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

"We cannot postpone any longer, it's damaging our reputation and credibility," the president wrote last month in a social media message.

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

Each have since been indicted, in cases that many experts have stated seem to be politically motivated and challenging to win in legal proceedings.

But the latest charges against a presidential opponent, former national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors assert.

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

This Details of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. Since departing the White House in 2019, he has emerged as a outspoken presidential opponent, even to call him "stunningly uninformed" and unfit for the presidency in his memoir.

Experts say that while there may be political motivations to target Bolton, the methods used to obtain an indictment and the proof compiled against him indicate a potentially stronger legal argument than the DOJ presented against Comey.

"These actions that's being claimed is both more severe and appears to have occurred over a significant duration," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton put the nation at risk by improperly retaining and transmitting classified information to relatives using unprotected methods, including AOL. Some of the documents were marked highly classified.

The indictment alleges that at a certain time a unauthorized user accessed to Bolton's account where documents were stored and sent an apparent warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

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

Retribution or a Substantial Legal Argument?

The schedule of his indictment - 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 time in the Trump government that was sharply negative of the president.

"Undoubtedly that the schedule of this indictment, when combined with others, has prompted questions about the strength of these charges, and why these charges are being filed at this time," stated Jamil Jaffer, founder and director of the National Security Institute.

However, he added, "should the DOJ is able to prove the facts stated and show the material is properly designated, his conduct may certainly have broken the statute".

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

"Situations that concern sensitive materials present challenges to try, but they can and are brought against both low-level and senior personnel, from occasionally," she explained.

Similarities to Examinations into Trump and Biden

Trump likewise faced allegations of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that matter was ultimately dismissed by a federal judge and voided by his return as president.

A special counsel additionally determined that ex-President Joe Biden wrongfully stored sensitive materials from his time as vice president, but failed to prosecute him.

Bolton's case bears similarities to Biden's classified documents matters, noted Mr Lesko, who previously held a senior national security position at the DOJ.

Rigorous protocols regulate the management of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton was aware the material he was transmitting was classified, and he had to knowingly transmit it to someone without authorization to receive it.

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

A More Conventional Prosecution

The process by which the DOJ brought this legal action will be closely examined, after Trump publicly expressed his desire to see his critics charged and some of those indictments came to fruition.

But Mr Lesko indicated in Bolton's case, authorities seem to have followed protocol.

"This Bolton case and eventually the indictment seemed to have observed the standard procedure including the rules and standards within the DOJ," he said.

Unlike Comey's short, two-page charge, Bolton's was a increasingly "traditional" filing that "clearly outlines the particulars concerning the facts and situation in this instance," Mr Lesko commented.

"It appears fairly consistent with a long line of precedents... where government officials mishandled and shared classified material."