Former President Donald Trump has consistently expressed his wish to see critics probed, exerting influence on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.
"We cannot postpone further, it's damaging our reputation and credibility," the leader stated recently in a Truth Social message.
"I was impeached me, and charged me (5 times!)" he declared, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's lawsuit.
Each have subsequently been indicted, in situations that many experts have said seem to be driven by politics and difficult to succeed in legal proceedings.
But the most recent charges against a Trump critic, ex national security adviser John Bolton, stand apart, legal experts and former prosecutors say.
"In my opinion, comparing Bolton's case to James' is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.
The Specifics of Bolton's Legal Situation
Bolton has been criminally indicted on federal charges related to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has become a vocal 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 gathered against him indicate a possibly stronger case than the Justice Department presented against James.
"This misconduct that's being alleged is simultaneously more serious and appears to have taken place over a significant period of time," commented Carissa Byrne Hessick, a academic 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 alleged that Bolton placed the country at danger by improperly retaining and transmitting sensitive documents to family members using insecure means, including AOL. Several of the documents were marked highly classified.
The indictment states that at one point a hacker gained access to Bolton's account where documents were stored and transmitted an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".
Bolton pleaded not guilty during a court appearance on Friday to 18 distinct counts of improperly handling sensitive materials.
Retribution or a Substantial Case?
The timing of his indictment - arriving on the heels of allegations against James - has revived concerns about political pressure on the legal system.
Trump once suggested Bolton belonged in jail, and called him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump government that was sharply negative of the leader.
"Undoubtedly that the timing of this charge, when combined with additional cases, has prompted questions about the strength of these allegations, and why these charges are being brought now," stated Jamil Jaffer, founder and director of the National Security Institute.
Nevertheless, he added, "if the Justice Department is capable to demonstrate the facts stated and demonstrate the material is correctly classified, his behavior may certainly have violated the law".
Prosecuting such a high-ranking official for improperly handling classified documents is "rare" but not unprecedented, said Carrie Cordero, a senior fellow at the Center for a New American Security.
"Cases that concern classified information pose challenges to try, but they can and are filed against both junior and senior officials, from occasionally," she explained.
Similarities to Examinations into Former President and President
Trump similarly encountered charges of improperly storing classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that matter was eventually dismissed by a court official and negated by his re-election as leader.
A independent investigator also found that former President Joe Biden improperly maintained sensitive materials from his period as second-in-command, but did not prosecute him.
Bolton's situation bears similarities to Biden's sensitive materials matters, noted Mr Lesko, who previously held a top national security position at the Justice Department.
Rigorous protocols govern the management of classified documents. To secure a conviction, the government must demonstrate that Bolton was aware the information he was sending was classified, and he had to intentionally transmit it to someone without authorization to receive it.
"Because of the sensitive character of the information at question in this case, we lack a great deal of details about why the prosecution contends elements like the personal notes and the additional information he shared by electronic message, and the reason there were classified," said Mr Jaffer.
A Increasingly Conventional Prosecution
The process by which the Justice Department brought this legal action will be closely examined, following Trump openly expressed his wish to see his critics prosecuted and several of those indictments materialized.
But Mr Lesko indicated in Bolton's situation, authorities appear to have adhered to protocol.
"The Bolton prosecution and ultimately the indictment seemed to have followed the regular procedure including the rules and standards within the Department of Justice," he stated.
Unlike Comey's brief, two-page charge, Bolton's was a increasingly "conventional" filing that "explicitly sets forth the details concerning the facts and circumstances in this instance," Mr Lesko said.
"It appears reasonably aligned with a series of cases... where government officials improperly handled and transmitted sensitive information."
