President Donald Trump has made no secret of his desire to see his critics investigated, pressuring the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our reputation and credibility," the president wrote last month in a Truth Social post.

"They impeached me twice, and indicted me (5 times!)" he said, referencing the four criminal cases he faced after leaving the White House in 2021 and James's civil case.

Both have since been charged in cases that many experts have said appear to be politically-motivated and difficult to win in court.

But the latest charges against a Trump critic, former national security adviser John Bolton, stand apart, legal specialists and former prosecutors say.

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

Bolton has been criminally indicted on federal charges pertaining to the alleged mishandling of classified information. Since leaving the White House in 2019, he has become a vocal Trump critic, going so far as 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 procedures used to secure an indictment and the evidence compiled against him indicate a potentially stronger case than the Justice Department brought against Comey or James.

"This misconduct that's being alleged is both more serious and appears to have occurred over a significant period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

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During his time as Trump's national security adviser, and after his 2019 White House departure, prosecutors alleged that Bolton put the country at risk by improperly retaining and transmitting classified information to family members using insecure means, including AOL. Some of the documents were labeled top secret.

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

Bolton pleaded not guilty during a court appearance on Friday to 18 separate charges of mishandling classified information.

Retribution or a strong case?

The timing of his indictment - coming on the tails of charges against Comey and James - has renewed questions about political pressure on the justice system.

Trump once suggested Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, wrote 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 charges, and why these charges are being brought now," said Jamil Jaffer, founder and executive director of the National Security Institute at the George Mason University Antonin Scalia Law School.

However, he added, "If the Justice Department is able to prove the facts alleged and demonstrate the information is properly classified, his conduct may very well have violated the law".

Charging such a high-ranking official for mishandling classified documents is "rare" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present challenges to prosecute, but they can and are brought against both low-level and high-level officials, from time to time," she said.

Similarities to investigations into Trump and Biden

Trump similarly faced charges of improperly storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately dismissed by a federal judge and negated by his re-election as president.

A special counsel also found that former President Joe Biden improperly stored classified documents from his time as vice president, but did not criminally charge him.

Bolton's case bears similarities to Trump's and Biden's classified documents issues, said Mr. Lesko, who also held a top national security role at the Justice Department.

Strict procedures govern the handling of classified documents. To win a conviction, the government must prove that Bolton knew the information he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to receive it.

"Because of the classified nature of the material at issue in this case, we don't have a lot of details about why the government believes things like the diary entries and the other information he communicated by email, and why there were classified," said Mr. Jaffer.

A more traditional prosecution

The process by which the Justice Department brought this case will be under scrutiny, after Trump publicly posted his desire to see his political opponents prosecuted and some of those indictments came to fruition.

But Mr. Lesko said in Bolton's case, prosecutors seem to have followed protocol.

"The Bolton prosecution and ultimately the indictment seemed to have followed the regular process including the rules and norms within the Department of Justice," he said.

Unlike Comey's brief, two-page indictment, Bolton's was a more "traditional" document that "clearly sets forth the details involving the facts and circumstances here," Mr. Lesko said.

"It seems fairly consistent with a long line of cases... where government officials mishandled and transmitted classified material." (BBC)

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