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Ex-President Donald Trump has repeatedly shown his desire to see critics investigated, exerting pressure on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's killing our standing and credibility," the leader wrote recently in a social media message.

"I was impeached twice, and indicted me (5 times!)" he said, referencing the four criminal cases he encountered after departing the White House in 2021 and James's civil case.

Each have since been charged, in situations that numerous specialists have stated appear to be politically motivated and difficult to succeed in legal proceedings.

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

"I would say, contrasting Bolton's case to James' is like comparing two different things," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Details of Bolton's Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has become a vocal presidential opponent, going so far as to describe him "stunningly uninformed" and unfit for office in his book.

Experts say that while there may be political motivations to go after Bolton, the procedures used to obtain an indictment and the proof compiled against him indicate a possibly more substantial legal argument than the DOJ presented against Comey.

"This misconduct that's being alleged is simultaneously more serious and appears to have taken place over a considerable duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton placed the nation at risk by wrongfully keeping and transmitting sensitive documents to family members using insecure means, including AOL. Some of the materials were labeled highly classified.

The indictment states that at one point a unauthorized user accessed to Bolton's account where documents were kept and transmitted an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to eighteen separate charges of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - arriving on the tails of charges against James - has revived concerns about political pressure on the legal system.

Trump once suggested Bolton should be in prison, and described him a "sleazebag". Bolton, for his part, wrote a publication about his experience in the Trump government that was highly critical of the president.

"Undoubtedly that the timing of this indictment, when paired with additional cases, has raised questions about the validity of these allegations, and the reason these counts are being brought now," said Jamil Jaffer, founder and executive director of the National Security Institute.

However, he continued, "should the DOJ is able to demonstrate the allegations alleged and demonstrate the information is properly classified, his behavior may certainly have broken the statute".

Charging such a senior figure for improperly handling sensitive materials is "rare" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern sensitive materials present difficulties to prosecute, but they can and are brought against equally low-level and high-level officials, from occasionally," she said.

Similarities to Investigations into Trump and Biden

Trump similarly faced allegations of improperly storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that matter was eventually dismissed by a federal judge and voided by his return as leader.

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

Bolton's situation shares characteristics to Biden's sensitive materials matters, noted Mr Lesko, who also held a senior security position at the DOJ.

Strict protocols regulate the handling of sensitive materials. To secure a guilty verdict, the government must prove that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled to receive it.

"Due to the sensitive nature of the material at question in this case, we don't have a great deal of details about the reasons the prosecution contends elements like the diary entries and the other material he shared by electronic message, and why there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The procedure by which the DOJ brought this case will be under scrutiny, after Trump publicly posted his desire to see his political opponents charged and several of those indictments materialized.

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

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

In contrast to Comey's short, concise charge, Bolton's was a more "traditional" document that "explicitly outlines the particulars concerning the circumstances and situation here," Mr Lesko said.

"It appears reasonably aligned with a long line of precedents... where government officials improperly handled and transmitted sensitive information."