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Former President Donald Trump has repeatedly expressed his wish to see opponents investigated, exerting pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our reputation and trustworthiness," the president wrote recently in a social media message.

"They impeached me, and charged me (5 times!)" he declared, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's civil case.

Both have since been indicted, in cases that many experts have stated seem to be politically motivated and difficult to succeed in court.

But the latest charges against a Trump critic, former 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.

This Details of Bolton's Legal Situation

Bolton has been formally charged on federal charges pertaining to the alleged mishandling of sensitive materials. Since leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to call him "remarkably ignorant" and unfit for the presidency in his book.

Specialists say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the evidence gathered against him indicate a possibly more substantial legal argument than the DOJ brought against James.

"These actions that's being alleged is both more severe and seems to have occurred over a considerable period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's national security adviser, and following his 2019 White House exit, authorities alleged that Bolton placed the country at risk by wrongfully retaining and sending classified information to relatives using insecure means, including AOL. Several of the documents were marked highly classified.

The charge states that at one point a hacker accessed to Bolton's account where files were stored and transmitted an apparent 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 18 separate charges of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

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

Trump once suggested Bolton should be in prison, and called him a "sleazebag". Bolton, for his part, authored a publication about his time in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this indictment, when combined with others, has prompted questions about the strength of these allegations, and why these counts are being filed at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the DOJ is able to prove the allegations alleged and show the information is correctly classified, his conduct may certainly have violated the law".

Prosecuting such a high-ranking figure for improperly handling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that concern classified information present difficulties to try, but they can and are brought against both junior and senior officials, from time to time," she explained.

Parallels to Examinations into Trump and Biden

Trump likewise faced allegations of improperly storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was eventually dismissed by a federal judge and voided by his return as president.

A special counsel additionally found that former President Joe Biden wrongfully stored sensitive materials from his period as vice president, but failed to prosecute him.

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

Strict protocols govern the management of sensitive materials. To secure a conviction, the prosecution must demonstrate that Bolton knew the information he was sending was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the sensitive character of the information at issue in this case, we don't have a lot of details about why the prosecution contends elements like the diary entries and the additional information he shared by electronic message, and why there were restricted," said Mr Jaffer.

A More Traditional Legal Action

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

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

"The Bolton prosecution and ultimately the charge appeared to have observed the standard procedure including the regulations and norms within the DOJ," he stated.

Unlike Comey's brief, concise charge, Bolton's was a increasingly "conventional" filing that "explicitly sets forth the particulars concerning the facts and situation in this instance," Mr Lesko commented.

"It seems fairly consistent with a long line of precedents... where government officials improperly handled and transmitted sensitive information."