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Ex-President Donald Trump has repeatedly expressed his wish to see critics probed, exerting influence on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our reputation and credibility," the president stated last month in a Truth Social message.

"I was impeached me, and indicted me (five times!)" he declared, mentioning the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that many specialists have stated appear to be politically motivated and difficult to win in court.

But the latest charges against a Trump critic, ex national security adviser John Bolton, stand apart, legal experts and former prosecutors assert.

"I would say, contrasting Bolton's case to James' is like equating apples to oranges," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of the Legal Situation

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

Specialists contend that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the proof compiled against him suggest a potentially more substantial case than the Justice Department brought against Comey.

"These actions that's being claimed is simultaneously more serious and seems to have taken place over a significant period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure 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 materials were marked top secret.

The indictment states that at a certain time a hacker gained access to Bolton's account where documents were stored and sent an seeming warning to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on Friday to eighteen separate charges of mishandling sensitive materials.

Political Motivation or a Substantial Case?

The schedule of his charge - coming on the tails of allegations against James - has renewed questions about political pressure on the legal system.

Trump previously suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump administration that was highly critical of the leader.

"There's no question that the timing of this charge, when paired with additional cases, has prompted questions about the strength of these allegations, and the reason these counts are being filed now," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the Justice Department is able to prove the facts alleged and demonstrate the information is correctly designated, his conduct may certainly have violated the statute".

Prosecuting such a senior figure for improperly handling classified documents is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information present difficulties to prosecute, but they may and are filed against both low-level and senior personnel, from time to time," she said.

Similarities to Investigations into Former President and Biden

Trump likewise faced allegations of improperly storing sensitive materials at his Mar-a-Lago property in Florida and hindering their return, but that case was ultimately dismissed by a court official and negated by his re-election as president.

A special counsel also found that ex-President Joe Biden improperly maintained sensitive materials from his period as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's classified documents issues, said Mr Lesko, who previously held a senior national security role at the DOJ.

Rigorous protocols govern the management of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was sending was restricted, and he had to knowingly transfer it to someone not entitled to obtain it.

"Because of the classified character of the material at question in this case, we don't have a lot of details about the reasons the government contends elements like the diary entries and the additional information he shared by email, and the reason there were restricted," said Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department brought this case will be closely examined, after Trump publicly posted his desire to see his critics charged and some of those charges came to fruition.

But Mr Lesko said in Bolton's case, authorities seem to have adhered to protocol.

"This Bolton prosecution and ultimately the charge seemed to have observed the regular process including the rules and standards within the Department of Justice," he said.

In contrast to Comey's short, concise indictment, Bolton's was a increasingly "conventional" document that "clearly sets forth the details concerning the circumstances and circumstances in this instance," Mr Lesko commented.

"It seems fairly aligned with a long line of precedents... where public servants mishandled and shared sensitive information."