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.

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.

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

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.

However, 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, as suggested by experts.