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Former President Donald Trump has repeatedly shown his desire to see critics investigated, applying pressure on the DOJ to charge 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 stated recently in a Truth Social message.

"They impeached me, and indicted me (five times!)" he declared, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Both have since been charged, in situations that many specialists have stated seem to be driven by politics and challenging to succeed in court.

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

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

This Details of Bolton's Legal Situation

Bolton has been formally charged on federal charges related to the alleged improper handling of classified information. After departing the White House in 2019, he has become a outspoken presidential opponent, even to call him "remarkably ignorant" and unsuitable for office in his book.

Experts say that while there may be political motivations to go after Bolton, the procedures used to secure an indictment and the proof gathered against him indicate a potentially more substantial legal argument than the Justice Department brought against James.

"These actions that's being alleged is simultaneously more serious and appears to have occurred over a considerable period of time," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House departure, authorities alleged that Bolton placed the nation at risk by improperly retaining and transmitting classified information to family members using unprotected methods, including AOL. Some of the documents were marked top secret.

The charge states that at one point a hacker gained access to Bolton's system where documents were kept and sent an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

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

Retribution or a Strong Case?

The timing of his charge - coming on the heels of allegations against James - has renewed questions about political pressure on the justice system.

Trump once suggested Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, authored a publication about his time in the Trump government that was highly critical of the leader.

"There's no question that the schedule of this charge, when paired with additional cases, has prompted doubts about the validity of these allegations, and why these charges are being filed now," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is able to demonstrate the facts alleged and demonstrate the information is properly classified, his conduct may very well have violated the law".

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

"Situations that concern sensitive materials present difficulties to try, but they may and are filed against equally low-level and high-level personnel, from time to time," she explained.

Parallels to Examinations into Former President and President

Trump similarly faced allegations of improperly keeping sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that matter was eventually thrown out by a court official and voided by his return as leader.

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

Bolton's case bears similarities to Trump's classified documents matters, noted Mr Lesko, who also held a senior national security position at the DOJ.

Rigorous protocols regulate the handling of sensitive materials. To secure a conviction, the government 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 obtain it.

"Due to the sensitive nature of the material at question in this case, we lack a lot of details about the reasons the government contends elements like the diary entries and the additional material he shared by email, and why there were classified," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the Justice Department brought this case will be under scrutiny, following Trump openly expressed his wish to see his critics charged and several of those indictments came to fruition.

But Mr Lesko said in Bolton's case, prosecutors seem to have followed protocol.

"The Bolton case and ultimately the charge appeared to have followed the standard process including the rules 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 "clearly sets forth the particulars involving the facts and circumstances here," Mr Lesko said.

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