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

"We cannot postpone any longer, it's damaging our standing and credibility," the leader wrote last month in a Truth Social post.

"I was impeached twice, and charged me (5 times!)" he said, referencing the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Both have subsequently been charged, in cases that many experts have said seem to be politically motivated and challenging to succeed in court.

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

"In my opinion, comparing Bolton's charges to Comey's is like comparing apples to oranges," said Mark Lesko, a ex acting US attorney for the Eastern District of New York.

The Specifics of the Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed improper handling of sensitive materials. Since departing the White House in 2019, he has become a vocal presidential opponent, even to describe him "stunningly uninformed" 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 charge and the proof gathered against him suggest a potentially stronger legal argument than the DOJ brought against Comey.

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

During his tenure as Trump's security advisor, and following his 2019 White House departure, prosecutors alleged that Bolton put the country at danger by wrongfully retaining and sending classified information to family members using insecure means, including AOL. Several of the documents were marked top secret.

The indictment alleges that at one point a unauthorized user gained access to Bolton's system where files were stored and transmitted an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct counts of mishandling classified information.

Political Motivation or a Substantial Legal Argument?

The schedule of his charge - arriving on the heels of charges against Comey - has revived questions about political pressure on the justice system.

Trump once suggested Bolton belonged in prison, and described him a "disreputable person". Bolton, for his role, wrote a book about his experience in the Trump government that was sharply negative of the president.

"There's no question that the timing of this charge, when combined with others, has raised doubts about the validity of these charges, and why these charges are being brought now," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "if the DOJ is able to prove the facts alleged and show the information is correctly classified, his conduct may certainly have broken the statute".

Prosecuting such a high-ranking official for mishandling classified documents is "rare" 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 brought against both junior and senior personnel, from occasionally," she explained.

Parallels to Investigations into Trump and Biden

Trump likewise faced charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and obstructing their return, but that matter was ultimately dismissed by a federal judge and negated by his re-election as president.

A independent investigator additionally found that former President Joe Biden improperly maintained sensitive materials from his period as second-in-command, but failed to criminally charge him.

Bolton's case shares characteristics to Biden's classified documents matters, noted Mr Lesko, who also held a top security role at the DOJ.

Strict protocols govern the management of classified documents. To win a guilty verdict, the government must prove that Bolton knew the material he was transmitting was classified, and he had to intentionally transmit it to someone without authorization to obtain it.

"Because of the sensitive character of the information at question in this case, we don't have a great deal of details about why the government contends things like the personal notes and the other information he shared by email, and the reason there were classified," said Mr Jaffer.

A Increasingly Conventional Prosecution

The procedure by which the DOJ initiated this case will be under scrutiny, after Trump publicly posted his wish to see his critics charged and some of those indictments materialized.

But Mr Lesko said in Bolton's situation, prosecutors seem to have adhered to protocol.

"This Bolton prosecution and eventually the charge seemed to have followed the regular procedure including the regulations and norms within the Department of Justice," he stated.

In contrast to Comey's short, concise indictment, Bolton's was a increasingly "traditional" filing that "clearly outlines the particulars involving the circumstances and circumstances in this instance," Mr Lesko said.

"It seems fairly consistent with a series of precedents... where public servants improperly handled and shared classified material."