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Ex-President Donald Trump has consistently expressed his desire to see critics investigated, exerting influence on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our standing and trustworthiness," the leader stated last month in a Truth Social post.

"I was impeached twice, and indicted me (five times!)" he said, referencing the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Both have since been charged, in situations that many experts have stated seem to be driven by politics and challenging to win in court.

But the latest charges against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and former prosecutors assert.

"I would say, contrasting Bolton's charges to Comey's is like comparing two different things," 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 mishandling of classified information. After leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to call him "stunningly uninformed" and unsuitable for office in his memoir.

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

"This misconduct that's being alleged is both more serious and appears to have taken place over a considerable period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House departure, authorities alleged that Bolton placed the country at danger by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

The charge states that at a certain time a unauthorized user gained access to Bolton's system where documents were kept and transmitted an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to 18 separate counts of improperly handling sensitive materials.

Political Motivation or a Substantial Legal Argument?

The schedule of his charge - arriving on the tails of charges against Comey - has revived questions about political pressure on the legal system.

Trump once implied Bolton should be in prison, and described him a "sleazebag". Bolton, for his role, authored a book about his experience in the Trump administration that was highly critical of the president.

"There's no question that the timing of this indictment, when paired with others, has raised doubts about the strength of these charges, and the reason these charges are being filed now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "if the DOJ is able to demonstrate the allegations alleged and show the material is correctly classified, his behavior may certainly have violated the statute".

Charging such a high-ranking official for mishandling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials present challenges to prosecute, but they can and are filed against both junior and high-level officials, from time to time," she explained.

Parallels to Investigations into Former President and President

Trump likewise faced allegations 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 federal judge and negated by his return as leader.

A independent investigator also determined that ex-President Joe Biden improperly stored classified documents from his period as second-in-command, but did not prosecute him.

Bolton's situation bears similarities to Trump's classified documents matters, noted Mr Lesko, who previously held a senior national security position at the Justice Department.

Strict protocols regulate the handling of classified documents. To win a guilty verdict, the government must demonstrate that Bolton knew the material he was transmitting was classified, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the sensitive nature of the information at question in this matter, we lack a great deal of details about why the prosecution contends elements like the diary entries and the additional information he shared by electronic message, and the reason there were classified," explained Mr Jaffer.

A More Conventional Prosecution

The process by which the Justice Department initiated this case will be closely examined, after Trump openly expressed his desire to see his political opponents prosecuted and several of those charges came to fruition.

But Mr Lesko indicated in Bolton's situation, prosecutors seem to have adhered to standard procedure.

"The Bolton case and ultimately the charge seemed to have followed the regular procedure including the regulations and norms within the DOJ," he said.

In contrast to Comey's brief, concise indictment, Bolton's was a more "traditional" filing that "explicitly sets forth the details concerning the circumstances and situation here," Mr Lesko said.

"It appears fairly consistent with a series of cases... where government officials mishandled and transmitted sensitive information."