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Former President Donald Trump has repeatedly expressed his desire to see critics probed, exerting influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and credibility," the president stated last month in a Truth Social message.

"They impeached twice, and indicted me (five times!)" he declared, mentioning the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Each have since been charged, in situations that numerous experts have said appear to be driven by politics and difficult to win in court.

But the most recent allegations against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors assert.

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

This Details of the Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of sensitive materials. After departing the White House in 2019, he has become a outspoken presidential opponent, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political reasons to go after Bolton, the methods used to obtain an indictment and the evidence gathered against him indicate a possibly more substantial case than the DOJ presented against Comey.

"This misconduct that's being alleged is simultaneously more serious 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.

Throughout his tenure as Trump's national security adviser, and following his 2019 White House exit, prosecutors claimed that Bolton placed the country at danger by wrongfully keeping and transmitting classified information 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 system where files were stored and transmitted an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

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

Political Motivation or a Substantial Legal Argument?

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

Trump previously suggested Bolton should be in prison, and described him a "disreputable person". Bolton, for his role, authored a book about his experience in the Trump government that was sharply negative of the president.

"Undoubtedly that the timing of this charge, when paired with others, has raised doubts about the validity of these charges, and why these counts are being brought at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is capable to prove the facts stated and show the material is correctly designated, his conduct may very well have violated the statute".

Prosecuting such a high-ranking figure for improperly handling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve sensitive materials pose difficulties to prosecute, but they may and are filed against both low-level and high-level personnel, from time to time," she explained.

Similarities to Examinations into Trump and President

Trump likewise encountered charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that matter was eventually dismissed by a federal judge and negated by his return as leader.

A special counsel also determined that ex-President Joe Biden improperly maintained sensitive materials from his time as second-in-command, but did not prosecute him.

Bolton's situation shares characteristics to Biden's classified documents issues, said Mr Lesko, who also held a senior national security position at the Justice Department.

Strict procedures regulate the management of sensitive materials. To win a conviction, the government 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 character of the information at issue in this matter, we lack a lot of details about why the prosecution believes elements like the diary entries and the other information he shared by electronic message, and the reason there were classified," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ initiated this case will be under scrutiny, after Trump publicly expressed his desire to see his political opponents charged and several of those charges came to fruition.

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

"The Bolton case and eventually the indictment seemed to have followed the regular process including the rules and standards within the DOJ," he said.

Unlike Comey's short, concise charge, Bolton's was a increasingly "conventional" document that "explicitly outlines the details concerning the circumstances and situation here," Mr Lesko said.

"It appears fairly aligned with a series of cases... where public servants improperly handled and shared classified material."