“MACHIAVELLIAN” AMBITIONS
The files reveal a man eager to cast himself as what he described as a Machiavellian figure. In multiple prompts to LLMs, Dougan generated manifestos portraying his departure from the U.S. as a calculated strategic move, not in order to avoid prosecution. “I did not flee the United States out of fear. I fled because I understood the game… I built my own terrain, my news websites,” he wrote.
In fact, Dougan fled Florida after the FBI raided his home and seized his electronic equipment amid an investigation into the publication of confidential information about thousands of law-enforcement officials, and for which he was later charged for wiretapping and extortion.
In one LLM prompt, Dougan provided a biographical draft and said to the Qwen model, accessed through Open WebUI: “I want to rewrite this into a more Machiavellian introduction, before I go into my confession about that the US and European authorities allege about me.” He also instructed a Qwen model to generate a “machiavellian dating profile that will intrigue women.” He added: “I’m also an international fugitive, my friends think I’m a real life James Bond.” The Qwen model complied.
In an undated letter addressed to Russian President Vladimir Putin, Dougan asked to be the public face of Russian hacking in the U.S., stating, “I put a face to the culprit and give Americans someone to blame – an American – My only wish now is for Russian citizenship and to see my children, and they can come to visit me here.” It is unclear whether the letter was ever sent.
However, Dougan’s 10 years in Moscow appear to have ended in frustration. The leaked files also expose a propagandist growing deeply disillusioned with his Russian overseers and lack of financial reward for his efforts, complaining of extreme burnout and internet censorship in the country making his work more difficult.
In comments to NewsGuard this week, Dougan appeared to brush off the impact of the leaks on his status in Moscow. “Really the worst thing in this [leak] was that I was talking shit about the blocking of the internet but you know, that’s nothing unusual. It made my life more difficult, and I’m sure nobody blames me,” he said via Signal messaging, referring to his complaints about internet limitations imposed by the government.
Asked by NewsGuard this week whether he had left Russia, Dougan replied, “Of course not. Why?”