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Former President Donald Trump has consistently shown his desire to see critics investigated, applying influence on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our standing and credibility," the president wrote recently in a social media message.

"They impeached twice, and indicted me (five times!)" he declared, mentioning the multiple legal proceedings he faced after leaving the White House in 2021 and James's lawsuit.

Each have since been indicted, in cases that many specialists have said seem to be politically motivated and difficult to succeed in legal proceedings.

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

"I would say, contrasting Bolton's case to Comey's is like equating two different things," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the supposed mishandling of classified information. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Experts contend that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the proof gathered against him suggest a possibly stronger case than the DOJ brought against Comey.

"This misconduct that's being claimed is both more serious and seems to have taken place over a considerable period of time," commented Carissa Byrne Hessick, a professor 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, authorities alleged that Bolton put the nation at risk by wrongfully keeping and transmitting sensitive documents to family members using insecure means, including AOL. Several of the materials were labeled highly classified.

The indictment alleges that at one point a hacker gained access to Bolton's system where files were stored and sent 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 distinct counts of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The timing of his indictment - arriving on the heels of charges against Comey - has revived questions about external influence on the legal system.

Trump once implied Bolton should be in prison, and called him a "sleazebag". Bolton, for his role, wrote a book about his experience in the Trump administration that was highly critical of the leader.

"There's no question that the timing of this indictment, when combined with additional cases, has prompted doubts about the validity of these charges, and why these charges are being brought 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 facts alleged and demonstrate the information is correctly classified, his behavior may very well have broken the law".

Prosecuting such a senior official for improperly handling sensitive materials is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve sensitive materials pose difficulties to prosecute, but they may and are filed against equally low-level and senior officials, from occasionally," she explained.

Similarities to Investigations into Former President and Biden

Trump likewise faced charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and hindering their return, but that matter was ultimately thrown out by a court official and voided by his re-election as president.

A independent investigator also found that ex-President Joe Biden wrongfully stored sensitive materials from his time as vice president, but did not prosecute him.

Bolton's situation bears similarities to Trump's classified documents matters, noted Mr Lesko, who also held a top national security role at the Justice Department.

Strict protocols govern the handling of sensitive materials. To secure a conviction, the government must demonstrate that Bolton knew the information he was sending was classified, and he had to knowingly transmit 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 particulars about the reasons the government contends things like the diary entries and the additional information he communicated by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The process by which the Justice Department initiated this case will be under scrutiny, following Trump openly posted his wish to see his critics charged and some of those charges came to fruition.

But Mr Lesko indicated in Bolton's case, prosecutors seem to have adhered to protocol.

"The Bolton prosecution and ultimately the charge seemed to have followed the standard procedure including the rules and norms within the Department of Justice," he stated.

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

"It seems reasonably aligned with a long line of cases... where government officials improperly handled and transmitted classified material."