Some of the most contested questions in political science and political economy revolve around the conditions under which democratization is likely to happen and when democracy becomes a stable institutional choice. This paper revisits the particular claim in the democratization literature that the type of colonization, and particularly the degree to which Europeans settled in a colony, fundamentally affected the probability that democratic institutions developed and became stable. We revisit this and several other theories of democratization by using a unique source of information – the Statesman’s Yearbook – on a large number of non-sovereign countries in the immediate aftermath of WWII. Analysis shows that neither the size of the European population nor the existence of institutions of higher education appear to be important for the subsequent democratization of countries decolonized during the latter half of the 20th century, while the existence of representative political bodies during the late colonial period clearly predicts the existence and stability of democracy in recent decades.