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Former President Donald Trump has consistently expressed his desire to see critics investigated, 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 damaging our standing and credibility," the president stated recently in a social media message.

"They impeached me, and charged me (5 times!)" he said, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

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

But the most recent allegations against a presidential opponent, former national security adviser John Bolton, differ significantly, legal experts and former prosecutors say.

"In my opinion, contrasting Bolton's case to James' is like comparing two different things," said Mark Lesko, a former acting US attorney 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 sensitive materials. After leaving the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to describe him "remarkably ignorant" and unsuitable for office in his memoir.

Specialists say that while there may be political motivations to target Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a possibly stronger legal argument than the Justice Department brought against James.

"These actions that's being alleged is simultaneously more severe and appears to have occurred over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and after his 2019 White House exit, prosecutors claimed that Bolton placed the nation at risk by improperly retaining and transmitting classified information to relatives 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 system where files were kept and sent an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to 18 separate charges of improperly handling classified information.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the heels of allegations against Comey - has renewed concerns about political pressure on the legal system.

Trump once implied Bolton should be in jail, and described him a "disreputable person". Bolton, for his role, authored a book about his time in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the timing of this indictment, when paired with additional cases, has prompted questions about the strength of these allegations, and the reason these charges are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is able to demonstrate the allegations stated and show the information is correctly designated, his behavior may very well have violated the statute".

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

"Situations that involve classified information present difficulties to try, but they can and are brought against equally junior and high-level personnel, from occasionally," she explained.

Parallels to Investigations into Former President and Biden

Trump similarly encountered allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their return, but that case was eventually thrown out by a court official and negated by his return as president.

A special counsel additionally found that ex-President Joe Biden wrongfully stored sensitive materials from his time as second-in-command, but failed to criminally charge him.

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

Rigorous protocols regulate the handling of classified documents. To win a conviction, the government must prove that Bolton knew the material he was sending was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the sensitive nature of the material at issue in this matter, we don't have a great deal of particulars about the reasons the prosecution contends elements like the diary entries and the other information he communicated by email, and the reason there were classified," said Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department initiated this case will be under scrutiny, following Trump openly posted 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 standard procedure.

"This Bolton case and ultimately the charge seemed to have followed the standard procedure including the rules and standards within the Department of Justice," he said.

In contrast to Comey's brief, concise charge, Bolton's was a more "traditional" filing that "explicitly outlines the details concerning the facts and situation here," Mr Lesko commented.

"It seems fairly aligned with a series of cases... where public servants mishandled and shared classified material."