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Former President Donald Trump has repeatedly shown his desire to see critics investigated, exerting influence 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 trustworthiness," the leader wrote recently in a social media post.

"I was impeached me, and charged me (5 times!)" he said, mentioning the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

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

But the latest charges against a Trump critic, ex national security adviser John Bolton, differ significantly, legal specialists and ex-prosecutors say.

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

This Specifics of the Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of classified information. Since leaving the White House in 2019, he has emerged as a vocal Trump critic, even to describe him "stunningly uninformed" and unsuitable for office in his book.

Specialists contend that while there may be political reasons to go after Bolton, the methods used to secure an charge and the proof gathered against him suggest a potentially more substantial legal argument than the Justice Department brought against James.

"These actions that's being alleged is simultaneously more severe and appears to have taken place 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 after his 2019 White House exit, authorities claimed that Bolton put the nation at danger by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Several of the documents were marked highly classified.

The indictment states that at a certain time a unauthorized user accessed to Bolton's system where documents were stored and transmitted 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 eighteen distinct counts of improperly handling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his charge - coming on the tails of charges against James - has renewed concerns about external influence on the justice system.

Trump previously implied Bolton belonged in jail, and described 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 timing of this indictment, when combined with others, has prompted questions about the strength of these allegations, and why these counts are being brought at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "if the Justice Department is able to demonstrate the facts alleged and demonstrate the material is correctly designated, his behavior may certainly have violated the law".

Charging such a high-ranking official for improperly handling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern sensitive materials pose challenges to try, but they can and are brought against equally low-level and high-level officials, from time to time," she explained.

Parallels to Investigations into Trump and President

Trump similarly faced allegations of improperly storing classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was eventually thrown out by a court official and negated by his return as leader.

A independent investigator additionally found that ex-President Joe Biden wrongfully maintained classified documents from his time as second-in-command, but did not prosecute him.

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

Rigorous procedures govern the management of classified documents. To win a conviction, the government must demonstrate that Bolton knew the information he was transmitting was classified, and he had to knowingly transmit it to someone not entitled to obtain it.

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

A Increasingly Traditional Prosecution

The process by which the Justice Department initiated this legal action will be under scrutiny, after Trump publicly expressed his desire to see his critics prosecuted and some of those charges materialized.

But Mr Lesko said in Bolton's case, authorities seem to have followed protocol.

"The Bolton case and ultimately the charge seemed to have followed the regular process including the rules and standards within the Department of Justice," he stated.

Unlike Comey's short, concise indictment, Bolton's was a increasingly "traditional" filing that "clearly sets forth the details concerning the circumstances and circumstances in this instance," Mr Lesko commented.

"It appears reasonably aligned with a series of precedents... where government officials mishandled and transmitted classified material."