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Former President Donald Trump has repeatedly expressed his wish to see critics probed, applying influence on the DOJ to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our standing and credibility," the leader stated recently in a Truth Social message.

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

Both have subsequently been indicted, in cases that many experts have said seem to be driven by politics and difficult to win in legal proceedings.

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

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

The Specifics of the Case

Bolton has been criminally indicted on national allegations related to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unfit for the presidency in his book.

Specialists contend that while there may be political reasons to go after Bolton, the methods used to obtain an charge and the evidence gathered against him suggest a potentially more substantial case than the Justice Department presented against James.

"This misconduct that's being alleged 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 after his 2019 White House exit, prosecutors alleged that Bolton put the nation at risk by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Several of the documents were marked top secret.

The indictment alleges that at one point a hacker gained access to Bolton's account where documents were kept and transmitted an apparent threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Substantial Legal Argument?

The schedule of his charge - coming on the tails of allegations against James - has renewed questions about political pressure on the justice system.

Trump previously suggested Bolton should be in jail, and described him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump administration that was sharply negative of the leader.

"There's no question that the timing of this charge, when paired with additional cases, has prompted questions about the validity of these allegations, and the reason these charges are being filed now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

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

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

"Situations that concern sensitive materials present difficulties to try, but they may and are brought against equally junior and senior personnel, from occasionally," she explained.

Parallels to Investigations into Former President and Biden

Trump likewise faced charges of improperly keeping classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was eventually dismissed by a federal judge and voided by his re-election as president.

A independent investigator also determined that ex-President Joe Biden improperly maintained sensitive materials from his period as second-in-command, but failed to prosecute him.

Bolton's case bears similarities to Trump's sensitive materials issues, said Mr Lesko, who previously held a senior security position at the Justice Department.

Rigorous procedures govern the handling of sensitive materials. To win a conviction, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the sensitive nature of the material at issue in this matter, we lack a lot of details about the reasons the government contends elements like the diary entries and the additional material he shared by electronic message, and why there were classified," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the Justice Department initiated this legal action will be closely examined, following Trump publicly expressed his desire to see his critics prosecuted and some 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 appeared to have observed the standard process including the regulations and standards within the DOJ," he stated.

In contrast to Comey's brief, two-page indictment, Bolton's was a more "conventional" document that "explicitly sets forth the particulars involving the circumstances and circumstances here," Mr Lesko said.

"It seems reasonably aligned with a series of precedents... where public servants mishandled and shared sensitive information."