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Former President Donald Trump has repeatedly expressed his wish to see critics investigated, exerting pressure on the Justice Department to charge former 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 stated last month in a Truth Social message.

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

Both have subsequently been charged, in situations that many experts have said seem to be driven by politics and difficult to win in legal proceedings.

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

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

This Specifics of the Legal Situation

Bolton has been formally charged on national allegations pertaining to the supposed improper handling of classified information. After leaving the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his book.

Experts contend that while there may be political motivations to target Bolton, the procedures used to obtain an indictment and the evidence gathered against him suggest a potentially stronger legal argument than the Justice Department presented against Comey.

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

During his tenure as Trump's national security adviser, and following his 2019 White House exit, authorities claimed that Bolton put the nation at danger by improperly keeping and sending classified information to relatives using unprotected methods, including AOL. Some of the documents were labeled highly classified.

The indictment alleges that at one point a hacker accessed to Bolton's account where documents were stored and sent an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on recently to eighteen distinct charges of mishandling sensitive materials.

Retribution or a Strong Legal Argument?

The timing of his indictment - arriving on the tails of charges against Comey - has renewed questions about political pressure on the legal system.

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

"There's no question that the timing of this indictment, when paired with additional cases, has raised questions about the strength of these charges, and the reason these counts are being filed now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "if the DOJ is able to demonstrate the allegations stated and show the information is correctly classified, his conduct may very well have violated the statute".

Prosecuting such a senior official for mishandling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials present challenges to prosecute, but they may and are brought against equally low-level and senior officials, from time to time," she explained.

Parallels to Investigations into Trump and President

Trump likewise encountered charges of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their return, but that matter was eventually dismissed by a federal judge and voided by his return as president.

A special counsel additionally determined that ex-President Joe Biden improperly stored sensitive materials from his period as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Trump's sensitive materials matters, noted Mr Lesko, who previously held a senior security position at the DOJ.

Rigorous procedures regulate the handling of sensitive materials. To secure a conviction, the government must demonstrate that Bolton was aware the material he was sending was classified, and he had to intentionally transfer it to someone without authorization to obtain it.

"Because of the classified character of the information at issue in this case, we lack a great deal of details about the reasons the prosecution believes things like the diary entries and the other material he communicated by email, and the reason there were restricted," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the DOJ initiated this case will be under scrutiny, after Trump publicly expressed his desire to see his critics charged and several of those indictments came to fruition.

But Mr Lesko said in Bolton's case, prosecutors appear to have adhered to standard procedure.

"The Bolton prosecution and eventually the indictment appeared to have followed the regular procedure including the regulations and standards within the DOJ," he stated.

In contrast to Comey's brief, concise indictment, Bolton's was a more "conventional" document that "clearly sets forth the particulars involving the facts and circumstances in this instance," Mr Lesko commented.

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