Former President Donald Trump has repeatedly expressed his desire to see critics probed, exerting influence on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.
"We can't delay any longer, it's damaging our standing and trustworthiness," the leader stated last month in a Truth Social message.
"They impeached me, and charged me (5 times!)" he declared, referencing the four criminal cases he faced after leaving the White House in 2021 and James's civil case.
Each have subsequently been indicted, in cases that many experts have said seem to be politically motivated and challenging to succeed in legal proceedings.
But the most recent allegations against a presidential opponent, ex national security adviser John Bolton, stand apart, legal specialists and ex-prosecutors say.
"In my opinion, comparing Bolton's case to James' is like comparing apples to oranges," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.
Bolton has been formally charged on national allegations pertaining to the supposed mishandling of sensitive materials. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unfit for the presidency in his memoir.
Experts say that while there may be political reasons to go after Bolton, the procedures used to secure an charge and the evidence gathered against him indicate a potentially stronger case than the DOJ brought against Comey.
"This misconduct that's being claimed is simultaneously more serious and seems to have occurred over a considerable duration," 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 after his 2019 White House departure, authorities alleged that Bolton placed the nation at danger by improperly keeping and sending classified information to family members using unprotected methods, including AOL. Some of the documents were marked highly classified.
The charge states that at one point a hacker gained access to Bolton's system where files were kept and sent an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".
Bolton entered a not guilty plea during a court appearance on Friday to 18 separate counts of improperly handling sensitive materials.
The timing of his indictment - arriving on the heels of charges against James - has renewed concerns about political pressure on the justice system.
Trump previously suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his part, wrote a publication about his experience in the Trump government that was sharply negative of the president.
"There's no question that the timing of this indictment, when paired with others, has prompted doubts about the strength of these charges, and the reason these counts are being filed now," said Jamil Jaffer, founder and director of the National Security Institute.
However, he added, "should the DOJ is able to demonstrate the allegations alleged and show the material is properly designated, his behavior may very well have violated the statute".
Charging such a senior official for mishandling classified documents is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.
"Situations that concern sensitive materials pose challenges to prosecute, but they can and are filed against both junior and senior personnel, from time to time," she said.
Trump likewise encountered charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was ultimately thrown out by a court official and voided by his return as leader.
A special counsel also found that ex-President Joe Biden improperly maintained sensitive materials from his period as second-in-command, but did not prosecute him.
Bolton's case bears similarities to Trump's sensitive materials issues, noted Mr Lesko, who also held a top security position at the Justice Department.
Strict protocols regulate the management of classified documents. To win a conviction, the government must prove that Bolton was aware the information he was sending was restricted, and he had to knowingly transmit it to someone without authorization to receive it.
"Due to the sensitive nature of the material at issue in this case, we don't have a lot of particulars about why the prosecution contends elements like the personal notes and the other information he shared by electronic message, and the reason there were classified," said Mr Jaffer.
The process by which the DOJ initiated this case will be under scrutiny, after Trump openly expressed his desire to see his critics charged and some of those indictments came to fruition.
But Mr Lesko said in Bolton's case, prosecutors appear to have followed standard procedure.
"This Bolton case and ultimately the indictment seemed to have followed the regular procedure including the rules and standards within the DOJ," he stated.
Unlike Comey's short, concise charge, Bolton's was a more "conventional" filing that "clearly outlines the particulars involving the facts and situation here," Mr Lesko said.
"It seems fairly consistent with a series of cases... where public servants improperly handled and transmitted classified material."
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