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Ex-President Donald Trump has repeatedly expressed his desire to see critics investigated, exerting pressure on the DOJ to charge former 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 wrote last month in a social media message.

"They impeached twice, and indicted me (5 times!)" he said, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's civil case.

Each have subsequently been indicted, in situations that numerous specialists have stated appear to be politically motivated and challenging to win in court.

But the latest allegations against a presidential opponent, ex security advisor John Bolton, stand apart, legal experts and former prosecutors assert.

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

The Details of the Case

Bolton has been criminally indicted on national allegations related to the alleged improper handling of classified information. After leaving the White House in 2019, he has become a outspoken Trump critic, even to describe him "remarkably ignorant" and unsuitable for office in his memoir.

Specialists contend that while there may be political reasons to go after Bolton, the procedures used to secure an charge and the proof gathered against him suggest a possibly stronger legal argument than the DOJ brought against James.

"These actions that's being claimed is simultaneously more severe and seems to have taken place over a significant period of time," 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 following his 2019 White House departure, prosecutors alleged that Bolton put the nation at danger by wrongfully retaining and sending classified information to relatives using insecure means, including AOL. Some of the documents were labeled top secret.

The charge alleges that at a certain time a unauthorized user accessed to Bolton's account where documents were stored and sent an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to eighteen separate counts of improperly handling sensitive materials.

Political Motivation or a Strong Case?

The schedule of his indictment - coming on the heels of charges against Comey - has renewed questions about political pressure on the legal system.

Trump once suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, authored a book about his experience in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this indictment, when combined with others, has prompted questions about the strength of these allegations, and why these counts are being filed 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 stated and show the information is properly designated, his behavior may very well have violated the law".

Prosecuting such a high-ranking figure for improperly handling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern sensitive materials pose difficulties to prosecute, but they can and are filed against equally low-level and senior personnel, from time to time," she explained.

Similarities to Examinations into Former President and President

Trump similarly faced charges of improperly storing classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that matter was ultimately thrown out by a court official and voided by his re-election as president.

A special counsel additionally determined that former President Joe Biden wrongfully stored sensitive materials from his time as second-in-command, but did not prosecute him.

Bolton's case bears similarities to Biden's classified documents matters, said Mr Lesko, who also held a senior security role at the DOJ.

Strict procedures regulate the management of classified documents. To win a guilty verdict, the government must prove that Bolton was aware the information he was sending was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the classified character of the material at question in this case, we lack a great deal of particulars about the reasons the prosecution believes things like the diary entries and the additional material he communicated by electronic message, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the DOJ brought this case will be closely examined, following Trump openly posted his desire to see his critics charged and several of those charges materialized.

But Mr Lesko said in Bolton's case, authorities appear to have followed standard procedure.

"This Bolton case and ultimately the indictment seemed to have followed the standard procedure including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's brief, concise charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details involving the circumstances and circumstances in this instance," Mr Lesko said.

"It appears reasonably aligned with a long line of cases... where government officials mishandled and shared classified material."