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Ex-President Donald Trump has consistently expressed his wish to see critics investigated, applying pressure on the DOJ to charge 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 wrote last month in a social media post.

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

Both have subsequently been charged, in cases that numerous experts have stated appear to be politically motivated and difficult to win in legal proceedings.

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

"In my opinion, contrasting Bolton's charges to James' is like comparing apples to oranges," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been criminally indicted on national allegations pertaining to the supposed improper handling of classified information. Since leaving the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unfit for office in his book.

Experts contend that while there may be political reasons to go after Bolton, the methods used to secure an indictment and the evidence gathered against him indicate a possibly more substantial case 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 significant period of time," commented Carissa Byrne Hessick, a academic 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 alleged that Bolton placed the country at risk by improperly retaining and transmitting classified information to relatives using insecure means, including AOL. Some of the materials were labeled top secret.

The indictment alleges that at a certain time a hacker gained access to Bolton's system where documents were kept and transmitted an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Substantial Case?

The timing of his charge - coming on the heels of charges against James - has revived concerns about external influence on the justice system.

Trump once implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, wrote a book 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 raised questions about the validity of these allegations, and the reason these counts are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "if the DOJ is capable to demonstrate the allegations alleged and show the information is correctly classified, his conduct may certainly have violated the statute".

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

"Cases that concern classified information present challenges to prosecute, but they may and are filed against both low-level and senior officials, from occasionally," she said.

Parallels to Investigations into Trump and Biden

Trump likewise faced charges of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately dismissed by a court official and negated by his re-election as president.

A independent investigator also found that ex-President Joe Biden improperly maintained classified documents from his time as vice president, but did not criminally charge him.

Bolton's case bears similarities to Trump's classified documents matters, noted Mr Lesko, who also held a senior national security role at the DOJ.

Strict protocols govern the management of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the material he was sending was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Due to the sensitive character of the information at issue in this matter, we lack a lot of particulars about why the government contends elements like the diary entries and the other material he communicated by electronic message, and the reason there were classified," explained Mr Jaffer.

A More Traditional Prosecution

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

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

"This Bolton prosecution and eventually the indictment appeared to have followed the regular process including the regulations and standards within the DOJ," he stated.

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

"It seems fairly aligned with a series of precedents... where public servants mishandled and transmitted sensitive information."