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

"We cannot postpone further, it's killing our standing and credibility," the president stated last month in a social media message.

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

Both have since been charged, in situations that many specialists have said seem to be driven by politics and challenging to succeed in legal proceedings.

But the latest charges against a presidential opponent, ex national security adviser John Bolton, stand apart, legal experts and former prosecutors say.

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

The Specifics of the Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of classified information. Since departing the White House in 2019, he has become a outspoken presidential opponent, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Experts contend that while there may be political reasons to target Bolton, the procedures used to obtain an charge and the proof gathered against him suggest a possibly stronger case than the Justice Department brought against James.

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

Throughout his time as Trump's security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton put the country at danger by improperly retaining and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the materials were marked top secret.

The charge alleges that at one point a unauthorized user gained access to Bolton's system where documents were stored and transmitted an seeming threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to eighteen separate counts of improperly handling classified information.

Political Motivation or a Substantial Case?

The timing of his charge - coming on the heels of charges against Comey - has renewed questions about political pressure on the legal system.

Trump previously implied Bolton belonged in prison, and described him a "disreputable person". Bolton, for his part, authored a publication about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the timing of this charge, when paired with additional cases, has raised questions about the strength of these allegations, and why these charges are being filed now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is capable to demonstrate the allegations stated and demonstrate the material is properly classified, his behavior may very well have violated the statute".

Prosecuting such a high-ranking figure for mishandling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information pose challenges to prosecute, but they may and are brought against both low-level and high-level officials, from time to time," she explained.

Similarities to Examinations into Trump and President

Trump similarly encountered charges of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was ultimately thrown out by a court official and voided by his re-election as leader.

A special counsel also determined that ex-President Joe Biden wrongfully maintained classified documents from his time as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's classified documents issues, noted Mr Lesko, who also held a senior security position at the Justice Department.

Rigorous procedures regulate the handling of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to intentionally transfer it to someone without authorization to receive it.

"Due to the sensitive character of the information at question in this matter, we lack a lot of particulars about why the government believes elements like the personal notes and the additional material he shared by email, and why there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The process by which the DOJ brought this legal action will be under scrutiny, following Trump publicly posted his wish to see his critics prosecuted and several of those charges came to fruition.

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

"This Bolton case and ultimately the charge appeared to have observed the regular procedure including the rules and norms within the DOJ," he said.

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

"It appears reasonably aligned with a long line of cases... where public servants mishandled and shared classified material."