Conservative attorney George Conway didn’t flinch when asked if he feared being next on Donald Trump’s so-called “enemies list.” During an interview on MSNBC’s “The Weekend: Primetime” on October 20, 2025, Conway was pressed by host Catherine Rampell about the recent federal grand jury indictment of former national security adviser John Bolton. “Yes or no answer, are you worried that you’re next? On the enemies list?” Rampell asked. Conway’s response was brief and pointed: “No.” He didn’t leave it there, adding, “Let him try.”
Conway’s confidence comes amid a whirlwind of controversy surrounding the indictment of John Bolton, a former Trump administration insider turned outspoken critic. Last week, a federal grand jury in Maryland indicted Bolton on eight counts of transmitting and ten counts of retaining national defense information, according to The Iola Register. Prosecutors allege that between the spring of 2018 and at least the late summer of 2025, Bolton shared more than a thousand pages of top secret national defense information with two unauthorized individuals—his wife and daughter—using nongovernmental messaging apps and email accounts. The indictment claims these transmissions included diary-like entries detailing his daily activities as national security adviser, information marked as top secret and linked to national defense.
Bolton, for his part, has fiercely denied any criminal wrongdoing. In a statement, he insisted, “My book was reviewed and approved by the appropriate, experienced career clearance officials. When my e-mail was hacked in 2021, the FBI was made fully aware. In four years of the prior administration, after these reviews, no charges were ever filed. Then came Trump 2 who embodies what Joseph Stalin’s head of secret police once said, ‘You show me the man, and I’ll show you the crime.’” According to The Hill, Bolton likened his indictment to the weaponization of the Justice Department, claiming he is the latest in a string of Trump’s perceived enemies to face criminal charges.
The charges against Bolton stem from his practice of keeping contemporaneous diary notes during his tenure in the Trump White House. Bolton has argued that he was within his rights to keep a diary based on his memory, particularly for his book, The Room Where It Happened. The Iola Register notes that the book was reviewed and cleared for publication by White House officials, specifically Ellen Knight, the official then in charge of vetting such books. Despite this clearance, the indictment makes much of the fact that the information Bolton is accused of mishandling did not appear in his book after the draft was reviewed by the White House.
Bolton’s defense is further complicated by the fact that one of his personal accounts was hacked by Iran in 2021. However, he disclosed the breach to the FBI and cooperated with federal investigators, who were already aware of Iranian efforts to assassinate both Bolton and then-Secretary of State Mike Pompeo. The indictment does not allege that Iran used any information from Bolton’s emails to harm the United States, a detail that underscores the ambiguous national security impact of the alleged leaks.
This prosecution has sparked a fierce debate over its underlying motivation. Editorials in both The Iola Register and The Korea Times point to political retribution as the driving force behind the charges. According to The Korea Times, Bolton’s indictment marks the third time a prominent Trump critic—after former FBI Director Jim Comey and New York Attorney General Tish James—has faced federal criminal charges. The editorial claims the real motivation is Trump’s “Lock Them Up!” agenda, accusing the Department of Justice of being used for political purposes.
The editorial further speculates that Trump either ordered Bolton’s prosecution directly or was unaware of it, both scenarios reflecting poorly on his leadership. “Trump personally has never been all that interested in the nuts and bolts of management or policy or government,” the editorial asserts. “He likes to speak to the cameras and see himself on television, but as for the daily decision-making, he mostly seems content to toss it over to the group of grifters and ideologues that populate his government.”
There’s also the suggestion that senior FBI officials, such as Kash Patel, may be acting independently to curry favor with Trump by pursuing cases against his critics. The Korea Times editorial warns that these prosecutions are “designed to intimidate” rather than secure convictions, arguing that “any respectable federal judge will laugh them out of court.” The piece calls for political solutions and congressional oversight, though it concedes that such action is unlikely under the current Trump-aligned Congress. “Perhaps the next one will,” the editorial muses, urging that the charges be dismissed and critics continue to speak out.
Bolton’s lawyer, Abbe Lowell, has also weighed in, maintaining that the diaries in question are the kind of records “that would be kept by a 40-year career official.” Lowell insists that “an objective and thorough review will show nothing inappropriate was stored or kept by Amb. Bolton.” He emphasizes that keeping personal notes for memoirs is a longstanding tradition among public officials, citing the example of Jimmy Carter’s national security adviser, Zbigniew Brzezinski, whose own journal entries informed his memoir, Power and Principle.
For Trump’s part, his public comments have been characteristically blunt. As The Iola Register reported, Trump called for Bolton’s prosecution as early as 2020, after the release of Bolton’s book. “He released massive amounts of classified, and confidential, but classified information. That’s illegal and you go to jail for that,” Trump said at the time. White House aides reportedly spent hours pressuring Ellen Knight to say classified information had been used in the book, but she refused, and the book was ultimately cleared for publication.
The Biden Justice Department did not pursue the case, but the Trump FBI raided Bolton’s office and home in August, according to The Iola Register. This escalation has only fueled claims that the prosecution is less about national security and more about settling political scores. The Korea Times editorial sums up the prevailing skepticism: “Those who have too publicly or forcefully criticized Trump or his administration are clear targets for political retribution in the form of weaponized justice, no actual wrongdoing needed.”
As the legal battle unfolds, the case raises pressing questions about the boundaries of presidential power, the independence of the Justice Department, and the risks faced by those who choose to speak out against the administration. For now, critics like George Conway remain undeterred, while Bolton’s fate will be decided in a courtroom that may ultimately have to weigh not just the facts of the case, but the larger implications for American democracy.
