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Former President Donald Trump has consistently expressed his desire to see critics investigated, applying pressure 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 leader wrote recently in a social media post.

"They impeached me, and charged me (5 times!)" he said, referencing the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

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

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

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

The Specifics of the Legal Situation

Bolton has been formally charged on national allegations related to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Experts say that while there may be political reasons to go after Bolton, the methods used to secure an charge and the evidence gathered against him suggest a potentially more substantial case than the Justice Department presented against James.

"These actions that's being alleged is both more serious and seems to have taken place over a significant period of time," 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 exit, authorities claimed that Bolton placed the nation at risk by wrongfully retaining and sending classified information to family members using unprotected methods, including AOL. Some of the documents were labeled top secret.

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

Bolton entered a not guilty plea during a hearing on recently to eighteen separate charges of improperly handling classified information.

Retribution or a Substantial Case?

The timing of his charge - arriving on the tails of charges against James - has renewed concerns about external influence on the justice system.

Trump previously implied Bolton should be in prison, and called him a "disreputable person". Bolton, for his role, wrote a publication about his time in the Trump government that was highly critical of the leader.

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

However, he added, "if the DOJ is capable to demonstrate the allegations stated and show the material is correctly classified, his behavior may certainly have broken the statute".

Charging such a senior figure 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 concern classified information pose challenges to prosecute, but they can and are filed against equally junior and high-level personnel, from occasionally," she explained.

Similarities to Examinations into Former President and President

Trump likewise encountered charges of improperly storing classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that matter was eventually thrown out by a federal judge and voided by his re-election as leader.

A independent investigator additionally found that ex-President Joe Biden improperly maintained sensitive materials from his time as vice president, but failed to criminally charge him.

Bolton's situation shares characteristics to Biden's sensitive materials issues, noted Mr Lesko, who also held a top security position at the Justice Department.

Rigorous procedures govern the handling of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to knowingly transmit it to someone without authorization to receive it.

"Due to the classified character of the material at issue in this matter, we don't have a great deal of details about the reasons the government believes elements like the diary entries and the additional material he communicated by electronic message, and the reason there were restricted," said Mr Jaffer.

A Increasingly Conventional Legal Action

The process by which the DOJ brought this case will be under scrutiny, following Trump publicly expressed his wish to see his political opponents charged and several of those indictments came to fruition.

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

"The Bolton prosecution and eventually the indictment appeared to have observed the regular process including the regulations and standards within the Department of Justice," he said.

In contrast to Comey's short, two-page indictment, Bolton's was a increasingly "conventional" document that "explicitly outlines the details involving the circumstances and situation here," Mr Lesko commented.

"It seems reasonably consistent with a series of cases... where government officials mishandled and transmitted sensitive information."