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Former President Donald Trump has consistently expressed his wish to see critics 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 killing our standing and credibility," the president wrote recently in a Truth Social message.

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

Both have since been indicted, in cases that numerous experts have said seem to be politically motivated and challenging to win in court.

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

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

The Details of the Case

Bolton has been criminally indicted on national allegations related to the alleged mishandling of sensitive materials. Since leaving the White House in 2019, he has become a vocal presidential opponent, even to call him "stunningly uninformed" and unfit for office in his book.

Experts say that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the evidence gathered against him indicate a potentially stronger case than the DOJ brought against James.

"These actions that's being claimed is both more severe and seems 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.

During his time as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton placed the country at danger by improperly retaining and transmitting sensitive documents to relatives using unprotected methods, including AOL. Several of the documents were marked highly classified.

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

Bolton entered a not guilty plea during a hearing on Friday to eighteen distinct counts of improperly handling classified information.

Political Motivation or a Substantial Case?

The timing of his indictment - coming on the heels of allegations against James - has revived concerns about political pressure 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 experience in the Trump government that was sharply negative of the president.

"Undoubtedly that the timing of this indictment, when combined with others, has prompted questions about the strength of these charges, and the reason these charges are being brought at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

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

Prosecuting such a senior figure for mishandling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern classified information pose challenges to prosecute, but they can and are filed against equally junior and high-level personnel, from time to time," she explained.

Similarities to Investigations into Former President and President

Trump similarly encountered allegations of wrongfully keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that matter was ultimately dismissed by a federal judge and voided by his re-election as president.

A independent investigator also found that former President Joe Biden improperly stored classified documents from his period as vice president, but failed to criminally charge him.

Bolton's case shares characteristics to Trump's sensitive materials matters, said Mr Lesko, who previously held a senior national security position at the DOJ.

Strict procedures regulate the management of sensitive materials. To win a guilty verdict, the prosecution must prove that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the sensitive nature of the material at issue in this matter, we lack a great deal of details about the reasons the prosecution believes elements like the diary entries and the additional material he communicated by email, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The process by which the Justice Department initiated this legal action will be under scrutiny, following Trump publicly expressed his desire to see his critics charged and several of those charges materialized.

But Mr Lesko indicated in Bolton's case, authorities seem to have adhered to standard procedure.

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

In contrast to Comey's brief, two-page indictment, Bolton's was a more "conventional" document that "clearly sets forth the details involving the circumstances and circumstances here," Mr Lesko commented.

"It seems fairly aligned with a long line of cases... where public servants mishandled and transmitted classified material."