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Ex-President Donald Trump has consistently expressed his wish 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 can't delay any longer, it's damaging our standing and trustworthiness," the president wrote last month in a social media post.

"They impeached twice, and charged me (5 times!)" he said, mentioning the multiple legal proceedings he faced after leaving the White House in 2021 and James's lawsuit.

Each have since been charged, in cases that many experts have said appear to be politically motivated and challenging to win in court.

But the most recent allegations against a Trump critic, ex national security adviser John Bolton, differ significantly, legal experts and former prosecutors say.

"I would say, contrasting Bolton's case to Comey's is like equating apples to oranges," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

This Specifics of Bolton's Case

Bolton has been formally charged on federal charges pertaining to the alleged improper handling of classified information. Since leaving the White House in 2019, he has become a outspoken Trump critic, even to describe him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists say that while there may be political reasons to go after Bolton, the methods used to obtain an charge and the proof gathered against him indicate a potentially more substantial legal argument than the Justice Department brought against Comey.

"This misconduct that's being alleged is simultaneously more severe and seems to have taken place over a considerable duration," said Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's national security adviser, and after his 2019 White House departure, prosecutors claimed that Bolton put the nation at danger by wrongfully retaining and transmitting classified information to relatives using unprotected methods, including AOL. Some of the materials were labeled highly classified.

The charge states that at a certain time a unauthorized user gained access to Bolton's system where documents were stored and sent an apparent warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on recently to eighteen distinct charges of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the tails of charges against Comey - has renewed questions about political pressure on the justice system.

Trump previously implied Bolton should be in prison, and called him a "sleazebag". Bolton, for his part, authored a publication about his experience in the Trump government that was sharply negative of the leader.

"There's no question that the schedule of this indictment, when combined with additional cases, has prompted doubts about the validity of these allegations, and why these charges are being filed at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is able to demonstrate the facts alleged and demonstrate the material is correctly designated, his conduct may certainly have violated the law".

Charging such a senior official for improperly handling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve classified information pose challenges to prosecute, but they may and are filed against equally junior and high-level personnel, from time to time," she explained.

Similarities to Investigations into Trump and Biden

Trump similarly encountered charges of improperly keeping classified documents at his Mar-a-Lago property in Florida and obstructing their return, but that matter was ultimately dismissed by a court official and negated by his re-election as president.

A independent investigator also determined that ex-President Joe Biden wrongfully maintained sensitive materials from his time as second-in-command, but failed to prosecute him.

Bolton's case shares characteristics to Trump's classified documents matters, said Mr Lesko, who previously held a top national security role at the DOJ.

Rigorous protocols regulate the management of classified documents. To win a guilty verdict, the prosecution must prove that Bolton was aware the material he was transmitting was classified, and he had to knowingly transfer it to someone not entitled to obtain it.

"Due to the classified character of the information at question in this case, we don't have a lot of particulars about why the government contends elements like the diary entries and the other information he communicated by electronic message, and why there were restricted," said Mr Jaffer.

A Increasingly Traditional Legal Action

The procedure by which the DOJ brought this legal action will be under scrutiny, after Trump publicly expressed his wish to see his political opponents prosecuted and several of those indictments materialized.

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

"This Bolton case and ultimately the charge appeared to have observed the regular process including the rules and norms within the Department of Justice," he said.

In contrast to Comey's brief, concise charge, Bolton's was a increasingly "traditional" document that "clearly sets forth the details concerning the facts and circumstances in this instance," Mr Lesko commented.

"It appears reasonably consistent with a long line of cases... where public servants mishandled and transmitted classified material."