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Ex-President Donald Trump has repeatedly shown his wish to see critics probed, exerting influence on the DOJ 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 credibility," the president wrote recently in a Truth Social message.

"They impeached twice, and indicted me (five times!)" he declared, referencing the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that numerous specialists have stated seem to be driven by politics and challenging to succeed in court.

But the most recent allegations against a Trump critic, former national security adviser John Bolton, differ significantly, legal experts and former prosecutors say.

"In my opinion, contrasting Bolton's case to James' 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 Legal Situation

Bolton has been formally charged on national allegations related to the supposed improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken presidential opponent, going so far as to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Experts contend that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the proof gathered against him indicate a possibly stronger case than the Justice Department presented against James.

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

During his tenure as Trump's security advisor, and following his 2019 White House exit, authorities alleged that Bolton put the nation at danger by wrongfully keeping and sending classified information to family members using insecure means, including AOL. Several of the materials were marked highly classified.

The charge alleges that at a certain time a unauthorized user gained access to Bolton's account where documents were stored and sent an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to 18 distinct counts of mishandling classified information.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the tails of allegations against Comey - has revived concerns about political pressure on the justice system.

Trump once suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his part, authored a book about his time in the Trump administration that was highly critical of the president.

"Undoubtedly that the schedule of this indictment, when combined with additional cases, has raised questions about the validity of these allegations, and the reason these charges are being filed now," said Jamil Jaffer, founder and director of the National Security Institute.

However, he continued, "should the DOJ is capable to prove the facts alleged and show the material is correctly designated, his conduct may very well have broken the law".

Prosecuting such a high-ranking figure for improperly handling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve sensitive materials present challenges to prosecute, but they can and are filed against equally low-level and high-level officials, from time to time," she explained.

Parallels to Investigations into Trump and Biden

Trump likewise encountered charges of wrongfully keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually dismissed by a federal judge and negated by his return as president.

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

Bolton's case shares characteristics to Trump's sensitive materials matters, said Mr Lesko, who previously held a senior security position at the Justice Department.

Rigorous procedures govern the handling of classified documents. To secure a conviction, the government must demonstrate that Bolton was aware the information he was sending was restricted, and he had to knowingly transmit it to someone not entitled to obtain it.

"Due to the classified character of the material at issue in this matter, we don't have a lot of particulars about why the prosecution believes things like the diary entries and the additional material he communicated by email, and why there were classified," explained Mr Jaffer.

A More Conventional Legal Action

The process by which the DOJ initiated this case will be closely examined, following Trump openly posted his wish to see his critics prosecuted and several of those charges materialized.

But Mr Lesko said in Bolton's case, authorities appear to have followed standard procedure.

"The Bolton case and ultimately the indictment appeared to have followed the standard process including the regulations and norms within the DOJ," he said.

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

"It appears fairly consistent with a series of precedents... where government officials improperly handled and shared sensitive information."