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

"We cannot postpone any longer, it's damaging our standing and credibility," the leader wrote recently in a Truth Social post.

"They impeached me, and charged me (five times!)" he declared, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in situations that many experts have stated seem to be driven by politics and difficult to succeed in court.

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

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

The Details of the Legal Situation

Bolton has been formally charged on national allegations pertaining to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has become a vocal presidential opponent, even to describe him "stunningly uninformed" and unfit for the presidency in his memoir.

Experts say that while there may be political motivations to target Bolton, the procedures used to obtain an charge and the proof compiled against him suggest a potentially stronger legal argument than the Justice Department brought against Comey.

"This misconduct that's being claimed is simultaneously more severe and appears to have taken place 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 following his 2019 White House departure, prosecutors alleged that Bolton put the nation at danger by wrongfully keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the materials were marked top secret.

The charge states that at one point a hacker gained access to Bolton's system where files were stored and transmitted an apparent threat to cause "the largest scandal 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.

Retribution or a Substantial Case?

The schedule of his charge - arriving on the tails of allegations against James - has revived questions about external influence on the justice system.

Trump previously suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, 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 raised questions about the validity of these charges, and why these counts are being filed now," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is able to prove the facts alleged and show the information is properly classified, his behavior may certainly have violated the statute".

Charging such a senior official for improperly handling sensitive materials is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern classified information pose difficulties to try, but they can and are brought against equally junior and senior personnel, from time to time," she explained.

Similarities to Examinations into Former President and Biden

Trump likewise faced allegations of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that case was ultimately thrown out by a federal judge and negated by his return as president.

A special counsel additionally found that former President Joe Biden wrongfully maintained classified documents from his time as second-in-command, but did not prosecute him.

Bolton's case bears similarities to Trump's sensitive materials issues, said Mr Lesko, who also held a senior security role at the DOJ.

Strict procedures govern the management of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton knew the material he was transmitting was restricted, and he had to intentionally transmit it to someone without authorization to obtain it.

"Because of the classified nature of the material at question in this matter, we don't have a lot of details about why the government believes things like the personal notes and the additional information he shared by email, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ initiated this legal action will be under scrutiny, after Trump openly posted his wish to see his political opponents charged and several of those indictments came to fruition.

But Mr Lesko indicated in Bolton's situation, authorities seem to have followed protocol.

"This Bolton prosecution and eventually the charge seemed to have followed the standard process including the regulations and norms within the DOJ," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a increasingly "conventional" filing that "clearly outlines the particulars involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears reasonably aligned with a long line of cases... where government officials improperly handled and shared sensitive information."