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Ex-President Donald Trump has repeatedly expressed his desire to see critics probed, applying influence on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our standing and credibility," the leader wrote last month in a social media post.

"They impeached twice, and indicted me (5 times!)" he declared, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's civil case.

Each have since been charged, in situations that numerous specialists have stated seem to be politically motivated and difficult to win in legal proceedings.

But the latest charges against a Trump critic, former security advisor John Bolton, stand apart, legal specialists and ex-prosecutors say.

"I would say, contrasting Bolton's charges to Comey's is like comparing apples to oranges," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the supposed mishandling of sensitive materials. Since leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to call him "stunningly uninformed" and unfit for the presidency in his book.

Experts say that while there may be political reasons to go after Bolton, the procedures used to secure an charge and the proof compiled against him suggest a possibly stronger case than the DOJ presented against James.

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

During his time as Trump's national security adviser, and after his 2019 White House exit, prosecutors claimed that Bolton put the country at risk by improperly retaining and sending classified information to relatives using unprotected methods, including AOL. Several of the documents were labeled top secret.

The charge alleges that at a certain time a hacker gained access to Bolton's account where files were stored and sent an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to 18 distinct counts of improperly handling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his charge - arriving on the heels of charges against Comey - has revived concerns about external influence on the justice system.

Trump once suggested Bolton should be in prison, and described him a "sleazebag". Bolton, for his part, authored a book about his time in the Trump administration that was highly critical of the president.

"There's no question that the timing of this indictment, when combined with additional cases, has raised doubts about the strength of these charges, and why these charges are being filed now," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the Justice Department is able to prove the allegations alleged and show the information is correctly classified, his conduct may certainly have broken the statute".

Prosecuting such a senior figure for improperly handling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern classified information pose difficulties to try, but they can and are brought against equally junior and high-level officials, from occasionally," she said.

Parallels to Investigations into Former President and President

Trump likewise encountered allegations of wrongfully keeping sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that case was ultimately thrown out by a federal judge and negated by his return as leader.

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

Bolton's situation shares characteristics to Biden's sensitive materials issues, noted Mr Lesko, who previously held a senior national security position at the Justice Department.

Rigorous procedures regulate the handling of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton knew the information he was sending was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the classified character of the information at question in this case, we lack a great deal of details about the reasons the government believes elements like the personal notes and the other information he communicated by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the DOJ brought this case will be under scrutiny, following Trump openly posted his desire to see his political opponents charged and several of those indictments came to fruition.

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

"This Bolton prosecution and ultimately the indictment seemed to have observed the regular process including the rules and norms within the Department of Justice," he said.

In contrast to Comey's brief, two-page charge, Bolton's was a more "traditional" filing that "clearly outlines the details involving the circumstances and circumstances in this instance," Mr Lesko said.

"It seems fairly aligned with a series of cases... where public servants mishandled and shared classified material."