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

"We can't delay any longer, it's killing our reputation and credibility," the leader wrote recently in a social media message.

"They impeached twice, and indicted me (five times!)" he said, mentioning the multiple legal proceedings he faced after departing the White House in 2021 and James's lawsuit.

Both have subsequently been indicted, in situations that numerous specialists have stated appear to be driven by politics and difficult to win in court.

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

"In my opinion, comparing Bolton's charges to James' is like equating two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of the Case

Bolton has been criminally indicted on national allegations pertaining to the supposed mishandling of classified information. Since departing the White House in 2019, he has become a vocal presidential opponent, even to call him "remarkably ignorant" and unfit for office in his memoir.

Experts say that while there may be political reasons to target Bolton, the procedures used to secure an charge and the proof gathered against him indicate a potentially stronger case than the Justice Department presented against James.

"These actions that's being alleged is both more serious and seems to have occurred over a considerable duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and after his 2019 White House departure, authorities claimed that Bolton placed the nation at risk by wrongfully keeping and transmitting sensitive documents to family members using unprotected methods, including AOL. Several of the materials were marked top secret.

The charge states that at one point a hacker accessed to Bolton's account where documents were stored and sent an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

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

Political Motivation or a Strong Legal Argument?

The timing of his charge - coming on the tails of allegations against James - has revived concerns about political pressure on the legal system.

Trump once suggested Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, authored a book about his time in the Trump government that was sharply negative of the leader.

"Undoubtedly that the schedule of this charge, when paired with others, has raised questions about the validity of these charges, and the reason these charges are being filed now," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "should the DOJ is capable to demonstrate the allegations alleged and demonstrate the information is properly classified, his conduct may certainly have broken the law".

Prosecuting such a senior 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 classified information present challenges to prosecute, but they may and are filed against both low-level and high-level officials, from time to time," she explained.

Similarities to Examinations into Former President and Biden

Trump similarly encountered allegations of improperly keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was ultimately thrown out by a federal judge and voided by his return as president.

A independent investigator additionally found that former President Joe Biden wrongfully stored classified documents from his period as second-in-command, but did not criminally charge him.

Bolton's case shares characteristics to Trump's classified documents matters, said Mr Lesko, who previously held a top security role at the DOJ.

Strict procedures govern the management of classified documents. To win a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was transmitting was classified, and he had to knowingly transmit it to someone not entitled to receive it.

"Due to the classified nature of the material at issue in this case, we don't have a lot of particulars about why the government believes things like the personal notes and the other information he shared by email, and why there were classified," explained Mr Jaffer.

A More Traditional Prosecution

The process by which the DOJ brought this case will be closely examined, following Trump openly posted his desire to see his critics prosecuted and some of those indictments materialized.

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

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

In contrast to Comey's brief, concise indictment, Bolton's was a increasingly "traditional" document that "explicitly outlines the details involving the facts and situation here," Mr Lesko commented.

"It seems reasonably aligned with a long line of cases... where government officials improperly handled and transmitted classified material."