While not named, I’m going to assume that much of this piece is about Dave “I’m not a conservative, I just play one on TV” Rubin. I’m not convinced the guy has much in the way of a privately held sincere political ideology. He strikes me as a grifter and nothing more than that.
Your hypothetical about Kellyanne Conway is intriguing, and it reminds me a lot of the Vonnegut novel Mother Night. About a German citizen who is recruited by the Americans during WW2, to infiltrate the Nazi party and become a spy for the Allied forces. He becomes the most famous and successful propagandist that the Nazis have. Problem is, the CIA disavows knowledge of him after the war is over, and he is tried as a war criminal. The novel is about whether he owns any of the moral responsibility for being a Nazi propagandist — he was, after all, only pretending, and yet it’s undeniable that he provided a great service to the Nazi’s efforts. A fantastic novel.