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Ex-President Donald Trump has repeatedly shown his wish to see opponents investigated, applying pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's killing our reputation and trustworthiness," the leader wrote last month in a social media message.

"I was impeached me, and indicted me (5 times!)" he said, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's lawsuit.

Both have subsequently been indicted, in cases that numerous experts have stated seem to be driven by politics and difficult to succeed in court.

But the most recent allegations against a Trump critic, ex national security adviser John Bolton, stand apart, legal experts and former prosecutors assert.

"In my opinion, contrasting Bolton's case to James' is like comparing two different things," said Mark Lesko, a former acting US attorney for the Eastern District of New York.

This Details of Bolton's Case

Bolton has been criminally indicted on national allegations pertaining to the alleged mishandling of classified information. After leaving the White House in 2019, he has become a outspoken Trump critic, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Specialists contend that while there may be political reasons to go after Bolton, the procedures used to secure an indictment and the proof compiled against him suggest a potentially stronger case than the DOJ presented against Comey.

"This misconduct that's being claimed is simultaneously more serious and appears to have occurred over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and after his 2019 White House departure, authorities alleged that Bolton placed the nation at danger by improperly retaining and transmitting classified information to family members using insecure means, including AOL. Several of the documents were marked top secret.

The indictment states that at a certain time a unauthorized user accessed to Bolton's account where files were kept and sent an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on recently to eighteen separate counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - arriving on the heels of allegations against Comey - has renewed concerns about political pressure on the justice system.

Trump once implied Bolton should be in jail, and described him a "sleazebag". Bolton, for his part, wrote a publication about his experience in the Trump government that was sharply negative of the president.

"Undoubtedly that the schedule of this indictment, when paired with others, has prompted doubts about the validity of these allegations, and why these charges are being brought at this time," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "if the Justice Department is capable to prove the facts alleged and show the information is correctly designated, his conduct may very well have violated the law".

Charging such a high-ranking official for mishandling classified documents is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern classified information pose difficulties to prosecute, but they may and are brought against both junior and high-level personnel, from time to time," she explained.

Parallels to Examinations into Former President and Biden

Trump similarly faced allegations of wrongfully keeping sensitive materials at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was eventually thrown out by a court official and voided by his re-election as president.

A independent investigator additionally determined that ex-President Joe Biden improperly maintained classified documents from his time as vice president, but failed to prosecute him.

Bolton's situation bears similarities to Trump's classified documents issues, noted Mr Lesko, who also held a senior national security role at the DOJ.

Rigorous procedures regulate the management of sensitive materials. To secure a guilty verdict, the prosecution must prove that Bolton knew the information he was sending was restricted, and he had to intentionally transmit it to someone not entitled to obtain it.

"Due to the sensitive character of the information at question in this matter, we don't have a great deal of particulars about the reasons the prosecution contends things like the diary entries and the additional information he shared by email, and why there were classified," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ brought this case will be closely examined, after Trump publicly posted his wish to see his critics prosecuted and some of those charges materialized.

But Mr Lesko said in Bolton's case, prosecutors seem to have followed protocol.

"This Bolton prosecution and ultimately the charge seemed to have observed the standard process including the rules and standards within the DOJ," he said.

In contrast to Comey's short, concise charge, Bolton's was a more "traditional" document that "clearly sets forth the details concerning the facts and circumstances here," Mr Lesko commented.

"It seems fairly aligned with a long line of cases... where government officials mishandled and shared classified material."