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

"We cannot postpone further, it's damaging our reputation and credibility," the leader stated last month in a Truth Social message.

"I was impeached me, and indicted me (5 times!)" he declared, referencing the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been charged, in cases that numerous experts have said appear to be politically motivated and difficult to win in legal proceedings.

But the most recent allegations against a Trump critic, ex security advisor John Bolton, stand apart, legal experts and ex-prosecutors say.

"In my opinion, 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 Details of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. After departing the White House in 2019, he has become a outspoken presidential opponent, even to describe him "remarkably ignorant" and unfit for the presidency in his memoir.

Experts contend that while there may be political motivations to target Bolton, the procedures used to secure an indictment and the evidence compiled against him indicate a potentially stronger case than the Justice Department presented against James.

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

Throughout his tenure as Trump's security advisor, and following his 2019 White House exit, prosecutors claimed that Bolton put the nation at risk by wrongfully retaining and transmitting classified information to relatives using unprotected methods, including AOL. Several of the materials were marked top secret.

The indictment alleges that at a certain time a hacker gained access to Bolton's system where files were stored and sent an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on recently to 18 separate counts of improperly handling classified information.

Retribution or a Substantial Legal Argument?

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

Trump previously suggested Bolton belonged in prison, and called him a "sleazebag". Bolton, for his role, authored a book about his time in the Trump government that was sharply negative of the president.

"Undoubtedly that the schedule of this indictment, when combined with additional cases, has raised questions about the validity of these allegations, and why these counts are being brought at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the Justice Department is able to prove the allegations stated and demonstrate the material is correctly classified, his conduct may certainly have violated the statute".

Charging such a senior figure for mishandling sensitive materials is "uncommon" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve sensitive materials present challenges to try, but they may and are brought against equally low-level and senior personnel, from time to time," she said.

Similarities to Investigations into Former President and Biden

Trump similarly encountered allegations of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was ultimately dismissed by a federal judge and voided by his re-election as president.

A independent investigator additionally determined that ex-President Joe Biden wrongfully stored classified documents from his time as vice president, but failed to criminally charge him.

Bolton's case bears similarities to Biden's classified documents issues, said Mr Lesko, who also held a top national security role at the DOJ.

Rigorous protocols regulate the management of classified documents. To secure a guilty verdict, the prosecution must demonstrate that Bolton knew the information he was sending was classified, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the sensitive nature of the material at issue in this case, we lack a lot of details about the reasons the prosecution contends elements like the diary entries and the other information he shared by email, and the reason there were classified," explained Mr Jaffer.

A Increasingly Traditional Prosecution

The process by which the Justice Department brought this legal action will be under scrutiny, after Trump openly expressed his wish to see his critics prosecuted and several of those charges materialized.

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

"The Bolton case and eventually the indictment appeared to have observed the standard procedure including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's short, concise indictment, Bolton's was a increasingly "traditional" filing that "explicitly sets forth the particulars concerning the facts and situation in this instance," Mr Lesko said.

"It appears reasonably consistent with a long line of cases... where public servants improperly handled and shared sensitive information."