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Former President Donald Trump has repeatedly expressed his desire to see critics probed, applying pressure on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our standing and trustworthiness," the president wrote last month in a Truth Social message.

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

Each have since been indicted, in cases that numerous specialists have said seem to be politically motivated and difficult to win in legal proceedings.

But the latest charges against a presidential opponent, former security advisor John Bolton, stand apart, legal experts and former prosecutors assert.

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

This Specifics of the Legal Situation

Bolton has been criminally indicted on national allegations related to the supposed mishandling of sensitive materials. Since departing the White House in 2019, he has become a outspoken Trump critic, even to describe him "remarkably ignorant" and unsuitable for the presidency in his memoir.

Experts say that while there may be political motivations to target Bolton, the methods used to obtain an charge and the proof gathered against him indicate a potentially stronger case than the Justice Department presented against James.

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

Throughout his time as Trump's security advisor, and after his 2019 White House departure, prosecutors alleged that Bolton put the nation at danger by improperly retaining and transmitting classified information to family members using unprotected methods, including AOL. Some of the materials were marked top secret.

The charge alleges that at one point a unauthorized user accessed to Bolton's system where documents were stored and sent an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".

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

Retribution or a Strong Legal Argument?

The timing of his charge - coming on the heels of allegations against Comey - has renewed questions about political pressure on the justice system.

Trump once implied Bolton should be in jail, and described him a "sleazebag". Bolton, for his role, authored a book about his time in the Trump administration that was highly critical of the president.

"There's no question that the schedule of this charge, when paired with additional cases, has prompted doubts about the strength of these charges, and why these counts are being filed at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "should the Justice Department is capable to prove the facts stated and show the material is correctly classified, his conduct may very well have violated the law".

Prosecuting such a senior figure for improperly handling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve sensitive materials present challenges to try, but they can and are brought against both low-level and high-level officials, from time to time," she explained.

Similarities to Examinations into Former President and President

Trump similarly encountered charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was ultimately thrown out by a federal judge and negated by his return as president.

A special counsel additionally found that ex-President Joe Biden improperly stored classified documents from his period as vice president, but failed to criminally charge him.

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

Strict protocols govern the management of classified documents. To win a conviction, the government must demonstrate that Bolton was aware the information he was sending was classified, and he had to intentionally transfer it to someone without authorization to receive it.

"Because of the classified character of the information at issue in this matter, we don't have a great deal of details about the reasons the government believes elements like the diary entries and the other material he shared by email, and why there were classified," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the Justice Department brought this case will be closely examined, after Trump publicly expressed his desire to see his political opponents prosecuted and several of those charges materialized.

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

"This Bolton prosecution and eventually the charge appeared to have followed the standard procedure including the regulations and standards within the DOJ," he stated.

In contrast to Comey's brief, two-page indictment, Bolton's was a more "conventional" document that "explicitly sets forth the particulars concerning the circumstances and situation in this instance," Mr Lesko commented.

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