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Former President Donald Trump has repeatedly shown his wish to see opponents probed, applying pressure on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our reputation and credibility," the president wrote recently in a social media message.

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

Each have since been charged, in situations that numerous experts have said appear to be politically motivated and difficult to succeed in court.

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

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

This Details of Bolton's Case

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has become a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unfit for the presidency in his memoir.

Experts contend that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the proof compiled against him suggest a potentially stronger legal argument than the DOJ presented against James.

"These actions that's being alleged is both more serious and seems to have taken place over a considerable period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and following his 2019 White House departure, prosecutors claimed that Bolton put the nation at danger by improperly keeping and transmitting classified information to family members using insecure means, including AOL. Some of the materials were marked highly classified.

The charge alleges that at one point a hacker accessed to Bolton's system where documents were kept and sent an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on recently to eighteen distinct charges of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the heels of allegations against Comey - has revived concerns about external influence on the legal system.

Trump previously suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, authored a publication about his experience in the Trump administration that was highly critical of the president.

"There's no question that the schedule of this indictment, when paired with additional cases, has prompted doubts about the validity of these charges, and the reason these charges are being filed now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the DOJ is able to prove the allegations alleged and show the information is correctly designated, his behavior may very well have broken the law".

Prosecuting such a senior official for mishandling sensitive materials is "uncommon" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern classified information pose challenges to try, but they can and are filed against equally low-level and senior officials, from time to time," she said.

Parallels to Investigations into Trump and President

Trump similarly encountered allegations of wrongfully keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was eventually dismissed by a federal judge and voided by his return as president.

A independent investigator also found that ex-President Joe Biden improperly maintained classified documents from his time as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's sensitive materials matters, noted Mr Lesko, who previously held a senior security position at the DOJ.

Rigorous protocols govern the management of classified documents. To secure a conviction, the government must prove that Bolton was aware the material he was sending was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the classified nature of the material at issue in this matter, we lack a great deal of details about why the prosecution believes things like the diary entries and the additional information he shared by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Traditional Legal Action

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

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

"This Bolton prosecution and ultimately the indictment appeared to have observed the regular process including the regulations and norms within the DOJ," he said.

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

"It appears fairly aligned with a long line of cases... where government officials mishandled and shared classified material."