Former President Donald Trump has consistently expressed his desire to see critics investigated, applying influence on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.
"We cannot postpone any longer, it's killing our standing and trustworthiness," the leader wrote last month in a social media message.
"I was impeached me, and charged me (5 times!)" he declared, referencing the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.
Each have since been charged, in cases that many experts have said appear to be politically motivated and challenging to succeed in court.
But the latest allegations against a presidential opponent, former security advisor John Bolton, stand apart, legal specialists and ex-prosecutors say.
"In my opinion, contrasting Bolton's charges to Comey's is like comparing apples to oranges," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.
The Specifics of Bolton's Case
Bolton has been criminally indicted on federal charges related to the alleged improper handling of sensitive materials. Since leaving the White House in 2019, he has become a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unfit for office in his memoir.
Experts say that while there may be political motivations to go after Bolton, the methods used to secure an charge and the proof compiled against him indicate a possibly more substantial case than the Justice Department presented against James.
"This misconduct that's being alleged is simultaneously more severe and seems to have taken place over a considerable period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.
During his tenure as Trump's security advisor, and following his 2019 White House departure, prosecutors alleged that Bolton put the country at danger by wrongfully retaining and transmitting sensitive documents to relatives using insecure means, 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 stored and sent an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".
Bolton pleaded not guilty during a court appearance on recently to eighteen separate counts of mishandling sensitive materials.
Political Motivation or a Substantial Case?
The timing of his indictment - coming on the tails of charges against James - has revived questions about external influence on the justice system.
Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, wrote a book about his time in the Trump government that was sharply negative of the leader.
"Undoubtedly that the schedule of this indictment, when combined with others, has prompted doubts about the validity of these charges, and why these charges are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.
However, he added, "if the Justice Department is able to demonstrate the facts alleged and show the material is properly classified, his behavior may certainly have violated the statute".
Prosecuting such a senior figure for improperly handling classified documents is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.
"Cases that concern classified information pose challenges to prosecute, but they may and are brought against equally junior and senior officials, from occasionally," she explained.
Parallels to Investigations into Former President and Biden
Trump likewise faced charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that case was ultimately thrown out by a court official and negated by his re-election as leader.
A independent investigator additionally determined that ex-President Joe Biden improperly stored classified documents from his time as second-in-command, but did not prosecute him.
Bolton's case shares characteristics to Biden's classified documents matters, said Mr Lesko, who previously held a top security position at the DOJ.
Rigorous protocols regulate the management of sensitive materials. To win a conviction, the government must demonstrate that Bolton knew the information he was sending was classified, and he had to intentionally transmit it to someone not entitled to obtain it.
"Due to the classified character of the material at issue in this matter, we don't have a great deal of particulars about the reasons the government believes things like the diary entries and the other material he communicated by email, and the reason there were restricted," explained Mr Jaffer.
A More Traditional Prosecution
The procedure by which the DOJ brought this legal action will be closely examined, following Trump publicly posted his desire to see his political opponents charged and some of those charges materialized.
But Mr Lesko indicated in Bolton's case, prosecutors seem to have followed protocol.
"The Bolton prosecution and eventually the indictment seemed to have followed the regular procedure including the rules and standards within the DOJ," he said.
Unlike Comey's brief, concise indictment, Bolton's was a increasingly "conventional" filing that "clearly sets forth the particulars involving the circumstances and situation here," Mr Lesko commented.
"It seems reasonably aligned with a long line of cases... where government officials mishandled and shared classified material."
