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

"We can't delay further, it's damaging our standing and credibility," the leader wrote last month in a social media message.

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

Both have since been charged, in cases that numerous experts have said appear to be politically motivated and challenging to win in court.

But the most recent charges against a Trump critic, ex national security adviser John Bolton, stand apart, legal specialists and former prosecutors assert.

"In my opinion, contrasting Bolton's case to Comey's is like equating two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Specifics of the Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the supposed improper handling of sensitive materials. After departing the White House in 2019, he has become a outspoken Trump critic, even to call him "stunningly uninformed" and unfit for the presidency in his book.

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

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

During his time as Trump's national security adviser, and following his 2019 White House departure, prosecutors claimed that Bolton put the nation at danger by improperly keeping and transmitting classified information to relatives using unprotected methods, including AOL. Some of the materials were marked top secret.

The charge alleges that at a certain time a hacker accessed to Bolton's system where documents were stored and sent an apparent warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct charges of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the heels of allegations against Comey - has revived concerns about external influence on the legal system.

Trump once implied Bolton should be in jail, and described him a "disreputable person". Bolton, for his part, wrote a publication about his experience in the Trump government that was highly critical of the leader.

"There's no question that the schedule of this indictment, when combined with others, has prompted questions about the strength of these charges, and why these charges are being brought at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "should the DOJ is able to prove the facts alleged and show the information is properly designated, his conduct may very well have violated the statute".

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

"Situations that concern classified information pose challenges to try, but they may and are filed against equally low-level and high-level officials, from time to time," she explained.

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 return, but that case was eventually dismissed by a court official and negated by his return as president.

A independent investigator also determined that ex-President Joe Biden wrongfully stored sensitive materials from his time as vice president, but failed to criminally charge him.

Bolton's case shares characteristics to Trump's sensitive materials issues, said Mr Lesko, who previously held a top national security position at the DOJ.

Strict procedures govern the handling of sensitive materials. To secure 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 obtain it.

"Due to the classified nature of the information at question in this case, we don't have a great deal of details 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," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the Justice Department brought this case will be under scrutiny, following Trump openly posted his desire to see his critics prosecuted and some of those indictments came to fruition.

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

"This Bolton prosecution and ultimately the indictment seemed to have observed the standard process including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a more "conventional" filing that "explicitly outlines the particulars involving the facts and situation here," Mr Lesko said.

"It seems reasonably consistent with a series of cases... where government officials improperly handled and transmitted sensitive information."