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- By Brittany Stone
- 11 Aug 2026
Ex-President Donald Trump has consistently shown his desire to see critics investigated, exerting pressure on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.
"We can't delay further, it's damaging our standing and trustworthiness," the president wrote recently in a social media message.
"They impeached me, and charged me (5 times!)" he said, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's civil case.
Each have subsequently been indicted, in cases that many specialists have stated appear to be politically motivated and difficult to succeed in court.
But the latest allegations against a Trump critic, ex security advisor John Bolton, stand apart, legal experts and former prosecutors say.
"I would say, contrasting Bolton's case to Comey's is like equating apples to oranges," said Mark Lesko, a former acting US attorney for the Eastern District of New York.
Bolton has been criminally indicted on national allegations related to the supposed improper handling of classified information. Since departing the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.
Specialists contend that while there may be political reasons to target Bolton, the procedures used to obtain an charge and the proof compiled against him suggest a potentially more substantial legal argument than the DOJ brought against James.
"These actions that's being alleged is simultaneously more serious and seems to have occurred over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.
Throughout his tenure as Trump's national security adviser, and following his 2019 White House exit, authorities claimed that Bolton placed the nation at danger by wrongfully keeping and sending classified information to relatives using insecure means, including AOL. Several of the documents were labeled top secret.
The charge states that at one point a hacker gained access to Bolton's account where files were stored and sent an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".
Bolton pleaded not guilty during a hearing on Friday to 18 distinct charges of mishandling sensitive materials.
The schedule of his charge - arriving on the tails of allegations against Comey - has revived questions about external influence on the legal system.
Trump previously suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his part, wrote a book about his time in the Trump administration that was highly critical of the president.
"Undoubtedly that the timing of this charge, when paired with additional cases, has raised questions about the validity of these allegations, and why these charges are being brought at this time," stated Jamil Jaffer, founder and director of the National Security Institute.
However, he added, "if the DOJ is able to demonstrate the allegations alleged and show the material is properly designated, his behavior may certainly have violated the statute".
Charging such a senior figure for improperly handling sensitive materials is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.
"Situations that involve sensitive materials present difficulties to prosecute, but they may and are filed against both junior and high-level personnel, from time to time," she explained.
Trump likewise encountered allegations of improperly keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately thrown out by a federal judge and negated by his return as president.
A independent investigator additionally found that former President Joe Biden improperly maintained classified documents from his period as second-in-command, but failed to criminally charge him.
Bolton's case bears similarities to Biden's classified documents issues, noted Mr Lesko, who previously held a senior security role at the Justice Department.
Rigorous protocols govern the management of sensitive materials. To win a conviction, the prosecution must demonstrate that Bolton was aware the material he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to receive it.
"Because of the sensitive nature of the information at issue in this matter, we lack a lot of details about why the prosecution contends elements like the personal notes and the additional information he shared by email, and why there were restricted," explained Mr Jaffer.
The procedure by which the Justice Department initiated this case will be closely examined, after Trump openly expressed his desire to see his critics charged and some of those charges came to fruition.
But Mr Lesko indicated in Bolton's situation, authorities appear to have adhered to standard procedure.
"This Bolton case and eventually the charge seemed to have observed the regular procedure including the regulations and norms within the Department of Justice," he stated.
Unlike Comey's short, two-page indictment, Bolton's was a more "conventional" filing that "explicitly sets forth the particulars involving the circumstances and situation in this instance," Mr Lesko commented.
"It seems fairly aligned with a series of precedents... where public servants mishandled and shared sensitive information."
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