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Former President Donald Trump has consistently expressed his wish to see critics probed, applying influence on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and trustworthiness," the leader stated last month in a Truth Social message.

"They impeached twice, and indicted me (five times!)" he declared, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's civil case.

Each have since been charged, in situations that many specialists have said seem to be politically motivated and challenging to win in court.

But the most recent charges against a presidential opponent, ex security advisor John Bolton, differ significantly, legal experts and ex-prosecutors say.

"I would say, comparing Bolton's case to Comey's is like equating two different things," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been formally charged on federal charges related to the alleged mishandling of sensitive materials. After leaving the White House in 2019, he has emerged as a outspoken Trump critic, even to call him "remarkably ignorant" and unfit for the presidency in his memoir.

Specialists say that while there may be political reasons to target Bolton, the procedures used to secure an charge and the proof compiled against him indicate a possibly stronger legal argument than the DOJ brought against Comey.

"These actions that's being claimed is simultaneously more severe and appears to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and after his 2019 White House exit, authorities claimed that Bolton put the country at risk by wrongfully retaining and transmitting classified information to family members using unprotected methods, including AOL. Some of the documents were labeled highly classified.

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

Bolton pleaded not guilty during a court appearance on recently to eighteen separate charges of mishandling classified information.

Political Motivation or a Substantial Legal Argument?

The timing of his charge - arriving on the heels of charges against James - has revived questions about political pressure on the legal system.

Trump once suggested Bolton should be in prison, and called him a "sleazebag". Bolton, for his part, authored a book 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 combined with others, has raised questions about the validity of these charges, and the reason these charges are being brought at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he added, "if the Justice Department is capable to demonstrate the allegations stated and demonstrate the information is properly designated, his conduct may very well have violated the statute".

Prosecuting such a high-ranking figure for mishandling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information present challenges to try, but they can and are brought against both low-level and senior personnel, from occasionally," she said.

Parallels to Examinations into Trump and President

Trump likewise faced charges of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was ultimately dismissed by a court official and voided by his re-election as president.

A special counsel additionally found that former President Joe Biden wrongfully maintained classified documents from his time as vice president, but failed to criminally charge him.

Bolton's case bears similarities to Trump's classified documents issues, noted Mr Lesko, who previously held a senior national security position at the DOJ.

Rigorous procedures regulate the handling of classified documents. To win a conviction, the prosecution must demonstrate that Bolton knew the material he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Because of the sensitive character of the information at question in this case, we don't have a great deal of particulars about the reasons the prosecution contends things like the diary entries and the other information he communicated by email, and the reason there were classified," explained Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ brought this legal action will be closely examined, after Trump openly posted his wish to see his political opponents prosecuted and some of those charges materialized.

But Mr Lesko said in Bolton's situation, prosecutors appear to have followed protocol.

"This Bolton prosecution and eventually the charge seemed to have followed the standard procedure including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's short, two-page indictment, Bolton's was a more "traditional" document that "clearly outlines the details involving the facts and circumstances here," Mr Lesko commented.

"It seems fairly consistent with a long line of precedents... where government officials improperly handled and transmitted sensitive information."