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

"We can't delay further, it's killing our standing and credibility," the leader wrote last month in a Truth Social message.

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

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

But the most recent charges against a presidential opponent, former security advisor John Bolton, differ significantly, legal experts and ex-prosecutors say.

"I would say, comparing Bolton's charges to Comey's is like equating two different things," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Details of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the alleged improper handling of classified information. After departing the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Experts say that while there may be political motivations to target Bolton, the methods used to obtain an charge and the evidence compiled against him indicate a possibly stronger legal argument than the DOJ brought against James.

"These actions that's being alleged is both more serious and appears to have taken place over a significant period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House exit, authorities alleged that Bolton placed the nation at danger by wrongfully retaining and transmitting classified information to relatives using unprotected methods, including AOL. Some of the materials were marked top secret.

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

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

Retribution or a Substantial Legal Argument?

The timing of his charge - coming on the tails of allegations against James - has renewed questions about political pressure on the justice system.

Trump previously suggested Bolton belonged in prison, and called him a "disreputable person". Bolton, for his part, wrote a publication about his experience in the Trump government that was highly critical of the leader.

"There's no question that the schedule of this charge, when paired with others, has prompted doubts about the validity of these charges, and why these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "should the DOJ is able to demonstrate the allegations stated and show the material is correctly classified, his behavior may very well have broken the law".

Charging such a senior official for mishandling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

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

Similarities to Examinations into Former President and Biden

Trump likewise encountered allegations of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was eventually thrown out by a court official and voided by his return as leader.

A special counsel also found that former President Joe Biden wrongfully stored sensitive materials from his time as vice president, but did not prosecute him.

Bolton's situation bears similarities to Biden's classified documents issues, said Mr Lesko, who also held a top security role at the DOJ.

Rigorous procedures regulate the management of sensitive materials. To secure a guilty verdict, the government must demonstrate that Bolton was aware the information he was sending was restricted, and he had to knowingly transmit it to someone not entitled to receive it.

"Due to the sensitive nature of the material at question in this case, we lack a great deal of particulars about the reasons the government believes things like the personal notes and the additional material he communicated by electronic message, and why there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the Justice Department initiated this case will be under scrutiny, following Trump publicly expressed his desire to see his political opponents charged and several of those indictments materialized.

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

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

In contrast to Comey's brief, two-page charge, Bolton's was a increasingly "traditional" document that "explicitly sets forth the particulars involving the circumstances and circumstances in this instance," Mr Lesko commented.

"It seems fairly aligned with a series of precedents... where public servants mishandled and shared sensitive information."