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Former President Donald Trump has repeatedly shown his wish to see critics investigated, exerting influence on the DOJ to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's killing our reputation and trustworthiness," the leader wrote last month in a Truth Social post.

"I was impeached me, and indicted me (5 times!)" he said, referencing the four criminal cases he faced after departing the White House in 2021 and James's lawsuit.

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

But the most recent charges against a Trump critic, ex security advisor John Bolton, differ significantly, legal experts and ex-prosecutors say.

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

The Details of the Case

Bolton has been formally charged on national allegations pertaining to the supposed 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 memoir.

Experts say that while there may be political reasons to go after Bolton, the methods used to secure an charge and the evidence compiled against him suggest a potentially more substantial legal argument than the DOJ brought against James.

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

Throughout his time as Trump's security advisor, and following his 2019 White House exit, authorities claimed that Bolton put the nation at risk by improperly retaining and sending sensitive documents to family members using insecure means, including AOL. Several of the materials were marked highly classified.

The charge alleges that at a certain time a unauthorized user accessed to Bolton's system where documents were kept and transmitted an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on Friday to 18 separate counts of mishandling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his charge - coming on the heels of charges against Comey - has revived questions about external influence on the legal system.

Trump once implied Bolton belonged in jail, and described him a "disreputable person". Bolton, for his part, authored a book about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the timing of this indictment, when paired with additional cases, has prompted questions about the validity of these allegations, and why these counts are being filed at this time," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "if the Justice Department is capable to demonstrate the facts stated and show the material is correctly classified, his behavior may certainly have broken the statute".

Prosecuting such a high-ranking official for mishandling classified documents is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern sensitive materials present challenges to try, but they can and are filed against both junior and senior officials, from time to time," she explained.

Parallels to Examinations into Trump and Biden

Trump likewise encountered charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was eventually dismissed by a federal judge and voided by his return as leader.

A special counsel also found that former President Joe Biden improperly maintained classified documents from his period as second-in-command, but failed to prosecute him.

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

Strict procedures govern the handling of classified documents. To secure a conviction, the government must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transfer it to someone without authorization to receive it.

"Due to the classified character of the material at question in this matter, we lack a great deal of details about why the government contends things like the diary entries and the additional information he shared by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Legal Action

The procedure by which the Justice Department initiated this legal action will be under scrutiny, after Trump publicly posted his wish to see his political opponents charged and some of those indictments materialized.

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

"This Bolton case and ultimately the charge seemed to have followed the regular process including the rules and norms within the Department of Justice," he stated.

Unlike Comey's brief, concise indictment, Bolton's was a more "conventional" document that "clearly outlines the details involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears reasonably consistent with a long line of precedents... where government officials improperly handled and shared sensitive information."