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Former President Donald Trump has consistently shown his wish to see opponents probed, exerting pressure on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our standing and trustworthiness," the president wrote last month in a social media post.

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

Both have since been charged, in cases that many specialists have said appear to be driven by politics and challenging to win in legal proceedings.

But the most recent allegations against a Trump critic, former security advisor John Bolton, stand apart, legal specialists and ex-prosecutors assert.

"In my opinion, contrasting Bolton's case to Comey's is like equating two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

This Specifics of the Legal Situation

Bolton has been formally charged on federal charges related to the alleged improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken Trump critic, going so far as to call him "remarkably ignorant" and unfit for office in his book.

Specialists say that while there may be political motivations to target Bolton, the methods used to secure an indictment and the proof gathered against him indicate a possibly stronger case than the DOJ presented against James.

"These actions that's being alleged is simultaneously more serious and seems to have taken place over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and after his 2019 White House departure, prosecutors claimed that Bolton placed the nation at danger by improperly keeping and sending sensitive documents to relatives using unprotected methods, including AOL. Several of the materials were labeled highly classified.

The indictment states that at one point a unauthorized user accessed to Bolton's account where documents were stored and sent an seeming 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 separate charges of improperly handling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his indictment - coming on the heels of charges against James - has renewed questions about external influence on the legal system.

Trump once suggested Bolton should be in prison, and described him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this indictment, when combined with additional cases, has prompted questions about the validity of these charges, and the reason these charges are being brought at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is able to demonstrate the allegations alleged and demonstrate the information is properly classified, his conduct may certainly have broken the statute".

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

"Situations that concern sensitive materials present challenges to prosecute, but they can and are brought against equally low-level and high-level officials, from time to time," she said.

Similarities to Investigations into Former President and Biden

Trump similarly faced allegations of improperly storing classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that matter was ultimately dismissed by a court official and negated by his return as president.

A special counsel additionally found that ex-President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Trump's sensitive materials matters, noted Mr Lesko, who also held a senior security position at the Justice Department.

Strict procedures govern the handling of sensitive materials. To win a guilty verdict, the government must demonstrate that Bolton was aware the information he was transmitting was classified, and he had to intentionally transfer it to someone without authorization to receive it.

"Due to the classified character of the information at question in this case, we don't have a great deal of details about why the prosecution contends things like the diary entries and the other material he communicated by email, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the Justice Department initiated this legal action will be under scrutiny, after Trump publicly expressed his wish to see his political opponents prosecuted and some of those indictments came to fruition.

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

"This Bolton prosecution and eventually the indictment appeared to have observed the regular process including the regulations and standards within the DOJ," he stated.

In contrast to Comey's short, two-page indictment, Bolton's was a more "traditional" filing that "explicitly sets forth the particulars involving the facts and situation here," Mr Lesko said.

"It appears fairly consistent with a long line of cases... where public servants mishandled and transmitted classified material."