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Ex-President Donald Trump has repeatedly shown his wish to see critics probed, applying pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's damaging our reputation and trustworthiness," the president stated last month in a social media message.

"They impeached me, and indicted me (5 times!)" he declared, referencing the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that many specialists have stated seem to be driven by politics and challenging to win in court.

But the latest allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and ex-prosecutors say.

"In my opinion, comparing Bolton's charges to James' is like comparing apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been criminally indicted on national allegations related to the supposed improper handling of classified information. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to call him "stunningly uninformed" and unfit for the presidency in his memoir.

Specialists contend that while there may be political motivations to target Bolton, the methods used to secure an charge and the evidence compiled against him suggest a potentially stronger case than the DOJ brought against Comey.

"These actions that's being claimed is simultaneously more serious and seems to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the nation at risk by improperly keeping and transmitting sensitive documents to family members using insecure means, including AOL. Some of the documents were marked highly classified.

The indictment states that at a certain time a unauthorized user gained access to Bolton's system where files were kept and transmitted an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to eighteen separate counts of improperly handling classified information.

Retribution or a Substantial Case?

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

Trump previously suggested Bolton belonged in prison, and described him a "disreputable person". Bolton, for his part, authored a book about his time in the Trump government that was sharply negative of the leader.

"There's no question that the timing of this charge, when paired with additional cases, has raised questions about the strength of these charges, and why these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "if the Justice Department is able to demonstrate the allegations alleged and show the material is properly classified, his behavior may certainly have broken the law".

Prosecuting such a senior figure for mishandling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials pose difficulties to prosecute, but they can and are filed against both junior and high-level officials, from occasionally," she explained.

Similarities to Investigations into Trump and President

Trump similarly encountered allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was eventually thrown out by a federal judge and negated by his re-election as leader.

A independent investigator additionally found that ex-President Joe Biden wrongfully stored sensitive materials from his period as second-in-command, but failed to prosecute him.

Bolton's case shares characteristics to Trump's classified documents matters, noted Mr Lesko, who previously held a top national security position at the DOJ.

Strict protocols regulate the handling of classified documents. To win a guilty verdict, the government must prove that Bolton knew the information he was sending was restricted, and he had to intentionally transmit it to someone without authorization to obtain it.

"Because of the classified nature of the information at issue in this case, we lack a lot of details about the reasons the government contends things like the diary entries and the additional material he communicated by email, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the DOJ initiated this case will be under scrutiny, following Trump publicly posted his desire to see his political opponents prosecuted and several of those indictments came to fruition.

But Mr Lesko indicated in Bolton's case, prosecutors appear to have adhered to protocol.

"This Bolton case and ultimately the charge appeared to have observed the regular 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 "clearly sets forth the particulars involving the facts and situation here," Mr Lesko commented.

"It seems fairly consistent with a long line of precedents... where government officials mishandled and transmitted sensitive information."