The historical development of the four main theories which have attempted to explain the relationship between cognitive style and ideological content—i.e., authoritarianism, extremism theory, context theory, and value pluralism theory—is analyzed from a rhetorical perspective. The discussion focuses on the manner in which the tensions between theoretical universalism and political critique have been “resolved” by theorists working in different historico-political contexts. While both these scientific and political values have been of central concern in theorizing the link between cognitive style and content, they are deeply incompatible because it is not possible to establish a fixed relationship between a personality dimension and the changing beliefs associated with different ideologies across time and place. This has prompted theorists aiming for universalistic accounts to define ideological orientation in terms of psychological processes rather than content, which, in turn, has compromised the critical potential of their theory. The paper concludes that the historical development of the literature may be understood in terms of dilemmatic counter-themes which, under different political circumstances, have been resolved in novel ways.