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Former President Donald Trump has consistently expressed his desire to see opponents investigated, exerting pressure on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our reputation and credibility," the leader wrote recently in a Truth Social post.

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

Each have subsequently been indicted, in situations that many specialists have said appear to be driven by politics and difficult to succeed in court.

But the latest charges against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors assert.

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

This Specifics of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. After departing the White House in 2019, he has become a outspoken presidential opponent, even to describe him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists say that while there may be political reasons to target Bolton, the methods used to obtain an indictment and the evidence compiled against him suggest a potentially more substantial case than the Justice Department presented against Comey.

"These actions 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 security advisor, and following his 2019 White House departure, authorities claimed that Bolton placed the country at risk by improperly retaining and sending sensitive documents to family members using insecure means, including AOL. Several of the documents were labeled top secret.

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

Bolton entered a not guilty plea during a hearing on recently to eighteen distinct counts of mishandling sensitive materials.

Political Motivation or a Substantial Legal Argument?

The timing of his indictment - arriving on the tails of allegations against Comey - has revived questions about external influence on the justice system.

Trump previously implied Bolton belonged in prison, and called him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this charge, when paired with others, has raised questions about the validity of these allegations, and why these charges are being brought now," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is able to prove the allegations alleged and show the information is properly designated, his conduct may certainly have violated the statute".

Charging such a senior official for mishandling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve sensitive materials present difficulties to prosecute, but they can and are filed against equally junior and high-level officials, from time to time," she said.

Parallels to Examinations into Trump and Biden

Trump similarly faced charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually dismissed by a federal judge and voided by his return as leader.

A independent investigator also determined that ex-President Joe Biden wrongfully stored classified documents from his time as second-in-command, but did not prosecute him.

Bolton's situation bears similarities to Biden's sensitive materials matters, said Mr Lesko, who previously held a top national security position at the Justice Department.

Strict protocols govern the management of sensitive materials. To secure a conviction, the government must prove that Bolton was aware the material he was transmitting was classified, and he had to knowingly transfer it to someone without authorization to obtain it.

"Due to the classified character of the information at issue in this case, we lack a great deal of particulars about the reasons the government believes things like the diary entries and the additional information he communicated by electronic message, and the reason there were classified," explained Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ initiated this case will be closely examined, following Trump publicly expressed his desire to see his critics charged and several of those indictments materialized.

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

"The Bolton prosecution and ultimately the charge seemed to have followed the regular procedure including the rules and standards within the DOJ," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a increasingly "traditional" document that "explicitly sets forth the particulars concerning the facts and situation here," Mr Lesko commented.

"It seems reasonably consistent with a long line of precedents... where public servants mishandled and transmitted classified material."