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

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

"They impeached me, and indicted me (5 times!)" he declared, referencing the four criminal cases he faced after departing the White House in 2021 and James's civil case.

Each have since been indicted, in cases that many specialists have said seem to be driven by politics and challenging to succeed in court.

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

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

This Specifics of Bolton's Case

Bolton has been formally charged on national allegations related to the alleged mishandling of sensitive materials. After leaving the White House in 2019, he has emerged as a outspoken Trump critic, even to describe him "remarkably ignorant" and unfit for office in his book.

Experts contend that while there may be political motivations to target Bolton, the methods used to secure an charge and the evidence compiled against him indicate a potentially more substantial legal argument than the DOJ presented against James.

"This misconduct that's being claimed is both more serious and appears to have occurred over a considerable period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

During his tenure as Trump's national security adviser, and after his 2019 White House departure, authorities alleged that Bolton put the nation at danger by wrongfully keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the documents were labeled highly classified.

The indictment states that at one point a hacker gained access to Bolton's system where files were kept and sent an apparent threat to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on Friday to 18 distinct counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his charge - coming on the heels of charges against Comey - has renewed questions about external influence on the legal system.

Trump previously suggested Bolton belonged in prison, and described him a "sleazebag". Bolton, for his part, wrote a book about his experience in the Trump administration that was highly critical of the president.

"There's no question that the timing of this indictment, when paired with others, has raised questions about the validity of these charges, and why these charges are being brought now," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is able to prove the allegations stated and demonstrate the information is properly classified, his conduct may certainly have broken the law".

Prosecuting such a high-ranking figure for improperly handling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Cases that involve sensitive materials pose challenges to try, but they can and are brought against equally junior and senior personnel, from occasionally," she explained.

Parallels to Investigations into Trump and President

Trump likewise encountered charges of improperly storing classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was eventually dismissed by a federal judge and voided by his re-election as president.

A special counsel additionally found that ex-President Joe Biden wrongfully stored sensitive materials from his time as second-in-command, but failed to criminally charge him.

Bolton's situation bears similarities to Biden's sensitive materials matters, noted Mr Lesko, who also held a senior security role at the Justice Department.

Strict protocols regulate the management of classified documents. To secure a guilty verdict, the government must prove that Bolton knew the information he was sending was classified, and he had to intentionally transfer it to someone without authorization to obtain it.

"Due to the sensitive nature of the information at issue in this matter, we don't have a great deal of details about the reasons the government contends things like the diary entries and the additional material he shared by email, and why there were classified," said Mr Jaffer.

A More Conventional Prosecution

The process by which the DOJ initiated this legal action will be closely examined, following Trump publicly posted his wish to see his political opponents prosecuted and several of those charges came to fruition.

But Mr Lesko indicated in Bolton's case, prosecutors seem to have followed protocol.

"This Bolton prosecution and ultimately the charge seemed to have observed the regular procedure including the regulations and standards within the DOJ," he stated.

In contrast to Comey's brief, two-page indictment, Bolton's was a increasingly "traditional" filing that "explicitly sets forth the details concerning the circumstances and circumstances in this instance," Mr Lesko commented.

"It seems fairly aligned with a long line of precedents... where government officials mishandled and shared sensitive information."