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Former President Donald Trump has consistently expressed his desire to see critics probed, 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 credibility," the leader stated recently in a social media message.

"I was impeached me, and indicted me (5 times!)" he declared, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's lawsuit.

Both have subsequently been indicted, in cases that numerous experts have said seem to be politically motivated and challenging to succeed in court.

But the latest charges against a presidential opponent, ex national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors say.

"I would say, contrasting Bolton's charges to James' is like comparing apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Details of the Case

Bolton has been formally charged on federal charges pertaining to the alleged mishandling of sensitive materials. After leaving the White House in 2019, he has become a vocal Trump critic, even to call him "remarkably ignorant" and unfit for office in his memoir.

Specialists say that while there may be political motivations to target Bolton, the procedures used to obtain an charge and the evidence gathered against him suggest a possibly stronger legal argument than the Justice Department brought against James.

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

Throughout his time as Trump's security advisor, and after his 2019 White House departure, authorities alleged that Bolton put the country at danger by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the materials were labeled top secret.

The charge alleges that at one point a unauthorized user accessed to Bolton's account where files were stored and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to eighteen distinct counts of improperly handling classified information.

Retribution or a Strong Legal Argument?

The timing of his charge - coming on the tails of allegations against James - has revived questions about political pressure on the legal system.

Trump once implied Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, authored a publication about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this charge, when paired with additional cases, has raised doubts about the strength of these allegations, and why these counts are being filed at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he continued, "if the Justice Department is capable to prove the facts alleged and show the information is properly designated, his behavior may very well have broken the statute".

Prosecuting such a senior figure for mishandling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern classified information present difficulties to prosecute, but they may and are filed against both low-level and senior officials, from occasionally," she explained.

Parallels to Examinations into Trump and President

Trump likewise faced charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was ultimately thrown out by a federal judge and voided by his return as president.

A special counsel also determined that former President Joe Biden wrongfully stored classified documents from his time as vice president, but did not criminally charge him.

Bolton's situation shares characteristics to Biden's classified documents matters, said Mr Lesko, who previously held a senior security role at the Justice Department.

Strict procedures regulate the handling of classified documents. To secure a guilty verdict, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the sensitive nature of the material at question in this matter, we don't have a great deal of particulars about the reasons the government believes elements like the personal notes and the other information he communicated by email, 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, after Trump publicly posted his wish to see his political opponents prosecuted and some of those charges materialized.

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

"This Bolton prosecution and eventually the indictment seemed to have observed the standard procedure including the regulations and norms within the DOJ," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a more "traditional" filing that "clearly outlines the particulars involving the circumstances and situation here," Mr Lesko commented.

"It appears reasonably aligned with a series of precedents... where government officials mishandled and transmitted sensitive information."