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Ex-President Donald Trump has repeatedly shown his wish to see opponents investigated, applying pressure on the DOJ to charge ex 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 post.

"I was impeached twice, and indicted me (5 times!)" he declared, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in cases that many experts have stated seem to be driven by politics and challenging to succeed in court.

But the most recent charges against a Trump critic, former security advisor John Bolton, stand apart, legal experts and former prosecutors assert.

"In my opinion, contrasting Bolton's charges to James' 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. Since leaving the White House in 2019, he has become a outspoken Trump critic, going so far as to call him "remarkably ignorant" and unsuitable for office in his memoir.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the proof compiled against him suggest a potentially stronger case than the DOJ presented against Comey.

"This misconduct that's being alleged is both more serious and seems to have occurred over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and after his 2019 White House departure, authorities claimed that Bolton put the nation at risk by wrongfully retaining and sending sensitive documents to relatives using unprotected methods, including AOL. Some of the documents were marked highly classified.

The charge alleges that at a certain time a hacker gained access to Bolton's account where files were stored and sent an apparent threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

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

Political Motivation or a Substantial Case?

The schedule of his charge - coming on the heels of allegations against James - has renewed concerns about external influence on the justice system.

Trump once implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the schedule of this indictment, when paired with others, has raised questions about the strength of these allegations, and why these counts are being filed at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to prove the allegations alleged and demonstrate the information is properly designated, his conduct may very well have violated the statute".

Prosecuting such a high-ranking official for improperly handling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information pose difficulties to prosecute, but they may and are filed against equally low-level and high-level officials, from occasionally," she said.

Parallels to Investigations into Former President and President

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

A independent investigator also found that ex-President Joe Biden improperly stored classified documents from his time as vice president, but failed to criminally charge him.

Bolton's case shares characteristics to Biden's classified documents issues, noted Mr Lesko, who previously held a top national security role at the Justice Department.

Strict protocols govern the handling of classified documents. To win a guilty verdict, the government must demonstrate that Bolton was aware the material he was sending was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Because of the classified nature of the material at question in this matter, we lack a lot of particulars about why the prosecution believes things like the diary entries and the other information he shared by email, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ initiated this case will be closely examined, after Trump publicly expressed his wish to see his political opponents prosecuted and some of those charges materialized.

But Mr Lesko indicated in Bolton's case, authorities seem to have adhered to protocol.

"This Bolton case and eventually the charge appeared to have observed the regular procedure including the rules and norms within the Department of Justice," he stated.

Unlike Comey's brief, concise charge, Bolton's was a more "conventional" document that "explicitly sets forth the particulars concerning the circumstances and situation here," Mr Lesko commented.

"It seems reasonably consistent with a long line of cases... where public servants improperly handled and transmitted classified material."