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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 cannot postpone any longer, it's damaging our reputation and credibility," the leader wrote recently in a Truth Social message.

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

Each have since been indicted, in situations that many specialists have said appear to be driven by politics and difficult to succeed in legal proceedings.

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

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

The Specifics of the Legal Situation

Bolton has been formally charged on federal charges related to the supposed improper handling of classified information. After departing the White House in 2019, he has emerged as a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unsuitable for the presidency in his book.

Specialists contend that while there may be political reasons to target Bolton, the procedures used to secure an charge and the evidence gathered against him suggest a potentially stronger legal argument than the Justice Department brought against James.

"These actions that's being alleged is both more severe and appears to have occurred over a considerable period of time," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and following his 2019 White House departure, prosecutors alleged that Bolton placed the country at risk by improperly keeping and transmitting sensitive documents to family members using unprotected methods, including AOL. Some of the materials were marked top secret.

The charge states that at one point a unauthorized user gained access to Bolton's account where files were stored and sent an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

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

Political Motivation or a Strong Case?

The schedule of his charge - coming on the heels of allegations against James - has renewed concerns about external influence on the justice system.

Trump previously suggested Bolton belonged in jail, and called him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump government that was sharply negative of the president.

"Undoubtedly that the schedule of this charge, when combined with others, has raised doubts about the strength of these allegations, and the reason these counts are being filed now," said Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is capable to prove the facts stated and show the material is correctly classified, his conduct may certainly have violated the statute".

Charging such a high-ranking figure for improperly handling classified documents is "rare" but not without precedent, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve classified information present challenges to try, but they can and are filed against equally low-level and high-level personnel, from occasionally," she explained.

Parallels to Investigations into Former President and President

Trump similarly faced allegations of wrongfully storing sensitive materials at his Mar-a-Lago resort in Florida and obstructing their recovery, but that case was ultimately thrown out by a federal judge and voided by his return as leader.

A special counsel also determined that former President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Biden's sensitive materials issues, said Mr Lesko, who previously held a top national security position at the DOJ.

Rigorous procedures regulate the management of sensitive materials. To secure a guilty verdict, the government must prove that Bolton knew the material he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Because of the sensitive character of the material at issue in this matter, we don't have a great deal of particulars about why the government believes elements like the diary entries and the additional information he communicated by electronic message, and why there were restricted," said Mr Jaffer.

A More Conventional Prosecution

The process by which the DOJ initiated this legal action will be under scrutiny, after Trump openly posted his desire to see his political opponents prosecuted and some of those indictments came to fruition.

But Mr Lesko indicated in Bolton's situation, authorities appear to have adhered to protocol.

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

In contrast to Comey's brief, concise charge, Bolton's was a more "conventional" filing that "explicitly sets forth the details involving the facts and situation in this instance," Mr Lesko commented.

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