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

"We can't delay further, it's killing our standing and credibility," the president stated last month in a social media message.

"I was impeached twice, and indicted me (5 times!)" he declared, mentioning the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Each have since been indicted, in cases that numerous specialists have said seem to be driven by politics and difficult to succeed in court.

But the most recent allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal experts and ex-prosecutors say.

"I would say, comparing Bolton's charges to James' is like comparing two different things," stated 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 federal charges pertaining to the alleged mishandling of classified information. Since departing the White House in 2019, he has become a vocal presidential opponent, even to describe him "remarkably ignorant" and unfit for office in his memoir.

Specialists contend that while there may be political motivations to target Bolton, the procedures used to secure an charge and the evidence compiled against him suggest a potentially more substantial legal argument than the Justice Department presented against James.

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

Throughout his time as Trump's security advisor, and following his 2019 White House exit, authorities claimed that Bolton put the country at risk by wrongfully retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were labeled highly classified.

The charge states that at one point a hacker accessed to Bolton's system where files were stored and sent an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The timing of his charge - coming on the heels of charges against Comey - has revived concerns about political pressure on the legal system.

Trump previously implied Bolton belonged in jail, and called him a "disreputable person". Bolton, for his role, authored a publication about his time in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this indictment, when paired with others, has raised doubts about the validity of these charges, and why these counts are being filed at this time," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is able to prove the allegations alleged and demonstrate the material is properly designated, his conduct may very well have violated the statute".

Charging such a senior figure for improperly handling 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 sensitive materials pose challenges to prosecute, but they may and are brought against equally low-level and senior officials, from time to time," she explained.

Parallels to Examinations into Former President and President

Trump similarly faced charges of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was ultimately thrown out by a federal judge and voided by his return as leader.

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

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

Rigorous protocols regulate the handling of classified documents. To secure a conviction, the government must demonstrate that Bolton knew the material he was sending was classified, and he had to intentionally transmit it to someone without authorization to obtain it.

"Due to the classified nature of the material at issue in this case, we lack a great deal of particulars about the reasons the prosecution contends things like the diary entries and the additional material he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A More Conventional Prosecution

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

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

"The Bolton prosecution and eventually the indictment appeared to have followed the regular procedure including the regulations and standards within the Department of Justice," he said.

In contrast to Comey's short, two-page indictment, Bolton's was a more "conventional" filing that "clearly outlines the particulars involving the facts and situation here," Mr Lesko commented.

"It seems fairly consistent with a series of cases... where government officials improperly handled and shared classified material."