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Ex-President Donald Trump has repeatedly expressed his wish to see critics probed, exerting influence 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 standing and trustworthiness," the president stated recently in a Truth Social message.

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

Each have since been charged, in cases that numerous specialists have said seem to be driven by politics and difficult to succeed in legal proceedings.

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

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

This Details of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the alleged mishandling of classified information. After departing the White House in 2019, he has become a vocal Trump critic, going so far as to describe him "stunningly uninformed" and unsuitable for office in his book.

Experts say that while there may be political reasons to go after Bolton, the procedures used to secure an charge and the proof gathered against him indicate a potentially more substantial case than the DOJ presented against Comey.

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

Throughout his time as Trump's national security adviser, and following his 2019 White House departure, prosecutors alleged that Bolton placed the country at risk by wrongfully keeping and sending sensitive documents to family members using insecure means, including AOL. Some of the documents were labeled highly classified.

The indictment alleges that at a certain time a hacker gained access to Bolton's system where documents were stored and transmitted an seeming warning to cause "the biggest controversy since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on recently to 18 distinct counts of improperly handling classified information.

Political Motivation or a Strong Legal Argument?

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

Trump once implied Bolton should be in jail, and described him a "sleazebag". Bolton, for his role, authored 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 others, has raised doubts about the strength of these charges, and the reason these counts are being brought now," stated Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "should the DOJ is able to demonstrate the allegations alleged and show the material is correctly designated, his conduct may very well have broken the statute".

Charging such a high-ranking figure for mishandling sensitive materials is "uncommon" but not without precedent, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve classified information pose difficulties to try, but they may and are filed against equally low-level and high-level officials, from occasionally," she said.

Parallels to Examinations into Trump and Biden

Trump similarly faced allegations of improperly storing classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was eventually dismissed by a federal judge and negated by his return as leader.

A independent investigator 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 situation bears similarities to Trump's classified documents matters, noted Mr Lesko, who also held a senior national security role at the DOJ.

Rigorous protocols regulate the handling of classified documents. To secure a conviction, the prosecution must demonstrate that Bolton knew the material he was transmitting was restricted, and he had to knowingly transfer it to someone not entitled to receive it.

"Because of the classified character of the material at question in this case, we lack a great deal of particulars about the reasons the government contends things like the personal notes and the additional material he communicated by electronic message, and the reason there were restricted," said Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ initiated this case will be under scrutiny, following Trump openly posted his desire to see his political opponents prosecuted and several of those indictments came to fruition.

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

"This Bolton prosecution and ultimately the indictment appeared to have followed the regular procedure including the regulations and standards within the Department of Justice," he stated.

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

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