Former President Donald Trump has consistently shown his wish to see critics investigated, applying pressure on the DOJ to prosecute former 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 Truth Social post.
"They impeached me, and indicted me (five times!)" he said, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.
Both have subsequently been charged, in situations that numerous specialists have stated seem to be politically motivated and challenging to win in legal proceedings.
But the most recent allegations against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors say.
"I would say, comparing Bolton's case to Comey's is like comparing apples to oranges," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.
Bolton has been formally charged on federal charges pertaining to the alleged improper handling of sensitive materials. Since leaving the White House in 2019, he has emerged as a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unfit for the presidency in his book.
Experts contend that while there may be political reasons to go after Bolton, the procedures used to secure an indictment and the evidence compiled against him indicate a potentially stronger legal argument than the Justice Department brought against Comey.
"This misconduct that's being alleged is both more serious and seems to have occurred over a significant duration," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.
During his tenure as Trump's national security adviser, and after his 2019 White House exit, prosecutors claimed that Bolton put the country at danger by wrongfully retaining and sending classified information to family members using insecure means, including AOL. Several of the documents were marked highly classified.
The indictment states that at one point a unauthorized user accessed to Bolton's system where documents were kept and sent an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".
Bolton entered a not guilty plea during a hearing on recently to 18 separate counts of improperly handling classified information.
The timing of his indictment - arriving on the heels of charges against Comey - has revived concerns about external influence on the legal system.
Trump previously suggested Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, authored a publication about his time in the Trump administration that was sharply negative of the president.
"Undoubtedly that the timing of this indictment, when combined with others, has raised doubts about the strength of these allegations, and why these counts are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.
Nevertheless, he added, "if the Justice Department is capable to demonstrate the allegations stated and demonstrate the information is correctly designated, his behavior may certainly have broken the law".
Prosecuting such a high-ranking figure for improperly handling classified documents is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.
"Situations that concern classified information present challenges to try, but they can and are brought against equally low-level and senior personnel, from occasionally," she said.
Trump similarly encountered allegations of improperly keeping classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was eventually dismissed by a federal judge and negated by his re-election as leader.
A independent investigator also found that ex-President Joe Biden improperly maintained classified documents from his time as vice president, but did not prosecute him.
Bolton's case shares characteristics to Trump's classified documents issues, noted Mr Lesko, who previously held a top security role at the DOJ.
Strict procedures govern the handling of sensitive materials. To win a conviction, the prosecution must prove that Bolton knew the material he was sending was restricted, and he had to intentionally transmit it to someone not entitled to receive it.
"Due to the classified character of the information at question in this case, we don't have a lot of particulars about why the government believes elements like the diary entries and the additional material he shared by electronic message, and the reason there were restricted," said Mr Jaffer.
The process by which the DOJ brought this legal action will be closely examined, following Trump publicly expressed his wish to see his critics prosecuted and several of those indictments came to fruition.
But Mr Lesko said in Bolton's case, authorities seem to have adhered to standard procedure.
"This Bolton case and ultimately the indictment appeared to have followed the standard procedure including the rules and norms within the Department of Justice," he said.
In contrast to Comey's short, concise charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details involving the circumstances and circumstances in this instance," Mr Lesko said.
"It seems fairly aligned with a long line of cases... where public servants mishandled and shared classified material."
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