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Ex-President Donald Trump has consistently expressed his desire to see opponents probed, exerting influence on the DOJ to charge ex 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 stated recently in a Truth Social post.

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

Each have since been indicted, in cases that many experts have said appear to be politically motivated and difficult to win in legal proceedings.

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

"I would say, comparing 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.

The Details of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. Since leaving the White House in 2019, he has become a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Specialists contend that while there may be political motivations to target Bolton, the procedures used to secure an indictment and the proof gathered against him indicate a possibly stronger legal argument than the Justice Department brought against Comey.

"These actions that's being claimed is both more serious and appears to have occurred over a considerable duration," said 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 departure, authorities alleged that Bolton put the country at risk by improperly retaining and transmitting sensitive documents to family members using unprotected methods, including AOL. Several of the documents were labeled highly classified.

The charge alleges that at one point a hacker gained access to Bolton's account where files were stored and transmitted an seeming 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 18 separate counts of mishandling sensitive materials.

Political Motivation or a Strong Case?

The timing of his indictment - arriving on the heels of charges against James - has renewed questions about political pressure on the justice system.

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

"Undoubtedly that the schedule of this indictment, when paired with others, has raised doubts about the validity of these charges, and why these charges are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "should the DOJ is able to prove the allegations alleged and demonstrate the information is correctly designated, his conduct may very well have broken the law".

Charging such a senior official for improperly handling classified documents is "rare" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

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

Similarities to Examinations into Trump and President

Trump likewise encountered charges of improperly 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 leader.

A special counsel additionally found that former President Joe Biden improperly maintained classified documents from his period as vice president, but failed to criminally charge him.

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

Strict procedures govern the management of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the sensitive nature of the information at question in this case, we lack a lot of details about why the prosecution believes elements like the personal notes and the other information he communicated by electronic message, and the reason there were classified," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the Justice Department initiated this case will be under scrutiny, after Trump openly expressed his desire to see his political opponents charged and some of those indictments came to fruition.

But Mr Lesko said in Bolton's case, prosecutors appear to have followed protocol.

"This Bolton prosecution and ultimately the indictment seemed to have followed the standard process including the rules and norms within the DOJ," he said.

Unlike Comey's short, two-page charge, Bolton's was a increasingly "traditional" filing that "clearly sets forth the particulars involving the circumstances and situation in this instance," Mr Lesko said.

"It appears fairly aligned with a long line of cases... where public servants mishandled and transmitted sensitive information."