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Former President Donald Trump has consistently shown his wish to see opponents probed, applying pressure on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our reputation and credibility," the leader wrote recently in a social media post.

"They impeached twice, and charged me (five times!)" he said, referencing the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Each have subsequently been indicted, in cases that many experts have stated seem to be driven by politics and difficult to win in legal proceedings.

But the latest charges against a Trump critic, former security advisor John Bolton, stand apart, legal specialists and ex-prosecutors say.

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

This Details of the Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged improper handling of sensitive materials. After departing the White House in 2019, he has become a outspoken presidential opponent, even to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Experts say that while there may be political motivations to target Bolton, the methods used to obtain an charge and the evidence gathered against him indicate a potentially stronger legal argument than the DOJ presented against James.

"This misconduct that's being alleged is both more serious and seems to have occurred over a considerable period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his time as Trump's national security adviser, and following his 2019 White House departure, prosecutors alleged that Bolton placed the nation at risk by improperly keeping and sending sensitive documents to family members using insecure means, including AOL. Several of the documents were marked top secret.

The charge alleges that at one point a unauthorized user gained access to Bolton's account where files were stored and sent an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a hearing on Friday to 18 distinct charges of improperly handling classified information.

Retribution or a Strong Legal Argument?

The timing of his charge - arriving on the tails of allegations against James - has revived questions about external influence on the legal system.

Trump once suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his role, authored a publication about his time in the Trump government that was sharply negative of the leader.

"There's no question that the schedule of this charge, when combined with additional cases, has raised questions about the validity of these charges, and the reason these charges are being brought now," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is capable to prove the facts stated and demonstrate the information is correctly designated, his behavior may certainly have broken the statute".

Charging such a senior figure for improperly handling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern sensitive materials present challenges to prosecute, but they may and are brought against equally low-level and high-level personnel, from occasionally," she explained.

Similarities to Investigations into Trump and President

Trump likewise encountered charges of improperly storing sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was ultimately thrown out by a court official and voided by his return as leader.

A independent investigator also determined that ex-President Joe Biden improperly stored classified documents from his period as second-in-command, but did not prosecute him.

Bolton's case bears similarities to Biden's classified documents issues, noted Mr Lesko, who previously held a top security role at the Justice Department.

Rigorous procedures govern the management of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton knew the information he was transmitting was classified, and he had to intentionally transfer it to someone not entitled to receive it.

"Because of the classified nature of the information at question in this case, we don't have a great deal of details about why the prosecution contends elements like the diary entries and the additional information he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Legal Action

The process by which the DOJ brought this legal action will be closely examined, following Trump publicly posted his desire to see his political opponents prosecuted and several of those charges came to fruition.

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

"The Bolton prosecution and eventually the indictment appeared to have observed the regular procedure including the rules and norms within the DOJ," he said.

In contrast to Comey's brief, concise charge, Bolton's was a more "conventional" filing that "clearly outlines the details involving the circumstances and circumstances here," Mr Lesko commented.

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