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

"We can't delay any longer, it's damaging our reputation and trustworthiness," the leader stated last month in a social media post.

"They impeached me, and charged me (5 times!)" he declared, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's civil case.

Both have since been charged, in situations that numerous experts have said seem to be politically motivated and difficult to succeed in court.

But the latest charges against a Trump critic, ex security advisor John Bolton, differ significantly, legal specialists and ex-prosecutors assert.

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

This Details of the Legal Situation

Bolton has been criminally indicted on national allegations related to the alleged improper handling of classified information. Since leaving the White House in 2019, he has emerged as a vocal Trump critic, even to describe him "remarkably ignorant" and unsuitable for office in his memoir.

Experts contend that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a possibly stronger legal argument than the DOJ brought against Comey.

"This misconduct that's being alleged is simultaneously more serious and appears to have occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and after his 2019 White House exit, authorities claimed that Bolton placed the nation at risk by wrongfully retaining and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the materials were labeled highly classified.

The indictment alleges that at a certain time a unauthorized user accessed to Bolton's account where documents were kept and sent an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to 18 separate counts of improperly handling classified information.

Political Motivation or a Strong Legal Argument?

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

Trump previously implied Bolton should be in prison, and called him a "disreputable person". Bolton, for his part, authored a publication about his time in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the schedule of this charge, when paired with additional cases, has prompted questions about the strength of these charges, and why these charges are being filed at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to prove the allegations alleged and show the material is properly designated, his conduct may certainly have broken the statute".

Prosecuting such a high-ranking official for improperly handling classified documents is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials present difficulties to try, but they can and are filed against both low-level and high-level officials, from occasionally," she said.

Parallels to Investigations into Trump and Biden

Trump similarly encountered charges of improperly storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was eventually dismissed by a federal judge and voided by his return as president.

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

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

Strict protocols govern the management of classified documents. To win a conviction, the prosecution must prove that Bolton knew the information he was sending was restricted, and he had to intentionally transmit it to someone without authorization to receive it.

"Due to the sensitive nature of the material at question in this case, we don't have a great deal of details about why the prosecution contends elements like the personal notes and the other material he communicated by electronic message, and why there were classified," explained Mr Jaffer.

A More Traditional Legal Action

The process by which the Justice Department initiated this legal action will be under scrutiny, after Trump openly posted his wish to see his political opponents charged and some of those indictments came to fruition.

But Mr Lesko said in Bolton's situation, authorities appear to have adhered to standard procedure.

"This Bolton case and eventually the indictment appeared to have observed the regular procedure including the rules and standards within the DOJ," he said.

Unlike Comey's short, two-page charge, Bolton's was a increasingly "traditional" document that "clearly outlines the details concerning the facts and situation in this instance," Mr Lesko said.

"It seems fairly consistent with a long line of cases... where government officials improperly handled and transmitted sensitive information."