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Former President Donald Trump has consistently shown his desire to see opponents investigated, 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 killing our reputation and trustworthiness," the leader wrote last month in a social media message.

"I was impeached twice, and indicted me (5 times!)" he declared, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's lawsuit.

Each have since been indicted, in cases that many specialists have said seem to be driven by politics and difficult to succeed in legal proceedings.

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

"I would say, contrasting Bolton's case to Comey's is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Case

Bolton has been formally charged on national allegations related to the supposed mishandling 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 unsuitable for the presidency in his memoir.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an charge and the proof compiled against him indicate a possibly stronger legal argument than the DOJ presented against James.

"These actions that's being alleged is simultaneously more severe and appears to have taken place over a significant duration," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and following his 2019 White House departure, prosecutors claimed that Bolton placed the country at risk by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled top secret.

The charge states that at a certain time a unauthorized user accessed to Bolton's system where documents were kept and transmitted an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on recently to 18 separate charges of mishandling sensitive materials.

Political Motivation or a Substantial Legal Argument?

The timing of his indictment - coming on the heels of allegations against Comey - has renewed concerns about external influence on the justice system.

Trump once suggested Bolton belonged in jail, and described him a "disreputable person". Bolton, for his part, authored a publication about his time in the Trump government that was highly critical of the president.

"There's no question that the timing of this indictment, when paired with others, has prompted doubts about the validity of these allegations, and why these charges are being brought at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "should the DOJ is capable to prove the facts stated and show the information is correctly classified, his conduct may very well have broken the statute".

Charging such a high-ranking official for improperly handling sensitive materials is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials present difficulties to prosecute, but they can and are brought against equally low-level and senior officials, from occasionally," she said.

Similarities to Investigations into Former President and Biden

Trump likewise faced allegations of wrongfully keeping 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 re-election as president.

A independent investigator also found that former President Joe Biden improperly stored classified documents from his period as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Biden's classified documents issues, said Mr Lesko, who also held a senior national security position at the Justice Department.

Strict protocols govern the management of sensitive materials. To secure a conviction, the prosecution must demonstrate that Bolton was aware the material he was sending was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Due to the classified character of the material at issue in this case, we lack a great deal of particulars about why the government believes elements like the diary entries and the additional information he communicated by electronic message, and why there were classified," said Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the DOJ brought this case will be closely examined, following Trump publicly expressed his wish to see his political opponents charged and several of those indictments came to fruition.

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

"The Bolton prosecution and eventually the charge appeared to have observed the regular procedure including the rules and norms within the DOJ," he said.

In contrast to Comey's brief, two-page charge, Bolton's was a more "conventional" filing that "clearly sets forth the details involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears fairly aligned with a series of precedents... where government officials mishandled and transmitted classified material."