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Ex-President Donald Trump has repeatedly shown his wish to see critics probed, applying pressure on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

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

"I was impeached twice, and charged me (5 times!)" he said, mentioning the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

Both have since been indicted, in situations that numerous specialists have stated appear to be driven by politics and challenging to succeed in court.

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

"I would say, comparing Bolton's case to Comey's is like equating apples to oranges," said Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of the Legal Situation

Bolton has been formally charged on federal charges related to the supposed mishandling of sensitive materials. After leaving the White House in 2019, he has become a vocal presidential opponent, going so far as to call him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political reasons to go after Bolton, the methods used to obtain an charge and the proof compiled against him indicate a potentially stronger legal argument than the Justice Department presented against James.

"These actions that's being claimed is simultaneously more serious and appears to have taken place 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 national security adviser, and after his 2019 White House departure, prosecutors alleged that Bolton placed the nation at danger by wrongfully retaining and transmitting classified information to family members using insecure means, including AOL. Several of the materials were marked highly classified.

The charge states that at one point a hacker accessed to Bolton's account where documents were stored and sent an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on recently to eighteen separate charges of improperly handling classified information.

Retribution or a Strong Case?

The timing of his charge - coming on the heels of charges against Comey - has renewed questions about political pressure on the justice system.

Trump once implied Bolton belonged in prison, and described him a "disreputable person". Bolton, for his part, wrote a book about his experience in the Trump administration that was sharply negative of the president.

"There's no question that the schedule of this charge, when combined with others, has prompted questions about the validity of these charges, and the reason these counts are being filed now," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "if the DOJ is capable to prove the allegations stated and demonstrate the information is properly designated, his behavior may certainly have broken the law".

Charging such a senior official for improperly handling sensitive materials is "rare" but not unprecedented, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that concern classified information pose difficulties to prosecute, but they can and are brought against both low-level and high-level officials, from time to time," she explained.

Similarities to Investigations into Trump and President

Trump likewise encountered charges of wrongfully keeping sensitive materials 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 determined that former President Joe Biden wrongfully stored classified documents from his period as vice president, but failed to criminally charge him.

Bolton's case shares characteristics to Trump's classified documents matters, said Mr Lesko, who also held a senior national security position at the Justice Department.

Strict protocols govern the handling of classified documents. To win a guilty verdict, the prosecution must prove that Bolton knew the information he was transmitting was classified, and he had to intentionally transfer it to someone without authorization to obtain it.

"Because of the classified character of the information at issue in this case, we lack a lot of details about why the prosecution contends elements like the personal notes and the additional material he shared by electronic message, and why there were classified," said Mr Jaffer.

A Increasingly Traditional Prosecution

The procedure by which the Justice Department initiated this case will be closely examined, following Trump openly posted his desire to see his critics prosecuted and some of those charges came to fruition.

But Mr Lesko said in Bolton's case, authorities seem to have followed protocol.

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

In contrast to Comey's brief, two-page indictment, Bolton's was a more "traditional" filing that "explicitly outlines the details concerning the circumstances and circumstances here," Mr Lesko commented.

"It appears fairly aligned with a long line of precedents... where public servants mishandled and shared sensitive information."