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Former President Donald Trump has repeatedly expressed his desire to see critics probed, 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 wrote recently in a Truth Social message.

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

Both have since been charged, in situations that numerous experts have said appear to be politically motivated and difficult to win in legal proceedings.

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

"In my opinion, contrasting Bolton's charges to Comey's is like comparing apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Legal Situation

Bolton has been formally charged on national allegations pertaining to the alleged improper handling of sensitive materials. After departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for office in his memoir.

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 potentially more substantial case than the DOJ brought against Comey.

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

Throughout his time as Trump's security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton put the nation at danger by improperly keeping and transmitting sensitive documents to family members using insecure means, including AOL. Several of the documents were labeled highly classified.

The indictment alleges that at a certain time a hacker gained access to Bolton's system where files were stored and transmitted an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate counts of mishandling sensitive materials.

Retribution or a Substantial Case?

The schedule of his charge - coming on the heels of charges against Comey - has renewed questions about political pressure on the justice system.

Trump previously suggested Bolton belonged in jail, and described him a "disreputable person". Bolton, for his role, authored a book 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 prompted doubts about the validity of these allegations, and why these counts are being brought at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "if the DOJ is able to prove the facts stated and demonstrate the information is correctly classified, his behavior may very well have broken the law".

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

"Cases that involve classified information present difficulties to try, but they can and are filed against both junior and high-level personnel, from occasionally," she said.

Parallels to Investigations into Former President and President

Trump similarly faced charges of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately thrown out by a federal judge and negated by his return as leader.

A special counsel also found that ex-President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but did not criminally charge him.

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

Strict protocols regulate the management of sensitive materials. To secure a conviction, the government must demonstrate that Bolton knew the material he was sending was restricted, and he had to intentionally transfer it to someone not entitled to obtain it.

"Because of the classified character of the material at question in this matter, we lack a great deal of particulars about why the prosecution believes elements like the personal notes and the additional information he communicated by electronic message, and why there were classified," explained Mr Jaffer.

A Increasingly Conventional Prosecution

The process by which the DOJ brought this legal action will be closely examined, following Trump openly expressed his desire to see his critics prosecuted and several of those charges materialized.

But Mr Lesko indicated in Bolton's case, prosecutors seem to have adhered to standard procedure.

"The Bolton case and ultimately the indictment appeared to have observed the standard process including the rules and norms within the DOJ," he said.

In contrast to Comey's brief, concise indictment, Bolton's was a increasingly "conventional" document that "clearly outlines the details involving the facts and situation here," Mr Lesko said.

"It seems fairly aligned with a series of cases... where government officials mishandled and transmitted classified material."