Legal experts say the John Bolton classified documents case will be more difficult for President Donald Trump’s critics to dismiss as a Trump vengeance play compared to the indictments of former FBI Director James Comey and New York Attorney General Letitia James.

Bolton, a national security adviser during Trump’s first administration and frequent Trump critic after it, pleaded not guilty on Friday to charges of mishandling classified information in an investigation that began during the Biden administration. 

The Biden administration’s Justice Department began investigating Bolton during a 2021 Iran hacking investigation. Some of the classified information in Bolton’s possession was allegedly obtained through the Iranian hack. Career federal prosecutors are reportedly more supportive of the Bolton prosecution than the other cases. 

“John Bolton, through his extensive government experience, is very aware of laws governing classified information,” John Malcolm, director of the Meese Center for Legal and Judicial Studies at The Heritage Foundation, told The Daily Signal. 

Malcolm noted that most cases of mishandling classified information only raise the possibility of the information falling into the wrong hands if not protected.

“Not only does this pose the possibility of falling into the wrong hands, but it appears that representatives of the Iran government accessed it,” added Malcolm, a former federal prosecutor. 

The charges against Bolton are also more serious than those levied against other Trump critics, Malcolm noted. 

Comey, the former FBI director, was charged with perjury in relation to allegedly instructing someone to leak classified information. James, the New York attorney general, was charged with allegedly improperly filling out mortgage paperwork. 

Further, Bolton’s indictment Thursday by a federal grand jury in Maryland is more detailed, running 26 pages with 18 counts, compared to the two-page Comey indictment and the five-page James indictment. 

“It is a pretty damning indictment to be sure for transmitting classified information and a great deal more detailed than the indictments of James Comey and Letitia James,” Paul Kamenar, counsel for the watchdog group National Legal and Policy, told The Daily Signal. 

Federal law enforcement says it obtained information from a foreign adversary’s spy service, including emails that allegedly show Bolton may have sent sensitive information on an unclassified system while working for the Trump White House. The information was allegedly sent to people helping him write his 2020 memoir, “The Room Where It Happened.”

In part, Bolton has used the fact the probe commenced under the Biden administration as a defense. 

“When my e-mail was hacked in 2021, the FBI was made fully aware. In four years of the prior [Biden] administration, after these reviews, no charges were ever filed,” Bolton said in a statement. “Then came Trump 2, who embodies what Joseph Stalin’s head of secret police once said, ‘You show me the man, and I’ll show you the crime.’”

However, Kamenar said if the charges are true, it could be more serious than other high-profile classified document cases. 

Two of those cases ended in guilty pleas. One was that of former Obama administration CIA Director and retired Gen. David Petraeus, and the other was that of former Clinton administration national security adviser Sandy Berger.

“Petraus and Berger got away with a slap on the wrist,” Kamanar said. “That’s unfortunate. But unlike the Bolton case, those cases showed no signs that a foreign adversary had access to the classified information.”

Petraus pleaded guilty to a misdemeanor charge in 2015 for sharing classified information with a biographer and girlfriend and was sentenced to probation. Berger was caught on video removing information from the National Archives reading room and stuffing it into his socks before his testimony to the 9/11 commission. He pleaded guilty in 2005 to a misdemeanor and paid a fine.

Likewise, Kamenar said other federal investigations of high-profile figures for alleged mishandling of classified information—including Trump, former President Joe Biden, and former Secretary of State Hillary Clinton—did not produce indictments but also had no suggestions that a foreign adversary accessed the documents. 

Bolton’s legal team could allege selective prosecution, but that could be a tough case to make, said Malcolm of The Heritage Foundation. 

“He can argue it’s selective prosecution or that he was targeted because he was considered an enemy of Trump,” Malcolm said. “Ultimately that’s a tough argument to make. … The seized documents are what they are.”

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