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Former President Donald Trump has consistently shown his desire to see critics investigated, applying pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

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

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

Each have since been indicted, in situations that many experts have stated appear to be driven by politics and challenging to succeed in court.

But the latest allegations against a Trump critic, ex national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors assert.

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

The Details of the Case

Bolton has been formally charged on national allegations pertaining to the alleged improper handling of sensitive materials. 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 the presidency in his book.

Experts say that while there may be political reasons to target Bolton, the methods used to secure an indictment and the evidence gathered against him suggest a potentially more substantial legal argument than the DOJ brought against Comey.

"This misconduct that's being alleged is both more severe 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 tenure as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton put the country at risk by improperly retaining and sending classified information to family members using insecure means, including AOL. Several of the materials were labeled highly classified.

The indictment states that at a certain time a unauthorized user accessed to Bolton's account where files were stored and sent an seeming threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on Friday to eighteen separate counts of mishandling sensitive materials.

Political Motivation or a Strong Case?

The schedule of his charge - coming on the heels of allegations against James - has revived questions about political pressure on the legal system.

Trump once implied Bolton belonged in prison, and called him a "disreputable person". Bolton, for his role, wrote a publication about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the timing of this charge, when paired with additional cases, has prompted doubts about the strength of these allegations, and the reason these counts are being filed at this time," said Jamil Jaffer, creator and executive director of the National Security Institute.

However, he added, "should the Justice Department is able to demonstrate the facts alleged and demonstrate the information is properly designated, his behavior may very well have violated the law".

Charging such a senior official for mishandling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials present difficulties to try, but they may and are brought against both low-level and high-level personnel, from occasionally," she said.

Parallels to Examinations into Trump and President

Trump similarly faced charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was eventually dismissed by a federal judge and negated by his re-election as president.

A special counsel additionally determined that ex-President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but failed to criminally charge him.

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

Rigorous procedures regulate the handling of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton knew the material he was sending was restricted, and he had to knowingly transmit it to someone not entitled to receive it.

"Due to the classified nature of the material at question in this matter, we lack a lot of details about why the prosecution contends elements like the diary entries and the other material he communicated by electronic message, and why there were classified," explained Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the DOJ brought this legal action will be closely examined, after Trump openly expressed his desire to see his critics charged and several of those indictments came to fruition.

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

"The Bolton case and eventually the indictment seemed to have observed the regular procedure including the rules and norms within the DOJ," he said.

In contrast to Comey's short, two-page charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the particulars involving the facts and circumstances here," Mr Lesko said.

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