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

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

"They impeached twice, and charged me (5 times!)" he declared, mentioning the four criminal cases he faced after leaving the White House in 2021 and James's lawsuit.

Both have subsequently been charged, in cases that many experts have said seem to be driven by politics and challenging to succeed in legal proceedings.

But the most recent charges against a Trump critic, former security advisor John Bolton, differ significantly, legal experts and former prosecutors say.

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

The Details of the Legal Situation

Bolton has been criminally indicted on federal charges related to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has emerged as a outspoken presidential opponent, even to call him "remarkably ignorant" and unsuitable for office in his memoir.

Specialists say that while there may be political motivations to target Bolton, the methods used to obtain an indictment and the evidence compiled against him indicate a possibly more substantial legal argument than the DOJ presented against Comey.

"These actions that's being claimed is both more serious and appears 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 tenure as Trump's security advisor, and after his 2019 White House departure, prosecutors alleged that Bolton put the nation at danger by improperly retaining and sending classified information to family members using unprotected methods, including AOL. Several of the documents were labeled top secret.

The indictment states that at one point a hacker accessed to Bolton's system where files were stored and sent an seeming threat to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a hearing on Friday to 18 separate counts of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the tails of allegations against Comey - has revived questions about external influence on the legal system.

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

"There's no question that the timing of this indictment, when paired with additional cases, has prompted doubts about the validity of these charges, and why these charges are being brought now," said Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is able to prove the allegations alleged and show the material is properly designated, his conduct may very well have violated the law".

Charging such a senior figure for improperly handling classified documents is "uncommon" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern sensitive materials present difficulties to try, but they may and are brought against both low-level and senior officials, from occasionally," she explained.

Similarities to Investigations into Former President and President

Trump similarly faced charges of improperly storing classified documents at his Mar-a-Lago resort 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 additionally determined that ex-President Joe Biden improperly stored sensitive materials from his period as vice president, but did not prosecute him.

Bolton's case shares characteristics to Biden's classified documents matters, noted Mr Lesko, who previously held a top national security role at the Justice Department.

Rigorous procedures govern the management of sensitive materials. To win a guilty verdict, the prosecution must demonstrate that Bolton was aware the information he was transmitting was classified, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the classified nature of the material at question in this matter, we don't have a great deal of details about the reasons the prosecution believes things like the diary entries and the other material he shared by electronic message, and why there were classified," said Mr Jaffer.

A More Traditional Legal Action

The procedure by which the Justice Department initiated this legal action will be under scrutiny, following Trump publicly posted his wish to see his critics prosecuted and several of those charges came to fruition.

But Mr Lesko said in Bolton's case, authorities seem to have adhered to standard procedure.

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

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

"It seems reasonably aligned with a series of cases... where government officials mishandled and shared sensitive information."