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Ex-President Donald Trump has repeatedly shown his wish to see critics probed, exerting pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

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

"They impeached me, and indicted me (five times!)" he said, mentioning the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

Each have since been indicted, in cases that many experts have stated appear to be driven by politics and difficult to succeed in court.

But the most recent charges against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and former prosecutors assert.

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

This Details of the Legal Situation

Bolton has been formally charged on federal charges related to the supposed mishandling of classified information. After departing the White House in 2019, he has become a outspoken presidential opponent, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists contend that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the evidence compiled against him suggest a possibly stronger case than the DOJ presented against Comey.

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

During his time as Trump's security advisor, and following his 2019 White House exit, authorities claimed that Bolton put the nation at danger by wrongfully keeping and transmitting sensitive documents to family members using insecure means, including AOL. Several of the documents were labeled top secret.

The indictment states that at one point a hacker accessed to Bolton's account where files were stored and transmitted an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to eighteen separate charges of improperly handling sensitive materials.

Retribution or a Strong Case?

The schedule of his indictment - arriving on the tails of charges against James - has renewed questions about political pressure on the justice system.

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his part, wrote a publication about his time in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this charge, when paired with others, has prompted doubts about the strength of these allegations, and why these charges are being filed now," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the DOJ is capable to demonstrate the allegations stated and show the material is correctly classified, his behavior may very well have violated the statute".

Prosecuting such a high-ranking figure for improperly handling classified documents is "rare" but not unprecedented, noted 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 both low-level and high-level officials, from occasionally," she explained.

Parallels to Examinations into Former President and Biden

Trump likewise faced charges of wrongfully storing classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that matter was eventually dismissed by a federal judge and voided 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 did not criminally charge him.

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

Strict protocols regulate the management of sensitive materials. To secure a conviction, the government must prove that Bolton knew the information he was transmitting was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the classified character of the material at question in this matter, we lack a lot of particulars about the reasons the government contends elements like the diary entries and the other material he communicated by email, and why there were classified," explained Mr Jaffer.

A More Traditional Legal Action

The process by which the DOJ initiated this case will be closely examined, following Trump openly expressed his desire to see his political opponents charged and some of those indictments materialized.

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

"This Bolton case and eventually the charge seemed to have observed the standard process including the rules and norms within the DOJ," he said.

In contrast to Comey's short, two-page charge, Bolton's was a more "traditional" filing that "clearly outlines the particulars concerning the circumstances and situation here," Mr Lesko said.

"It seems reasonably consistent with a long line of cases... where public servants mishandled and shared sensitive information."