This essay revisits the debate on the motives of the Flemish nationalist historian Hendrik Jozef Elias to collaborate during the Second World War. Using the concept of teleology, this essay will reassess certain conceptions about the life and career of Elias. First, it will argue that Elias held a unique teleological perspective on national history. Contrary to other Flemish nationalist historians who envisioned history as one long progress towards national independence, Elias adhered to the principles of the early conceptualization of teleology – ambiguity and human freedom/will – to envision history as constituting a plethora of different national communities, each with its own idea and will that was formed by their corresponding historical circumstances. This unique teleological perspective consequently influenced Elias’ subsequent political career. By characterizing his own era as a national community possessing a historically defined will, Elias believed that it was imperative for an individual to adhere to this will once history had made it clear. Consequently, this meant that he had no other choice but to collaborate to support his national community’s will. In addition, Elias believed he had to continue to adhere to this will, even when historical circumstances changed, spelling the end not only of his historically defined national community, but of his own political career as well.