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Former President Donald Trump has consistently shown his wish to see critics probed, applying influence on the DOJ to prosecute former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's killing our reputation and trustworthiness," the president stated last month in a Truth Social message.

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

Both have since been indicted, in cases that numerous experts have stated appear to be politically motivated and challenging to succeed in court.

But the latest allegations against a Trump critic, former national security adviser John Bolton, differ significantly, legal specialists and ex-prosecutors say.

"In my opinion, contrasting Bolton's case to Comey's is like comparing two different things," stated Mark Lesko, a former acting US attorney 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 classified information. Since leaving the White House in 2019, he has emerged as a outspoken Trump critic, going so far as to describe him "remarkably ignorant" and unsuitable for the presidency in his book.

Specialists say that while there may be political reasons to go after Bolton, the procedures used to obtain an charge and the proof gathered against him suggest a possibly stronger legal argument than the DOJ brought against James.

"This misconduct that's being alleged is both more serious and appears 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 tenure as Trump's security advisor, and following his 2019 White House departure, authorities alleged that Bolton placed the country at risk by improperly keeping and transmitting sensitive documents to relatives using insecure means, including AOL. Several of the documents were marked highly classified.

The indictment alleges that at a certain time a unauthorized user gained access to Bolton's system where documents were kept and sent an apparent warning to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a court appearance on Friday to 18 distinct charges of mishandling classified information.

Retribution or a Substantial Case?

The timing of his charge - coming on the heels of charges against James - has revived concerns about external influence on the legal system.

Trump previously implied Bolton should be in prison, and described him a "disreputable person". Bolton, for his part, authored a publication about his experience in the Trump administration that was highly critical of the president.

"Undoubtedly that the timing of this charge, when combined with additional cases, has prompted 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 demonstrate the allegations stated and show the information is correctly classified, his conduct may certainly have violated the statute".

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

"Cases that involve classified information pose challenges to try, but they can and are filed against both junior and high-level personnel, from occasionally," she said.

Similarities to Investigations into Trump and President

Trump likewise faced allegations of wrongfully keeping sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was eventually thrown out by a court official and voided by his re-election as leader.

A independent investigator also determined that former President Joe Biden wrongfully maintained classified documents from his time as second-in-command, but failed to prosecute him.

Bolton's situation shares characteristics to Trump's sensitive materials issues, said Mr Lesko, who also held a top national security position at the Justice Department.

Rigorous procedures govern the management of sensitive materials. To win a conviction, the government must demonstrate that Bolton was aware the information he was transmitting was restricted, and he had to intentionally transfer it to someone not entitled to receive it.

"Due to the sensitive character of the information at issue in this case, we don't have a great deal of details about why the government contends things like the personal notes and the additional information he communicated by email, and why there were restricted," said Mr Jaffer.

A More Traditional Prosecution

The procedure by which the Justice Department initiated this legal action will be under scrutiny, following Trump publicly expressed his wish to see his political opponents charged and some of those charges came to fruition.

But Mr Lesko indicated in Bolton's case, authorities appear to have adhered to standard procedure.

"This Bolton case and eventually the indictment seemed to have followed the regular procedure including the regulations and norms within the DOJ," he stated.

In contrast to Comey's short, concise charge, Bolton's was a more "traditional" filing that "explicitly outlines the details involving the circumstances and circumstances in this instance," Mr Lesko said.

"It seems fairly consistent with a long line of cases... where government officials mishandled and transmitted sensitive information."