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Former President Donald Trump has repeatedly shown his desire to see opponents investigated, applying pressure on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's killing our reputation and trustworthiness," the president stated recently in a social media message.

"They impeached me, and charged me (5 times!)" he declared, referencing the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Each have subsequently been indicted, in situations that many experts have stated appear to be politically motivated and difficult to win in legal proceedings.

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

"I would say, contrasting Bolton's charges to James' is like equating two different things," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed mishandling of classified information. After leaving the White House in 2019, he has become a vocal Trump critic, even to call him "stunningly uninformed" and unfit for the presidency in his memoir.

Experts say that while there may be political reasons to target Bolton, the procedures used to secure an charge and the proof compiled against him suggest a potentially stronger case than the DOJ brought against James.

"This misconduct that's being alleged is simultaneously more serious and seems to have occurred over a significant duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and after his 2019 White House exit, authorities alleged that Bolton put the nation at danger by improperly retaining and sending sensitive documents to family members using unprotected methods, including AOL. Several of the documents were labeled top secret.

The charge states that at one point a hacker accessed to Bolton's system where files were stored and transmitted an seeming threat to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to eighteen distinct charges of mishandling sensitive materials.

Retribution or a Strong Legal Argument?

The timing of his charge - arriving on the heels of allegations against James - has revived concerns about political pressure on the legal system.

Trump once suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his role, wrote a book about his time in the Trump administration that was highly critical of the leader.

"Undoubtedly that the schedule of this indictment, when paired with additional cases, has prompted doubts about the strength of these charges, and the reason these charges are being brought now," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is able to demonstrate the allegations alleged and demonstrate the information is correctly classified, his conduct may certainly have violated the law".

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

"Cases that concern classified information pose difficulties to prosecute, but they can and are filed against both low-level and high-level officials, from time to time," she explained.

Parallels to Investigations into Former President and Biden

Trump similarly encountered charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately thrown out by a federal judge and voided by his return as leader.

A independent investigator additionally determined that ex-President Joe Biden improperly stored classified documents from his period as vice president, but did not prosecute him.

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

Rigorous protocols regulate the management of classified documents. To secure a conviction, the government must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to obtain it.

"Due to the sensitive nature of the material at issue in this matter, we lack a lot of details about the reasons the prosecution believes elements like the diary entries and the other information he communicated by email, and why there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The procedure by which the DOJ brought this case will be closely examined, following Trump openly posted his desire to see his critics prosecuted and several of those indictments came to fruition.

But Mr Lesko indicated in Bolton's case, prosecutors seem to have adhered to protocol.

"This Bolton prosecution and ultimately the indictment appeared to have observed the standard procedure including the regulations and norms within the Department of Justice," he said.

In contrast to Comey's short, two-page charge, Bolton's was a increasingly "traditional" document that "clearly outlines the details involving the circumstances and circumstances here," Mr Lesko said.

"It appears fairly aligned with a series of precedents... where public servants mishandled and transmitted sensitive information."