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Ex-President Donald Trump has consistently shown his wish to see opponents investigated, exerting pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and trustworthiness," the president stated recently in a Truth Social message.

"I was impeached twice, and indicted me (5 times!)" he declared, referencing the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Both have since been indicted, in cases that numerous experts have said seem to be driven by politics and difficult to win in court.

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

"I would say, comparing Bolton's charges to James' is like equating two different things," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

This Details of the Case

Bolton has been formally charged on national allegations related to the supposed improper handling of classified information. Since leaving the White House in 2019, he has emerged as a vocal presidential opponent, even to call him "stunningly uninformed" and unsuitable for office in his book.

Experts contend that while there may be political reasons to go after Bolton, the methods used to obtain an charge and the evidence compiled against him suggest a possibly more substantial legal argument than the Justice Department presented against Comey.

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

During his time as Trump's security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton placed the nation at danger by improperly keeping and sending classified information to family members using unprotected methods, including AOL. Some of the materials were labeled top secret.

The charge alleges that at one point a hacker gained access to Bolton's system where documents were stored and transmitted an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to eighteen separate charges of mishandling sensitive materials.

Political Motivation or a Strong Case?

The timing of his indictment - coming on the heels of allegations against Comey - has renewed concerns about political pressure on the justice system.

Trump previously suggested Bolton should be in jail, and described him a "sleazebag". Bolton, for his part, authored a publication about his experience in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this indictment, when combined with others, has prompted doubts about the validity of these charges, and why these charges are being brought now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "if the Justice Department is capable to prove the allegations stated and demonstrate the material is properly classified, his conduct may very well have violated the law".

Charging such a senior official for mishandling classified documents is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials present challenges to try, but they may and are brought against equally low-level and senior personnel, from time to time," she explained.

Similarities to Investigations into Former President and President

Trump similarly faced charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that matter was ultimately thrown out by a court official and voided by his re-election as president.

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

Bolton's situation shares characteristics to Trump's sensitive materials issues, noted Mr Lesko, who previously held a senior national security position at the DOJ.

Strict protocols regulate the management of sensitive materials. To secure a guilty verdict, the government must demonstrate that Bolton knew the information he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the classified nature of the information at question in this matter, we don't have a great deal of details about the reasons the government contends things like the diary entries and the other information he shared by email, and why there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The process by which the DOJ initiated this case will be closely examined, following Trump openly expressed his wish to see his political opponents charged and some of those charges materialized.

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

"The Bolton prosecution and ultimately the indictment seemed to have observed the regular process including the rules and norms within the DOJ," he said.

In contrast to Comey's short, two-page charge, Bolton's was a more "conventional" filing that "explicitly sets forth the details involving the circumstances and situation in this instance," Mr Lesko commented.

"It seems reasonably aligned with a long line of precedents... where public servants improperly handled and shared sensitive information."