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Former President Donald Trump has consistently expressed his wish to see opponents probed, exerting pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's damaging our reputation and trustworthiness," the leader stated recently in a Truth Social post.

"They impeached twice, and charged me (5 times!)" he said, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's civil case.

Both have since been indicted, in situations that many specialists have said appear to be driven by politics and difficult to win in legal proceedings.

But the latest allegations against a Trump critic, ex security advisor John Bolton, stand apart, legal specialists and former prosecutors assert.

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

The Details of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. Since departing the White House in 2019, he has emerged as a vocal Trump critic, even to call him "stunningly uninformed" and unsuitable for office in his memoir.

Experts contend that while there may be political reasons to go after Bolton, the methods used to secure an charge and the evidence gathered against him indicate a possibly stronger legal argument than the Justice Department brought against Comey.

"This misconduct that's being claimed is simultaneously more severe and appears 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 following his 2019 White House exit, authorities claimed that Bolton put the nation at danger by improperly retaining and transmitting sensitive documents to family members using insecure means, including AOL. Several of the materials were labeled highly classified.

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

Bolton entered a not guilty plea during a court appearance on Friday to 18 separate charges of improperly handling sensitive materials.

Political Motivation or a Strong Case?

The timing of his charge - arriving on the heels of allegations against Comey - has revived concerns about external influence on the justice system.

Trump previously suggested Bolton should be in jail, and described him a "sleazebag". Bolton, for his role, authored a publication about his time in the Trump government that was sharply negative of the president.

"There's no question that the schedule of this charge, when combined with additional cases, has raised doubts about the strength of these allegations, and the reason these charges are being filed now," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "should the DOJ is capable to prove the allegations alleged and demonstrate the material is properly designated, his conduct may certainly have violated the statute".

Charging such a senior figure for mishandling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

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

Parallels to Investigations into Trump and Biden

Trump likewise encountered charges of wrongfully keeping classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that matter was ultimately thrown out by a federal judge and negated by his re-election as leader.

A special counsel additionally determined that ex-President Joe Biden wrongfully maintained sensitive materials from his time as vice president, but did not prosecute him.

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

Strict protocols regulate the management of sensitive materials. To secure a conviction, the prosecution must prove that Bolton was aware the material he was sending was classified, and he had to knowingly transfer it to someone without authorization to receive it.

"Because of the sensitive nature of the material at issue in this case, we lack a great deal of particulars about why the prosecution contends elements like the diary entries and the additional material he shared by electronic message, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ initiated this case will be under scrutiny, after Trump publicly expressed his desire to see his critics prosecuted and several of those charges came to fruition.

But Mr Lesko said in Bolton's situation, prosecutors seem to have followed standard procedure.

"The Bolton prosecution and ultimately the charge appeared to have followed the standard procedure including the rules and norms within the DOJ," he stated.

In contrast to Comey's short, concise charge, Bolton's was a more "conventional" filing that "clearly outlines the details concerning the facts and circumstances here," Mr Lesko said.

"It seems reasonably aligned with a series of precedents... where government officials mishandled and transmitted classified material."