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Former President Donald Trump has repeatedly shown his wish to see opponents investigated, applying influence on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and credibility," the leader stated last month in a Truth Social message.

"I was impeached me, and charged me (5 times!)" he declared, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Both have subsequently been indicted, in cases that many experts have said appear to be driven by politics and difficult to win in court.

But the latest allegations against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and former prosecutors assert.

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

The Specifics of Bolton's Case

Bolton has been criminally indicted on national allegations pertaining to the alleged improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists say that while there may be political reasons to go after Bolton, the procedures used to obtain an charge and the proof compiled against him indicate a potentially stronger legal argument than the Justice Department presented against Comey.

"These actions that's being claimed is both more severe and appears to have taken place over a significant duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and after his 2019 White House exit, prosecutors claimed that Bolton placed the country at risk by improperly retaining and sending classified information to relatives using unprotected methods, including AOL. Several of the documents were labeled highly classified.

The charge alleges that at one point a hacker accessed to Bolton's account where files were kept and transmitted an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Strong Case?

The timing of his charge - arriving on the heels of allegations against Comey - has renewed concerns about external influence on the justice system.

Trump previously implied Bolton belonged in prison, and described him a "sleazebag". Bolton, for his part, authored a book about his time in the Trump administration that was highly critical of the president.

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

However, he continued, "if the DOJ is able to prove the allegations alleged and demonstrate the information is properly classified, his conduct may certainly have broken the statute".

Prosecuting such a senior official for mishandling sensitive materials is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose challenges to prosecute, but they can and are brought against equally junior and senior officials, from time to time," she said.

Parallels to Investigations into Trump and President

Trump likewise faced allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that matter was ultimately thrown out by a court official and negated by his return as president.

A special counsel also determined that former President Joe Biden improperly maintained sensitive materials from his time as vice president, but failed to prosecute him.

Bolton's case bears similarities to Biden's sensitive materials issues, noted Mr Lesko, who previously held a top security role at the Justice Department.

Strict procedures regulate the management of classified documents. To win a guilty verdict, the government must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Because of the classified character of the material at question in this case, we don't have a great deal of particulars about the reasons the government believes things like the diary entries and the other information he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department brought this legal action will be under scrutiny, after Trump publicly expressed his desire to see his critics charged and several of those charges materialized.

But Mr Lesko said in Bolton's situation, prosecutors seem to have followed standard procedure.

"This Bolton case and eventually the indictment seemed to have followed the standard process including the rules and norms within the Department of Justice," he stated.

In contrast to Comey's brief, two-page indictment, Bolton's was a more "conventional" filing that "explicitly sets forth the particulars involving the facts and situation here," Mr Lesko said.

"It appears reasonably aligned with a series of cases... where public servants mishandled and transmitted sensitive information."