noted Mr Lesko, who also held a top national security position at the Justice Department.

Strict protocols govern the handling of classified documents. To secure a guilty verdict, the government must demonstrate that Bolton knew the information he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to receive it.

"Due to the classified nature of the information at question in this matter, we don't have a lot of particulars about the reasons the prosecution contends things like the diary entries and the additional material he shared by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the DOJ initiated this case will be closely examined, after Trump publicly posted his desire to see his political opponents charged and several of those charges materialized.

But Mr Lesko said in Bolton's case, authorities appear to have followed protocol.

"This Bolton case and eventually the charge seemed to have followed the standard procedure including the regulations and norms within the Department of Justice," he said.

In contrast to Comey's brief, concise indictment, Bolton's was a increasingly "conventional" filing that "explicitly sets forth the particulars involving the circumstances and situation here," Mr Lesko said.

"It appears reasonably consistent with a series of precedents... where public servants mishandled and shared sensitive information."