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

"We cannot postpone further, it's damaging our standing and trustworthiness," the president wrote last month in a Truth Social post.

"They impeached twice, and charged me (5 times!)" he said, mentioning the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Both have subsequently been indicted, in cases that many experts have said seem to be driven by politics and challenging to win in legal proceedings.

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

"In my opinion, comparing Bolton's case to Comey's is like comparing apples to oranges," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of Bolton's Case

Bolton has been criminally indicted on federal charges pertaining to the alleged improper handling of sensitive materials. Since leaving the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to call him "stunningly uninformed" and unfit for the presidency in his memoir.

Experts say that while there may be political reasons to target Bolton, the methods used to obtain an indictment and the evidence compiled against him indicate a possibly more substantial case than the DOJ presented against James.

"These actions that's being claimed is both more serious and appears to have occurred over a considerable duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House departure, prosecutors alleged that Bolton placed the nation at danger by wrongfully retaining and transmitting sensitive documents to family members using insecure means, including AOL. Some of the materials were marked highly classified.

The indictment alleges that at a certain time a unauthorized user accessed to Bolton's account where files were stored and sent an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on recently to 18 distinct charges of mishandling sensitive materials.

Political Motivation or a Strong Case?

The schedule of his indictment - arriving on the heels of charges against Comey - has revived questions about external influence on the legal system.

Trump once implied Bolton should be in prison, and called him a "sleazebag". Bolton, for his role, wrote a publication about his time in the Trump administration that was highly critical of the president.

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

However, he continued, "if the Justice Department is capable to prove the allegations stated and demonstrate the material is properly classified, his behavior may very well have broken the law".

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

"Situations that involve classified information present challenges to prosecute, but they may and are filed against both junior and high-level officials, from time to time," she explained.

Parallels to Examinations into Former President and Biden

Trump likewise faced 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 president.

A special counsel additionally found that ex-President Joe Biden improperly stored sensitive materials from his time as vice president, but did not criminally charge him.

Bolton's case shares characteristics to Trump's sensitive materials issues, said Mr Lesko, who also held a senior security role at the Justice Department.

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

"Due to the sensitive nature of the information at question in this matter, we don't have a great deal of particulars about why the government believes elements like the personal notes and the other information he shared by electronic message, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The process by which the Justice Department brought this legal action will be closely examined, after Trump openly expressed his wish to see his critics charged and some of those indictments materialized.

But Mr Lesko said in Bolton's situation, prosecutors appear to have adhered to protocol.

"The Bolton prosecution and ultimately the indictment appeared to have followed the regular process including the rules and standards within the DOJ," he said.

Unlike Comey's short, concise charge, Bolton's was a more "conventional" document that "clearly outlines the details concerning the facts and situation in this instance," Mr Lesko said.

"It appears fairly consistent with a series of precedents... where government officials improperly handled and shared sensitive information."