Ex-President Donald Trump has consistently shown his wish to see opponents probed, applying influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.
"We cannot postpone any longer, it's damaging our reputation and credibility," the leader stated last month in a social media post.
"They impeached twice, and indicted me (five times!)" he said, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.
Both have since been charged, in situations that many specialists have stated appear to be driven by politics and challenging to succeed in court.
But the most recent allegations against a Trump critic, former national security adviser John Bolton, stand apart, legal experts and former prosecutors say.
"I would say, comparing Bolton's charges to Comey's is like equating two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.
Bolton has been criminally indicted on federal charges pertaining to the supposed improper handling of sensitive materials. After departing the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "stunningly uninformed" and unfit for the presidency in his book.
Experts say that while there may be political reasons to target Bolton, the procedures used to secure an indictment and the evidence gathered against him indicate a potentially stronger legal argument than the DOJ presented against Comey.
"These actions that's being alleged is both more severe and appears to have occurred over a significant period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.
During his time as Trump's security advisor, and after his 2019 White House departure, authorities alleged that Bolton put the country at risk by wrongfully retaining and sending sensitive documents to family members using insecure means, including AOL. Some of the materials were labeled highly classified.
The charge states that at a certain time a unauthorized user accessed to Bolton's account where files were stored and transmitted an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".
Bolton pleaded not guilty during a court appearance on Friday to eighteen distinct charges of mishandling classified information.
The timing of his charge - coming on the heels of allegations against James - has renewed concerns about political pressure on the justice system.
Trump once implied Bolton should be in jail, and described him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump government that was highly critical of the president.
"Undoubtedly that the schedule of this charge, when paired with others, has raised doubts about the validity of these allegations, and the reason these counts are being filed at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.
Nevertheless, he added, "if the DOJ is able to demonstrate the facts alleged and show the material is correctly designated, his conduct may certainly have violated the statute".
Prosecuting such a high-ranking official for mishandling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.
"Cases that involve sensitive materials present challenges to try, but they may and are filed against both low-level and high-level officials, from time to time," she said.
Trump similarly encountered allegations of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was ultimately thrown out by a federal judge and voided by his return as president.
A special counsel also found that ex-President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but failed to prosecute him.
Bolton's case shares characteristics to Biden's sensitive materials issues, said Mr Lesko, who also held a top security role at the DOJ.
Rigorous protocols govern the management of classified documents. To win a guilty verdict, the government must prove that Bolton knew the material he was transmitting was classified, and he had to intentionally transfer it to someone without authorization to obtain it.
"Because of the classified character of the material at issue in this matter, we lack a lot of particulars about why the government contends things like the diary entries and the additional information he communicated by electronic message, and why there were classified," said Mr Jaffer.
The process by which the Justice Department initiated this case will be closely examined, after Trump openly posted his wish to see his critics prosecuted and some of those charges materialized.
But Mr Lesko indicated in Bolton's situation, authorities seem to have adhered to standard procedure.
"The Bolton case and ultimately the indictment seemed to have followed the standard procedure including the rules and standards within the DOJ," he said.
In contrast to Comey's brief, two-page indictment, Bolton's was a increasingly "conventional" filing that "clearly sets forth the details concerning the facts and circumstances in this instance," Mr Lesko commented.
"It appears fairly consistent with a series of cases... where government officials mishandled and transmitted classified material."
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