Baron Heinrich Freiherr von Stackelberg is remembered for his market typology and his principles of political economics. However, he also stands out for his singular admiration of authoritarian political regimes. The purpose of this article is therefore to rethink and reinterpret elements that will help us gain a fuller understanding as to why Stackelberg adopted such a political stance. These elements derive from the information that has already been identified by historians of political economy. We intend to delve into certain aspects of Stackelberg’s controversial life, especially in relation to his personality, his profile, and his upbringing, and demonstrate that lurking in the background of his conception of the market was a radical worldview.