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Ex-President Donald Trump has repeatedly expressed his wish to see critics investigated, exerting influence 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 trustworthiness," the leader stated recently in a social media message.

"I was impeached me, and charged me (5 times!)" he declared, mentioning the multiple legal proceedings he faced after departing the White House in 2021 and James's civil case.

Each have subsequently been indicted, in situations that numerous experts have said appear to be driven by politics and challenging to win in legal proceedings.

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

"In my opinion, comparing Bolton's case to James' is like equating two different things," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of Bolton's Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of sensitive materials. Since leaving the White House in 2019, he has emerged as a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for the presidency in his memoir.

Experts contend that while there may be political reasons to go after Bolton, the methods used to secure an indictment and the proof gathered against him indicate a potentially stronger case than the DOJ brought against Comey.

"These actions that's being alleged is both more severe and seems to have occurred over a considerable 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 following his 2019 White House exit, prosecutors alleged that Bolton placed the nation at risk by wrongfully retaining and transmitting classified information to relatives using insecure means, including AOL. Several of the materials were marked highly classified.

The indictment states that at one point a unauthorized user gained access to Bolton's account where documents were kept and transmitted an seeming threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to 18 distinct charges of mishandling classified information.

Retribution or a Substantial Legal Argument?

The timing of his indictment - arriving on the heels of allegations against Comey - has revived questions about political pressure on the justice system.

Trump previously implied Bolton belonged in jail, and described him a "sleazebag". Bolton, for his part, authored a book about his time in the Trump government that was sharply negative of the leader.

"There's no question that the schedule of this indictment, when paired with others, has prompted questions about the validity of these allegations, and the reason these counts are being filed at this time," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to prove the facts alleged and show the material is properly classified, his conduct may certainly have broken the statute".

Charging such a senior official for improperly handling sensitive materials is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information present challenges to try, but they can and are brought against equally junior and high-level officials, from occasionally," she said.

Similarities to Investigations into Former President and President

Trump similarly encountered charges of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that case was ultimately dismissed by a court official and voided by his return as leader.

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

Bolton's case shares characteristics to Trump's classified documents issues, said Mr Lesko, who previously held a top security position at the Justice Department.

Rigorous procedures regulate the handling of classified documents. To secure a guilty verdict, the government must prove that Bolton knew the information he was sending was restricted, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the classified nature of the material at question in this case, we don't have a great deal of details about why the prosecution believes things like the diary entries and the additional material he shared by electronic message, and why there were classified," said Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department initiated this case will be closely examined, following Trump openly posted his desire to see his political opponents charged and several of those indictments came to fruition.

But Mr Lesko indicated in Bolton's situation, prosecutors seem to have adhered to protocol.

"The Bolton case and eventually the indictment seemed to have followed the regular process including the regulations and standards within the Department of Justice," he said.

In contrast to Comey's short, concise indictment, Bolton's was a more "conventional" filing that "clearly sets forth the particulars concerning the facts and situation here," Mr Lesko said.

"It seems reasonably consistent with a series of precedents... where public servants improperly handled and shared sensitive information."