Former President Donald Trump has repeatedly expressed his desire to see opponents probed, exerting pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.
"We cannot postpone any longer, it's damaging our reputation and credibility," the leader wrote last month in a Truth Social message.
"They impeached twice, and indicted me (five times!)" he said, mentioning the four criminal cases he encountered after leaving the White House in 2021 and James's lawsuit.
Both have since been charged, in cases that many experts have said seem to be driven by politics and challenging to succeed in legal proceedings.
But the most recent allegations against a Trump critic, ex national security adviser John Bolton, differ significantly, legal experts and former prosecutors say.
"I would say, comparing Bolton's case to James' is like comparing two different things," stated Mark Lesko, a ex federal prosecutor for the Eastern District of New York.
Bolton has been formally charged on national allegations pertaining to the alleged mishandling of sensitive materials. After departing 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 office in his book.
Experts say that while there may be political motivations to go after Bolton, the methods used to secure an indictment and the evidence compiled against him suggest a possibly stronger case than the Justice Department presented against Comey.
"This misconduct that's being claimed 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 time as Trump's security advisor, and following his 2019 White House departure, authorities claimed that Bolton placed the nation at danger by improperly keeping and sending classified information to family members using insecure means, including AOL. Some of the materials were marked top secret.
The indictment alleges that at a certain time a unauthorized user gained access to Bolton's system where documents were kept and sent an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".
Bolton entered a not guilty plea during a hearing on recently to 18 separate charges of improperly handling classified information.
The schedule of his indictment - arriving on the heels of allegations against Comey - has revived questions about political pressure on the legal system.
Trump previously suggested Bolton belonged in jail, and called him a "disreputable person". Bolton, for his part, wrote a book about his experience in the Trump administration that was sharply negative of the leader.
"Undoubtedly that the timing of this indictment, when paired with additional cases, has prompted questions about the validity of these allegations, and why these counts are being brought now," stated Jamil Jaffer, creator and executive director of the National Security Institute.
However, he continued, "if the Justice Department is able to demonstrate the facts alleged and demonstrate the material is correctly designated, his conduct may certainly have broken the statute".
Charging such a high-ranking official for mishandling sensitive materials is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.
"Cases that involve classified information pose challenges to try, but they may and are filed against equally low-level and senior personnel, from occasionally," she said.
Trump similarly encountered allegations of improperly keeping sensitive materials at his Mar-a-Lago property in Florida and hindering their recovery, but that case was ultimately dismissed by a court official and negated by his re-election as president.
A special counsel also found that ex-President Joe Biden wrongfully stored classified documents from his time as second-in-command, but failed to criminally charge him.
Bolton's situation bears similarities to Biden's sensitive materials issues, said Mr Lesko, who previously held a top security role at the Justice Department.
Rigorous procedures govern the handling of classified documents. 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 obtain it.
"Because of the sensitive character of the information at issue in this matter, we don't have a lot of particulars about why the government contends things like the diary entries and the other information he communicated by email, and the reason there were restricted," explained Mr Jaffer.
The process by which the DOJ initiated this case will be closely examined, after Trump openly posted his desire to see his critics prosecuted and several of those charges materialized.
But Mr Lesko indicated in Bolton's case, prosecutors seem to have adhered to protocol.
"The Bolton case and eventually the indictment seemed to have observed the standard process including the rules and standards within the Department of Justice," he said.
Unlike Comey's short, concise indictment, Bolton's was a more "conventional" filing that "clearly sets forth the details involving the facts and situation here," Mr Lesko said.
"It seems fairly aligned with a series of cases... where public servants mishandled and transmitted sensitive information."