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Former President Donald Trump has consistently expressed his wish to see opponents investigated, exerting influence on the Justice Department to charge ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's damaging our standing and credibility," the president wrote recently in a social media message.

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

Each have subsequently been charged, in cases that numerous experts have stated appear to be driven by politics and difficult to win in legal proceedings.

But the latest allegations against a Trump critic, former national security adviser John Bolton, differ significantly, legal specialists and ex-prosecutors say.

"In my opinion, contrasting Bolton's case to James' is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Specifics of the Case

Bolton has been criminally indicted on federal charges pertaining to the supposed improper handling of sensitive materials. Since leaving the White House in 2019, he has become a vocal Trump critic, going so far as to call him "stunningly uninformed" and unfit for office in his book.

Experts say that while there may be political motivations to target Bolton, the procedures used to obtain an indictment and the evidence gathered against him indicate a potentially stronger case than the Justice Department presented against Comey.

"These actions that's being claimed is simultaneously more serious and seems to have occurred over a significant period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his tenure as Trump's security advisor, and after his 2019 White House departure, prosecutors claimed that Bolton placed the country at risk by improperly keeping and transmitting sensitive documents to relatives using unprotected methods, including AOL. Some of the documents were labeled top secret.

The indictment alleges that at a certain time a hacker accessed to Bolton's system where documents were stored and sent an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were leaked".

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

Political Motivation or a Strong Legal Argument?

The schedule of his charge - arriving on the heels of allegations against James - has revived concerns about external influence on the legal system.

Trump previously implied Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, wrote a publication about his time in the Trump government that was sharply negative of the president.

"There's no question that the timing of this charge, when paired with additional cases, has raised questions about the strength of these allegations, and the reason these charges are being filed at this time," stated Jamil Jaffer, creator and executive director of the National Security Institute.

Nevertheless, he continued, "should the DOJ is able to prove the allegations alleged and demonstrate the material is correctly classified, his conduct may certainly have broken the statute".

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

"Cases that concern classified information present challenges to prosecute, but they may and are brought against equally low-level and senior personnel, from time to time," she explained.

Parallels to Investigations into Former President and Biden

Trump similarly encountered allegations of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was eventually thrown out by a federal judge and voided by his return as president.

A special counsel additionally found that former President Joe Biden improperly stored sensitive materials from his period as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's classified documents matters, said Mr Lesko, who also held a top security role at the Justice Department.

Rigorous procedures regulate the management of sensitive materials. To win a conviction, the government must prove that Bolton was aware the information he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to obtain it.

"Due to the classified character of the material at question in this matter, we lack a great deal of particulars about the reasons the prosecution contends things like the diary entries and the other material he communicated by email, and why there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ initiated this case will be under scrutiny, after Trump publicly expressed his wish to see his political opponents charged and several of those charges materialized.

But Mr Lesko said in Bolton's situation, authorities seem to have adhered to protocol.

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

In contrast to Comey's brief, concise indictment, Bolton's was a more "traditional" filing that "explicitly sets forth the particulars concerning the facts and circumstances here," Mr Lesko said.

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