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

"We cannot postpone further, it's killing our reputation and trustworthiness," the leader stated last month in a Truth Social post.

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

Both have since been charged, in cases that many experts have stated appear to be driven by politics and difficult to succeed in court.

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

"In my opinion, comparing Bolton's case to Comey's is like comparing apples to oranges," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of the Case

Bolton has been criminally indicted on national allegations related to the alleged mishandling of classified information. After departing the White House in 2019, he has become a vocal presidential opponent, even to call him "stunningly uninformed" and unfit for office in his book.

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

"This misconduct that's being claimed is simultaneously more severe and seems to have taken place over a significant duration," said Carissa Byrne Hessick, a academic 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, authorities claimed that Bolton put the country at danger by wrongfully retaining and transmitting classified information to family members using insecure means, including AOL. Several of the materials were marked top secret.

The charge alleges that at one point a unauthorized user accessed to Bolton's account where files were kept and transmitted an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on Friday to eighteen separate charges of improperly handling classified information.

Retribution or a Strong Legal Argument?

The timing of his indictment - arriving on the tails of allegations against James - has renewed questions about political pressure on the legal system.

Trump once suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, wrote a book about his experience in the Trump government that was sharply negative of the president.

"Undoubtedly that the timing of this charge, when paired with others, has prompted doubts about the strength of these charges, and the reason these charges are being brought now," said Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the DOJ is able to demonstrate the facts stated and show the information is correctly classified, his behavior may very well have broken the statute".

Prosecuting such a senior figure for improperly handling sensitive materials is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to try, but they may and are filed against both junior and senior personnel, from occasionally," she said.

Parallels to Examinations into Trump and Biden

Trump similarly faced allegations of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that matter was ultimately dismissed by a federal judge and negated by his return as president.

A special counsel also determined that ex-President Joe Biden wrongfully stored classified documents from his time as second-in-command, but failed to criminally charge him.

Bolton's case shares characteristics to Trump's classified documents issues, noted Mr Lesko, who previously held a top security position at the Justice Department.

Strict protocols govern the management of classified documents. To secure a guilty verdict, the government must demonstrate that Bolton was aware the material he was sending was classified, and he had to intentionally transfer it to someone not entitled to receive it.

"Due to the classified character of the information at question in this matter, we don't have a great deal of particulars about why the prosecution contends things like the personal notes and the additional information he shared by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, after Trump publicly expressed his wish to see his critics prosecuted and several of those charges came to fruition.

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

"This Bolton prosecution and eventually the indictment appeared to have followed the standard process including the regulations and standards within the Department of Justice," he stated.

In contrast to Comey's brief, two-page indictment, Bolton's was a increasingly "traditional" filing that "explicitly outlines the particulars concerning the facts and situation here," Mr Lesko said.

"It appears fairly consistent with a long line of precedents... where government officials mishandled and transmitted sensitive information."