This paper considers the historical contexts in which theories of legal pluralism grew and developed between the final third of the nineteenth century and the first half of the twentieth century. Theories of the state as a pluralistic system, as opposed to the absolute supremacy of state-made law, were the focus of German legal historical scholarship in the late nineteenth century, represented by the towering figure of Otto von Gierke. Gierke's image of a pluralist German Middle Ages largely influenced legal scholarship in Europe, even affecting the Italian scholar Santi Romano, whose book on the “legal order” has been considered a milestone in the construction of pluralist legal theories. Once passed from a legal historian like Gierke to a theorist like Romano, the model of a pluralist legal order returned to legal historiography, inspiring the innovative historical interpretation of medieval law proposed by Francesco Calasso. Gierke was a conservative, right-wing socialist, and Romano was a fascist and counselor of the fascist Italian government. Calasso, on the contrary, was a liberal opponent of the fascist regime. The three versions of legal pluralism, then, decline the same basic vision in three different ways, being influenced by the political contexts in which the three authors operated.