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Former President Donald Trump has repeatedly shown his desire to see critics probed, applying influence 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 trustworthiness," the leader wrote last month in a social media message.

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

Each have since been charged, in situations that many experts have said appear to be politically motivated and difficult to win in court.

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

"I would say, comparing Bolton's charges to James' is like comparing two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

This Details of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unfit for the presidency in his memoir.

Specialists contend that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a potentially stronger legal argument than the Justice Department presented against Comey.

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

During his time as Trump's security advisor, and following his 2019 White House exit, prosecutors alleged that Bolton put the country at danger by wrongfully retaining and transmitting classified information to relatives using insecure means, including AOL. Some 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 kept and sent an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on recently to 18 distinct charges of improperly handling sensitive materials.

Retribution or a Substantial Case?

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

Trump previously implied Bolton belonged in prison, 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 president.

"There's no question that the schedule of this indictment, when combined with additional cases, has prompted questions about the validity of these allegations, and why these counts are being brought at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is able to prove the facts alleged and show the material is correctly classified, his behavior may certainly have broken the statute".

Prosecuting such a senior figure for improperly handling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve classified information present challenges to try, but they can and are filed against both low-level and high-level personnel, from time to time," she explained.

Similarities to Investigations into Trump and President

Trump similarly faced allegations of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their return, but that matter was eventually thrown out by a court official and negated by his return as president.

A special counsel also determined that former President Joe Biden improperly stored classified documents from his time as vice president, but did not criminally charge him.

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

Rigorous protocols regulate the management of sensitive materials. To win a guilty verdict, the prosecution must prove that Bolton was aware the material he was sending was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the sensitive character of the material at issue in this matter, we don't have a lot of details about why the prosecution contends elements like the diary entries and the other material he communicated by email, and why there were restricted," said Mr Jaffer.

A Increasingly Traditional Legal Action

The procedure by which the DOJ initiated this legal action will be closely examined, following Trump openly posted his wish to see his political opponents charged and some of those charges materialized.

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

"The Bolton case and ultimately the indictment appeared to have followed the standard process including the regulations and standards within the DOJ," he said.

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

"It appears fairly aligned with a series of cases... where government officials improperly handled and shared sensitive information."