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

"We can't delay further, it's killing our standing and trustworthiness," the leader stated recently in a social media post.

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

Both have subsequently been charged, in cases that numerous specialists have said seem to be politically motivated and difficult to win in legal proceedings.

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

"I would say, contrasting Bolton's charges to Comey's is like comparing apples to oranges," stated Mark Lesko, a former acting US attorney for the Eastern District of New York.

The Specifics of Bolton's Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the supposed improper handling of classified information. After departing the White House in 2019, he has become a outspoken Trump critic, even to describe him "remarkably ignorant" and unsuitable for office in his book.

Experts contend that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the evidence gathered against him suggest a potentially stronger case than the DOJ brought against Comey.

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

During his time as Trump's national security adviser, and following his 2019 White House exit, authorities alleged that Bolton placed the nation at risk by wrongfully retaining and transmitting 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 hacker gained access to Bolton's account where files were stored 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 recently to 18 distinct charges of mishandling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - arriving on the tails of allegations against Comey - has renewed concerns about political pressure on the justice system.

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, wrote a publication about his experience in the Trump administration that was highly critical of the leader.

"There's no question that the schedule of this charge, when paired with additional cases, has raised doubts about the strength of these charges, and why these counts are being brought now," said Jamil Jaffer, creator and director of the National Security Institute.

However, he continued, "if the Justice Department is able to prove the facts alleged and show the material is correctly classified, his behavior may certainly have violated the law".

Charging such a high-ranking figure for improperly handling sensitive materials is "uncommon" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information present difficulties to prosecute, but they can and are brought against both junior and senior officials, from time to time," she explained.

Parallels to Investigations into Trump and President

Trump likewise encountered allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their return, but that case was eventually dismissed by a court official and negated by his return as leader.

A special counsel also found that ex-President Joe Biden wrongfully stored classified documents from his time as second-in-command, but did not criminally charge him.

Bolton's case bears similarities to Trump's classified documents issues, said Mr Lesko, who previously held a senior national security role at the Justice Department.

Strict protocols regulate the handling of sensitive materials. To secure a conviction, the prosecution must prove that Bolton was aware the material he was sending 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 lot of details about the reasons the prosecution contends 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 Prosecution

The process by which the Justice Department brought this case will be under scrutiny, following Trump openly expressed his wish to see his political opponents prosecuted and some of those indictments came to fruition.

But Mr Lesko said in Bolton's situation, authorities appear to have followed standard procedure.

"This Bolton case and eventually the charge seemed to have observed the standard process including the regulations and standards within the DOJ," he stated.

In contrast to Comey's short, concise indictment, Bolton's was a more "traditional" filing that "explicitly sets forth the particulars involving the circumstances and situation in this instance," Mr Lesko said.

"It seems fairly aligned with a series of precedents... where public servants improperly handled and shared classified material."