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Former President Donald Trump has repeatedly shown his desire to see critics 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 damaging our reputation and trustworthiness," the president wrote last month in a Truth Social post.

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

Both have since been indicted, in situations that numerous experts have said appear to be driven by politics and challenging to win in legal proceedings.

But the most recent charges against a presidential opponent, former security advisor John Bolton, stand apart, legal specialists and ex-prosecutors assert.

"In my opinion, contrasting Bolton's charges to James' is like equating apples to oranges," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Specifics of the Case

Bolton has been criminally indicted on federal charges related to the supposed improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a vocal Trump critic, going so far as to call 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 procedures used to obtain an indictment and the evidence gathered against him suggest a potentially more substantial case than the DOJ brought against James.

"These actions that's being claimed is simultaneously more serious and appears to have occurred over a significant period of time," said 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 alleged that Bolton put the nation at risk by improperly retaining and sending classified information to relatives using insecure means, including AOL. Some of the materials were labeled highly classified.

The indictment alleges that at a certain time a unauthorized user gained access to Bolton's system where files were kept and sent an seeming warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on Friday to eighteen distinct counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the tails of charges against James - has revived questions about political pressure on the justice system.

Trump previously suggested Bolton should be in prison, and called him a "sleazebag". Bolton, for his role, wrote a book about his experience in the Trump administration that was highly critical of the president.

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

Nevertheless, he added, "if the DOJ is able to prove the allegations stated and demonstrate the information is correctly classified, his conduct may certainly have broken the statute".

Charging such a high-ranking official for improperly handling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve classified information pose challenges to try, but they may and are filed against both low-level and high-level personnel, from occasionally," she said.

Parallels to Investigations into Former President and President

Trump likewise encountered charges of improperly storing classified documents at his Mar-a-Lago property in Florida and obstructing their recovery, but that case was eventually thrown out by a federal judge and voided by his return as leader.

A independent investigator additionally determined that former President Joe Biden improperly stored sensitive materials from his period as vice president, but did not criminally charge him.

Bolton's case bears similarities to Biden's sensitive materials issues, noted Mr Lesko, who also held a senior national security position at the DOJ.

Rigorous procedures regulate the handling of classified documents. To secure a conviction, the prosecution must prove that Bolton knew the information he was sending was restricted, and he had to intentionally transmit it to someone without authorization to obtain it.

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

A Increasingly Traditional Legal Action

The procedure by which the DOJ initiated this legal action will be under scrutiny, after Trump openly expressed his desire to see his critics charged and several of those charges materialized.

But Mr Lesko said in Bolton's case, authorities appear to have followed protocol.

"This Bolton prosecution and eventually the charge appeared to have observed the standard procedure including the rules and standards within the DOJ," he said.

In contrast to Comey's short, two-page charge, Bolton's was a more "traditional" document that "explicitly outlines the details concerning the facts and circumstances here," Mr Lesko said.

"It seems reasonably consistent with a series of cases... where public servants improperly handled and shared sensitive information."