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

"We cannot postpone further, it's killing our reputation and credibility," the president stated recently in a social media message.

"I was impeached twice, and charged me (five times!)" he said, mentioning the four criminal cases he faced after leaving the White House in 2021 and James's civil case.

Each have subsequently been indicted, in cases that many experts have stated appear to be driven by politics and difficult to succeed in legal proceedings.

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

"In my opinion, comparing Bolton's case to James' is like equating two different things," stated Mark Lesko, a former federal prosecutor for the Eastern District of New York.

The Details of Bolton's Legal Situation

Bolton has been criminally indicted on federal charges related to the alleged mishandling of sensitive materials. After departing the White House in 2019, he has become a vocal presidential opponent, going so far as to describe him "stunningly uninformed" and unfit for the presidency in his memoir.

Experts say that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the proof compiled against him suggest a possibly stronger legal argument than the Justice Department presented against Comey.

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

During his tenure as Trump's security advisor, and after his 2019 White House departure, authorities alleged that Bolton put the country at risk by wrongfully keeping and transmitting classified information to family members using insecure means, including AOL. Some of the materials were labeled top secret.

The charge states that at a certain time a hacker gained access to Bolton's system where files were kept and transmitted an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a hearing on Friday to 18 distinct counts of improperly handling classified information.

Retribution or a Strong Legal Argument?

The schedule of his indictment - arriving on the heels of allegations against Comey - has revived concerns about political pressure on the legal system.

Trump previously implied Bolton belonged in jail, and described him a "disreputable person". Bolton, for his part, authored a publication about his time in the Trump government that was highly critical of the leader.

"Undoubtedly that the timing of this indictment, when combined with others, has prompted doubts about the strength of these allegations, and the reason these charges are being brought at this time," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he added, "should the DOJ is able to demonstrate the facts alleged and show the information is correctly designated, his conduct may certainly have violated the statute".

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

"Situations that involve classified information pose challenges to try, but they may and are brought against both junior and senior officials, from occasionally," she said.

Parallels to Examinations into Former President and Biden

Trump similarly faced allegations of improperly storing sensitive materials at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was ultimately dismissed by a federal judge and voided by his return as president.

A special counsel also found that former President Joe Biden wrongfully stored sensitive materials from his period as vice president, but failed to criminally charge him.

Bolton's situation bears similarities to Trump's sensitive materials matters, said Mr Lesko, who previously held a senior security role at the Justice Department.

Strict protocols govern the management of classified documents. To secure a conviction, the government must demonstrate that Bolton was aware the material he was transmitting was restricted, and he had to knowingly transmit it to someone not entitled 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 the reasons the government believes elements like the diary entries and the other information he communicated by email, and the reason there were restricted," explained Mr Jaffer.

A More Traditional Legal Action

The procedure by which the DOJ brought this legal action will be under scrutiny, following Trump openly expressed his desire to see his critics prosecuted and several of those charges came to fruition.

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

"This Bolton prosecution and eventually the indictment seemed to have observed the standard process including the rules and standards within the DOJ," he said.

In contrast to Comey's brief, concise indictment, Bolton's was a increasingly "conventional" document that "clearly outlines the particulars involving the facts and circumstances in this instance," Mr Lesko commented.

"It appears fairly consistent with a series of precedents... where public servants mishandled and shared classified material."