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

"We cannot postpone further, it's killing our standing and trustworthiness," the leader stated recently in a Truth Social post.

"They impeached me, and charged me (5 times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in cases that many experts have stated seem to be driven by politics and difficult to win in court.

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

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

This Details of the Case

Bolton has been formally charged on federal charges related to the supposed mishandling of sensitive materials. Since departing the White House in 2019, he has become a vocal presidential opponent, even to call him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Specialists contend that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the evidence compiled against him suggest a possibly stronger legal argument than the Justice Department presented against Comey.

"This misconduct that's being alleged is both more severe and seems to have taken place 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 security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton placed the nation at danger by improperly retaining and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

The indictment states that at a certain time a unauthorized user gained access to Bolton's system where files were kept and sent an apparent warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on Friday to 18 separate charges of mishandling classified information.

Retribution or a Strong Case?

The timing of his indictment - arriving on the heels of allegations against James - has revived questions about external influence on the justice system.

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

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

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

Charging such a high-ranking figure for mishandling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve sensitive materials present challenges to prosecute, but they may and are filed against equally junior and high-level officials, from occasionally," she said.

Parallels to Investigations into Trump and Biden

Trump similarly encountered charges of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was ultimately thrown out by a federal judge and negated by his re-election as leader.

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

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

Rigorous procedures govern the handling of sensitive materials. To win a conviction, the government must demonstrate that Bolton knew the information he was transmitting was restricted, and he had to intentionally transmit it to someone without authorization to obtain it.

"Due to the sensitive nature of the information at question in this case, we lack a lot of details about the reasons the prosecution contends elements like the personal notes and the additional material he communicated by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

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

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

"The Bolton prosecution and ultimately the indictment seemed to have observed the regular process including the rules and standards within the DOJ," he stated.

Unlike Comey's short, concise indictment, Bolton's was a more "traditional" document that "clearly sets forth the particulars involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears reasonably aligned with a long line of cases... where government officials improperly handled and shared sensitive information."