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

"We can't delay further, it's damaging our reputation and credibility," the president stated recently in a Truth Social message.

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

Both have since been charged, in situations that numerous experts have said appear to be politically motivated and challenging to win in legal proceedings.

But the most recent allegations against a Trump critic, ex security advisor John Bolton, stand apart, legal specialists and former prosecutors assert.

"I would say, contrasting Bolton's case to Comey's is like comparing apples to oranges," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Details of the Case

Bolton has been formally charged on federal charges related to the alleged improper handling of classified information. After departing the White House in 2019, he has become a vocal presidential opponent, going so far as to call him "remarkably ignorant" and unsuitable for the presidency in his book.

Experts 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 indicate a possibly more substantial legal argument than the Justice Department brought against Comey.

"This misconduct that's being claimed is simultaneously more severe and seems to have taken place over a significant period of time," commented 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 alleged that Bolton placed the country at risk by wrongfully keeping and transmitting classified information to family members using unprotected methods, including AOL. Some of the documents were marked top secret.

The charge states that at one point a unauthorized user accessed to Bolton's system where documents were kept and transmitted an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to eighteen distinct charges of improperly handling classified information.

Political Motivation or a Substantial Legal Argument?

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

Trump previously implied Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, authored a publication about his experience in the Trump government that was highly critical of the leader.

"There's no question that the timing of this indictment, when combined with others, has prompted questions about the validity of these charges, and the reason these counts are being filed at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "should the DOJ is able to prove the allegations stated and show the information is properly designated, his conduct may very well have violated the statute".

Prosecuting such a senior official for improperly handling classified documents is "rare" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information pose challenges to try, but they can and are filed against both low-level and senior officials, from time to time," she explained.

Parallels to Examinations into Trump and President

Trump similarly encountered charges of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was ultimately thrown out by a federal judge and voided by his return as leader.

A special counsel also determined that ex-President Joe Biden improperly stored sensitive materials from his time as vice president, but failed to criminally charge him.

Bolton's case bears similarities to Biden's classified documents issues, said Mr Lesko, who also held a top national security role at the DOJ.

Rigorous procedures govern the management of classified documents. To win a conviction, the government must prove that Bolton knew the material he was sending was restricted, and he had to knowingly transfer it to someone without authorization to obtain it.

"Because of the classified nature of the material at issue in this case, we don't have a lot of particulars about the reasons the government contends things like the personal notes and the other information he communicated by electronic message, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the DOJ brought this legal action will be closely examined, after Trump openly posted his desire to see his political opponents charged and some of those charges materialized.

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

"The Bolton case and eventually the charge seemed to have followed the regular procedure including the rules and standards within the Department of Justice," he stated.

Unlike Comey's short, concise charge, Bolton's was a increasingly "traditional" filing that "clearly outlines the particulars involving the facts and situation in this instance," Mr Lesko said.

"It appears reasonably consistent with a series of cases... where government officials mishandled and shared sensitive information."