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Ex-President Donald Trump has repeatedly expressed his desire to see opponents probed, exerting pressure on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our reputation and trustworthiness," the leader wrote last month in a Truth Social message.

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

Both have since been indicted, in situations that numerous experts have stated seem to be politically motivated and difficult to succeed in legal proceedings.

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

"I would say, contrasting Bolton's case to James' is like equating apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on national allegations pertaining to the supposed mishandling of sensitive materials. Since leaving the White House in 2019, he has emerged as a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts say that while there may be political motivations to go after Bolton, the procedures used to obtain an charge and the evidence compiled against him suggest a potentially more substantial legal argument than the DOJ presented against James.

"This misconduct that's being alleged is both more severe and appears to have occurred over a considerable period of time," said 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 alleged that Bolton placed the country at danger by wrongfully keeping 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 gained access to Bolton's account 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 distinct counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the tails of allegations against Comey - has revived concerns about political pressure on the justice system.

Trump once suggested Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, wrote a book about his experience in the Trump government that was sharply negative of the leader.

"Undoubtedly that the schedule of this charge, when paired with additional cases, has prompted questions about the validity of these allegations, and why these counts are being filed at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "should the DOJ is able to prove the allegations alleged and show the information is correctly designated, his conduct may certainly have broken the law".

Prosecuting such a high-ranking figure 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 concern sensitive materials present difficulties to try, but they can and are brought against equally junior and high-level personnel, from occasionally," she explained.

Similarities to Investigations into Trump and President

Trump likewise encountered charges of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was eventually dismissed by a court official and voided by his return as leader.

A special counsel also determined that ex-President Joe Biden improperly maintained classified documents from his period as vice president, but did not criminally charge him.

Bolton's case bears similarities to Biden's classified documents issues, noted Mr Lesko, who previously held a top security position at the Justice Department.

Rigorous procedures regulate the handling of sensitive materials. To secure a guilty verdict, the prosecution must prove that Bolton was aware the material he was transmitting was classified, and he had to intentionally transmit it to someone without authorization to receive it.

"Because of the classified character of the material at issue in this case, we don't have a great deal of particulars about the reasons the prosecution contends elements like the diary entries and the other material he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, after Trump openly posted his desire to see his critics prosecuted and several of those charges came to fruition.

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

"The Bolton case and eventually the indictment appeared to have observed the standard procedure including the regulations and norms within the DOJ," he stated.

Unlike Comey's brief, two-page charge, Bolton's was a more "conventional" document that "explicitly outlines the particulars involving the facts and situation in this instance," Mr Lesko commented.

"It appears fairly aligned with a long line of precedents... where public servants mishandled and transmitted classified material."