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Ex-President Donald Trump has repeatedly expressed his wish to see critics investigated, applying pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone further, it's killing our standing and credibility," the president wrote recently in a social media message.

"I was impeached me, and indicted 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 since been indicted, in situations that many specialists have said seem to be politically motivated and challenging to win in legal proceedings.

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

"I would say, contrasting Bolton's case to James' is like comparing two different things," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of the Case

Bolton has been formally charged on national allegations related to the supposed improper handling of sensitive materials. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, even to call him "remarkably ignorant" and unsuitable for office in his book.

Experts say that while there may be political reasons to target Bolton, the procedures used to obtain an charge and the proof gathered against him indicate a potentially more substantial legal argument than the DOJ presented against Comey.

"This misconduct that's being claimed 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 time as Trump's national security adviser, and after his 2019 White House exit, authorities claimed that Bolton put the nation at risk by improperly retaining and transmitting classified information to family members using unprotected methods, including AOL. Several of the materials were marked highly classified.

The indictment alleges that at a certain time a hacker accessed to Bolton's account where documents were stored and transmitted an seeming threat to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on recently to eighteen distinct counts of improperly handling classified information.

Retribution or a Substantial Legal Argument?

The schedule of his indictment - arriving on the tails of allegations against Comey - has revived concerns about political pressure on the justice system.

Trump once suggested Bolton should be in jail, and called him a "disreputable person". Bolton, for his role, wrote a publication about his time in the Trump government that was highly critical of the president.

"Undoubtedly that the timing of this charge, when combined with others, has prompted questions about the strength of these charges, and the reason these charges are being filed now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is capable to demonstrate the allegations alleged and demonstrate the material is properly classified, his conduct may certainly have broken the law".

Prosecuting such a high-ranking figure for mishandling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that involve sensitive materials present difficulties to try, but they may and are brought against both junior and senior officials, from time to time," she explained.

Similarities to Investigations into Former President and Biden

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

A special counsel also determined that former President Joe Biden wrongfully maintained classified documents from his period as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's sensitive materials issues, said Mr Lesko, who also held a senior national security role at the Justice Department.

Rigorous procedures regulate the management of classified documents. To secure a conviction, the government must demonstrate that Bolton was aware the material he was sending was restricted, and he had to intentionally transfer it to someone without authorization to obtain it.

"Because of the classified character of the material at question in this case, we don't have a lot of details about the reasons the government believes elements like the personal notes and the additional information he communicated by electronic message, and why there were restricted," said Mr Jaffer.

A More Traditional Legal Action

The procedure by which the Justice Department brought this legal action will be closely examined, following Trump openly expressed his wish to see his political opponents prosecuted and some of those charges came to fruition.

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

"This Bolton prosecution and eventually the charge appeared to have observed the standard process including the regulations and norms within the DOJ," he said.

Unlike Comey's short, concise indictment, Bolton's was a more "conventional" filing that "explicitly outlines the details concerning the circumstances and circumstances in this instance," Mr Lesko commented.

"It seems fairly aligned with a series of cases... where government officials improperly handled and transmitted classified material."