Former US national security advisor John Bolton and the President Donald J. Trump share traits neither probably knew they had. The latter, for one, is far more war mongering than he let on to American voters, evidenced by his recently failed, disastrous foray into attacking Iran. Bolton, on the other hand, has been a consistent war addict, the neocon’s preferred position in projecting US power through what the British used to call might. Earlier in June, Trump had the fantastic gall to say this about the man who had a brief stint as his own moustachioed national security advisor from 2018 to 2019: “I never thought [Bolton] was a smart person, that he was a radical right in terms of war, not in terms of other things. He was. He wanted to go to war with anybody that opened their mouth, anybody that talked, and I used him for a purpose, you know.” Yet another one of the president’s mirror portraits.
Trump went on to note Bolton’s involvement with the administration of President George W. Bush where “he created a lot of problems, but he always wanted to kill people in war, and that was okay for me, as long as I didn’t listen to him, which I never did.” Listening to Israel’s Benjamin Netanyahu must have been quite something else.
That other commonly shared trait between the two is a rather sketchy approach to handling classified documents. In October 2025, a grand jury indicted Bolton for the discovery of private journal entries, private notes and assortment of classified material from his time as national security advisor. Many of the “diary” entries about his daily activities contained, among other things, military plans for adversarial foreign governments, covert US activities in various theatres, and intelligence on adversarial heads of state. This might have stayed buried but for the hacking activities of, as the Department of Justice put it, “a cyber actor believed to be associated with the Islamic Republic of Iran”. (The hack of Bolton’s personal email account was reported after he left office in September 2019 with one glaring omission: he did not tell the FBI or anyone else in government that the account contained national defence information.) How fitting in its symmetry that both Bolton and Trump have found themselves bedevilled by the same country of their ire.
The documents in question were sent to two of Bolton’s family members who were not authorised to access, receive or possess the classified material in question. These were conveyed via non-governmental email accounts and a non-governmental messaging platform yet to be approved for processing classified information. Copies of the said documents were also kept, without permission, at his Bethesda home.
The list of counts in the indictment proved menacing: eight for transmission and 10 for retaining classified defence information. On June 26, Bolton entered a guilty plea to one count of retaining national defence information in a federal court in Maryland, thereby resolving all 18 counts. He faces a maximum prison term of 60 months and has agreed to pay a fine of US$2.25 million. The plea agreement also notes that neither he nor his survivors will be able to collect any annuity or federal retirement pay.
The officials at hand to make the announcement uttered the expected platitudes. Kelly O. Hayes, US Attorney for the District of Maryland, was in good form in talking about the priority of the attorney’s office as keeping Americans safe and ensuring that “anyone who endangers our national security will be brought to justice.” Hayden O’Byrne, Acting Deputy Assistant Attorney General, spoke of how the case “ought to send a message to other public officials whom the public has entrusted with classified, national defense information. If you wilfully mishandle these state secrets, the Department of Justice, led by the National Security Division, will investigate and prosecute you to the fullest extent of the law.”
Where to start with such remarks, other than to note the misdeeds of that most highly ranked of officials entrusted with the most sensitive of state secrets, one Donald Trump? The president’s appallingly lax approach to classified documents has teetered on the criminal. Such conduct, however, has never been punished. Following his first presidency, Trump faced a grand jury indictment bristling with 40 felony counts regarding the mishandling of classified documents arising from that term. The June 8, 2023 indictment against Trump and his alleged co-conspirator Waltine Nauta, who had been stationed as a valet in the White House during the presidency, noted his retention of “hundreds of classified documents” including information on defence and weapons capabilities of the US and foreign countries, US nuclear programs, potential vulnerabilities of the US and its allies to military attack and plans for possible retaliation given that eventuality. These had been secreted among newspapers, press clippings, letters, notes, cards, photographs and other miscellaneous material in “scores of boxes” which were duly transported to his Mar-a-Lago Club in Palm Beach, Florida.
In July 2024, and just days after an attempt was made on his life, Judge Aileen Cannon granted the motion of Trump’s legal team to dismiss the case. He had successfully argued before his own appointee, that most satisfying state of affairs for an accused, that the DOJ’s appointment of special prosecutor Jack Smith violated the Appointments Clause of the US Constitution. Smith’s prosecution did not accord with “the role of Congress in the appointment of constitutional officers, and the role of Congress in authorizing expenditures by law”. That role could not “be usurped by the Executive Branch or diffused elsewhere”.
Smith, an appointee of former Attorney General Merrick Garland, initially appealed the decision. He was subsequently requested to dismiss the case with Trump’s return to the White House, as the DOJ is barred from prosecuting sitting presidents. In February this year, the same judge granted the president’s request to permanently prevent the release of Smith’s report on Trump’s handling of classified documents at his Mar-a-Lago residence. The report, comprising two volumes, had been submitted to Garland on January 7, 2025. In words that said much about the foundering Republic, Judge Cannon thought releasing the second volume of the report regarding the handling of the classified documents would cause “irreparable damage” to the president and “contravene basic notions of fairness and justice.” It would certainly reveal the sheer slovenliness of the leader of the free world when dealing with matters classified.
As that old idiom goes, the fish rots from the head down, and the second administration has not disappointed with its singular treatment of sensitive security information. Dare one forget that caricature of carelessness called Signalgate, when then national security advisor Michael Waltz added Jeffrey Goldberg of The Atlantic to a Signal chat chain containing details on forthcoming military strikes on Yemen. These included sequencing details of the attacks, information about the targets and weapons that would be used. No counts levelled there, except perhaps that of risible stupidity. For that mighty achievement, Waltz was made ambassador to the United Nations.
Trump, currently reigning in a kingdom beyond prosecution, has been splenetic in his attitude to Bolton, whom he accused, most richly, of using classified information in his unflattering account of the Trump administration in The Room Where It Happened. For Trump, power is an exercise of personal grievance and petty remonstrance. No slight is undeserving enough of punishment. Bolton tattled about the room where things happened; he just did not read it very well. Not so smart after all.