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Ex-President Donald Trump has repeatedly shown his wish to see critics probed, applying pressure on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our reputation and trustworthiness," the leader wrote last month in a social media post.

"I was impeached twice, and indicted me (5 times!)" he said, referencing the four criminal cases he faced after departing the White House in 2021 and James's civil case.

Each have subsequently been indicted, in situations that many specialists have stated seem to be politically motivated and difficult to win in legal proceedings.

But the most recent charges against a presidential opponent, former national security adviser John Bolton, stand apart, legal specialists and ex-prosecutors say.

"In my opinion, comparing Bolton's charges to Comey's is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged mishandling of sensitive materials. Since leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the evidence gathered against him suggest a possibly more substantial legal argument than the DOJ brought against James.

"This misconduct that's being alleged is simultaneously more serious and seems to have taken place over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and after his 2019 White House departure, prosecutors alleged that Bolton placed the country at risk by wrongfully retaining and sending classified information to relatives using unprotected methods, including AOL. Some of the materials were marked highly classified.

The indictment states that at a certain time a hacker accessed to Bolton's system where files were kept and sent an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on recently to 18 distinct charges of mishandling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his indictment - coming on the heels of charges against James - has renewed questions about political pressure on the justice system.

Trump previously implied Bolton belonged in prison, and described him a "disreputable person". Bolton, for his part, wrote a book about his time in the Trump government that was highly critical of the president.

"There's no question that the timing of this indictment, when combined with others, has prompted doubts about the validity of these allegations, and why these charges are being brought now," said Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "if the Justice Department is capable to prove the allegations alleged and demonstrate the material is properly classified, his behavior may certainly have violated the law".

Prosecuting such a high-ranking official for mishandling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose challenges to try, but they may and are filed against equally low-level and senior personnel, from occasionally," she said.

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 return, but that case was ultimately dismissed by a federal judge and voided by his return as leader.

A independent investigator additionally determined 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, noted Mr Lesko, who also held a top national security role at the Justice Department.

Rigorous procedures govern the management of sensitive materials. To win a conviction, the prosecution must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transmit it to someone without authorization to obtain it.

"Due to the classified character of the information at issue in this case, we don't have a lot of details about why the government contends elements like the diary entries and the additional information he shared by email, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The process by which the Justice Department initiated this case will be under scrutiny, following Trump publicly expressed his wish to see his political opponents prosecuted and some of those indictments came to fruition.

But Mr Lesko indicated in Bolton's case, authorities seem to have followed protocol.

"This Bolton prosecution and ultimately the indictment appeared to have observed the standard process including the regulations and norms within the Department of Justice," he stated.

In contrast to Comey's brief, concise charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details involving the facts and situation in this instance," Mr Lesko said.

"It appears fairly consistent with a long line of cases... where government officials mishandled and shared sensitive information."