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Ex-President Donald Trump has repeatedly expressed his desire to see opponents investigated, exerting influence on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our reputation and trustworthiness," the leader stated recently in a Truth Social post.

"They impeached twice, and indicted me (five times!)" he said, mentioning the four criminal cases he faced after leaving the White House in 2021 and James's civil case.

Both have subsequently been charged, in cases that many specialists have stated appear to be politically motivated and challenging to succeed in court.

But the most recent allegations against a Trump critic, ex national security adviser John Bolton, stand apart, legal experts and ex-prosecutors say.

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

The Details of Bolton's Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of classified information. After departing the White House in 2019, he has become a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists contend that while there may be political reasons to target Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a possibly stronger case than the DOJ presented against James.

"These actions that's being claimed is both more serious and appears to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House exit, prosecutors claimed that Bolton placed the country at danger by improperly retaining and sending sensitive documents to family members using unprotected methods, including AOL. Several of the documents were marked highly classified.

The charge alleges that at one point a unauthorized user gained access to Bolton's system where files were kept and transmitted an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on recently to 18 separate counts of improperly handling sensitive materials.

Retribution or a Substantial Case?

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

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

"There's no question that the timing of this charge, when paired with others, has raised doubts about the strength of these charges, and the reason these charges are being brought at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is able to prove the allegations stated and show the information is properly designated, his behavior may certainly have violated the statute".

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

"Cases that concern sensitive materials present difficulties to try, but they may and are brought against equally junior and senior officials, from time to time," she said.

Parallels to Examinations into Trump and President

Trump similarly encountered charges of improperly storing sensitive materials at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually dismissed by a federal judge and negated by his return as leader.

A independent investigator additionally found that former President Joe Biden improperly stored sensitive materials from his time as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Trump's classified documents matters, said Mr Lesko, who also held a senior national security position at the DOJ.

Strict protocols regulate the management of sensitive materials. To win a guilty verdict, the prosecution must prove that Bolton knew the information he was sending was classified, and he had to intentionally transfer it to someone not entitled to obtain it.

"Due to the sensitive character of the material at issue in this matter, we lack a lot of details about the reasons the prosecution contends things like the personal notes and the other information he shared by email, and the reason there were restricted," said Mr Jaffer.

A More Traditional Prosecution

The process by which the Justice Department brought this case will be closely examined, following Trump publicly posted his desire to see his political opponents prosecuted and some of those charges came to fruition.

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

"The Bolton case and ultimately the indictment seemed to have followed the regular procedure including the rules and standards within the Department of Justice," he stated.

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

"It seems fairly aligned with a long line of precedents... where government officials mishandled and shared classified material."