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Ex-President Donald Trump has repeatedly expressed his wish to see critics investigated, applying pressure on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's damaging our reputation and trustworthiness," the president wrote recently in a social media message.

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

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

But the latest allegations against a Trump critic, former security advisor John Bolton, differ significantly, legal experts and former prosecutors say.

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

This Specifics of Bolton's Legal Situation

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

Specialists say that while there may be political motivations to go after Bolton, the methods used to secure an charge and the proof compiled against him suggest a potentially stronger case than the Justice Department brought against James.

"These actions that's being claimed is both more serious and seems 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 tenure as Trump's national security adviser, and after his 2019 White House departure, prosecutors claimed that Bolton placed the country at danger by improperly retaining and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were marked top secret.

The charge states that at a certain time a hacker accessed to Bolton's system where documents were kept and transmitted an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on recently to 18 separate charges of mishandling classified information.

Retribution or a Substantial Legal Argument?

The timing of his indictment - coming on the heels of charges against Comey - has revived questions about political pressure on the legal system.

Trump previously suggested Bolton should be in prison, and called him a "sleazebag". Bolton, for his part, wrote a book about his time in the Trump administration that was sharply negative of the leader.

"Undoubtedly that the timing of this indictment, when combined with others, has raised questions about the validity of these charges, and why these charges are being filed at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is capable to prove the facts stated and show the information is properly classified, his conduct may certainly have violated the law".

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

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

Parallels to Investigations into Former President and Biden

Trump similarly encountered allegations of improperly keeping classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that case was ultimately thrown out by a federal judge and negated by his return as leader.

A independent investigator also found that former President Joe Biden improperly maintained sensitive materials from his time as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Biden's classified documents issues, noted Mr Lesko, who previously held a top national security position at the DOJ.

Rigorous protocols govern the management of classified documents. To win a conviction, the prosecution must demonstrate that Bolton was aware the information he was sending was restricted, and he had to intentionally transmit it to someone not entitled to obtain it.

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

A Increasingly Traditional Prosecution

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

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

"The Bolton prosecution and ultimately the charge seemed to have followed the regular procedure including the rules and norms within the Department of Justice," he stated.

Unlike Comey's short, two-page charge, Bolton's was a more "traditional" document that "clearly outlines the particulars involving the circumstances and circumstances here," Mr Lesko commented.

"It seems reasonably aligned with a series of cases... where public servants mishandled and shared classified material."