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Former President Donald Trump has consistently expressed his desire to see critics investigated, applying influence on the Justice Department to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our standing and credibility," the president stated recently in a social media post.

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

Each have subsequently been indicted, in situations that many specialists have said appear to be politically motivated and challenging to succeed in legal proceedings.

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

"I would say, comparing Bolton's case to Comey's is like comparing apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges pertaining to the alleged mishandling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal Trump critic, going so far as to call him "remarkably ignorant" and unsuitable for office in his memoir.

Experts contend that while there may be political motivations to go after Bolton, the methods used to obtain an charge and the evidence compiled against him indicate a potentially more substantial legal argument than the DOJ presented against James.

"This misconduct that's being alleged is both more serious and seems to have taken place over a considerable period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's national security adviser, and following his 2019 White House exit, authorities alleged that Bolton put the country at risk by wrongfully retaining and sending sensitive documents to relatives using insecure means, including AOL. Several of the materials were marked highly classified.

The indictment states that at one point a hacker accessed to Bolton's account where documents were stored and sent an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on recently to eighteen distinct charges of mishandling classified information.

Political Motivation or a Strong Case?

The timing of his charge - coming on the tails of charges against James - has renewed concerns about political pressure on the justice system.

Trump previously suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump government that was highly critical of the leader.

"There's no question that the schedule of this charge, when paired with others, has raised questions about the strength of these charges, and the reason these charges are being brought at this time," said Jamil Jaffer, creator and director of the National Security Institute.

However, he added, "should the DOJ is able to prove the allegations stated and demonstrate the information is properly designated, his conduct may certainly have violated the law".

Charging such a senior official for improperly handling classified documents is "uncommon" but not unprecedented, 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 may and are filed against both low-level and high-level officials, from occasionally," she explained.

Similarities to Investigations into Former President and Biden

Trump similarly encountered allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was ultimately dismissed by a court official and voided by his return as president.

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

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

Strict procedures regulate the management of sensitive materials. To win a guilty verdict, the government must prove that Bolton knew the material he was sending was restricted, and he had to knowingly transmit it to someone without authorization to receive it.

"Due to the sensitive character of the material at question in this case, we lack a lot of details about why the prosecution contends elements like the diary entries and the additional material he communicated by electronic message, and why there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department initiated this case will be under scrutiny, following Trump openly expressed his desire to see his critics prosecuted and several of those indictments materialized.

But Mr Lesko indicated in Bolton's situation, prosecutors appear to have followed protocol.

"This Bolton case and ultimately the indictment seemed to have followed the standard procedure including the rules and norms within the DOJ," he said.

In contrast to Comey's short, concise indictment, Bolton's was a increasingly "traditional" filing that "clearly outlines the details involving the circumstances and circumstances here," Mr Lesko commented.

"It seems fairly aligned with a series of cases... where government officials improperly handled and transmitted classified material."